italy tours 2 weeks

BEST of Italy in 2 Weeks: Detailed 14-Day Itinerary (+Map & Planning Tips)

By Author Jurga

Posted on Last updated: June 3, 2024

Planning a trip to Italy for the first time and getting overwhelmed? You are not alone! We get this question all the time: ‘What is the best Italy itinerary for a first trip’ ?

In all honesty, there is no one ‘best’ way to plan a trip to Italy. It’s a big and incredibly beautiful country and pretty much everywhere is worth visiting. But if this is your first trip to Italy and you don’t know where to start, I recommend focusing on the ‘musts’ – some of the most beautiful places in Italy that everyone should see at least once in a lifetime.

To help you plan a trip, in this guide, we share a detailed 2-week Italy itinerary that brings you to all the most famous places in the country : Rome, Florence, Venice, Milan, but also the famous Leaning Tower of Pisa, Tuscan countryside, Cinque Terre, Amalfi Coast, Pompeii, and a few other destinations that should be at the top of every Italy bucket list.

Will you see everything in Italy in two weeks? No, definitely not! But if you want to see the main highlights and get a good idea of what Italy is about, this itinerary is a great first introduction to this amazing country. And take my word for it – you will want to go back and explore more!

So why do we recommend 2 weeks? In my opinion, you really need at least two weeks in order to quickly see all the ‘musts’ in Italy. If you have just a week or ten days, don’t worry – Italy is still more than worth a trip (it always is!). But if you want to cover all the main highlights, you’ll really need at least 12-15 days.

In this article, we focus on helping you make the most of your first trip and plan the most complete Italy itinerary in 2 weeks. At the bottom of this guide, you can also find our additional suggestions on places to see if you have more time.

Good to know: You can visit Italy in any season and this trip itinerary is suitable for any time of the year. Some coastal areas might be a bit deserted in winter, but if you absolutely want to see them, it’s possible too.

Also, this itinerary is structured in such a way that you don’t have to change hotels too often . This will save you time for practicalities and leave more time to explore.

Since most of the places covered in this Italian itinerary are cities, we DO NOT recommend renting a car for this trip . You can’t do much with a car in Rome or in Venice and you can easily travel between the main cities by train . And for those few places where it would be useful to have a car, you can take day tours (you can find all this info in our article).

If you want to explore a few places in northern Italy deeper, you could rent a car after you visit Venice and then return it in Milan . Depending on what exactly you want to see, it might make sense to consider hiring a car for this part of the trip.

How to use this itinerary: As you’ll see, this 2-week trip starts in Rome and ends in Milan . Both cities have major international airports and it’s quite easy to find flights to/from Rome or Milan from pretty much anywhere in the world. Of course, you can do the trip in the other direction, or you can also make a round trip starting and ending at any of the cities mentioned below . This itinerary is solely meant to give you an idea of what can be done and how you can plan a 2-week trip to Italy.

MAP: To help you get a better idea of where all these places are located, we also created a map indicating all the places covered by our itinerary.

Take a look!

This is our recommended Italy itinerary that covers all the best places in two weeks:

Day 1: Arrival in Rome

There is no better place to start your Italian vacation than in the Eternal City – the capital city of Italy – Rome .

For this itinerary, I recommend that you spend at least 3 full days in Rome: 2 days in the city itself, plus make a day trip to Pompeii and the Amalfi Coast. This way, you won’t have to change hotels too often and can see (albeit very shortly) some of the best places in southern Italy as well.

Depending on when your flight arrives, you might be able to see some of the landmarks of Rome on the first day already.

TIP: If you can make it, I highly recommend joining an evening walking tour of the city’s highlights – it’s a great first introduction to the city!

Accommodation: Stay in Rome for 4 nights. Here you can find our guide to the best area to stay in Rome . We recently stayed at 9Hotel Cesari and loved it (especially the breakfasts on their rooftop terrace). On a bit lower budget, Hotel Accademia is an excellent choice, and you’ll find many other hotels in the same area.

Days 2-3: Rome

While two days are really short for Rome, if you plan well, you can see most of the ‘musts’ in just 2 days.

We recommend focusing on the main attractions, such as the Vatican , the Colosseum , and all the famous sights in the historic city center (Trevi Fountain, Pantheon, etc.). In addition, you can also add one or two more local experiences such as e.g. a food tour . It will make your visit more memorable and also a bit more relaxing!

Good to know: Be sure to book your tickets/tours for the Colosseum and also for the Vatican in advance!!! Both are extremely popular attractions and tickets often sell out (in high season, sometimes a few weeks in advance). Tip! This Rome Tourist Card allows you to book timed entry tickets for both these attractions in one place, so you’ll also immediately see what is open on the day when you are there (and can adjust your itinerary if needed).

TIP: If you didn’t get the tickets in advance and they are sold out, you can usually still join one or the other guided tour (they usually have access to tickets that are reserved for tour groups). In any case, at least for the Colosseum and the Roman Forum, we highly recommend going with a guided tour rather than on your own. We took this amazing tour that also includes the Colosseum Underground and Arena Floor (these levels are not included with the regular ticket).

For more info on what to see and how to best plan your time, please see our 2-day Rome itinerary below . This itinerary includes all the top sights that you absolutely shouldn’t miss, a detailed schedule, as well as our experience-based tips on how to make the most of your short visit. Check it out!

LEARN MORE: How to see the best of Rome in 2 days

Day 4: Pompeii & Amalfi Coast day trip from Rome

You could easily spend this day in Rome and find plenty to do too. But if you want to make the most out of your two weeks in Italy, we recommend visiting Pompeii and the Amalfi Coast as a day trip from Rome . You don’t necessarily have to do it on day 4 of this itinerary; days 2 or 3 would work too, so you can move things around depending on your preference.

It’s quite a long drive to get to Pompeii from Rome, but if this is your first time in Italy and you want to see as many of the most famous places, then it’s probably worth it.

There are various tours that visit Pompeii and either Mt Vesuvius , Amalfi Coast , or Naples from Rome in one day. Any of these tours will be rushed if you only have a day, but all are really nice and you can’t really go wrong with either option.

• If visiting in the warmest months (+-March to October), we recommend this tour . It includes Pompeii and the Amalfi Coast.
• If visiting in the lower season, we recommend this tour . In winter, it brings you to Pompeii and Naples.

TIP: If you’re just interested in the city of Naples, you can also easily come here for a day by train from Rome. In that case, see our recommended 1-day Naples itinerary . Here you can also find a more detailed guide to the best things to do in Naples .

And if you have a few days extra to add to your Italy itinerary, definitely consider spending more time in this area. In that case, you could probably better fly to Naples first, before going to Rome.

Alternative: If you don’t feel like doing a 12-13-hour day tour to Pompeii and rather stay in Rome, it’s a great choice too. In that case, we recommend getting a bit off the beaten path and visiting some of the most incredible ancient sites in Rome .

We recently did this amazing e-bike tour that brings you to the famous Appian Way, Roman aqueducts, and catacombs.

And with the extra time left in the city, you could visit some of the hidden gems of Rome or see some of the best viewpoints .

Day 5: Rome to Florence & visit Florence

Next on your Italy itinerary is Tuscany , one of the most beautiful regions in the country. We recommend basing yourself in Florence for the next few days. Florence is one of the most beautiful cities in Italy and is well worth a visit, but there are also some really nice places that you can see nearby. With just a few days here, you’ll have difficulties choosing where to go and what to skip!

Florence is just a short ride from Rome (+-1.5 hrs by train). Try to get an early train so you have enough time to explore the city after you arrive and drop off your luggage at your hotel.

On the first day in Florence, be sure to visit the musts, such as the Duomo Cathedral, the Uffizi Gallery, and/or Accademia Gallery . Depending on your interests, you can visit one or all three, but be sure to plan it well.

Good to know: All these places require a ticket and are extremely popular, so it’s essential to get tickets/tours in advance! Having your sightseeing itinerary well-planned upfront is the only way not to miss any of the most important sights and keep your Italian vacation enjoyable without feeling overwhelmed.

TIP: If you want to see as many of the musts in a short time, we recommend this popular tour that includes both – Uffizi Gallery and Accademia Gallery. Afterwards, visit the Florence Cathedral and climb the Dome (be sure to get a timed-entry ticket !).

Then, stroll the streets of the city center and see some of the main highlights that don’t absolutely require tickets or reservations – such as Ponte Vecchio, Piazza della Signoria, Basilica Santa Croce, etc.

LEARN MORE: One Day in Florence

You’ll still have some additional time to explore Florence in the next days, but – depending on the day trips you choose – it will likely be just a few hours in the evenings after you get back from a tour. That’s why we recommend visiting the places that require a ticket on your first day already.

In the evenings, you can also enjoy some of the best sunset views from the nicest rooftop bars in Florence .

Needless to say, if you can add an extra day in Florence, you’ll be able to explore the city at a much more relaxed pace. But this counts for pretty much every place in this itinerary…

READ ALSO: Best Things to Do in Florence

Accommodation: Stay in Florence for at least 3 nights. Florence city center isn’t that big, but – to make things easier with the luggage and tours, stay somewhat close to the railway station. For one of our recent trips to Florence, we booked Hotel Croce di Malta – the location is excellent, they have a pool, and you can’t beat those rooftop views! On a bit lower budget, B&B Le Stanze del Duomo is one of the best price-quality hotels in the center!

Day 6: Tuscany day tour from Florence

While there’s plenty to see and do in Florence to fill a few days, you’ll likely want to see some of the famous Tuscan countryside as well.

So on your second day in Florence, we recommend taking a day tour to some of the nicest towns of Tuscany .

You could just take a train and visit the cities like Siena or Pisa on your own, but you would likely only see one town that way (and waste too much time in transit). Also here – if you want to make the most of your time, it’s best to go with an organized tour that visits a few of the very best places in a day.

TIP: We recommend this highly-rated day tour . It brings you to the Leaning Tower of Pisa, the beautiful city of Siena, the charming medieval town of San Gimignano, and more. You could never see all these places in just a day on your own.

If you rather not join a tour, then take a train to Siena. Here you can find our guide to the best things to do in Siena , including a sample itinerary for your first. As an absolute minimum, don’t miss the Siena Cathedral !

Day 7: Cinque Terre day trip from Florence

Next is another place that’s probably high on your Italy bucket list – Cinque Terre . The famous 5 villages on the Ligurian coast are among the most visited and most photographed places in Italy.

If you plan well, it’s possible to see the best of Cinque Terre in just a day, also if you are visiting from Florence. You could take a train to La Spezia and on to Cinque Terre, following our detailed 1-day Cinque Terre itinerary . If you decide to go on your own, be sure to also read our practical tips for visiting Cinque Terre .

However, Cinque Terre is very popular and extremely busy (especially in the high season from March to October). So planning a quick visit here might be overwhelming…

TIP: If you want to see all the best places without having to plan anything, you’ll be glad to know that there are also some organized day tours from Florence to Cinque Terre. This highly-rated tour is one of the very best options for a day trip from Florence and covers all the musts in Cinque Terre.

Alternative/ addition day: If you are visiting Italy in the low season, you may want to skip Cinque Terre and visit Bologna instead (it’s just 40 minutes by train from Florence). Or, you could also add a stop in Bologna when traveling between Florence and Venice.

One day is enough to see the main sights in Bologna and it’s worth it if you can squeeze it in. But – as already mentioned before – you can add extra days pretty much everywhere in this itinerary and still not see it all…

READ ALSO: Florence to Bologna Travel Info & Best Things to Do in Bologna

Day 8: Florence to Venice & explore Venice

The second part of this 2-week Italy itinerary takes you to northern Italy. The next stop is Venice , just about 2.5 hrs from Florence by train. Venice is one of the most unique cities in the world and so no Italy trip itinerary would be complete without visiting here!

If you take a train early in the morning, you’ll be in Venice by noon, which leaves you plenty of time to get acquainted with the city and see some of the main highlights. We recommend spending 2 nights here, so you have 1.5 days, plus two evenings in Venice. Venice is magical at night – the city is so pretty and you can appreciate it so much more without all the day tourists around.

On your first day, you could tick some of the must-see places on your Venice bucket list. One of the musts is St. Mark’s Square and Cathedral (one of the most beautiful churches in Italy ), and the other – Doge’s Palace , just next door. Needless to say, these are very popular attractions, so also here you have to book your tickets (or tours) in advance.

TIP: We recommend a tour like this that covers some of the musts in the most efficient way. Ideally, opt for an afternoon tour, so that you don’t have to rush in order to get there on time.

After that, explore the city center on foot, see Rialto Bridge and the Grand Canal. You should also take a Venetian gondola ride , which is another must-do in Venice!

READ ALSO: How to see the best of Venice in 1 day

Accommodation: Stay in Venice for 2 nights. To make things easy for yourself, you could stay close to the railway station – e.g. Hotel Carlton On The Grand Canal is a very good option and usually great value for the money. Alternatively, if you don’t mind taking a water bus to the more centrally-located places, check out H10 Palazzo Canova close to Rialto Bridge or Bauer Palazzo not too far from San Marco Square. For the ultimate Venitian experience, take a look at the famous luxury Hotel Danieli .

Day 9: Venice

Today, you have an entire day to explore Venice and its surroundings . You could opt to spend the day in the city, or you could also take a half-day trip to the nearby islands Murano, Burano, and Torcello (there are various boat tours that visit the islands in 4-6 hours ).

While not an absolute must, a visit to these islands is a nice opportunity to see some smaller Italian towns. Murano is famous for its glass-blowing factories, Burano – for its lace, and Torcello – for its Byzantine basilica. In addition, the towns are very colorful and picturesque, and completely different from Venice.

There is so much to see and do in Venice that you will easily fill the entire day in the city. So it all depends on your interests and how many activities you want to pack into your itinerary.

As a minimum, in addition to the places mentioned before, we recommend going to the top of St. Mark’s Campanile for some of the best views over the city and the Venetian Lagoon. In some seasons, it is now possible to reserve the tickets in advance (do it!). Otherwise, you’ll have to queue and wait a long time. If you can do it first thing in the morning or in the late afternoon, it will be easier to plan the rest of your day.

TIP: If you are looking for something special to do in Venice in the evening, check out this dinner cruise on the Venetian lagoon . Alternatively, see if there’s something interesting going on at Teatro La Fenice .

And if you can squeeze in an extra day in your itinerary, Venice is definitely worth a longer stay. In that case, check out our 3-day Venice itinerary for some inspiration on what to see and do depending on how much time you have.

READ ALSO: Best things to do in Venice

TIP: Next on your itinerary is Verona, Lake Garda, and Lake Como. If you want to explore these areas deeper, Venice would be a good place to rent a car for the remainder of this trip (we use and recommend this website for the best car rental deals ). You can easily visit Verona by car, drive to (and maybe even around) Lake Garda, visit Lake Como, and then return the car in Milan.

Renting a car in Italy is normally not expensive, but driving and parking in the small towns by the lakes – especially in high season – can be very challenging.

Anyway, the rest of the itinerary below is created assuming you take a train. But you can easily adjust it if you decide to drive.

Day 10: Venice to Verona & explore Verona

The next stop on this Italian itinerary is Verona , one of the most romantic cities in Italy. It gets this reputation because of Shakespeare’s “Romeo and Juliet”, and Juliet’s House is one of the top attractions in the city.

The train ride between Venice and Verona takes about 1.5 hours, so you’ll have a big part of the day left to explore Verona. The city is quite compact and you should be able to see all the musts in a day.

As a minimum, be sure not to miss the Verona Arena , built 2000 years ago (best get a priority ticket for this one). Also the views from Torre dei Lamberti and the earlier-mentioned Juliet’s House with its famous balcony are must-see in Verona.

Just as in all the other cities, you can also find some really nice Verona city tours led by locals. There are walking tours , a very nice bike tour , and this food tour is very popular as well. The nice thing about Verona is that it’s not that big, and so you can see a lot at a rather relaxed pace.

LEARN MORE: Best Places to See & Things to Do in Verona

Accommodation: Stay in Verona for 2 nights. We recommend Hotel Milano & SPA***S – it offers excellent price/quality in the city center. And yes, it also has a beautiful rooftop terrace with an amazing view – something we recommend in every city in this itinerary because we love staying at hotels with nice rooftop terraces ourselves. It makes any city visit so much more memorable!

Day 11: Lake Garda day trip from Verona

Lake Garda is one of the most beautiful lakes in Italy and if you have an extra day in your itinerary, it’s well worth planning a short visit here as well. This is especially the case if you are traveling in the warmer months.

If you don’t mind changing hotels more often, you could stay in Sirmione on your way between Verona and Milan. However, keep in mind that there is no direct train from Verona to Sirmione, so you’ll have to travel by bus or train + bus, or arrange a private transfer. To make it easier and simpler to plan, you can just visit Lake Garda as a (half) day trip from Verona. It’s good not to have to pack/ unpack every day.

You can come here by public transport and explore on your own. In that case, be sure to decide in advance where you’ll visit – just Sirmione or also some other towns along the lake, and research the public transport options to get back to Verona in the evening. See our Lake Garda itinerary suggestions on how to spend a day here.

There’s also a nice half-day tour from Verona that visits Sirmione town and includes a short boat ride on the lake. Sirmione is one of the best places to see at Lake Garda and the one that’s the easiest to visit if you don’t rent a car and/or don’t have at least a few days in the area.

TIP: If you take a half-day tour to Lake Garda, you’ll have a free afternoon in Verona. If visiting on weekends in summer (Thursday to Sunday, from +- mid-June to early September), you can attend an opera at the Verona Arena . It’s a really special experience!

Alternative: If you decide to skip Lake Garda altogether, then you could add an extra day in Florence or in Bologna as mentioned before. Or – if you visit Lake Garda with a half-day tour, you could take a train to Milan in the afternoon already and save some time in your itinerary this way.

Day 12: Verona to Milan & explore Milan

The final destination in this 2-week Italy itinerary is Milan , where you can also visit the beautiful Lake Como nearby.

One of Italy’s biggest and richest cities, Milan is also one of the most fascinating places in the country. It has such a unique mix of old, historic places and modern contemporary lifestyle and architecture. Plus, if you like Italian fashion and want to do some shopping, Milan will not disappoint either.

The train ride from Verona to Milan takes about 1.5 hours, and since you have almost two days for the city alone, you should be able to see all the musts in a rather relaxed way.

On your first day in Milan, you could visit the two main attractions – the Duomo Cathedral and see Leonardo Da Vinci’s Last Supper . There are also some great tours that visit The Last Supper and some of them also bring you to the Cathedral. It’s also well worth visiting the Duomo rooftop , but you can leave it for the next morning as well.

Good to know: Also here, whatever you decide, be sure to book tickets/ tours for the most popular places in advance! Tickets for The Last Supper are often sold out a few months upfront, but finding a guided tour is much easier (they pre-book tickets and can usually accommodate last-minute bookings as well).

Accommodation: Stay in Milan for 3 nights. Hotel Dei Cavalieri Milano Duomo is a great option right in the heart of the old town.

Day 13: Milan

Today, you have an entire day to explore Milan . Visit the highlights in the old city center, but don’t miss the modern part of the town either!

For more information on what to see and do and how to plan your day, please see our recommended 1-day Milan itinerary . It includes all the musts and the details on how to best plan your time.

If you already visited the Duomo and/or Duomo Terraces and/or Da Vinci’s Last Supper the day before, just adjust your itinerary accordingly.

If you have some time left, you can go shopping in the center or visit Designer Outlet Serravalle (although this one will likely require an entire day).

In the evening, head to the Navigli district , aka the canals of Milan. It’s a very nice and lively neighborhood with lots of restaurants, bars, and cafes – a perfect place to end the day of sightseeing.

LEARN MORE: Best Things to Do in Milan

Day 14: Lake Como day trip from Milan

On the last day of your 2 weeks in Italy, we recommend visiting another famous lake in northern Italy, Lake Como . Located just near Milan, it’s an easy day trip destination and a wonderful addition to any Italian itinerary!

Just as with Lake Garda, you could visit Lake Como on your own. In that case, simply take a train from Milan to one of the towns (Como or Varenna are both good options) and then explore further.

However, ideally, you also take a boat trip on the lake and visit several of the nicest towns of Lake Como instead of one. And for that, it’s easier to join an organized tour and have them guide you to all the best places without having to plan or arrange anything.

TIP: We recommend this highly-rated day tour. It brings you to Como (including Villa Olmo), Bellagio , and Varenna – some of the most scenic places on Lake Como. It would be very difficult to plan a similar trip and see all of these sights in just a day on your own (mainly because tours use private transportation and don’t have to waste time waiting for trains or delayed ferries).

Also here, you could easily spend more time at Lake Como than just a day. In that case (or if you rather not take a tour even if visiting for just a day), you may want to read our guide with tips for visiting Lake Como .

READ ALSO: Top Places to See & Things to Do in Lake Como

So, this is it – the ultimate Italy itinerary that allows you to see ALL THE BEST PLACES in 2 weeks. Of course, there’s much more to see and do in Italy than the destinations covered here. But if you want to visit all the ‘musts’, this sightseeing itinerary does exactly that.

We planned this Italy itinerary in such a way that it starts and ends at the biggest towns with major international airports, Rome and Milan. There are lots of direct flights to/from both of these cities to many other places in the world. So it should be quite easy to plan your trip in such a way that you can fly home from Milan.

And if you absolutely want to make a loop, a round trip starting and ending in Rome, you can simply take a train from Milan to Rome, and fly out of there. The fast train between the two cities takes about 3.5 hours.

Good to know: If you take regular trains in Italy, you can just get a ticket at a station. However, if you opt for high-speed trains between the main cities (recommended), it’s best to reserve your seat in advance. You can use the official Trenitalia website for that, but keep in mind that standard tickets are usually non-refundable. We also recommend checking this website for all the best options for train tickets .

If you have more time…

If you have more time in Italy, you could add extra days pretty much anywhere in this itinerary and you’ll find plenty to do. We already included some additional recommendations above. And here are a few extra suggestions:

• You could add some extra time at the Amalfi Coast and also visit Capri Island and Naples . So instead of visiting this area on a day trip from Rome, you could stay here for several days. See our Amalfi Coast itinerary and Naples day trips for more suggestions on what to see and do there, and this guide for more information about the best areas to stay in Naples . You could easily add at least 5 days to your Italy trip itinerary just for this area – there’s so much to see!
• If visiting in summer, I also highly recommend adding at least a few days in the beautiful Italian Dolomites . You could rent a car in Venice and visit the mountains for a few days, continuing past Verona and Lake Garda and on to Milan. Here you can find some Dolomites itinerary suggestions and our guide on where to stay in the Dolomites .
• Tuscany is another area where you could easily add a few extra days. There are so many beautiful places to see! See our Tuscany itinerary for some additional inspiration for the best Tuscan towns .
• Bologna , one of the foodie destinations in Italy, is another nice addition to any Italy itinerary. You could just visit for a day from Florence, or spend several days here as well. Also Rimini , Ravenna , and San Marino are all worth a visit. See our Emilia Romagna itinerary for more information about these places.

…. I could go on and on. As you can see, there’s plenty to see in Italy to fill another few weeks or months. And once you visit this incredible country, you’ll definitely want to come back and explore more.

But for your first trip, this is a very complete itinerary that shows you the best of Italy in two weeks .

Yes, this itinerary is quite packed and yes, you’ll probably want to stay longer at many places you visit. But it gives you an amazing overview of what Italy is about, and you can always plan a repeat trip to the areas that you liked the most. You can also find a lot more travel inspiration in our Italy travel guide .

READ ALSO: Italian Food – traditional dishes to try in every region

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Tuesday 5th of March 2024

Please offer your ideas and suggestions for a 1-week trip to Italy in May 2024. We only have a short time to visit so any guidance to enjoy Italy in a few days will be so helpful!

Thursday 7th of March 2024

Hi Shannah, there are so many options, so pick the places that interest you the most. And don't overdo it in terms of too many different locations. With a week in Italy and if it's your first trip, you could visit Rome (2-3 days + potentially a day trip to Pompeii/Amalfi e.g. like this), Florence (1 day in the city and one day trip, e.g. to Tuscan towns like this or to Cinque Terre - see this tour), and Venice (1-2 days). Of course, you can just visit one specific region, but there are literally thousands of options, so you have to see what interests you the most. Hope this helps. For more details about all these places, please see our article above.

Monday 26th of February 2024

We are to Italy/Switzerland for 3 weeks in August. We are starting in Switzerland for a week then two weeks in Italy starting with Milan and working our way down as far south as the Amalfi Coast. We are a bit stressed because we finally booked our flights and then read that August is the worst time to travel to Italy due to the weather, horrendous crowds and Italy national holiday starting August 15 when Italians and other Europeans go to the coastal cities (where we wanted to end our trip) an overcrowd those areas.

Do you have any tips on places to go to make an August trip most enjoyable? We prefer some areas that are beautiful, nice to stroll around, eat and see some sights, but don't have to go to all the main tourist attractions. We'd love some suggestions that help us get off the beaten path vs. all the main highlights. I've been to Venice, Florence, Rome once before and my husband has not been at all, but doesn't care too much about all the 'must sees' besides Rome. We plan to leave from Rome airport, but want to try to make it further south to Amalfi coast first.

Any suggestions would be super helpful!

Tuesday 27th of February 2024

Hi Erica, I'm afraid that what you read is correct. Italy can be crazy busy in August, especially in coastal areas. That being said, the cities are usually deserted (=locals are gone), but places like Rome are full of tourists so you won't be alone. The best way to avoid the biggest crowds is to skip the most popular seaside destinations. Amalfi Coast, Italian Riviera, Cinque Terre, Capri, Rimini, etc. will be crowded at that time of the year. But if you book accommodations in advance and plan your sightseeing activities in the mornings, it could be manageable. Of you visit places like e.g. Amalfi Coast, you will have to pre-book everything, not just hotels and excursions, but also restaurants. If you go more inland and stay in smaller villages, you can have a perfectly enjoyable trip. A few years ago, we were in Tuscany in the second half of August and it was great. But we started our days early, did most of the sightseeing in the mornings, and when it started to get busy everywhere, went back to our accommodation and spent the warmest hours by the pool. In the evenings, we usually visited smaller towns, but it was really busy everywhere, parking was not easy, etc. So you need more patience, especially if you go to the main tourist hotspots. Take a look at these articles for some additional tips: Amalfi Coast Travel Tips (don't rent a car here!!!) Where to Stay on the Amalfi Coast Where to Stay in Capri Rome Travel Tips Lake Como Travel Tips If you like nature, consider spending some time in the Italian Dolomites. It will also be very busy, but different than at the sea. Also there, top places and most popular hikes will be crowded, so start your days early. Or avoid the top places and you can have a very enjoyable visit. The nearby Trentino region is much quieter, but it's popular with locals = August is the peak season. You can find some inspiration in this article - most activities are definitely not just for kids. Having said all this, when you travel somewhere from the other side of the world, it's just normal that you want to see the top spots. The best tip I can give you is to try to get a bit off the beaten path in addition to the top places, AND book as much as possible in advance. Good luck and enjoy your trip. Italy is always a good idea and I'm sure you'll have a wonderful time!

Sunday 22nd of October 2023

Hello Jurga,

A great article to read through! Me, the wife and two kids (11 and 14) are planning a trip through Italy next Summer. He have 6 weeks off for summer, so we're looking at a 2-3 week trip through Italy probably. With the kids I don't want to be rushing so do you recommend staying longer in some of these locations? More hotels don't phase us.

Monday 23rd of October 2023

Hi Matthew, so much depends on your interests! With the kids in the summer, you may want to spend some more time in the nature rather than sightseeing in big cities. So you could add Italian Dolomites to your itinerary. Also, you could spend more time at the Naples/Capri/Amalfi Coast and/or Italian Riviera (around Cinque Terre). Also places like Lake Garda and Lake Como offer a great mix of nature, sightseeing, and some relaxing time by the pool. There are so many options. That's why it's really difficult to help our readers with specific itineraries. Pick the places that interest you the most, plan a few longer stays once in a while so that you can all wind down and relax a bit, and realize that whatever you do, there is no way you can see everything in Italy in 3 or even 6 weeks. You'll want to go back ;). Good luck with the choices!

Madonna Hanes

Thursday 19th of October 2023

I'm thinking of coming out to Italy for 10 days, 2 days for flights, and 8 days for touring Italy. What do you recommend and where? Thanks advance.

I was thinking September.

Hi Madonna, so much depends on your interests and on the season when you travel and - as you can probably imagine - the possibilities are endless. But if it's your first trip to Italy and you want to see 'the musts', then I'd probably concentrate on the main cities - Rome (3 days), Florence (3 days), and Venice (2 days). In Rome, I'd probably just stay in the city - there's a lot to see. Take a look at this itinerary for some ideas. In Florence, take a look at these suggestions on what to do in a day. In addition, you can always take one or two day trips from Florence like this day trip that visits Siena, Pisa, and Tuscan countryside, and/or a day tour to Cinque Terre. In Venice, see this itinerary. In addition, you could take a (half)day trip to the nearby islands. Hope this helps.

Friday 11th of August 2023

Hello, Jurga. Your article is an absolute gem!!! I learned so much from it. I am planning a trip to Italy and i was going to follow your itinerary but we are only going for 12 days not 14. What do you recommend skipping? Thank you in advance

Hi Maya, that's a tough one since there is so much to see. You also didn't say when you are traveling. For example, in the winter you could skip some of the coastal areas/nature (e.g. Amalfi Coast from Rome on day 4, Tuscan countryside or Cinque Terre (days 5-6), or Lake Garda and Lake Como (days 11 and 14). In the warm season, the choice is much more difficult. Just see what interests you less and let it go. There is no way to see everything in Italy in 3-4 weeks, let alone 12 days, so you always have to make choices. Good luck!

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2 Week Italy Tours & Trips

Filter for departure dates and price to find the right 2 week Italy tour with TourRadar. Choose from 145 trips with 3,360 customer reviews, that range from 11 up to 14 days.

145 Italy 14 Days tour packages with 3,360 reviews

In-depth Cultural Historical

Best of Italy

"It was 'The Best of Italy' indeed. We have learned so much of Italy so far." Eric, traveled in May 2022

In-depth Cultural Active

Ultimate Italy

"Thoroughly enjoyed the tour. It was my first tour as a solo traveler and I had great time and met some amazing people." VK, traveled in August 2014

In-depth Cultural Family Coach / Bus +1

Italy's Best

"Well planned, the rest excellent. I enjoyed it very much, and of course I will travel with you again." Rosalinda, traveled in October 2019

In-depth Cultural Family Christmas & New Year +1

Tutta l'Italia

"The hotels and transfers between each city were smooth and successful. This was a good tour to see many cities." Bridget, traveled in July 2023

In-depth Cultural

Journeys: Iconic Italy National Geographic Journeys

"The tour was an amazing mix of included activities and feee time. The small group size made the tour much more enjoyable." Tara, traveled in May 2019

In-depth Cultural Family

Italia Amore Mio (Small Group)

"Great sites,,,,,,,,,,,,,,," Wenceslao, traveled in April 2024

In-depth Cultural Active Explorer Christmas & New Year +2

Mamma Mia! - 13 Days/12 Nights

"The guides were probably one of my favorite parts of the trip because after spending so much time with them they began to feel like more of a friend than a tour guide which was awesome!" Avery, traveled in June 2024

• €100 deposit on some dates

Highlights of Sicily & Southern Italy

"One of the best tour we have being a true Sicilian experience would highly recommend." Elena, traveled in April 2018

Explorer Historical

Highlights of Sicily

Best of Italy (Summer, 13 Days)

"We saw and experienced more than I could have imagined or hoped for. He went out of his way to make every moment special." Anthony, traveled in September 2019

What people love about 2 Week Italy Tours

mecol was great. went above and beyond

This is a self-directed tour. The tour leader is there to make sure the transportation goes smoothly and to ensure the hotels are arranged. Besides a couple of group dinners, you are expected to make your own site-seeing arrangements. Communications from the tour operator, prior to the tour departure date, are sparse and you do not receive a lot of detailed scheduling Information. The tour leader was knowledgeable and very helpful.

This tour is great for seeing numerous cities and historical sites in Italy, a one day trip over the border into Lugano, Switzerland was just a true delight and icing on the cake. I have now learned that the Cosmos level is the "budget" label for Globus, so expect mostly 3 star hotels that are located outside of the major cities. This wasn't too much an issue as public transportation (metro/bus) or taxi's are available from each hotels if needed. Some of the hotels have poor air conditioning so if that's a priority for you then consider a Globus level tour instead. Overall, the hotel we clean. We found it difficult to plan our excursions as the itinerary they provide is very vague with regards to the times of the optional excursions, but these were clarified on day one as we asked our tour director and she was able to tell us if we had enough time to do some of things we wanted to do that weren't offered. Expect to get up early as the bus is usually on the road by 7:30 am, but that's necessary to get to the sites before the crowds. As far as the optional excursions go, the first dinner in Rome was a bit of a disappointment as it wasn't in central Rome, the food was mediocre and the service was fair, the highlight was two elderly Italian men playing and singing live music - famous old Italian songs- a lot of us complained about this so maybe Cosmos will change that venue? The other excursions are well worth it, takes the hassle out of dealing with transportation and getting tickets. The ones not to miss are the Tuscan Farm Dinner, Lugano Switzerland Cable Car, Capri, Pompeii. I would recommend this tour for those who don't require a luxury hotel, I am glad we were able to experience it!

Regions in Italy

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Fearlessly Italy

2-Week Italy Itinerary – A Step-By-Step Guide To 14 Days In Italy

You’ve been planning a 2 week Italy itinerary for a while and still feel in a stalemate? Don’t worry, you’re not alone. The country is so packed with things to do, wonderful places to visit, and great Italian food to try that anyone traveling to Italy for the first time is bound to feel overwhelmed.

If you don’t want the burden of the logistics, you can book one of the best Italy tours , but if you prefer to travel independently, fret not, we’re here to help.

This guide of ours, even though extensive and detailed, will only touch the most popular cities you can’t miss in 2 weeks in Italy. Those places you really can’t afford to miss if it’s your first time in this beautiful country.

We will squeeze as much as we can into a two-week Italy tour itinerary. It’s not strictly a Rome Florence Venice itinerary, it includes also other places, but it’s pretty classic.

Table of Contents

Is 2 weeks long enough in Italy?

If it’s your first trip, 2 weeks is a pretty good amount of time to get the grasp of what to expect from an Italian holiday, to experience the local culture, to visit the most famous and classic landmarks, and to fall in love with the country.

Two weeks in Italy is enough if you do proper planning. Whether you are planning a classic 2-week Italy itinerary or a more alternative one, you need to keep in mind that there will always be places you won’t be able to include. Which is the best excuse to plan a second trip or more!

Should I go to Italy for 2 weeks or 3 weeks?

If you are planning a country-wide itinerary, I think you will need at least two weeks to cover the most important landmarks. Of course, if you can afford 3 weeks in Italy you can either include more regions and places or stay longer in the cities you are visiting.

For example, you could stay a week in Rome, 5 days in Florence, or devote 4 to 5 days to the Campania region and enjoy a more complete experience.

14 Days In Italy – A Step-By-Step Itinerary

Granted, with so much to see, planning your best 2-week Italy itinerary is not easy. Our extensive guide will provide you with the essentials to organize a perfect vacation on your own. If you are visiting for the first time, 2 weeks in Italy are enough to see the main attractions in the main cities.

Planning 14 days in Italy allows you to explore the classics such as Rome, Florence, and Venice. If you want to enjoy a place longer, visit more attractions or take some day trips, you can easily spend 3 weeks in Italy. If you have less than two weeks in Italy, you can avoid some of the attractions in each city and stay one day less. Here, we give you the tools to plan a trip to Italy on your own.

If it’s not your first time or you have more than two weeks in Italy, check out our other guides on specific areas like Sardinia, Sicily in the cities of Catania and Agrigento, and Trentino Alto Adige, both its cities and the Dolomites mountain range.

We will see when is the best time to visit Italy depending on what type of holiday you want, we will suggest the best car rentals in case you want to embark on an Italy road trip, we will tell you what to pack and obviously what to visit to make your holiday smooth and unforgettable.

This guide will empower you to plan a trip to Italy on your own. For each city, we will provide you with the best day tours if you wish to optimize the time of your 2 weeks Italy itinerary and have more in-depth information. At the end of this guide, you will also find a selection of the best tours to Italy in case you want a hassle-free holiday where expert organizers take care of the details and the logistics for you.

Map Of Your 14 Days In Italy

Where to go: a cool itinerary for two weeks in italy, milan – 2 days.

Milan is Italy’s “Wall Street”, a bustling financial hub that attracts businessmen for work or business-oriented travelers. However, with a long history and a good deal of historical landmarks and artistic attractions, Milan has been imposing itself also as an exciting tourist destination for travelers from all over the world. On your 2-week Italy itinerary, we suggest spending 2 days in Milan . If you want to stay less, you can also visit most attractions in Milan in 1 day .

Some of the most important places to visit in Milan are:

• The Duomo. The most popular among Milan’s landmarks, the city’s cathedral is a must. Its Gothic facade never fails to bedazzle visitors and passers-by, the inside is a fascinating journey into Milan’s history and culture, and its rooftop gives you a great view of the city and its architecture.  Click here for Walks of Italy’s Best of Milan Tour that includes a visit to The Last Supper and the Duomo’s rooftop .
• Sforza Castle. Residence of one of Milan’s most prominent families, the Sforza Castle today hosts several exhibitions, both temporary and permanent, as well as being a cultural center.
• Galleria Vittorio Emanuele II. Known as Milan’s parlour, this long covered gallery is lined with cafes and shops of the most exclusive brands. It’s close to the Duomo’s square, so you can’t miss it!
• Da Vinci’s The Last Supper. Don’t miss the famous mural painting by Leonardo Da Vinci in UNESCO-listed Santa Maria delle Grazie church, beautiful Renaissance building by architect Donato Bramante.
• La Scala Opera House. Milan’s opera house, this is a beautiful Neoclassic building worth a visit even if you are not going to see the performances. You can visit both La Scala and the museum but call first because if there are rehearsals you can’t visit the theatre hall.
• Navigli. Milan’s canals are a great place for a walk both day and night. This is one of the favorite hangouts for aperitivo , dinner or a night out.

READ MORE: Check out our extensive guide to Milan to find out what to do if you have more time .

Hotels in Milan – Some suggestions

• High-end. Bulgari Hotel Milano , Four Seasons Hotel Milano , Mandarin Oriental, Milan .
• Mid-range. Hotel NH Collection Milano CityLife , Hyatt Centric Milano Centrale , Hotel Milano Scala , The Street Milano Duomo .
• Budget. B&B Hotel Milano Portello , Hotel RossoVino Milano , QUO Milano hostel .
• Apartments. CA Foscari Loft & Factory , ApartHotel Bossi .

Check out Booking for more accommodation options in Milan for every type and price.

The next stop in your two-week trip to Italy is La Serenissima, so book your Milan to Venice train and get to one of the world’s most romantic cities. Click here to check timetables and prices with Omio .

Venice – 2 to 3 Days

One of the most popular destinations in Italy, Venice is as gorgeous as it gets. Unprecedented views, a unique urban landscape, and a long history are the perfect combination for an unforgettable trip. And if you go for the Carnival, the colorful and fascinating masks will add to the charm of the city.

How many days in Venice? We suggest 2 to 3 but it really depends on how much time you have, how much you want to enjoy and explore the city and, last but not least, on your budget.

Some of the things to do in Venice in your two weeks in Italy are:

• Piazza San Marco. One of the key landmarks in Venice that make the city famous is its central Piazza San Marco, the very first place tourists visit. Surrounded by San Marco Basilica and the Doge’s Palace, this piazza is really gorgeous.
• St. Mark’s Basilica. One of the most symbolic buildings in Venice, San Marco Basilica is a gorgeous piece of Oriental-style architecture dating back to the 11th century. Click here to book the exclusive tour of St. Mark’s Basilica after closing time .
• Doge Palace.  Standing exactly where it stood throughout the centuries, the majestic Palazzo Ducale is an important piece of the city’s republican past. Get a VIP entrance to the Doge Palace with Walk of Italy’s Secret Passages tour .
• Jewish Ghetto. Europe’s oldest Jewish ghetto, Venice one was created in 1516 and is now a lovely neighborhood to stroll around the city’s traditional architecture and eat delicious local treats.
• Canals and Bridges. The beauty of Venice is in its architecture and this is directly related to its unusual layout. Instead of streets, in Venice you have canals and bridges, instead of buses, you will take the boat or if you don’t mind forking out good cash, a gondola. One of the most scenic things to do in Venice is certainly strolling around its bridges, Rialto and the Bridge of Sighs being the most famous. Click here to book Venice Boat Tour to visit the city and its bridges from the water and cruise the Grand Canal .
• Gallerie dell’Accademia. This art gallery hosts the largest collection of Venetian paintings from the Byzantine and Gothic 14th century to the Renaissance.
• Basilica dei Frari. Often neglected by the hasty traveler, this monumental Basilica is 102 meters long and boasts an impressive collection of artwork and 17 altars. It’s also the resting place of several notables, from Antonio Canova to Titian to several Doges.

Hotels in Venice – Some suggestions

• High-end. The Gritti Palace , The St. Regis Venice , Hotel Danieli, Venice .
• Mid-range. Hotel Papadopoli Venezia , Hotel Monaco & Gran Canal , Palazzo Veneziano – Venice Collection , Ruzzini Palace Hotel .
• Budget. Ca’ Pedrocchi , Dimora Marciana , Locanda Antica Venezia , Ai Cherubini .
• Apartments. Corte Barozzi Venice Suites , San Gregorio Venice Apartments , Casa del Carro 2 Grand Terrace Apartment , Palazzo Paruta & Wellness Suites .

Check out Booking for more accommodation options in Venice for every type and price.

Unless you are part of an organized tour, from Venice to the Cinque Terre, I definitely suggest you take the train as it’s cheap, comfortable and you can find different times of departure. Click here to book and see the prices on Omio (GoEuro) .

If you are skipping the Italian Riviera, check out our Venice to Florence train guide to keep planning your trip!

Cinque Terre – 2 Days

The quaint villages of the Italian Riviera never fail to bedazzle travelers from all over the world. If you want to spend three weeks in Italy, you can stay a bit longer in the Liguria region and explore also cities like Genoa and La Spezia.

Close to La Spezia, the capital of the province, are also beautiful places like Lerici and Tellaro, sea resorts cherished by writers and artists. Being on the coast, you will find great fish restaurants. Alongside the five scenic villages, part of the Cinque Terre , La Spezia’s coastline boasts also other towns worth a stop, such as Portovenere, Le Grazie, and Levanto.

The five villages known as Cinque Terre are:

• Monterosso al Mare. It’s the largest of the five towns and boasts also the largest beach on the coastline. Which is why it’s the most popular both day and night for evening parties and entertainment.
• Manarola. Famous for its Nativity Scene set for Christmas , here you can also visit 14th-century San Lorenzo Church and the remains of the local stronghold.
• Vernazza. This is a very scenic village, some consider it the most beautiful. It has two beaches and several nice restaurants. You will spend your time wandering up and down its cobbled alleys.
• Corniglia. The smallest and tallest village of the Cinque Terre, here you can visit its famous churches and sanctuaries as well as the remains of old Genoese strongholds.
• Riomaggiore. The closest village to La Spezia city, from its train station you can start the famous Via dell’Amore hiking route and the dock from where to take the ferries for the local tours and cruises.

From Cinque Terre to Florence, too, you can take the train. First, a regional to get to La Spezia and Genoa, then a high-speed train to Florence. Click here to check timetables and prices with Omio .

If you are visiting the Italian Riviera as a day trip from Florence, you can check out our guide on the different ways to reach it and how to get to Cinque Terre from Florence by train .

Florence – 3 to 4 Days

The birthplace of the Renaissance and included in most tours, very likely your Italy travel itinerary will have at least two days in Florence . Here, we suggest three to four days, but if you have only ten days in Italy , two is also enough to get a taste of the city.

The city’s history was heavily influenced by the rule of the Medici family, and today we can still see much of their legacy. Walking around Florence will fill you with beauty and culture. Enjoy its ancient art and architecture all around the city center, walk along the Arno River and linger on the Ponte Vecchio bridge for some shopping and photo snapping.

Best things to do in Florence

We wrote a full guide to Florence , if you wish to stay longer and see more places.

• Duomo and Giotto’s Bell Tower. Santa Maria del Fiore Cathedral and the adjoining bell tower and gorgeous Baptistery are possibly the most photographed and visited landmarks in Florence. For sure one of the first places travelers head to as soon as they arrive and a must even if you are wondering what to do in Florence in one day . Click here for a full experience of Florence Duomo and Michelangelo’s David.
• Uffizi Gallery. A huge art collection, at the Uffizi you will find the paintings and statues of some of the world’s most famous artists such as Leonardo Da Vinci, Botticelli, Caravaggio, Raphael, Cimabue and many others. Here the line is very long, so if you want to skip it and optimize your time inside the museum with a guide, check out Walks of Italy’s 3-hour Uffizi Tour comprehensive also of Palazzo Vecchio.
• Santa Maria Novella Basilica. Located near Florence’s main train station, this beautiful Dominican basilica built with a mix of Gothic and Romanesque styles includes great artwork, paintings, chapels, a big garden, and a cloister.
• Pitti Palace. Residence of many of Florence’s ruling families, Palazzo Pitti today is a large complex of art galleries and royal apartments.
• Boboli’s Gardens. Adjoining the Pitti Palace, the elegant Giardini di Boboli were built in 1418 when Luca Pitti bought this vast land intending to build a mansion (Pitti Palace will be built 40 years later). One of Florence’s largest parks, Boboli Gardens are one of the most important examples of Italian gardens of the 16th century.
• San Lorenzo Cathedral. The personal cathedral of the powerful Medici family, San Lorenzo huge church also hosts a museum showing the donations received over the centuries, most of them by the same Medicis. Close is also the burial place of the Medicis, known as Cappelle Medicee.

Hotels in Florence – Some suggestions

• High-end. Portrait Firenze – Lungarno Collection , Rocco Forte Hotel Savoy , The St. Regis Florence , Four Seasons Hotel Firenze , Hotel Lungarno – Lungarno Collection .
• Mid-range. Donati Luxury Tower Suites , Hotel Bernini Palace , Hotel Number Nine , Arte’ Boutique Hotel .
• Budget. Il Gattopardo B&B , Eco Urban B&B , Cicerone Guest House , Hotel Art Atelier .
• Apartments. Modarno Exclusive Apartments , Windows on Florence , Casa del Sarto , Residenza Marchesi Pontenani .

Check out Booking for more accommodation options in Florence.

The whole region of Tuscany is amazing, so if you can stretch your holiday a couple more days, you might like to explore also other cities such as Siena and Pisa  and the countryside with a day trip from Florence to the Chianti region and San Gimignano town. Click here to check availability and price .

Florence is not too far from Rome, with Trenitalia’s Frecciarossa or Frecciargento high-speed trains, it takes an hour and a half. Click here to book and see the prices on Omio .

READ MORE: How to plan a perfect trip to Florence

Rome – 4 to 6 Days

The capital of the ancient Roman empire boasting some 3000 years of history and rich civilization, the places to visit in Rome are endless. From the archaeological sites of the Roman Forum to the quaint neighborhood of Trastevere to the Vatican City, the more you manage to devote to Rome, the better you will experience the city. It goes without saying that Rome is a must-see, especially if it’s your first 2-week trip to Italy.

Having a hard time planning your Rome trip? We design your itinerary and guide you through the planning!

Some of the things to do in Rome in your 2 weeks in Italy include:

• Colosseum. Possibly the most famous and photographed landmark in Rome, the Coliseum was built in 70 AD to host fights among gladiators, public shows, animal hunts and even naval battles.
• Roman Forum. Located in the valley between the Palatine and the Capitoline Hills, the Roman Forum was the heart of ancient Rome, where senators and public figures held their speeches, where they organized the city’s markets, court trials and pretty much everything concerning public life. Click here for the VIP Colosseum and Roman Forum Tour .
• Baths of Caracalla. Gorgeous ancient public baths, they included also a gym, a library, and different rooms for the bath experience and a wellness center. They are often skipped for lack of time, but if you can make it, they are really beautiful.
• Vatican City. The seat of Christendom and papal residence for centuries, the Vatican City is packed with sites to visit such as the Sistine Chapel, the Vatican Museums and obviously St. Peter’s Basilica. If you want to fully enjoy the Vatican, the best thing you can do is to skip the lines, especially to the museums and the basilica. In this case, the convenience of booking a tour, apart from VIP access, is that your guide will take you directly to the places you shouldn’t miss. The Vatican is really big!  Click here to see Walks of Italy’s Private Vatican Tour .
• Trastevere. A gentrified former working-class neighborhood, Trastevere is the place to go for a good night out. During the day, however, you can also visit the Museum of Roman Popular Traditions which sometimes also hosts temporary exhibitions and Villa Farnesina where are Raphael’s frescoes.
• Hadrian Mausoleum. Built by Emperor Hadrian as his own funerary mausoleum in the 2nd century, this is also known as Castel Sant’Angelo and is located along the Tiber River, giving beautiful views both day and night.
• Pantheon. A very old building, it was a temple devoted to all gods built with an “oculus”, a hole in the big dome to symbolize direct contact with the divine. Now it’s a Catholic church that hosts several tombs of members of the former royal family and of the famous painter Raphael.
• Piazza Navona. Huge elliptical piazza in the city center not far from the Pantheon, Piazza Navona has three fountains, the largest being Bernini’s Four Rivers Fountain standing in front of Borromini’s Sant’Agnese church.
• Spanish Steps. Rome’s most famous staircase, the Spanish Steps lead to St. Trinità dei Monti church, ordered by French king Louis XII, while at the bottom you can view Bernini’s sculpture known as La Barcaccia.
• Trevi Fountain. An absolute must, especially if you are visiting Rome for the first time, is Trevi Fountain, the gorgeous baroque fountain built between 1732 and 1762.

Rome is divided into “Rioni”, neighborhoods, and each of them has its own landmarks and personality. From Prati to Trastevere to Testaccio and Ostiense , countless are the things to see in Rome, the restaurants where you can try the traditional food, the park where to run, jog or chill out for an afternoon, the museums, the palaces and more. To get around and see how to best enjoy Rome, check out my full guide of the city , or click here to see what are the best Rome tours if you wish to save some time but still visit the most important sites.

My eBook “ Tasting Rome by Neighbourhood ” suggests five daily Rome itineraries in as many districts, giving you the chance to explore the popular and lesser-known areas of the city stopping to eat in the best restaurants along the way. All the meals of the day are covered, from breakfast to dinner, with some suggestions also for aperitif and gelato.

Hotels in Rome – Some suggestions

I wrote several guides to navigate the huge landscape of Rome hotels:

• Best 5-star Rome hotels
• Best boutique hotels in Rome
• Best budget hotels in Rome
• Best cheap hotels in Rome
• Best hotels near Termini Station
• Best hotels near the Pantheon in Rome
• Top hotels near the Spanish Steps in Rome
• Top hotels near Piazza Navona in Rome
• Top hotels near the Trevi Fountain in Rome
• Best hotels near the Colosseum in Rome
• Best hotels in Rome city center
• Best hotels near the Vatican in Rome
• Best family-friendly Rome hotels
• Best hotels in Trastevere
• Most romantic hotels in Rome

Check out Booking for more Rome hotel options.

Your next stop when planning a 2 week trip to Italy for the first time is Naples, the gorgeous capital city of the Campania region not too far from Rome. With Trenitalia high-speed trains you will reach it in a little more than an hour. Click here to book and see the prices on Omio (GoEuro) .

Naples and the Amalfi Coast – 3 Days

Famous for having invented the pizza, alongside delicious cuisine, Naples has a lot to offer to the curious traveler who wants to dig deep into the local history and culture. If you stay for 2 days in Naples , you will have plenty of time to walk around its city center, enjoy the view of the Vesuvio volcano and the beach, explore its wonderful coastline, and soak in its rich tradition.

Some of the best things to do in Naples in your 2 weeks in Italy include:

• Royal Palace. Naples’ Palazzo Reale is located in Piazza del Plebiscito, an old square that in the Middle Ages was used for public tournaments and shows in the age of the Bourbons. It has been made pedestrian so now it’s the place where locals and tourists like to relax in a historical promenade.
• Archaeological Museum. Launched in 1816, Naples’ Museo Archeologico displays a huge collection of ancient relics, among which you will find relics from Pompeii and others from the Greek-Roman age, Etrurian and Egyptian, and ancient coins from a private collection.
• Duomo.  Naples’ Santa Maria Assunta Cathedral shows the paintings of Luca Giordano and is the place where locals worship San Gennaro, patron of the city. Here you can also see the Treasure of San Gennaro and all the precious donations given by kings, presidents, and leaders of the world for centuries.
• Spaccanapoli. This is the long road built by the Romans to better organize the city, and it runs from the Quartiere degli Spagnoli to Forcella district. Wandering this road you will also wander the city’s history and multifaceted society. Here, in fact, you are going to see old buildings, churches, shops, abusive street vendors, and local restaurants that release the unique scent of Napoli’s cuisine.
• Sansevero Chapel and the Veiled Christ. A hidden gem near Spaccanapoli is Cappella Sansevero where you can admire the incredible sculpture of the Veiled Christ (Cristo Velato), a masterpiece by Giuseppe Sanmartino where you will totally mistake the marble veil that covers the body of the Christ for a fine fabric!
• Underground Naples. Beneath the surface, you can visit another Naples, the hidden spots, and nooks that citizens have used for different purposes such as shelter during the bombings, the hideout for the runaway criminals, and the water springs. Today, you can visit also museums, the relics found after ongoing archaeological diggings, and the Bourbons Gallery.
• Pompeii and Ercolano. I know time is short, but once you are in Naples, we recommend you devote a day to visit the ruins of the ancient cities of Pompei and Ercolano, destroyed by the Vesuvio eruption in 70 AD. They are very easy to reach via a short ride on the Circumvesuviana train and you can spend there the whole day. Click here to see reviews and prices for the tours and activities available in Pompeii .

Hotels in Naples – Some suggestions

• High-end. Grand Hotel Parker’s , ROMEO Napoli , Grand Hotel Vesuvio .
• Mid-range. Santa Chiara Boutique Hotel , Prestige Rooms Chiaia , NapoliMia Boutique Hotel .
• Budget. Le Corti del Re , Hotel Bella Napoli , Sant’Angelo Suites .
• Apartments. Appartamenti Mergellina , Borgo 1313 Apt , La Casa sul Nilo .

Check out Booking’s website for more hotel options.

Hotels in the Amalfi Coast – Some suggestions

• High-end. Hotel Conca d’Oro in Positano, Positamy in Positano,
• Mid-range. Le Muse Suite in Sorrento, Villa Setteventi in Positano, Amalfi Luxury House ,
• Budget. Ambrosio Relais in Sorrento, B&B MoMi Sorrento , Residenza Ester .
• Apartments. Sorrento Apartments , Lucy’s House in Amalfi, Amalfitano Apartments .

Once your 14 days in Italy are over, you can either take your flight back home from Naples or take a train to Rome and your flight from Fiumicino International Airport.

Hidden gems + alternative Italy itineraries

If you like to discover also more offbeat destinations or you can afford a longer holiday, say 3 weeks in Italy, you can really add some interesting places to your Italy itinerary.

For example, let’s say that you are back in Rome after this two-week Italy trip and you have one extra week.

For a lovely alternative, you can catch a plane to Sardinia and enjoy a fantastic offbeat destination! To be able to stray off the bigger cities and explore its traditional soul, make sure you rent a car.

Your experience in Sardinia will depend on the season. If you are traveling in summer, especially in July and August, what you can do will be pretty much limited to the beach because it’s really hot. Not too bad, considering that Sardinia is surrounded by wonderful beaches and the turquoise Mediterranean Sea. Famous are the beaches of the Costa Smeralda and the northern coast where you can find cool European vacation rentals .

If you go in spring or fall, you can enjoy a more authentic experience by exploring the towns of the inland. Places like Orgosolo, Oristano, Ghilarza, and San Sperate will make for lovely trips to immerse in the local culture.

In winter, I suggest a stop in Mamoiada for their Mamuthones festival. You can see these ancient masquerades on the night of the 16th of January or in February for Carnival. Carnival is a fantastic occasion to visit also towns like Oristano where they celebrate it with the Sartiglia or Ottana where they have the masks of Boes and Merdules, always coming from ancient times and farming-themed.

If it’s your first time in Sardinia, I also suggest you explore the city where you land, which is going to be either Cagliari, Bosa, or Alghero . All of them are extremely fascinating and are surrounded by interesting places for a potential day trip.

Northern Italy

If you enjoy the northern cities and want to explore more of them, a nice alternative is to explore the Trentino Alto Adige region or the beautiful city of Turin .

The region of Trentino Alto Adige is heaven for nature lovers. For scenic treks, choose any of the destinations in the Dolomites from the stunning Madonna di Campiglio to Molveno Lake to the Marmolada.

If you are more of a cultural traveler, you can explore charming cities like Trento , Bolzano , Rovereto, and Merano, or quaint towns like Bressanone and Levico. In Trentino Alto Adige, when you are not skiing, you can visit the castles scattered around the region like Castel Thun and Castel Beseno or sacred places like San Romedio Sanctuary perched on a cliff.

City slickers will probably enjoy a couple of days in Turin. The cool capital of the Piedmont region opens up to a myriad of different opportunities.

If you are fond of Christian history, you can visit the Duomo to see the Holy Shroud, while other types of spirituality will be attracted by esoteric places such as Piazza Statuto, Portone del Diavolo (Gates of Hell), and Chiesa della Gran Madre di Dio.

In Turin, you can definitely enjoy great food, indulge in an evening aperitif, and sip their traditional bicerin coffee drink . For some great day trip, head to the Baroque Basilica of Superga or Venaria Reale royal palace.

Not sure if you’d rather visit Milan or Turin ? Our tips will help!

Bologna and Emilia Romagna

Foodies on the lookout for some alternative destinations to include in their 2-week Italy itinerary should consider Bologna . Showcasing a very elegant architecture, the streets of the city center are covered with porticoes, making it more pleasant to walk in both summer and winter.

Being the capital of the Emilia-Romagna region, it goes without saying that the food in Bologna is hearty, delicious, and pretty fulfilling. Tuck into lasagna, piadina, tortellini, and all types of stuffed pasta in ragout sauce before moving on to the next destination.

Other fantastic places to visit in the region are Ravenna, the last capital of the western Roman Empire and packed with gorgeous Byzantine mosaics that have been declared UNESCO world heritage sites, Parma and the surrounding castles, Modena and Maranello for sports cars fans, and Rimini and Riccione in summer.

It’s really hard to leave Sicily off your trip. Whether you are following a classic 2-week Italy itinerary or a more alternative one, Sicily is the largest Italian island and packed with amazing cities, activities, foods, and historical sites to discover.

Whether you land in Palermo or Catania, I suggest taking your time to explore your port of arrival before moving on. Palermo is Italy’s “most Arab” city. Showcasing a suggestive combination of Christian and Muslim sacred sites and decorative patterns, in Palermo you can easily spend a week doing every day something different.

Of course, the region deserves to be visited far and wide, so I’ll understand if you move onto the next harbour sooner. Get lost in the maze of alleys of Mazara del Vallo where you will spot architectural and artistic influences from the Romans, the Punics, the Saracens, and the Normans. This beautiful town is famous for its pristine beaches lapped by a crystal azure sea.

Carry on to Agrigento where, apart from enjoying the local beaches, you can also visit the town and the famous Valle dei Templi Greek ruins. Before leaving Sicily, make sure you consider visiting also places like Syracuse, Ragusa, Taormina, and the beautiful Catania for its charming architecture and an excursion on the Etna Mount.

Take more day trips

Alternatively, you can spend more days in some of the cities suggested in our classic 2 weeks in Italy itinerary and take some day trips.

From Florence, you can enjoy a great day trip to Pisa , Lucca, or Siena . Or other fantastic towns such as San Gimignano, Arezzo, and obviously the wonderful vineyards of the Chianti region.

There are also plenty of day trips you can take from Rome . You can visit the beautiful Viterbo also known as the city of popes, the scenic Bracciano on its namesake lake, Cerveteri for Etruscan history and necropolis, and Tivoli for two wonderful UNESCO World Heritage Sites.

From Venice, you can head to Verona for a day and come back in the evening. Venice is a big group of islands, so when you are done with the main attractions in Piazza San Marco and the Jewish Quarter, head to the picturesque harbors of Burano, Torcello, Pellestrina, and Sant’Erasmo.

Some other great day trips from Venice in the Veneto region include Treviso, Padova, Rovigo, Vicenza, and Belluno for a great holiday in the Dolomites.

From Naples, I highly recommend you visit Pompeii. History buffs can even devote two days to this wonderfully preserved ancient Roman city because it’s huge and all parts are very interesting and revealing of the local life before the Vesuvius destroyed it. More great day trips from Naples include Sorrento, the Amalfi Coast, and the city of Caserta for its gorgeous “Reggia” royal palace.

The possibilities are endless, and soon we’ll be publishing a full northern Italy itinerary and an exciting offbeat Italy itinerary!

Essential tips for two weeks in Italy

Best time to travel to italy.

Boasting a mild climate and the advantages of four seasons, depending on what your ideal holiday is, any time is good to visit Italy.

Do you like skiing? Explore the beautiful Dolomites in Trentino Alto Adige. Do you prefer chilling out in the sun? Discover the gorgeous beaches in Sardinia in summer.

As far as the main cities go, any month is good to visit. In Rome, Florence and Venice there are so many things to see and do that really any season is good. If you are quite free to choose your holiday time, I would probably avoid July and August as they are very crowded and can be very hot. So not so pleasant to walk around the city center.

Spring and Fall are both great seasons to visit the big cities both to avoid the crowds and to have a more pleasant climate.

How to get around Italy

Italy has a great and very widespread railway system, so if you are traveling independently, you can totally rely on Trenitalia or Italo Treno. After each major city, I mentioned the transport you can book to get to your next stop but Italy railway is great to reach also smaller towns and even tiny villages. The perfect way of traveling around Italy for two weeks.

If you are visiting the cities and towns within the railway network, you are covered. But if you are planning on getting off the train route, relying solely on the buses might not be as straightforward. So for example, if you want to visit the Tuscany countryside or some parks outside Rome, I suggest you rent a car. Definitely, the best option when planning a 2-week Italy road trip. Click here for more info and to book a car in Italy .

What to pack for Italy

As Italy has four seasons, you can decide what to pack once you know when you are traveling. Spring is a very popular season thanks to its mild weather, but it can sometimes be tricky as temperatures change all of a sudden.

My advice would be to wear different layers so that you can cover in the evening when it’s usually colder. If you are planning a 2-week trip to Italy in Spring, make sure you pack some pretty flexible clothes.

The beginning of the Fall in Italy is pretty nice as the summer heat is mostly gone and the winter cold has not arrived yet. Mostly, you can wear light clothes and carry a jacket, a light jumper, and a light scarf for the evening. Make sure you pack an umbrella.

If you are wondering what to pack for Italy for the winter, it’s pretty straightforward: warm clothes, a jacket, a coat, warm trousers, and sweaters. Quite straightforward is also packing for a summer Italy trip: shorts, t-shirts, sandals, or summer runners, and obviously a bikini if you are going to the beach!

For some peace of mind, especially on public transport, you might want to wear anti-theft clothes. Clever Travel Companion has a pretty wide choice of models, colors, and clothes such as scarves, boxers, leggings, tops, t-shirts, women’s underpants, and more. Click here to check models and prices.

How much money do you need for 2 weeks in Italy?

If you are really traveling on a budget, you should consider putting aside around 1500€ (1600$), international flights excluded. If you prefer mid-range accommodation rather than hostels or cheap B&Bs and to treat yourself to some restaurant lunch or dinner, a budget of 2000€ (2100$) per person will be more likely.

Accommodation prices will vary depending on the location and on the season. Rome in November will be cheaper than in December , April , or even August . Generally speaking, Italy in December will be more expensive than in January or in November . Also, hotels in Naples will be more affordable than in Venice.

When it comes to food, if you wish to save some good bucks, you can opt for street food on the go, which is delicious and you are bound to find plenty of specialties.

The cost of local transport depends on how you travel. Domestic flights are usually more expensive than trains and buses, including bullet trains. You can find some offers and promotions but it’s a matter of luck. Of course, if you need to go from Milan to Palermo quickly, a flight is the best option.

High-speed trains are more expensive than regional and Intercity trains, but obviously faster. They are more affordable than flights and in some cases I think a better choice. For example, if you are going from Milan to Rome, or from Florence to Rome, the bullet train will take you from city center to city center so you are going to save time and money of the airport transfers.

Regional trains are recommended if you wish to stop in smaller towns where Trenitalia’s Freccia trains and Italo fast trains don’t stop.

Finally, if you are traveling on a shoestring and want to save also in public transport, check out bus schedules and routes. This is the cheapest option but also the slowest. This means that you either need to stay in Italy for more than two weeks, sacrifice some destinations, or skip some landmarks.

READ MORE: Tips for planning a perfect trip to Italy

Which is better Amalfi Coast or Cinque Terre?

If you are traveling with kids and planning cultural sightseeing, the Amalfi Coast should be your choice. The Cinque Terre is a good option if you want to do some hiking between the towns and visit other cities of the Italian Riviera and Liguria region such as Levico, Genoa , and La Spezia.

Amalfi Coast is the destination for celebrities and families. Its location close to Naples, Pompeii, Caserta, and Sorrento allows for a great cultural holiday.

Both Amalfi Coast and Cinque Terre are summer destinations because they are on the coast and in winter most tourism resorts and facilities are closed. Plus, bad weather might cause landslides and heavy rain.

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How to Spend 2 Weeks in Italy (Itinerary for 14 Perfect Days!)

Planning your first trip to Italy may feel overwhelming–but this (repeatedly) tried-and-tested itinerary for 2 weeks in Italy will have you relaxing into la dolce vita in no time!

For those who are new here, we are Kate and Jeremy Storm, travel bloggers and Italy travel addicts who have cumulatively spent more than a year each, over the course of many trips, exploring Italy in-depth.

After more trips (and plates of pasta) than we can count , our desire to return to Italy just keeps growing: there will always be more villages to explore, natural beauty to marvel at, and, of course, pasta and wine to enjoy.

Helping travelers plan their Italy itineraries is one of our passions, and we have repeatedly tested this guide to 14 days in Italy on friends, family, and ourselves many times over the course of several years!

So far, we have personally made our way to 14 of Italy’s 20 regions, from the imposing Dolomites of South Tyrol to the beaches of Sicily.

We’ve also “lived” for 2 months in Rome, and one month each in Florence and Bologna , enjoying a slower pace of Italy travel.

Suffice it to say that after all the time we’ve spent in Italy, we have some opinions about how to make your first trip to Italy truly unforgettable… and this Italy itinerary is what we suggest.

Some links in this post may be affiliate links. If you make a purchase through one of these links, we may earn a small commission at no extra cost to you. Please see our disclosure policy for more detail.

For first-time visitors, 2 weeks in Italy is the perfect amount of time to hit the country’s most famous and classic spots, see which ones you love, and (if you’re anything like us) fall head-over-heels in love with the country to the point that you’ll leave planning your next trip back.

This is the 2 week Italy itinerary we recommend to first-time visitors, including our friends and family, and we won’t be straying off the beaten path much here.

These first 14 days in Italy will be all about the classics–follow this trip and you’ll be spending a lot of time watching postcards come to life!

(And yes, this is a fairly long Italy blog post–feel free to use the table of contents below this paragraph to jump around as needed.)

Table of Contents

After Planning Your 2 Week Italy Itinerary…

How we structured this itinerary for 14 days in italy, the perfect itinerary for 2 weeks in italy, more (or less) than 2 weeks in italy, getting around italy, when to visit italy for 2 weeks, what to pack for italy, your 2 week italy itinerary map.

… we’d love to help continue to plan your trip to Italy in more detail here on Our Escape Clause!

We have been writing about Italy travel since 2016, and have amassed a collection of 100+ Italy blog posts available for free on this website, covering everything from the best hidden gems in Rome to what a coperto is (and why you should expect to pay one).

Cities like Rome and Venice are among our absolute favorites in the world, and we write about them extensively–but if you’re interested in getting off the beaten path in Italy, we have lots of options for that, too, from enjoying the mosaics of Ravenna to taking a road trip in Puglia .

One of my favorite things to write is detailed itineraries (like this one!), and we have suggestions for  Rome ,  Florence ,  Venice ,  Cinque Terre , the  Amalfi Coast ,  Milan ,  Naples , and more (and in the cases of some cities, several versions depending on how long you have to explore!).

I’ll link relevant blog posts throughout this 2 week Italy itinerary, but of course, I could never hope to include links to them all!

Head to  our Italy archives  to view all of our Italy blog posts in order, or if you’re looking for details on a particular destination, the search bar at the top right of the page (or at the top of the pop-out menu on mobile) is a great tool to use.

You also may want to check out the comment section at the bottom of this post–over the years, dozens of travelers have refined their own Italy itineraries there!

We structured this 2 week Italy itinerary as a point-to-point trip covering Rome, Florence, the Tuscan countryside, Cinque Terre, and Venice.

In this way, you’ll have a chance to experience many of the most popular places to visit in Italy over the course of 2 weeks, without doubling back or over-stuffing your schedule.

While some travelers like to include Milan, Lake Como, and/or the Amalfi Coast over the course of 2 weeks, we have found that with roughly 14 days (and often some jet lag) to work with, less is more.

We’ve opted for Venice over Milan and Lake Como due to personal preference, and opted for Cinque Terre over the Amalfi Coast due to geographic convenience and the ease with which it can be seen over a short period of time.

However, ultimately, the destinations that appeal to you most should be at the top of your Italy bucket list, and this itinerary for Italy in 2 weeks can be adjusted accordingly.

Days 1-4 in Italy: Rome

Rome’s highlights rank among the most famous sights in the world: who hasn’t dreamed of seeing the Colosseum in person, of walking across St. Peter’s Square, and of admiring the masterpiece that is the Sistine Chapel?

Three full days in Rome (excluding travel days) will give you plenty of time to see the best of what Rome has to offer, while also leaving plenty of time in your 2 weeks in Italy itinerary for all of the other destinations along the way.

If you happen to be lucky enough to have an extra couple of days in Italy, though–say 15 or 16 days, or perhaps less jetlag to contend with than some visitors–we highly recommend extending your time in Rome before adding time to any other destination on this 2 week Italy itinerary.

It’s simply impossible to run out of incredible things to do in Rome, which is why we have happily spent months there!

(It’s also worth pointing out that if you do have a bit of extra time in your schedule, booking an organized day trip to the Amalfi Coast is doable, if a long, day that is popular with ambitious travelers!).

Top Things to Do in Rome

Tour the colosseum + palatine hill..

Strolling through the center of Ancient Rome for the first time is an unforgettable experience!

Definitely don’t miss it during your first trip to Italy: you can buy skip-the-line tickets here (highly recommend for people visiting during summer/high season), or book the tour we enjoyed here .

Visit Vatican City.

The magnificent Sistine Chapel, the iconic St. Peter’s Basilica, the lovely St. Peter’s Square: for being such a tiny country, visiting Vatican City has a lot to offer!

We recommend using skip-the-line passes here as well, you can purchase them here .

We wrote a full guide to visiting Vatican City , so won’t repeat ourselves too much here, but in short, plan ahead, cover your shoulders, and touring the Vatican Museums on Friday night is worth it if you have the chance.

Stroll through Centro Storico.

The Trevi Fountain, the Pantheon, the Spanish Steps, Campo de Fiori: what do all of these famous things to do in Italy have in common with each other?

They’re all within walking distance of each other in Rome’s Centro Storico!

We also recommend seeking out a few of Rome’s hidden gems as you explore, including easy-to-access spots like Galleria Sciarra and Galleria Spada .

One of the best things about visiting Rome is just how much beauty is hidden in plain sight.

Things to Consider When Visiting Rome

Rome has two major downsides for a tourist: crowds and heat.

You can beat the bulk of both by traveling in the shoulder season (we personally think that October is the perfect month to visit Italy, and Rome is remarkably uncrowded in winter ), and/or waking up extra early to enjoy the city before everyone else gets out of bed.

For example, some of the best photos of the Trevi Fountain, Colosseum, and Spanish Steps that we’ve taken were snapped around dawn!

That being said–there are a million ways to get off the beaten path in Rome no matter when you visit!

While touristic hotspots like the Colosseum and Spanish Steps are nearly always crowded, fascinating places like the Capuchin Crypt, the Palazzo Doria Pamphilj, the Basilica of St. Paul Outside the Walls, plus the neighborhoods of Testaccio, Ostiense, and Monti in general, are just a few of the many great places to enjoy Rome without dense crowds.

Where to Stay in Rome

La Cornice Guesthouse  — We loved this little guesthouse! It was extremely clean and comfortable, and VERY affordable for Rome.

La Cornice is set slightly outside the main tourist areas, but an easy 5-minute walk to the metro and a 20-minute ride got us to the Colosseum and other major sights.

Our favorite part of La Cornice? Eating a nearby Joseph Ristorante for lunch, which we not only enjoyed during this trip but have returned to repeatedly in the years after.

Check rates & book your stay at La Cornice Guesthouse!

Hotel Condotti  — Located just around the corner from the Spanish Steps (and consequently the Piazza di Spagna metro station), you couldn’t ask for a better location in Rome!

Well-reviewed and boasting exceptionally clean rooms, Hotel Condotti is the perfect choice for a traveler with a midrange budget (or even a luxury traveler–this hotel also holds some impressive-looking suites!) who would like to be within walking distance of the best that Centro Storico has to offer.

Check rates & book your stay at Hotel Condotti!

Pantheon Inn  — If you’re looking for a building with classic Italian charm in the heart of Rome, this is it.

Located right behind the Pantheon and within reach, the Pantheon Inn offers a quiet, peaceful escape in the middle of bustling Rome.

You will need to walk a bit to the metro stop–but since the walk will take you through the heart of the beautiful Centro Storico, we doubt you’ll mind.

Check rates & book your stay at the Pantheon Inn!

Days 5-7 in Italy: Cinque Terre

No first trip to Italy would be complete without a visit to this beautiful coastline!

After leaving Rome, head north to Cinque Terre for coastal views, hiking, adorable fishing villages, and plenty of fresh seafood.

We recommend traveling from Rome to Cinque Terre (specifically Monterosso al Mare) via train , which should take about 4-6 hours depending on the route.

Since all 5 of the Cinque Terre villages are easily connected by train (or ferry during the summer!), feel free to stay in whichever one appeals the most, or even in nearby Levanto or La Spezia to save a tiny bit of cash.

Top Things to Do in Cinque Terre

Hike between the villages..

Sadly, many of the hikes at Cinque Terre have been closed for landslides–but the magnificent Blue Path trail between Monterosso al Mare and Vernazza (which is highly recommended!) and between Vernazza and Corniglia are open and ready for visitors!

We recommend stopping by one of the visitor centers for the latest information on available hikes.

Watch the sunset from Manarola.

Arguably the most famous of Cinque Terre’s villages due to its postcard-worthy view, Manarola is the perfect place to watch the sun sink behind the sea (preferably with a glass of local wine in hand).

Eat all the pesto and seafood.

Pesto is local to the Ligurian coast, and that makes Cinque Terre one of the best places to indulge in it in all of Italy!

Pesto happens to be one of my favorite foods, so I may be slightly biased, but in my opinion, it’s an unforgettable part of visiting Cinque Terre.

As the villages of Cinque Terre are fishing villages at their heart, the seafood here is also absolutely delicious.

Things to Consider When Visiting Cinque Terre

While it would be tempting to bring a car to Cinque Terre to have access to your own transportation and a more direct way to get to Cinque Terre from Rome and to Florence after your visit, the roads do not make for an easy drive.

Parking can also be a challenge around the villages–if possible, we’d recommend relying on the train, ferry, or the famous trail to get around Cinque Terre .

Keep an eye on closures to both the trains and the trails between the villages, however.

Strikes can happen that will shut down the train (which happened to us way back in May 2016!), and the trails can sometimes be washed out and therefore closed.

The trails also often close during the offseason, so if you’re planning a winter trip to Italy, don’t count on being able to hike between all the villages.

Why Cinque Terre instead of the Amalfi Coast?

I addressed this above, but it’s understandably a popular question when planning a trip to Italy for 2 weeks, and I wanted to expand on it here!

Italy’s Amalfi Coast is truly a marvel, but it makes less geographic sense for this itinerary than Cinque Terre.

Visiting the Amalfi Coast would require traveling south from Rome when the bulk of this 2 weeks in Italy itinerary focuses on the northern half of the country.

If you have your heart set on visiting the Amalfi Coast, you can certainly swap it out for Cinque Terre, but bear in mind that the travel times involved would be cumbersome, especially if you don’t want to cut days from the rest of the destinations on your Italy itinerary.

Cinque Terre also has the benefit of being smaller than the Amalfi Coast, making it easy to explore most or all of the villages over a short amount of time.

If you absolutely don’t want to cut any destinations and are determined to visit both Cinque Terre and the Amalfi Coast, handing the reins to the experts and booking and organized day trip to the Amalfi Coast from here is your best bet ( this one gets rave reviews ).

Where to Stay in Cinque Terre

Of the 5 villages of Cinque Terre, the only one we would recommend not staying in is Corniglia, as it’s the most difficult to get in and out of.

Other than that, all the villages have their perks–Monterosso al Mare has the biggest beach, Manarola has the most Instagram-famous viewpoint, and Vernazza and Riomaggiore are simply drop-dead gorgeous.

Bear in mind that many properties in Cinque Terre can involve a climb to reach them, so if mobility is a concern, be sure to double-check the location.

Most properties will offer porters to carry your luggage for you for a small fee, so if clamoring through town with your luggage doesn’t sound like fun, be sure to ask your hotel about their services!

Here are a few very well-reviewed properties to consider during your time in Cinque Terre:

Luciano Guesthouse (Riomaggiore)  — This is where we stayed during our most recent visit to Cinque Terre, and we can’t recommend it enough!

The property was clean and lovely, and the customer service offered by Francesco and his wife during our stay was absolutely top-notch. We would be thrilled to stay again!

Check rates & book your stay at Luciano Guesthouse!

Scorci di Mare (Riomaggiore) — Want to stay a 3-minute walk from the beach and see the sea from your window?

If so, the popular Scorci di Mare is the perfect spot for you!

Check rates & book your stay at Scorci di Mare!

Da Baranin (Manarola) — Cinque Terre is expensive, there’s no getting around it.

For a budget option, consider Da Baranin–you’ll need to climb up and down a steep hill as a trade-off, but you’ll get to stay in Manarola for a very affordable price tag!

Check rates & book your stay at Da Baranin!

Days 8-11 in Italy: Florence + the Tuscan Countryside

Tuscany is one of our favorite regions in Italy–and not just because we could spend a lifetime eating and drinking there (though we could).

The towns are beautiful and distinct, Florence is a dream of a city, the history is interesting, and the golden tinge to the light that you see in pictures of Tuscany isn’t photoshop–it just really looks like that.

While there’s no such thing as too much time in Tuscany, 3 days in Tuscany will give you a chance to explore the best of Florence in about 1.5-2 days, and also give you time to visit at least one other Tuscan city or small town, and/or head out wine tasting.

Pisa is a popular choice that is close to Florence, but unless you’re truly dying to see the leaning tower, we’d recommend Siena, Lucca , or Montepulciano instead.

If you’re looking for small-town day trips from Florence , San Gimignano, Volterra , Arezzo , and Montefioralle (near Greve in Chianti) are all stunning, and though it is in Umbria rather than Tuscany, we adored our visit to the village of Orvieto as well.

If you’re hoping to enjoy some wine tasting and town-hopping, this is an excellent opportunity to get a lot of value out of a guided tour: this wildly popular day trip from Florence is a fantastic way to taste a variety of what Tuscany has to offer (literally and figuratively).

Top Things to Do in Florence

Visit some of the best renaissance art on the planet..

The Uffizi Gallery (home of the Birth of Venus) and the Galleria dell’Accademia (home of Michelangelo’s David) are both home to undisputed world treasures that deserve to be admired during your 2 weeks in Italy.

We definitely recommend booking skip-the-line tickets to both galleries to avoid waiting in their very long lines (we once showed up to the Uffizi without pre-booked tickets and ended up giving up on visiting after nearly an hour of waiting).

You can purchase skip-the-line tickets to the Galleria dell’ Accademia here and to the Uffizi here .

Try your hand at a cooking class.

We may be a bit biased, given how much we adore Tuscan food, but if you want to take a cooking class during your 14 days in Italy, we recommend doing it here.

We adored our day taking this cooking class and years later, we still talk about it being one of our favorite days spent in Tuscany!

From the views of the countryside to the beautiful farmhouse the class is hosted in, to the sublime food, it is truly an experience to remember.

Seek out the best views of the city.

From the ever-popular viewpoints of Piazzale Michelangelo and the cupola of the Duomo to lesser-known spots like the Rose Garden and Palazzo Vecchio, there’s no doubt that Florence is a city that deserves to be admired from all angles.

We’ve rounded up the best views of Florence here –personally, we have a soft spot for the view from the top of Palazzo Vecchio.

Take a day trip to the Tuscan countryside.

Wine, plus incredible Tuscan food, plus rolling countryside, plus stunning villages–a day trip to some of Tuscany’s remarkable villages and wineries is bound to be a day that you’ll never forget.

This incredibly popular day trip is a fabulous option!

Things to Consider When Visiting Florence and Tuscan y’s Countryside

Three days in Tuscany gives you a couple of options as far as lodging: you can either stay in Florence the whole time and take day trips out, you can stay in a smaller city the whole time and simply take a day trip to Florence, or you can split it up–two nights in one city, and one in another.

Personally, we’d recommend sticking with one place to stay–this Italy itinerary is already fast-paced, so there’s no reason to take up extra time moving hotels in Tuscany.

We’ve visited Tuscany many times with both structures , and love both for different reasons .

You truly can’t go wrong with either option–I’d stay in Florence if you’re more of a city person, and in a surrounding Tuscan town if you’re more interested in the countryside.

If you stay in the countryside, you will definitely want to rent a car for this portion of your Italy itinerary.

Where to Stay in Florence

B&B Le Stanze del Duomo  — Though Florence hotels can be a bit pricey and stretch the definition of “budget”, B&B Le Stanze’s beautiful rooms and impeccable location in Florence will be sure to have you swooning!

Check rates & book your stay at B&B Le Stanze del Duomo!

Hotel Silla — Located just a hop, skip, and jump from the Arno River, we loved our stay at Hotel Silla!

The hotel itself is lovely and quiet, the included breakfast a nice touch, and the location perfect: you have easy access on foot to all that Florence has to offer, without having to worry about crowds or noise.

We’d be happy to check in again!

Check rates & book your stay at Hotel Silla!

Hotel Lungarno  — Nestled right against the Arno River and home to one of the best views of the Ponte Vecchio in Florence (not to mention some of the best views of the rest of Florence from their top deck), Hotel Lungarno is our personal “if we ever  really  want to splurge” hotel in Florence.

You can’t go wrong using Hotel Lungarno as your base during your Italy vacation!

Check rates & book your stay at Hotel Lungarno!

Days 12-14 in Italy: Venice

Canals, canals, and more canals: Venice is simply a ridiculously beautiful place, and despite its somewhat controversial reputation, we absolutely adore it (yes, even during the summer !).

Definitely make sure that you climb St. Mark’s Campanile for an amazing view of the city, check out Libreria Acqua Alta (one of our favorite bookstores in the world!), walk across the Rialto Bridge, and spend ridiculous amounts of time wandering aimlessly around the small streets and lesser-known canals–that is truly Venice at its best.

If you have good weather while in Venice, also consider a day trip out to Murano or Burano for another view of Venetian life!

We’ve written extensively about Venice, in large part because we adore the city and know that unfortunately, not everyone walks away with the same impression.

We recommend taking a look at our suggested 2 day Venice itinerary and guide to the best hidden gems in Venice as you plan your trip here!

Top Things to Do in Venice

Tour the doge’s palace + st. mark’s basilica..

Venice has a truly fascinating history–for a city that is now known mostly for its beauty, flooding, and risks of sinking, it can be hard to recall that once upon a time, there was a true and powerful Venetian Empire.

Learning about the history of Venice’s government (it included  many  councils) and how it acquired its wealth is a fabulous way to get to know the city on a deeper level–and the buildings themselves are incredibly impressive, too.

We recommend taking a tour here if at all possible–it truly adds so much context.

This tour of the Doge’s Palace + St. Mark’s Basilica is very popular and a great option!

Stroll through Venice’s beautiful sestieri.

Venice is divided into six districts, or sestieri, and each sestiere has its own distinct flavor and beauty.

San Marco and San Polo are the most popular (read: crowded), and while they are absolutely gorgeous, we recommend making time for a walk through some of the others as well.

Castello, Cannaregio, Dorsoduro , and San Croce all have a lot of beauty, canals, and quiet streets to offer.

Hit the water and enjoy Venice’s canals.

While the gondolas are (deservedly) famous, there are indeed ways to experience Venice’s canals on any budget.

Whether you want to splurge on a private gondola ride, opt for the mid-range shared gondola option, or stick to a budget and tour the Grand Canal via Vaporetto , there’s a canal option open to you!

Our guide to gondola rides in Venice will help you know what to expect, or, if you want to find a way to enjoy a gondola ride for just 2 Euro (not a typo!), here’s how to find a traghetto .

Things to Consider When Visiting Venice

Especially if you’re visiting during the summer, Venice will be both crowded and expensive.

It’s still absolutely worth it to go, but like in Rome, consider early wake-up calls to get the most out of your experience.

Some of our best memories of Venice are of walking through the city before the shops even start opening–and we’ve often found that we get our best photos of Venice then, too.

Keep in mind that if you want to take an iconic gondola ride, you’ll be paying a pretty penny–80 Euro/gondola worth.

After enjoying more than one gondola ride in Venice, we can confirm that they are worth it to the right traveler–but you can absolutely have a fabulous trip to Venice without one, too.

Where to Stay in Venice

Hotel Casa Boccassini  — This cute hotel easily met our needs during our first trip to Venice!

The room was simple but clean, and the shared bathroom was a fair trade in exchange for their competitive prices in a great location in Cannaregio.

The bathroom was clean and we had a sink in our room, both of which always make shared bathroom situations much easier.

The courtyard of the hotel was beautiful!

The hotel was a simple and beautiful 10-minute walk from the Rialto Bridge and just a 5-minute walk from the Vaporetto to the airport.

Check rates & book your stay at Hotel Casa Boccassini!

Hotel Lisbona  — We decided to check into Hotel Lisbona for one reason: we wanted to stay on a canal!

If you’re looking to stay right on a canal in Venice without paying luxury prices, we can heartily recommend Hotel Lisbona.

The building is beautiful and definitely has that oh-wow-I’m-in-Venice effect (especially when you look out the windows), the customer service is great, and the included breakfast is tasty.

The central location (it’s around a 5-minute walk to Piazza San Marco) couldn’t be better.

The downside? The room we stayed in was  tiny –but to be staying right on a Venetian canal in such an amazing location, we definitely considered the trade-off worth it.

Check rates & book your stay at Hotel Lisbona!

Hotel Danieli  — If you’re looking for a true luxury experience for your 2 days in Venice–the kind of hotel stay that you’ll remember for the rest of your life–look no further than the iconic Hotel Danieli, located inside 3 former palazzos along the Riva degli Schiavoni.

Every detail has been looked after here, and everything from the furniture to the breakfast to the location (mere steps from the Bridge of Sighs) to the truly stunning lobby will ensure you have an absolutely unforgettable trip to Venice.

Even if you don’t check in, consider dropping by the bar to see the beautiful lobby for yourself!

Check rates & book your stay at Hotel Danieli!

Italy has an endless amount of places to see, and no 2 weeks in Italy itinerary could dream of covering the whole country.

If you’re visiting over the summer (or over the winter and you like to ski) and find yourself with more time in Italy, consider heading to the South Tyrol region to experience the Dolomites (also known as the Italian Alps).

You could also head to Lake Como and stop off at Milan along the way, or stay further east after leaving Venice and hit up the stunning Verona .

Bologna , which is known as one of Italy’s great foodie cities, is another wonderful choice, and also includes the option of a day trip to the microstate of San Marino .

And, while Bologna is the most famous place to visit in Emilia-Romagna, we’d be remiss not to point out Ravenna (home to absolutely incredible UNESCO-recognized mosaics) and Parma (the origin of parmigiano-reggiano and a delightful city) as well.

South of Rome, you could head to the incredible Amalfi Coast or the stunning island of Capri , and stop off for a day along the way to eat pizza in Naples .

Further south, the stunning beaches and towns of Puglia make for a memorable summer trip to Italy.

Even with all that, you’re still barely scratching the surface of Italy (and of course, every single one of the destinations included in this 2 week Italy itinerary could easily take up more time as well)–but that’s ultimately a good thing.

If there’s one thing that we’re certain of after more than a year of exploring, it’s that there is always a reason to plan another vacation in Italy.

With One Week in Italy

If you only have roughly one week to spend in Italy, we–heartbreaking though it is–recommend cutting at least one of the destinations suggested on this 2 week Italy itinerary. 

Personally, we’d first cut Cinque Terre (especially if you’re visiting outside the summer season), leaving the trifecta of Rome-Florence-Venice intact.

We go into this further in our guide to spending a week in Italy , as well as provide other suggestions on how to make the most of a short Italy itinerary.

If you need to cut a second destination, let geography be your guide, and trim off whichever destination will take the most time to reach based on your travel plans.

I know it’s incredibly hard to cut destinations, but rushing to a new place almost every day will eat up way too much time that should be spent experiencing Italy.

And ultimately, any given two, or even one, of the destinations covered in this Italy itinerary, could make for a magnificent trip.

With 3 Weeks in Italy

If you have an extra week to tack onto this 2 week Italy itinerary, lucky you!

You’re in for a real treat with a whole 3 weeks in Italy.

Our personal recommendation would be to use that extra week to add on Naples, Pompeii , and the Amalfi Coast.

If you’re a fast-paced traveler, you could cover those destinations in 4-5 days and spend the remaining time sampling Milan and Lake Como ( the town of Bellagio is just as picturesque as the pictures imply).

With that, you’ll cover the vast majority of the country’s best-known sights on your trip to Italy!

Alternatively, if you’re more of a slow, immersive traveler, use the extra week to really dig into one of the regions already included on this Italy itinerary.

Tuscany or Rome would be our pick (and you can technically take a very long day trip to Pompeii or Naples from Rome if you want to try to get the best of both worlds).

Within each of the destinations outlined in this 2 weeks in Italy itinerary, walking will likely be your most common method of getting around, and also half the fun of traveling Italy!

You’ll probably want to mix in some public transportation as well, particularly in Rome, but strolling through destinations like Venice and Florence is by far the best way to explore them.

Getting between destinations, however, is a different story–here’s a quick outline of transportation within Italy.

Trains rule on-the-ground travel in Italy: if you’re not going to rent a car, it’s likely you’ll be getting around Italy by train.

Every train we have taken in Italy has been comfortable and pleasant, but keep in mind that strikes can occasionally interfere with travel.

We definitely recommend booking your train tickets in advance if you’re traveling on Italy’s high-speed trains, as these tickets can increase in price as the dates get closer.

If you’re traveling on the regional train, you don’t need to worry about booking ahead, as the prices are fixed. 

We typically travel Italy by train with Trenitalia, Italy’s national company, but Italo (a private company) is also excellent for some routes.

In Lombardy (where Milan and Lake Como are located), you’ll also see Trenord-branded trains.

You can check prices and compare rates, schedules, and more on Omio to ensure you’re getting the best deal on train (or bus) travel in Italy.

We use Omio regularly throughout Europe and have always had good experiences with it.

If you do happen to buy a train ticket at the station (for a day trip, perhaps), keep in mind that paper train tickets  must  be validated before boarding the train in Italy, and failing to do so could result in a hefty fine, being thrown off the train at the next stop, and an enormous headache.

As far as we’re concerned, that’s another reason to book online, as showing the tickets on your phone to the conductor is just fine.

Shop train tickets for your 2 week Italy trip today!

Renting a car to drive through Italy is a popular option, especially in places like Tuscany, but there are a few things you’ll want to consider before you do.

Keep in mind that cars are restricted from driving into the historical centers of most cities, including Florence and Venice, and failure to adhere to these rules (even accidentally) can result in strict fines that you sometimes find out about through the mail months after the fact (my dad and a good friend have both been fined for driving in Italy via a summons after returning home).

For that reason, as well as issues with extremely limited parking in cities, we recommend limiting car rental when possible to time spent in smaller villages and towns.

While we love taking road trips in Italy , this itinerary for 14 days in Italy doesn’t require one, with the possible exception of renting a car for a couple of days to explore smaller villages in Tuscany.

If you do want to rent a car in Tuscany, know that an international driver’s permit is required for renting a car in Italy and must be obtained in your home country before arriving.

Sometimes car rental companies ask for it, sometimes they don’t (same with the police), but in our opinion, it’s not worth taking the risk–add this to your list of things to take care of being starting your 2 week Italy trip if you plan on renting a car.

Also, keep insurance in mind!

Thanks to Italy’s (somewhat deserved) reputation for less-than-cautious drivers, some travel insurance companies will not cover you while driving in Italy, or charge an extra fee to do so. Be sure to double-check before you book.

If renting a car is the right choice for you, we recommend browsing Discover Cars , and aggregate for finding rental cars in Europe (and beyond, though they’re most popular in Europe).

Discover Cars will search both local and international brands that have available cars for your dates, and allow you to compare prices, reviews, and inclusions side-by-side.

Shop rental cars for your Italy vacation today!

Bus travel in Italy is much less common than in some other European countries, mostly because of their well-developed train system.

You can find some buses available, however, especially among smaller cities and villages (we’ve used local buses in South Tyrol several times), as well as throughout certain parts of southern Italy.

If you’re having trouble deciding how to get around a certain destination.

In addition to trains, you can also browse some long-distance buses via Omio .

If you’re hoping to be careful of your budget during your 2 week Italy trip, we recommend looking into flights for the Rome to Venice (or vice versa) leg of this itinerary.

Trains are a comfortable, romantic, and easy way to travel, and they also often cost more than budget flights do!

There’s no such thing as a bad time to spend 2 weeks in Italy, but some seasons are definitely more convenient to travel in than others.

Summer is the most popular season and will bring warm weather, lots of sunshine, and lots of tourists.

Prices will be at their highest, but the beaches will be at their best–if you’re hoping to swim at Cinque Terre, you’ll want to plan a summer trip.

Winter is the offseason and will bring colder temperatures, rain, and gray skies.

Prices will be at their lowest, and crowds will be as small as they ever get.

The Christmas season can bring increased crowds, but also the benefit of experiencing Christmas decor and markets (though fair warning–these have nothing on the Christmas markets in Austria and Germany! Check out Bolzano for something close.).

Personally, our favorite times to travel to Italy are the spring and especially the fall.

T he crowds are less than in the summer, spring brings beautiful blooms, and fall brings the olive harvest (after tasting fresh olive oil in Tuscany, I don’t know how we ever lived without it).

The weather is a bit riskier during the spring and fall than during the summer, but we have never had much of an issue with it.

T he occasional rainy or cool day is worth it to us for the tradeoff of not being hot and crowded, and October is our personal favorite month to visit Italy.

Ultimately, though, whenever you have a chance to plan a 14 day Italy trip, take advantage of it: every month of the year brings distinct upsides and challenges, but each and every one of them is worth the trade-off.

Planning a packing list for 2 weeks in Italy can be a challenge of its own!

We have a full Italy packing list here, but to get you started here are a few things to be sure to bring on your trip to Italy.

These days, we prefer just to leave valuables in our Pacsafe during the day.

Option C: Hope you get lucky with the weather (but fair warning, we’ve never been avoided rain entirely during a trip to Italy!).

Bring a small pack of tissues, toss them in your day bag, and you won’t have to worry about it.

I’ve been using it for more than 5 years now and am now working on my second volume, and I absolutely adore it!

I use them on all boats and the occasional bus, and if things get really bad, take some Non-Drowsy Dramamine as well.

Before heading off for your 2 weeks in Italy, be sure to read through our complete Italy packing list !

Take This Map With You! Click each highlight to pull up the name of the destination. To save this map to “Your Places” on Google Maps, click the star to the right of the title. You’ll then be able to find it under the Maps tab of your Google Maps account! To open the map in a new window, click the button on the top right of the map.

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About Kate Storm

In May 2016, I left my suburban life in the USA and became a full-time traveler. Since then, I have visited 50+ countries on 5 continents and lived in Portugal, developing a special love of traveling in Europe (especially Italy) along the way. Today, along with my husband Jeremy and dog Ranger, I’m working toward my eventual goal of splitting my life between Europe and the USA.

148 thoughts on “How to Spend 2 Weeks in Italy (Itinerary for 14 Perfect Days!)”

I’m in Veneto, and so am biased about what I write about Italy. You covered some great places like CInque Terre and beautiful Toscana. I totally agree about heading to see the Alps, the Dolomiti is a must too. Beautiful photos to accompany the post too!

Thanks, Lisa! We’re hoping to make it back to see even more of Italy in 2018–maybe we’ll make it to more of Veneto this time!

Do the 3 chimney hike, you will not be disappointed!

Italy, why can’t I quit you… I have been reading about how dreary Italy can be in the winters. I think you are right that fall would be the best time to visit. I loved how clear all of your photography was.

Thanks, guys! I know what you mean–we can’t quit Italy, either.

I went in October 1-14, 2021, we had one evening of rain in Venice but we went to a concerto and the rain was over when we came out of the concert!!! I had the best trip ever!!!!!! My daughter planned it and she did an excellent job, Naples to Rome to Florence to Tuscany to Venice to Cortina to Venice train to Naples to Mt. Vesuvius to Pompeii to Verti to Amalfi Coast. It was an amazing trip and I want to go back too.

How many days did you stay in each of these places on your trip to Italy?

What was your itinerary day to day. What method of transportation? Thanks!

Could you please share more details? would love to do this itinerary Summer of 2023!

A great article for first timer to Italy. I have sent this to my partner and I hope he reads it, I have dreamed of coming to Italy since I was a young girl. My parents went to Italy and always spoke of Venice and Muranos Island and of course glassware. Your photos are spectacular.

Hope you get to make that trip happen soon, Nicole! Italy is as amazing as advertised. 😀

Italy is such a cool destination and this is the perfect guide to plan a trip in two weeks. I have been to Rome once and your pictures of Trivi Fountain is amazing as during my visit it was mainly crowded. Did you explore the islands near Venice too ?

No chance to go to the islands, sadly–the weather didn’t cooperate with us too well in Venice. Hopefully next time! We’d especially love to go to Burano.

I was actually wondering where you were off next, after reading your Rome post 🙂 although not a big fan of Italy overall, I am a huge fan of Tuscany… I only got to spend 2 days in Florence a few years back, so it is definitely on my travel list! Love your pics!

Florence is definitely worth a return visit–the food alone would be, in our opinion! 😉

I visited Italy for the first time last year, travelling to Rome and it was magical. The amount of culture is unbelievable, I would love to travel to Florence or Naples next time!

I hope you get that return trip, Lottie! Italy never gets dull, that’s for sure.

Your pictures are really enticing. A trip to Italy would be incomplete without taking up a culinary class or 2 in Tuscany. Cinque Terre looks particularly interesting too. Will get back to you for travel-planning. 🙂 Cheers!!

You’re totally right, Aditi–our cooking class in Tuscany was one of our highlights of our month there this year! Food in general is such a big part of traveling in Italy, it really adds something to the whole experience.

I agree with you that one cant get enough of Italy…and this time I really mean it! So much cosy villages and site to explore…and not to mention the food! I have been to Italy many times before living in the country next to so I think you have chosen a great destinations for a two weeks itinerary for a first-timer! I hope to visit the northern and souther part of Italy this summer!

Oh, it must be so much fun to live in Italy! I’m sure it comes with its challenges as well, like any destination, but if we could pick somewhere to live for a year, Italy would be VERY high on the list!

Eat, Pray, love put Italy on my map. And, I am so glad it did. I really enjoyed my time in Italy. And, without knowing I almost followed your first-time visitor itinerary. The country is so beautiful that one time is not enough. I am aching to go back. Maybe this year it will happen.

Hope you get to go back, Archana! No such thing as too many trips to Italy, right?!

A nice itinerary that you have suggested. Did all these except for cinque Terre. Wish someone had advised me then to do that. I hope to go back to Italy again to see this. Cheers

Agreed–we hope we get to go again soon, too! 🙂

Curious, how did you decide the order of your destinations? We’re doing 15 days in Italy and flying into Rome. We’re trying to visit Venice, Florence, Cinque Terre, Tuscany then Amalfi Coast before returning to Rome for our flight home. Any advice on the best order?

We actually put this itinerary together based on a couple of months worth of travel in Italy, so we didn’t follow these steps exactly in order (though we’ve visited all of these destinations, some more than once!).For your trip, assuming you’re flying out of Rome as well, I’d personally probably structure it as: Rome to Cinque Terre, Cinque Terre to Florence/Tuscany, Florence/Tuscany to Venice, and Venice to the Amalfi Coast (you’ll need to stop by Rome again) before returning home.

No matter what way you do it, you’re going to have a lot of travel time in there–you’re covering quite a bit of the country.Honestly, I’m tempted to say you should skip either Cinque Terre or the Amalfi Coast (the Amalfi Coast would make more sense to cut geographically, hence why it didn’t make this itinerary) and slow the pace a bit, but I know that’s much easier said than done–when you have a limited number of days, you want to see it all!

Not sure how you’re planning on getting around, but I’d consider saving some time and flying from Venice back to Rome–budget airlines (including Ryanair) fly in/out of both those cities, and if you plan in advance, you may be able to get very low fares. Also consider booking any train tickets you need in advance–fares go up dramatically the closer your dates get.

Hope you guys have an amazing trip! Italy is absolutely incredible. ?

Hi Jeremy and Kate, Warm greetings from India. I discovered your blogsite recently and this is really amazing 🙂 I wanted a favor from you guys, I will be travelling to Italy soon, for some office work in mid march. I will stay at Siena for 14 days. Can you please please please recommend me a travel plan or at least help me with details of rail travel? I intend to see Rome on one weekend, Venice and Milan on other weekend. I intend to travel Florence and Pisa during weekdays, when we get time off. I wish to hear from you guys… Love from India <3

Hi, Akshay! That’s not a service that we offer, but I can say that we used Trenitalia for our train tickets and were very satisfied with them. I recommend booking as soon as you know your dates, because prices do get more expensive over time. I think seeing Venice and Milan in a single weekend will likely be too much–unless you’re dying to see Milan in particular, I’d recommend skipping it and heading right to Venice. Good luck!! Hope you have an incredible trip.

We leave for our first Italy trip next week! I am so excited! When we were first planning our trip we were trying to pack too much into 14 days. We settled on flying into Venice for two days, heading to Modena for two days, traveling to the Umbria region for 5 and ending in Rome where we fly out.

Oh, that is so exciting! It’s definitely tempting to try to stuff too many destinations into too few days, but your trip sounds wonderful. I hope it helps you fall in love with Italy!!

Hello- We are traveling to Italy for first time in August 2018. Flying in to Venice and staying for 3 nights. Then to Florence for 4 nights, and on to Rome for 6. Flying back to US from Rome. Question– Should we decrease time in Rome to add 1-2 nights in Naples or Sorrento to see Amalfi Coast? We will do day trip from Rome –> Naples –> Pompeii, but just curious if we should try to squeeze in Amalfi Coast. Thank you!

Hi Vicki! It’s hard to say without knowing your general travel style (how badly do you want to see the beach?), but our recommendation would be to stick with Rome for 6 nights, or to add on an additional night onto Florence and potentially use that as a day trip to Cinque Terre (you’ll need a car to do that, but it’s a shorter drive than Rome –> Sorrento). Good luck with your planning–your trip sounds fabulous!

Thanks so much Kate! The attraction to Amalfi Coast is b/c we have heard how beautiful it is- but it does does sound far for a day trip from Rome. I keep reading about Cinque Terre but we are not big hikers (knee issues…!). Would Cinque Terre be worth a day trip (train?) on the way to Florence from Venice? Thank you so much for your help! Vicki

A day in Cinque Terre on the way to Florence, perhaps… but you’d need a whole day, and likely need to spend a night. There’s no direct train from Florence to Levanto (the larger village near the Cinque Terre villages), unfortunately, so traveling by train between the two without a car is harder than it appears looking at a map. Travel from Venice to Cinque Terre will likely take an entire day as well, but you could add one Cinque Terre day in between two travel days if you’d like! 🙂

Kate, Thank you so much– this has been enormously helpful! I think we’ve decided to take the train from Venice to Florence, spend 4 full days in Florence and just explore that beautiful area. We know we need at least two full days in Florence, but welcome any/all suggestions about surrounding area day trips. Grazie!!

Hi Vicki! Some of our favorite Florence towns include San Gimignano, Volterra, and Lucca–all great day trips. 🙂 Siena is also popular. If you have a car, there are natural hot springs in Tuscany that are supposed to be beautiful, but we haven’t made it there ourselves yet. Our “Romantic Things to Do in Tuscany” post has some great ideas as well–you don’t necessarily need to be traveling with a partner for them, either! 😉

Vicki- who are you booking with. This is the exact trip myhusband wants but couldn’t find it. flying to venice for 3 nights, florence for 4 nights, then Rome.

I’m not sure what Vicki is planning, but if you guys are planning the trip yourselves, I’d fly to Venice, take the train to Florence, and then the train to Rome before flying home. I’m not sure of any group tours that follow that route, though I’m sure they exist!

Hi Kate, in your scenariou do you fly back home from Venice or Rome back home

It’s up to you and how the flights work to/from your destination.

In a perfect world, it’s easiest to fly into Rome and out of Venice.

However, if flights are much more expensive that way vs booking a round trip ticket, you can also take the high-speed train from Venice back to Rome to fly out. The fastest trains on that route take just under 4 hours, but you’d need to book those tickets in advance.

This post is a great guide for traveling through Italy. My friends and I traveled to Italy on a rented car and visited some of these places. I advise everyone to visit here!

Thanks, Dylan! So glad you guys had a great time.

Parking can also be a challenge around the villages–if possible, we’d recommend relying on the train or Cinque Terre’s famous trail to get between the villages. And it is very good, because in Ukraine it is big problem!^(

Yes, absolutely, but it can be convenient to drive to La Spezia and take the train into the 5 villages from there. 🙂 Easier than taking the train all the way from Florence for sure!

This is amazing blog! My husband and I are traveling to Italy for our honeymoon in June. Could you guys shed some light on car rental and driving in Italy? Is it driver friendly with interpretable directions? My husband wants to bring a GPS – is this too ridiculous? Thank you!! Also, have you been to Capri?

Hey Natalie! Congrats on your wedding–we got married 5 years ago this June. 🙂 🙂 Italy is reasonably simple to drive in when you consider the quality of the roads (decent) and navigation (decent). That being said, drivers are aggressive and driving in cities is a headache–at the very least, I’d ditch the car in major cities. Depending on your itinerary, I doubt you’ll need a car for your whole trip–I’d consider where it would be more of a hindrance than a help (basically any large city and any surrounding smaller cities/towns that you can connect to by train) and go from there.

I am so happy I came across your blog! We leave 9/8/18 from California and arrive in Rome on Sun. 9/9 @ 6pm My initial thought was to take the fast train to Venice on Mon. 9/10 and then work our way down to Florence, CT, Rome.. but now i am wondering if i should fly to Venice on 9/10 after a good nights rest instead of train to save time.. its the same price! Or do you suggest head straight to CT from Rome, then on to Florence, Venice and fly back to Rome to finish our trip there?? I saw you suggested above to go to CT from Rome..

I am trying to not overwhelm ourselves as i really don’t want to spend all my time on a train or stressed out.. But i feel like these are the 4 places we want to see this time around.. (i had to talk myself out of Amalfi, Lake Garda, etc.!.. i want to see it all!) Also, this will be our honeymoon! We will be there for a total of 13 nights.

Hey Amanda! Congrats on your upcoming wedding!!

September is the perfect time for a honeymoon in Italy, it’s one of our favorite months here. 🙂 I definitely understand the difficulty of cutting things down, lol–there’s never enough time!

As far as starting in Rome or Venice, it’s mostly personal preference. I wrote the itinerary this way for two reasons: 1) most people fly into Rome, and 2) If I had to choose, I think Venice makes a better last destination than first. They’re both crowded and touristy, of course, but seeing the best of Rome requires a lot of effort and activities–the Colosseum, touring the Vatican, etc.

Venice definitely has some great sights, but you could also spend a couple of days strolling aimlessly around the city while eating endless gelatos and still come away feeling like you “saw Venice”–in other words, it’s not as demanding as Rome IMO.

Plus… after flying all the way from California, I’m guessing you’ll be ready to see Italy once you get here, not jump on another train/plane! But ultimately, it’s your call–I don’t think either direction would be a mistake.

I do definitely recommend flying over train travel for the Rome to Venice route, as it’ll definitely save you time–anything that saves you time and stress on a honeymoon is a good idea. 🙂

Hi there, I am taking my wife for 2 weeks coming up next month. We are staying in Cortona, Italy in Tuscancy and making day excursions to Florence, Pisa and other towns within a day of Cortona. For the second week, would it be better to start off in Venice and make our way to Rome and/or Cinque Terre or do I see about a last minute cruise from Venice through the Mediterranean. Downside would be that we wouldn’t see as much of Italy. We don’t want to be on the go 24-7 but we do want to experience Italy. Your comments are appreciated!

Both of those options sound amazing, so it’ll really just be down to personal preference!

I don’t know the cruise itinerary, but I would imagine that the cruise will focus more on natural beauty + beaches, and a a trip to Rome would be more focused on history (with still a sprinkling of beaches in that week if you hit up Cinque Terre).

If this is your first trip to Italy, I personally would forgo the cruise to focus on Italy itself, but there is definitely no right or wrong answer to that!

Great advice and itineraries, thanks so much! We’re planning an 8-10 day trip to Italy during the last 2 weeks of August and are thinking Venice, Florence and Rome (not necessarily in that order). I’m wondering if it would be a better plan to split the time between Venice and Florence and plan to see Rome during a trip during a shoulder season (we also have 2 weeks available to travel after Christmas ). Your thoughts on whether to cut the itinerary to 2 vs 3 cities during the hotter “touristy” time of year? Thanks!

That’s a tough question! Knowing you have another opportunity to travel after Christmas, I would probably lean toward cutting one city and sticking to two–it’ll be a more relaxing trip that way, and there’s more than enough to do in any two of those cities to keep you entertained for 8-10 days. I know it’s a hard call, though!

Hello, it was nice reading your and other people’s ideas. We are going to be 71 and 72 this coming April-May when I am planning our trip to Italy. I have been before and love the trains and agree with all. But, dealing with luggage on trains is not the easiest especially as we get older. I need to book lodging before the flights and we have enough miles. If we take the train, are there taxis at all the stations to get us and luggage to where we stay? And, any idea how much or if they take credit cards like I know they do in NYC? He suggested driving for that reason, but I think finding parking with the lodging, or at the sights, would be the worse problem. Do you agree? I was thinking of mid May, but have read that May is pricey. Do you think late April is warm? I don’t want to lug jackets. My idea for 2 weeks: fly to Rome, 3 days; to Assisi, Perugio, Siena- find a place in either area for a day or 2; Florence, 3 days;Pisa 1 day; Cinque Terre/LaSpezia, 2 days; Venice -maybe drive thru Verona, 2 days.

Hi Roberta! Yes, I can definitely see how the luggage on and off trains can be difficult. There are taxis at most of the stations, but they don’t tend to take credit cards. Uber is available in Rome, but no other city on your itinerary. I would say that driving is definitely more trouble than it is worth for larger cities like Florence, Rome, and Venice–you could consider driving to Cinque Terre, but you’ll likely just be leaving the car at the hotel the whole time.

I’m not sure what your budget is, but some hotels will also offer an airport (and possibly train station?) pick up service–for a fee, of course, but they would be able to help with the luggage.

Late April is a bit unpredictable with the weather–it may already be getting warm in Rome, but Venice will almost certainly still be jacket weather. You never know, though! We were in central Italy during late April this year (Bologna/Emila-Romagna) and we still wanted light jackets until around the beginning of May.

Hope this helps! 🙂

Hey! Came across your blog and this is super helpful. Even reading through all the comments.

My wife and I are flying into and out of Rome in September and have 14 days in Italy. We were thinking after arriving in Rome hopping on a train to Venice and staying there for about 3 and a half days then taking the high speed train to Naples and spending some time in Sorrento and that area for about 4 days and ending in a Rome for about 4-5 days. I’m not counting the days where it’s mostly traveling.

Do you think this is feasible? Should we add a city worth seeing or is it too spread out to really enjoy it? We want to make the best of it since we may not get back there soon but I also don’t want us running around so much that it becomes in enjoyable.

I appreciate your feedback!

It is feasible! You’ll be tired, but it looks like you have enough time to work with. If you have your heart set on those destinations, I’d look at a budget flight instead of a train for Rome/Venice and back–round trip fares can be quite inexpensive on discount airlines like Ryanair, and I know they have lots of flights between both cities.

With a 14 day trip, I would personally be tempted to trim a day from each of those destinations and add in another city (Florence/Tuscany would be my personal first pick), but you certainly don’t need to, and you guys know your pace best.

If you’re 100% sure on dates, I’d check on flight and train prices *now*–the high-speed trains that go between multiple regions of Italy (ie, the Rome–>Venice and Venice–>Naples trains) can be pricey, and the prices do increase as the dates get closer. With regional trains that stay in one area (just Lazio or just Veneto, for example), the prices are fixed and you can just buy whenever. 🙂

Have fun!! September is a magical time to be in Italy, I’m sure your trip will be wonderful.

Hi I Loved your itinerary, am thinking of something similar in October for my family. Could I ask what your final budget was for travel and accommodation / tickets etc please? Many thanks Carly

We put this itinerary together based on several months traveling in Italy, so it’s hard to extrapolate out what we would have spent. Speaking generally, I would say 140 Euros/couple/day, adding additional funds for kids, is a comfortable midrange budget in Italy, though you can easily do it on a far smaller or far bigger budget as well. If you plan to rent a car in Italy, that will eat into costs and you may want to budget extra for that.

Your travel blog is perfection! We are looking to surprise our daughters with a trip next summer and you have covered everything on our wish list.

Thanks, Jodi! That sounds like so much fun–I would have been thrilled to have my parents surprise me with an Italy trip! 😀

Hello I am in the process of planning a summer trip to Italy with our kids. We are flying into Venice ( award travel) and was planning to stay 2 nights, then stay 5 nights in Tuscany and then head to Positano for 5 nights. Will fly home from Naples or Rome. On our first trip to Italy we did Florence, Cinque and Rome. I was dreaming of a farmhouse/villa stay in Tuscany but so far they are all a Saturday to Saturday stay. We arrive in Venice on a Monday and was planning Tuscany for a Wednesday arrival for 5 nights. Wondering if we should skip Positano and go somewhere for 5 nights before Tuscany? Or should we fly from Venice to Naples , visit Amalfi area and then head back to Tuscany? Or maybe you know a place that doesn’t require a week stay in Tuscany? Is there a Tuscan town you recommend for a good home base? Trying to make the best use of our time. I am getting confused 🙂 Our kids are teens. Appreciate your thoughts!

Hi Sally! It all depends on what you’re looking for–Positano is beautiful, but if you’d rather stick to a closer geographic area, Verona and Emilia-Romagna (possibly based in Verona) would be good options between the two. For beaches, there’s always Elba in Tuscany (though that can be a little harder to get to). I don’t know of any Tuscan villas offhand that aren’t only Saturday-Saturday, but I would guess that VRBO and maybe Airbnb would be your best bets for that. We use VRBO for our multi-generational family trips to Tuscany. 🙂 Tuscany is one of our favorite places, so I’d have a hard time saying you can go wrong with a base there! Siena and Lucca are both great options if you’re wanting something smaller than Florence, but you’ll definitely need a car for day trips if you’re wanting to explore the region (and especially if you’re staying outside the city center).

I enjoyed reading your blogs very much. My family and i will have only 5 days in Italy, as a side trip from Germany. Where would you recommend that we must visit, as a first timer to Italy? Also, are there flights/trains that go directly to Florence?

Ahh, that’s a hard one! The answer is, of course, wherever you are most invested in going–but in my personal opinion, I’d pick Tuscany. It’s easy to navigate, incredibly beautiful, and very classically “Italian” for first-time visitors. It’s also one of our favorite places in the world, so I’m a bit biased. 🙂 There are flights and trains that go directly to Florence, but on that timeline and coming all the way from Germany, I’d definitely fly. If you’re open to budget airlines, be sure to check Pisa–it’s about 20-30 minutes outside of Florence, and most of the budget airlines fly there instead of directly to Florence.

We are heading to Italy (first time for me) next fall with 2 other couples and are just now starting to research. Your blog is amazing and really is helping us formulate our trip. Have you ever cruised the coast of Italy ( i want to see as much as possible going for 2 weeks) and know we cant see it all but wondered how a cruise (small less then 300 people) might help us see all those amazing sights on the water – 7 day then heading into shore and seeing the other parts of Italy.

We haven’t had the chance to cruise the coast of Italy (yet), but it’s actually on our list of Italy trips we hope to take one day.

If your goal is to see as much as of Italy as possible, I would say the benefits of the cruise depend on where exactly it goes and what your priorities are. I’d check and see how much land time there is vs cruising time, etc. It’ll definitely cut into your time in Italy itself, but it would also undoubtedly be a beautiful and unforgettable experience in its own right. The coast of Italy is incredibly gorgeous!

Did you take the picture of the Tuscan countryside that is right before the “Cars” section of this blog? If so, where is that at?

Yes we did!

It was taken at a winery outside of San Gimignano–those are the towers of San Gimignano that you can see in the far distance. Unfortunately, I didn’t note the name of the winery at the time, but there are similar views all throughout the area!

Kate, My husband and I are planning to go back to Italy next October.our past trips were Florence, Tuscany and a Rome. This time we’re going to Umbria area and the Amalfi coast probably 14 days total. My question is what order do you suggest? Last trip we felt like we should have done Rome first then Tuscany, Rome was hustle bustle and Tuscany was laid back and relaxing..we felt we should have stayed in Tuscany last. What place would you suggest starting and ending with.

If you’re looking to start with hustle and bustle and then end with somewhere relaxing, I’d recommend starting with the Amalfi Coast and then heading onto Umbria! As a bonus, you’ll then be near the coast a tiny bit earlier in the season, so hopefully some of the warm weather will hold out for you (and it very well might–we’re in Rome right now, and even though we’re into the second half of October, it’s 80F and sunny out!).

Hi, Thank you for sharing this itinerary – so helpful as we have never travelled to Italy and are planning our first trip later this year. We would also like to visit Pompeii. How long would you spend there and where would you stay to include this stop. Thanks so much

I’m actually working on a Pompeii/Mount Vesuvius guide that should be published sometime this month, so be sure to check back for more detail, but here’s the short version–it depends on how much time you have.

If you only have right around 2 weeks in Italy and don’t want to cut any other destinations, you can do Pompeii as a day trip from Rome. However, the only way to feasibly do that well (especially on a first trip to Italy) is to book an all-day tour, and it’s about 6 hours of driving roundtrip.

Alternatively, you can stay in Naples and visit independently. Naples feels very different from the rest of this Italy itinerary, which focuses on north and central Italy instead of the south of the country, but it is a lovely city with some fascinating things to do, the world’s best pizza, and easy access to Pompeii. It’s considered “dirty” by many, but it doesn’t personally bother us a bit, and we don’t think time there is wasted.

For Pompeii itself, you really only need one day, and with some solid planning, a base in Naples, and an alarm clock, you can squeeze in a visit to the crater of Mount Vesuvius or Herculaneum that day as well.

If you wanted to visit via Naples and keep most of this itinerary structure, add on a stop after Rome. You could then double back to Cinque Terre or simply swap Cinque Terre for the Amalfi Coast, which is very close to Pompeii and Naples, before heading up to Florence + Venice.

Hi. I am visiting Italy in April and would like to go to the Dolomites. I will be staying at Peschiera del Garda for 5 nights. Will I be able to visit the Dolomites from this place? Will Dolomites be accessible in early May?

We haven’t been to Peschiera del Garda, but there are plenty of day trips to the Dolomites sold that leave from there, so you should be safe. 🙂 The Dolomites are pretty accessible–depending on altitude you may still see some snow in early May and certainly some colder temperatures, but you should be able to access the mountains to experience some beautiful views (I’m assuming you’re not planning on doing any intense hiking since you’re basing yourself near Lake Como).

Hi! I am trying to plan a trip to Italy for May. We want to go to Venice, but have also heard that there are new laws for tourists and how expensive it is during this time of year. I know it is so overly visited by tourists, and just wanted to ask you if you think it is worth it. It would be at the end of our trip, and only 2 days. If not, we may stay south. Thanks!

It’s an interesting question, Hannah. We’ve personally only visited Venice in the late fall, so we haven’t experienced the summer crowds ourselves–but we know they are intense.

If you have always wanted to see Venice, I do think it’s worth it–no matter how many cities call themselves “the Venice of X place”, there truly is only one Venice. It’s an incredibly unique and beautiful city.

However, you will definitely pay for the privilege–it’s expensive, and there will be crowds in May, especially if you go toward the end of the month.

I’d recommend pricing out hotels and activities for your dates, adding up the estimated cost, and asking if you think that number–including the cost of getting to/from Venice–is justified based on how much you want to see it.

If you don’t mind crowds, have always wanted to see the city, and don’t mind the cost (much)–go.

If you’d prefer to visit somewhere less congested and Venice is somewhere you’re considering visiting just because it’s an obvious choice and not because you’re excited to see it specifically, look at staying further south.

This is WONDERFUL! My fiance and I are planning a two week trip to Italy from the States. Any chance you have a rough estimate on how much to budget for all of this? Thanks so much!

Thank you, Marissa! Plane tickets will be incredibly dependent on where you are flying from in the USA–Las Vegas, Orlando, NYC, Chicago, Atlanta, and sometimes Boston are all places to check for budget airline flights if you’re looking to save cash and those are an option for you. To help with budgeting on the ground, we put together this post: https://www.ourescapeclause.com/trip-to-italy-cost/

Hopefully that helps give you a general idea!

That’s a really informative article Kate!

I need some advice from you. I am planning to visit Italy on my honeymoon in late November. I know it’s not an ideal season for sightseeing and getting around, but would you recommend including Catania or Malta in the itinerary during that time of the year? With some quick research I noted that these locations offer warmer weather, but I never saw these places covered in any itineraries available online. Would you be aware of any reason for that?

Thanks in advance!

Late November will really be too late in the year for any swimming, but Sicily and Malta will still be beautiful.

Catania is not generally considered to be a great place to sightsee in Sicily–Taormina, Siracusa, and even Palermo are all more popular. We skipped Catania ourselves for this reason, so I can’t offer any personal advice there. We did love Palermo, which is Sicily’s other major airport hub.

The best way to find itineraries for Malta would be to search for those itineraries alone–it’s not usually combined with Italy (not sure if that’s what you were searching?). It is a lovely place, and if you’re content to sightsee on land and skip some of the more summery activities, I think a November trip could be fun.

Other than weather, etc, if you want to include either Catania or Malta in your trip, the other two things I’d check on are flights (many budget flights to/from beach destinations are seasonal and won’t be running in November), and for Malta, whether anything you want to do is closed for the season.

Also, I’m not sure if you’re looking for a particular kind of trip, but depending on how late in November you go, you may be able to check out some Christmas markets in Italy and/or Malta, so keep an eye out for those!

Congratulations on your marriage–hope you have a wonderful trip!

Great article thank you so much! We just really don’t have interest in Venice (I know it’s weird) but would you suggest we could easily sub in Milan/Como for Venice?

You can! Milan and Venice can be reached in roughly the same amount of time from Florence, give or take depending on your train route. If you’re looking for other places in northern Italy to consider, you might like to take a look at Verona or Bologna as well. 🙂

This is a great and detailed article to aid in starting up creating one’s itinerary! I doubt 2 weeks would be even close to being enough if I wanted to see most of Italy in one go, especially since I am dying to see Milan, Lake Garda and Amalfi Coast!

– Laura

I’ve finally come to the conclusion that no amount of time is enough for Italy! I don’t think we’ll ever be done going back. 🙂 We still need to make it to Lake Garda (and Lake Como, and Lago di Braies, and Lago di Sorapis…) ourselves.

Thank you for the information. Q: If we ignore the time to travel, cost and all other extranal factors. Which is a better place to see Cinque Terre or Amalfi Coast?

Q: What other place in a differnt country in europe can I travel from Italy for a three day trip?

Have a good say!!

For your first question, personally we slightly prefer Cinque Terre, but it really just comes down to personal preference at that point! Both are phenomenal, neither is objectively better.

You can go just about anywhere in Europe for 3 days from Italy, as there are budget flights from all the major cities to just about anywhere on the continent! If you are looking for something geographically close and/or you don’t want to take a plane, Slovenia, Austria, Switzerland, France, etc, are easy to reach from the north, San Marino is accessible from Emilia-Romagna and the surrounding area, and Malta, Spain, and Croatia are accessible by ferry, just to give you a few ideas!

Very engaging and informative read! Enjoyed your blog. In process of planning trip to Italy in mid November. Flying in at Milan and out from Rome. 1N(Night) Milan 3N Dolomites 2N Venice 3N Cinque Terre 3N Florence/Tuscany 2N Rome 2N Naples

Love for mountains and offbeat places (less crowded) places. On a budget trip, depending on public transport.

(1) If you can suggest base location /or (BnB or Hostel) for Dolomites and Naples (2) Any other location, where exploring around would not be straight forward as will be dependent on public transport (3) Is the itinerary good mix of days and routes? If you think by any ways can swap days / location..please do recommend

Thanks so much, Niket! That trip sounds amazing, if a little fast-paced for our tastes. 🙂

For the Dolomites, Cortina d’Ampezzo and Bolzano are two of the “bigger” cities (and I use bigger loosely) that people use for a base. There are plenty of small towns as well, but keep in mind that in November there could be snow, etc, to contend with the higher you go, and public transportation options will be fewer and a bit more complicated.

For Naples, the biggest thing to keep in mind is the hills! The further you stay from Piazza del Plebiscito, the more hills you’ll climb. We stayed in the budget hotel linked in this post on our first visit to Naples and liked it well enough (the nearby escalators to get down the hill definitely helped): https://www.ourescapeclause.com/one-day-in-naples-itinerary/

As for the route, I personally would cut Cinque Terre and/or the Dolomites, as in mid-November the weather isn’t likely to be great and you have a lot of places that you’re covering. I’d be tempted to give over another night to Venice and another two nights to Rome in exchange, but that’s entirely personal preference!

I’d also recommend not counting too much on getting to see a particular hike, etc, in the Dolomites. It’s very likely that it will be cold, rainy, and maybe even snowy by mid-November, though undoubtedly still beautiful!

Thanks for the great ideas and tips. We’re a family of 4 thinking of a 2-week trip to Italy next summer and your itinerary could be a possibility (in reverse, as we’d start in Venice). Can you suggest any good self-catering or apartment rental options for the itinerary? Or trustworthy websites to try? Thank you in advance!

Hi Dee! Depends on what you’re looking for, size of group, etc, but for self-catering apartments we generally book through Booking.com or Airbnb. For villas/large groups, we’ve found excellent properties through VRBO. We highly recommend a country villa for a couple of nights in Tuscany if it fits your group and budget!

Hi Kate, very helpful blog indeed, thanks. I am struggling to work out the perfect itinerary because I need to visit Bologna for business. My plan ( which can be tweaked ) is to fly into ROME March 2 arriving 7 am and fly out March 16 at 11 am. I need to arrive Bologna 11th evening, and leave 14th evening or 15th morning. I can move my dates 1-2 days before or after. I am very keen on Amalfi coast, tuscany ( since i love tuscan wine ); florence, rome and Venice. Cinque terre is captivating in the pics too. I can skip pisa/ lucca. Would love to hear your comments, thanks

Personally, I’d strongly recommend cutting a couple of destinations from your list. While technically you can make it work (especially using day trips), that will be a very exhausting trip and the coastal destinations won’t be at their best in March. At most, I’d pick 3 destinations in addition to Bologna to visit.

You could potentially do something like this, give or take:

Rome Florence + Tuscan countryside (as one stop, you can day trip to the countryside from Florence or visa versa) Bologna 11-14 Venice OR Amalfi Coast with your remaining days (Venice would probably be easier).

That’s my suggestion, but ultimately it’s your call! I’ve certainly squeezed extra destinations I couldn’t bear to leave out before. 🙂

Hi Karen, Thanks for your advice. I will now consider the following, feel free to let me know if this is doable. day 1-3 Venice day 4-7 Florence ( 2 days in city; 1 day trip siena/ san gimignano/ chianti; 1 day trip hiking in cinque terre ) day 8-10 roma day 11-14 bologna for business What do you think? Tony

That sounds very doable and like a great trip!

We are in the planning stages of our 2+ week adventure of Italy. Travel is slated for May of 2021 which will include my wife, 2 daughters and I. We plan to fly into Milan or Venice depending flight tickets. We will rent a car and go for it. We want to drive along the entire coast of Italy with possible multi day stops in some of the bigger cities. Plan to stay in hostels, BnB and occasional hotels. For sure spend a 3 days in Silicy. Thoughts?

Hi Daniel! Sounds like quite the odyssey you guys have planned!

My first thought is that I hope that “+” on the 2+ weeks is pretty flexible if you want to drive the whole coast of Italy! That’s an extremely ambitious plan if you want to stop and see much along the way and also fit in 3 days in Sicily.

If your time frame is set at around 2 weeks in Italy, I’d consider road-tripping one portion of the country (since you mentioned flying into Venice or Milan, maybe driving from there to a few stops in Tuscany and/or Emilia-Romagna/Veneto/Lombardy along the way depending on what you want to see and then flying to Sicily to close out your trip.

If you have your heart set on driving the whole thing, I’d either try to extend your time or accept you’ll spend a lot of time in the car, finding and paying for parking, walking from parking lots into the towns and villages you’re visiting, and generally getting from place to place. Driving in Italy isn’t impossible by a long shot and we’ve done it plenty, but by the time you add in all the logistics, Google maps estimates tend to fall a bit short of how long it actually takes to get to each place!

Your blog is so incredibly helpful, thank you! Planning my 1st trip to Italy with my teen girl who’s graduating. Will us two females traveling alone feel safe? I want to not hassle with buses and need some tour guides, private cars. Etc over buses. I can probably do train but needs to be easy cause I get lost easy LOL. I will need everything bought ahead of time and planned out to the T so I won’t be stressed. I want to go about 20 nights but want to see allot then.

Sorry clicked send before I asked my question LOL. Can you please help me itinerary order. I want to spend 20 nights total. 2 in Rome, 2 in Lake Como, 4 in Florence Tuscany area (please list 2 towns for me to stay in there), 2 in Dolomite area, then 1 night in these places venice, Almfia coast, postitano, sorrento, Vernannza, riomaggiore, portofino, bolzano, and Bari. Am I missing any must see places? Is this doable? Also one last place is I want to see at least one place in Croatia. I don’t know which is better dubernick or split and how to fit it in? Maybe fly out of there? Help please thanks so much!

Hi Becky! Sounds like some amazing destinations you have on your list!

In Tuscany, if you want to stay in two places I’d personally probably do Florence + Siena or Lucca if you don’t want to drive, or Florence + a country house/apartment near Montepulciano or Siena if you do plan to drive!

Your wish list sounds amazing but honestly, with 20 nights that’s probably going to be a bit too much. I’d probably cut Bari altogether, and choose two coastal destinations max (Amalfi Coast area with Positano/Sorrento, or Cinque Terre with Riomaggiore/Vernazza, or Portofino, or Croatia).

For choosing between Split and Dubrovnik if you do decide to do Croatia, we have a whole post on that–search “Split or Dubrovnik” in the top righthand corner of the site and it’ll come up. 🙂

I haven’t personally taken a whole trip in Italy alone, but I have many friends who travel solo as women in Italy and love it, and I’ve never had any big problems going out alone, etc. Italy is very used to tourists and generally feels very safe to travel.

Hope that you guys have a wonderful trip, and happy graduation to your daughter!

Hello – planning to go in January for 30th bday. How do you feel about this choice of month?

Thanks, Haylee

It all depends on what you’re looking for!

You’ll need a coat, and gray/rainy days are worth preparing for, but on the other hand, prices will be lower (in a normal year, who knows what will happen this year), the crowds MUCH lighter, and all the sights still beautiful.

We sure wouldn’t turn down a January trip to Italy!

Thanks Kate Storm , Your article is so incredibly helpful. Verona, Liguria, Sicily, Abruzzo, Milan the best places you can live in Italy. I like u r article.

Thank you for your very informative article.I am interested in staying in Puglia.Could you recommend a small authentic village on the coast with access to public transport.What would your ideal itinerary for the Puglia region be.Thanks again

Hi Frances! Sadly our planned 2020 trip to Puglia got cancelled, so I can’t offer any personal recommendations there yet. Hope that changes soon!

Kate, I can’t get enough of your articles!! We are a family of 4 (2 teen boys), traveling to Italy for the first time! We will be flying into Venice the morning of June 2 2022 and out of Rome June 16. I would love your opinion on our proposed itinerary- trying to keep everyone happy and see a lot without cramming in too much! We will likely be hitting the “high points” when it comes to museums and churches. Right now, we’re looking at… 2-6 Venice 6-8 Cinque Terre 8-11 Tuscany/Florence 11-15 Rome 16 fly home Would you allocate it any differently traveling with two teen boys (14 and 17)? And/or add in any day trips? Thank you so much!

Aw, thank you for making my day, Rachel! Truly my favorite part of my job is knowing I help people plan their trips. 🙂

Your itinerary looks great! I’d consider moving one day from Venice (I adore it, but it’s a small city) to either Cinque Terre or to Florence/Tuscany.

A second full day in Cinque Terre would allow you to either spend some time at the beach or hike more, while an additional day in Florence/Tuscany would give you a chance to spend 2 full days in Florence (here’s our suggested itinerary for that: https://www.ourescapeclause.com/2-days-in-florence-itinerary/ ) as well as take a day trip out to the countryside.

There are some wonderful day trip options from Rome that you may want to look into since you have 4 full days there (here’s a post: https://www.ourescapeclause.com/best-day-trips-from-rome-italy/ ) but you can easily keep yourselves busy in the city as well!

Hope you guys have an amazing time! June is a beautiful month to be in Italy. 🙂

Hello, We are planning to travel to a Italy for 3 weeks (the end of March – beginning of April). Do you have any extra insight for traveling with children? Ages: 13 yrs, 8 yrs, 1yr old. I want an easy, mellow trip but still want to hit the major sights. What should we add or take away from your itinerary?

Hi! Unfortunately, we don’t have any experience traveling in Italy with children that young, but generally speaking, the itinerary should work as long as you’re willing to cut down the number of activities in each destination (so fewer museums, basically). I’d definitely recommend skip-the-line tickets everywhere you go! I know that Rome has a popular children’s museum, as well, and several of the popular hikes in Cinque Terre are doable with your 8 and 13-year-old.

Your blog is amazing, Kate! I am booking a surprise trip for my partner and we are set to visit Italy for 14 days in April 2022. He is a huge history and art buff, I am definitely planning on including Rome, Florence/Tuscany and Venice from your 2 week itinerary. In your opinion would adding in Naples in place of Cinque Terre be stretching it too thin?

Thanks in Advance! Dani

Thanks so much, Dani!

A surprise trip to Italy–that’s one lucky partner you have! LOL.

Yes, you can absolutely swap Naples for Cinque Terre, and I’m sure an art/history buff would love it. A fast train (not regional train) from Rome will probably be your most efficient way of getting there.

Fair warning, since I’m not sure of your travel style, Naples is definitely a bit less manicured than the other cities on your list. I adore it and highly recommend a visit, but just got in expecting a bit more grit (and the best pizza of your life).

Day trips to Pompeii, Herculaneum, and the Amalfi Coast are very doable from Naples as well.

Amazing post! I have always been fascinated by Italy and its historic colosseum. However, I never got a chance to visit there due to my hectic work schedule and other commitments. But, I will be getting some time off during Christmas. And while I was looking for an interesting travel itinerary, I stumbled upon your blog. It does give me some amazing suggestions that will help me to experience the best that Italy has to offer.

Hello…we are looking to go in 2023 to Italy and were considering this itinerary…We need to make sure we are in Florence/Tuscany on June 18…Is this a bit agressive? Would you consider something different and what is the best way to get around…Car or Train? You also noted day trips from these different places…would Naples be one?

Travel to Venice 1 Venice 2 Venice 3 Travel to Lake Como to Milan 4 Milan 5 Travel to Cinque Terre 6 Cinque Terre 7 Cinque Terre 8 Cinque Terre 9 Travel to Florence 10 Florence/Tuscany 11 Florence/Tuscany 12 Florence/Tuscany 13 Travel to Rome 14 Rome 15 Rome 16 Rome 17 Travel Home 18

That looks like a wonderful itinerary, and very reasonable for the most part!

The only exception is that you have “travel to Lake Como to Milan” in one day… doing a quick stopover at Lake Como would be difficult, I’d choose either Lake Como or Milan to visit.

You may also want to move one day from Cinque Terre to either Tuscany or Milan/Lake Como, but that’s a personal preference.

You can easily use the train for all of these places except possibly some of the smaller Tuscan towns, if you plan to visit them. For that, you could either rent a car for a couple of days or book a day tour!

For Naples, you can take a day trip from Rome, but it’s fairly long. If you plan to visit Pompeii and/or the Amalfi Coast as part of that, plan for a VERY long day and absolutely book a tour! We have a very reputable one listed in our Rome day trips guide: https://www.ourescapeclause.com/best-day-trips-from-rome-italy/

Hi! Thank you for sharing this wonderful itinerary. We are leaving San Francisco 5/25 and arriving in Rome on May on 5/26 and flying out of Venice on 6/9. I’m hoping we are getting in and out just before the big summer rush and heat! We were considering adding one extra day in Rome and I was wondering what the logic is for going to C/T before Florence? On the map it appears going Rome/Florence/CT/Venice might make the most sense, but I’m sure there is a reason I am not seeing. Would also love to hear your recommendations for the three full days in Florence for a family of 4 including a 15 and 18 year old! Thanks!

That’s an excellent time to be in Italy, you guys are going to have an incredible time. 🙂

The logic for going to Cinque Terre before Florence is two-fold. First, if you travel by train instead of by car (which I highly recommend for this itinerary), you can travel from Rome to Cinque Terre along the coast without switching trains, and you won’t go through Florence or need to double back at all. You’ll also have some beautiful views of the coast along the way!

The second is simply to break up what you’re seeing on the trip. While Florence and Rome are two very different cities, they’re the most similar of the 4 destinations on this itinerary, and going to Cinque Terre in between them gives you an opportunity to mix things up instead of condensing more art museums/churches/cobblestone streets (all things I adore, just to be clear!) into one portion of the trip and risk getting burned out.

For the 3 days in Florence, I would recommend more-or-less following our 2 day Florence itinerary (which I’m going to be updating with a bit more detail in the next few weeks, as we just got back from our latest trip!), and then taking a day trip into the Tuscan countryside with the 3rd day, whether that’s by booking a tour or going independently.

Here’s the itinerary: https://www.ourescapeclause.com/2-days-in-florence-itinerary/

For day trips, many popular tours include Siena, a small town like San Gimignano, and a winery visit. If you’d like something a bit different due to having teens with you, other options include Lucca (you can also add a stop in Pisa if you like), Volterra, Arezzo, Bologna… the sky is the limit! We have a full guide to day trips from Florence here: https://www.ourescapeclause.com/best-day-trips-from-florence-italy/

Hello! I am so happy I found your blog! Such great hints and tips for each of the areas you are recommending. We are heading to Italy for a wedding in Volterra. Flying into Florence and renting a car. After the wedding we are staying and for a week and ultimately ending up in Milan. What are your thoughts on breaking up the trip? Some of the places of interest from your blogs: Livorno, Pisa, Lucca, Cinque Terre (?), Rapallo or a beach, Genoa (?), Milan, Lake Como

I feel like we definitely have too many places we want to see be for such a short time. Would love your input, given we will have a car. 4 adults

Thank you so much! Back to google!

What a beautiful place for a wedding! Volterra is incredible (here’s our post on the town if you haven’t seen it: https://www.ourescapeclause.com/volterra-italy/ )

As for where to go the week after the wedding, you’re right that your dream list is a bit long, but which areas you pick are totally up to you!

Personally, I’d recommend doing either Lucca + Pisa + Cinque Terre or Milan + Lake Como + *maybe* one other Tuscan town/city before leaving the area after the wedding.

Lucca makes a great base in Tuscany (here’s our post: https://www.ourescapeclause.com/things-to-do-in-lucca-italy/ ) and also has the benefit of being within a quick ride of Pisa for a day trip. You can realisitically day trip to Cinque Terre from Lucca more easily than from Florence, too, or move to the beach and stay a couple of days.

I love that area, so that’s what I would do if it were my trip. 🙂

However, Lombardy is also stunning! In addition to Milan and Lake Como, with a full week you could also add a visit to Verona, Bergamo, or even Venice. However, I’d be tempted to split the difference and do about 2 days in Milan, 2-3 days in the Como area, and stay in Tuscany after the wedding to explore a different Tuscan city before heading to Lombardy.

Hope that helps! You have the benefit of your wish list being pretty well grouped geographically, which gives you more flexibility. 🙂

Hello! Wow your blog is so incredibly helpful. My husband and I are planning a ~2 week trip to Italy at the end of July/early August (I know… it’s soon!), and we’re looking at doing basically this itinerary. I’m curious though – this is a 14 day itinerary but I believe only 9 days are accounted for in your post. 2 days in Rome, 2 days in Cinque Terre, 3 days in Florence/Tuscany, and lastly 2 days in Venice. Is that right? Am I missing something? My husband is really interested in seeing the Dolomites. Is that something you think we could throw in there with that 9 day itinerary? Thanks so much! Really appreciated your recommendations.

Yes, it’s because the way I laid out this itinerary doesn’t include the days you’re actually traveling between destinations, these are the full days you’re in each area. 🙂 I know it’s a bit confusing, which is why I switched to a day-by-day layout on future itineraries!

It would be hard to squeeze the Dolomites (or any 5th destination) into a 2-week trip without being extremely rushed, especially because the Dolomites really need more than a day. If he has his heart set on seeing them, I’d consider swapping one of these destinations for the mountains!

Fantastic descovery is your site as Ive just decided last minute to go to Italy. Im under a particular schedule going there since Im going for 6 weeks but two of those will have to be remote work. So after two weeks of travel one week of remote work. Have 100 questions for you but if there would be just one, what would be the places you would stop for about a week,considering most my days will be working.

for sure will have more questions for you as I was thinking of using one of those week to go travel in a near by country etc.

Ah, that’s a delightful problem to have but a very hard question to answer!

Really, any city or reasonably-sized town that appeals to you is a great option. If you need to use video or send large files, I’d opt for a city and keep an eye on wifi speeds. If you don’t need particularly fast wifi, just about anywhere (other than perhaps some very rural places) will do.

We’ve worked for a month at a time from Rome, Florence, and Bologna, and for a week from many, many places including Naples, Palermo, Otranto, Verona, Venice… basically, the sky is the limit!

Personally, we find quiet neighborhoods in medium-to-large cities generally excellent to work from–plenty of convenience and infrastructure, as well as lots to see on your times off.

I just found your blog today & I’m actually obsessed with all the info you’ve posted! I’m trying to jump start my exploration of the world with my boyfriend so I’m currently trying to plan our Italy trip for 2024! It will be both of our first times & I’ve just been hooked onto reading this 2 week guide… I wanted to ask though as first timers, what would the best itinerary breakdown of each city be for us? As far as how many days in each city & what to do in order to check it off our first timer list? Also if you had to choose between Sept/October to travel to Italy which one would you choose?! I love love love this blog of yours & will continue to reach for it as I plan future trips for my boyfriend & I! (:

Thank you so much, Tori!

The itinerary here, as written, is great for first-timers, but where you start and finish can be swapped depending on whether Rome or Venice is easiest to fly in and out of based on where you’re coming from.

September and October are two of my absolute favorite months to visit Italy, so it’s hard to choose!

September will be warmer and a bit more crowded, and depending on the year and which week in September you may even enjoy some late-summer style weather. That’s great for visiting places like Cinque Terre.

October is cooler, with a higher risk of rain (especially later in the month), but the food is delicious, many of the harvests start, there are fewer crowds, and many perfect weather days. I often say Tuscany is the perfect October destination.

You really can’t go wrong with either month!

Hi Kate, So happy I stumbled upon your blog – most helpful of everything I’ve found online so far! Would love guidance on planning our trip for March 11-25, 2023. This will be the first time in Italy for my husband and near-adult kids – ages 16 and 18. I was in Rome, Florence, Siena and San Gimignano for about ten days, 25yrs ago and have been dreaming of going back ever since!!

The challenge is that we have to spend about 3 days in Paris as part of this 2-wk trip, and i don’t know how best to organize that. I’d like to go to Rome and Florence for sure; everything else is open. We’ll be flying to/from Florida and don’t know if we should go to Paris first, last… or if it’s just unrealistic to try to do all of it. Maybe we should do 5 days in Paris and the rest in just Rome and Florence? Also, ideally, we’d be in Paris for all or part of a weekend, which makes it even more challenging! (Meeting French cousins there and they have to work during the week.)

Here’s a bit about us: we have lots of energy and are willing to get up early and stay out late and take trains and planes at odd times :). We’re good travelers and are flexible, and yet this shouldn’t be a wild ride – it should have an easy pace but be full of sights, sounds, tastes, and discovery. Cities and small quaint charming towns are superb; we can probably skip coastal towns on this trip since we live near the beach in FL 🙂 If you disagree, do speak up! Happy to take trains and walk a lot, and use the discounted airline you mentioned, as long as it’s safe (!).

I haven’t looked at the rest of your blogs yet; wondering if you also have recs for olive oil and/or a balsamic tastings/tours and if there’s a guide or an app for being gluten free in Italy!

Thanks SO much in advance for any advice you can offer! Much appreciated!

Happy to help! You guys seem to be the perfect candidates for a busy trip, which is a great thing. 🙂

If you want to squeeze it all in, I’d recommend either starting in Paris or ending in Rome, or vice versa. If you can find good open-jaw tickets to these cities, your plan is ambitious but doable.

Assuming you start in Paris, I’d plan about 3-4 days there.

Your long travel day will be between Paris and Florence–you can either fly, or take a high-speed train to Milan followed by one to Florence (book early to ensure the best prices and direct routes). Both will be a long day, but the train is more fun. 🙂 We use Omio to plan our long train routes.

In Florence/Tuscany, you can allot 5-6 days. I’d plan to spend at least 2 full days in the city, and then more in smaller towns. You can either take day trips from Florence (by train, car, or tour), or head to southern Tuscany for a few days.

Southern Tuscany is where you’ll find the Val d’Orcia, as well as gorgeous towns like Montepulciano: https://www.ourescapeclause.com/things-to-do-in-montepulciano-italy/

If you want to take a day trip to Florence but are looking for a different (but still convenient) home base, Siena (as you know) and/or Lucca are amazing cities: https://www.ourescapeclause.com/things-to-do-in-lucca-italy/

From there, you can wrap up with a few days in Rome, which will give you time to see the major sites. We have lots of Rome posts, but here’s an example of what you can see with 2 days there: https://www.ourescapeclause.com/2-days-in-rome-itinerary/

Olive oil tours will be at their peak in the late fall (when the harvest is), so it doesn’t overlap with your trip. Traditional balsamic vinegar hails from Modena, which is out of the way for you. However–a good enoteca will be able to offer you delicious tastings of both, and you’ll find those all across Italy (you’ll be spoiled for choice in Tuscany in particular).

As far as being gluten-free goes, that is not my area of expertise, but I can recommend checking out the guides and translation cards from Jodi at Legal Nomads–she’s a longtime foodie and travel writer who has traveled the world with celiac.

Have an amazing trip!

Hi Kate, I am planning for the first ever european trip for my wife (40) and son (14). I have travelled in other countries of europe for business purpose. I have decided for a two weeks trip to Italy in 2nd half of May 2023. The following is a very very high level itinerary. I am yet to drill down. I have 13 full days. Day 1 – Arrival in Rome @ 2 pm. Take a walk in the evening. Day 2 – Colosseum, Roman Forum etc. Day 3 – Vatican City Day 4 – Travel to Florence Day 5 – Florence Day 6 – Florence Day 7 – Florence Day 8 – Cinque Terre Day 9 – Cinque Terre Day 10 – Cinque Terre/Camogli??? Day 11 – Travel to Venice Day 12 – Venice Day 13 – Venice Day 14 – Venice Day 15 – Travel to Rome and take a departure flight @ 4pm

I am not sure if I should cut down somethings and include any other spots. Can you please review the itinerary and suggest amendments?

Sounds like the workings of a great trip!

I’d consider moving one of your Florence days to Rome unless you’re planning to use the third day in Florence to take a day trip to the Tuscan countryside/smaller towns. You could also move your third day in Venice to Rome instead. Rome is definitely the biggest city of what’s on your list!

If you want to see the Riviera beyond Cinque Terre, I’d look into Portovenere–it’s sometimes called the “sixth town” of Cinque Terre, is easily accessible by ferry, and is much less crowded due to being a bit harder to access than the others.

I’d recommend booking your trains from Cinque Terre to Venice and Venice to Rome well in advance, as you’ll definitely want to take the high-speed trains for those routes.

Hope you have a fantastic first trip to Italy!

Thanks Kate for such a quick response! After doing some more research, I changed the sequence of the travel so that it is easier to fly out of Rome. Some people suggest to remove CT and increase the days for other 3 big cities. I am confused. 🙂 What do you suggest? Day 1 – Fly in to Rome @ 2pm. Travel to Venice by train. Day 2,3 – Venice (Yet to plan detailed itinerary) Day 4 – Travel to Florence Day 5,6,7 – Florence and nearby areas (Yet to plan detailed itinerary) Day 8 – Travel to Cinque Terre Day 9,10,11 – Cinque Terre (Yet to plan detailed itinerary) Day 12 – Travel to Rome Day 13, 14 – Rome ( 1 day colosseum etc. and 1 day vatican city) Day 15 – Travel back from Rome to India

I definitely agree that it’s a good idea to move some of your Cinque Terre time to Rome!

While you definitely can enjoy 3 full days in Cinque Terre, with your schedule, 1-2 is plenty. Better to have another day in the Eternal City. 🙂

Hi, Kate: We are traveling to Italy in May and June. Your site has been invaluable in our planning. My first of what I’m sure will be many questions is what train stations in Venice (to travel to Florence) and Florence (to travel to Rome) do we want to use? We are staying as close to the center of those cities as possible.

Hi Elizabeth,

I’m so glad to hear that!

In Venice, you’ll want to use Venezia Santa Lucia (which is right on the Grand Canal).

For Florence (both to and from), you’ll want Firenze Santa Maria Novella (which is a 10-minute walk from the Duomo).

Those are the “main” train stations in each city, so most ticket-booking options should suggest them to you automatically!

I have never been to Italy but am going in July so found your blog really helpful! My daughter will be doing an abroad program in Siena so I will fly over with her 12 days early. Is it a stretch to want to visit Rome, Florence, Cinque Terre, Venice and Lake Como within this time frame when she has to be in Florence on day 12? It would mean flying to Rome and going north from there to hit everything but would have to circle back to Siena. I’d love your two cents on where to fly into- thinking maybe even Switzerland since wanting to see Lake Como. Thank you!

Your daughter is going to have such a wonderful time!

All of the places you mentioned are fantastic, but yes, that’s really too much to fit into 12 days (since you mention your daughter needs to be in Florence on day 12, I’m assuming this is more or less an 11 day trip).

If it were me, I’d focus on Venice, Rome, and Florence.

Flying into Venice would probably be most convenient, though Rome would work as well.

Taking the high-speed train from Venice to Rome (you’ll want to book those tickets in advance) and then traveling from Rome to Florence by train after sightseeing down south will likely make the most sense.

As far as Cinque Terre goes, a day trip from Florence to Cinque Terre isn’t ideal, but it can be done and in your case may be a way to squeeze in a taste of the coast. We go into more detail on how to do that well here: https://www.ourescapeclause.com/florence-to-cinque-terre/

I hope that helps a bit and that you guys have a magnificent time in Italy!

HI Kate! your blog was very helpful. I would love to have your opinion on my upcoming trip. I am taking a transatlantic cruise from NYC to Rome; arriving in Civitavecchia on 10 May 2024. I am lucky and don’t have a time frame. Since Italians take their time… I’m going to embrace that after years of a stressful job, I’m traveling solo as at 37. I want to be loose with my plans, do you think buying tickets for places like the Colosseum just a few days in advance is risky? I was planning on my travel day to purchase tickets for those things. I also have a general route planned and I would love your opinion one this. Since I disembark in Civitavecchia I was going to spend 4 nights in Rome (this is the only things I have booked). -4 night in Rome -2/3 nights in Naples/ Amalfi Coast (I also would like to go further south but not sure where.) -Travel Day to Florence I might stay a night in Assisi or Siena -3/4 nights in Florence with a day trip to Pisa and Lucca -2 nights in Cinque Terre -I think I should go to Genoa or Milan after – I also want to spend a night in the Tuscan country side (Under the Tuscan Sun like) -1 night in Bologna -1 night in Bolozno/ Ortisei for the Seceda -2 nights in Venice I would really like to experience some real Italian life and this trip is really a scouting trip for a possible move to Italy.

Sounds like a wonderful trip!

In May, booking a few days in advance for most places (including the Colosseum) should be just fine in mid-May. There are a few attractions in Italy (climbing to the top of the Duomo’s cupola in Florence and visiting The Last Supper in Milan are two of them) that require planning further in advance year-round, but for travelers who are flexible with their plans, most things are doable a few days in advance.

All of the places you have mentioned are wonderful, but I do think you’ll find there are too many of them! Since you’re going to be booking as you go, I’d just stay open to extending your stays and visiting fewer places.

I’m not sure if you have a timeline for your trip, but after weeks of traveling it’s safe to say continuing to change hotels every night to every other night will stop being appealing. Plus, traveling more slowly is one of the biggest benefits of traveling for longer–it’s worth slowing down for.

We are going to Italy in September/October for about 2-3 weeks. Will visit Rome, Florence, Tuscany and Umbria areas. At the end of our trip we would like to visit Assisi, montepulciano , perugia. Our concern is how to get around in those areas. We don’t really want to rent a car but will if that is our only option, what is your suggestion on this?

It’s doable, but takes a bit of finagling!

The train stations for each of those places are outside the city center (1-3 miles away or so), so you’ll need to take a bus or taxi from the train station to the historic center.

I have been reviewing your site for the last few weeks and my fiancé and I have decided on two weeks in Italy. We’re thinking of flying into Rome and flying home from Venice.

We have never taken such a huge trip before and I’m curious if it makes sense to book the flights and have the book ends planned and then start doing booking of the meat of travel afterwards? Or should we have everything planned and booked before we even book the flights?

Hi Jessica!

Personally, we always opt to book the flights first and then fill in the rest of the trip from there. Flight deals and times can impact your starting and ending points, and possibly even shuffle your trip around by a day here or there.

Everything else–with rare exceptions like festivals, very trendy hotels, etc–is much more flexible compared to flights.

Just going over your blog and absorbing everything! I have a trip planned that has us arriving in Milan on April 29th and leaving out of Rome on May 19th so I’m planning on working our way from top to bottom.

Rough plan currently is Milan -> Venice -> Bologna -> Florence -> Cinque Terre? -> Naples -> Amalfi Coast? -> Rome With some day trips mixed in there, most likely to Siena, Pompeii, maybe Lucca/Pisa or somewhere else.

Would you recommend going to Cinque Terre which we would do closer to the start of May or go to Amalfi Coast which would be closer to mid May? Since you mentioned a day trip from Florence to Cinque Terre is not the easiest, would it make sense to go to the Amalfi Coast instead so I don’t have to backtrack through Florence to get down to Rome or Naples? I’m also concerned about the weather as Cinque Terre is more north and it will be earlier in the month vs Amalfi Coast being more south and more mid month.

What would your itinerary look like with roughly 3 weeks that works top to bottom?

For both Cinque Terre and the Amalfi Coast in May, you’ll really be gambling with the weather–it might be gorgeous swimming weather, it might be rainy and chilly (happened to us on our May trip that covered both places a few years ago–you’ll notice I’m wearing long sleeves and jeans in some Cinque Terre photos), or anywhere in between.

Weather aside, since we can’t control that, prices will probably be a bit lower in early May than mid-May, and the Amalfi Coast is the more expensive destination of the two overall–if cost is a factor, that’s something to keep in mind.

If you’re open to trimming Cinque Terre, it will certainly streamline your itinerary by cutting a transition, so I’d consider it if you’re not married to the idea of visiting two coastal destinations.

A few other day trip ideas you might consider if you have time: Parma or Ravenna from Bologna, Lake Como from Milan, and Montepulciano and/or some of the other Tuscan hill towns from Florence.

Your route is very similar to what we’d cover if trying to hit the highlights in 3 weeks, I’d just make sure to cut anywhere that feels like an obligation in order to give more time to the places you’re most excited for (any one of those cities would be an amazing place to spend a week or more).

Happy planning!

Thanks for the info! I’ve done some more research and currently have the following plan

Day 1 – Milan – Arrive late at night Day 2 – Milan – half day and then train to Venice. Half day in Venice Day 3 – Venice – Full Day Day 4 – Venice – Check out of hotel and explore Venice until ready to leave for Bologna. Night in Bologna Day 5 – Day trip to Modena and Parma Day 6 – Check out of hotel. Day in Bologna until ready to leave for Florence Day 7 – Florence – Full day Day 8 – Florence – Full day Day 9 – Florence – Sienna or Pisa/Luca day trip or Chianti wine tour. Day 10 – Florence – Sienna or Pisa/Luca day trip or Chianti wine tour. Day 11 – Train from Florence to Naples or Sorrento and then day trip from Sorrento to Naples. Day 12 -Sorrento – Day trip to Pompeii? Day 13 – Sorrento – Day trip to Capri? Day 14 – Amalfi Coast Day 15 – Amalfi Coast Day 16 – Amalfi Coast Day 17 – Rome half day? Or full day or arrive late night and just have 3 days in rome? Day 18 – Rome Day 19 – Rome Day 20 -Rome Day 21 -Half Day in Rome fly home

I’d like to do a wine tour of the Chianti region but I’m not sure if it’s something I should try to do with a Siena, San gimignano, and Chianti tour or dedicate a full day to it and have Siena/San gimignano as it’s own day. If I dedicate a full day to it I would have to take a day from Bologna, Rome or Amalfi coast. What are your thoughts on this? Do you think we have too much time in the Amalfi coast? I’m thinking of using Sorrento as a base for a few days as I’d like to visit Pompeii, Naples and Capri and then a few days stay possibly in Ravello. Or maybe take Day 17 away from Rome and give it to Florence. That would leave us with 3 and a half days in Rome.

Love to hear all your thoughts on my above plan and what changes you would make or places that you would switch out.

These are the places that I’ve wrote down that I don’t think are worth visiting this trip Assis Lake Como Cinque Terre Padova Vicenza Verona

and these are the places that I’m still thinking about Orvieto Arezzo

Do you think Orvieto or Arezzo are worth swapping out for Siena or Lucca/Pisa.

I’d actually recommend taking any extra time to smooth out the very beginning of the itinerary–day 2 in particular isn’t going to leave a lot of room for sightseeing, in between checking into/out of two hotels, transiting to a new city, etc. Depending on which city interests you more, I’d consider adding a day to either Milan or Venice. As it stands, you probably won’t do more than a few hours of actual sightseeing in Milan–up to you if that’s the pace you’re looking for!

I do think you can get away with 3 full days in Rome–more is always lovely, but 3 is a solid start.

Same with the Amalfi Coast–you can certainly have a wonderful time there with the extra day, but I wouldn’t say you need it. Sorrento is an excellent base and you can easily see a lot of the region from there.

Siena, Orvieto, Arezzo, and Lucca are all wonderful. Pisa is fun, but I wouldn’t call it an absolute must-do unless you’re dying to see the leaning tower–of the five, it’d be the one I’d prioritize least. Other than that, you can’t go wrong with any of them.

As far as whether to visit the Chianti region as an entirely separate day or combine with Siena/San Gimignano, I’d say that depends on how much of a wine fan you are. Personally, we enjoy wine tastings but one in a day (especially the way they pour in Tuscany!) is plenty for us, and we prefer to mix in sightseeing. If you’re visiting Tuscany for wine in particular and are very interested in learning about the various varietals, etc., though, you might consider separating them out.

Thanks so much Kate!

I was not overly interested in Milan other than the Duomo and Galleria Vittorio which is why I was only planning on spending the afternoon there before heading off to Venice. I didn’t want to skip over Milan entirely but I feel like our time is better spent in other locations.

Do you think it makes sense to split our time in Naples and Sorrento? Stay in Naples for say 2 days to explore Naples and Pompeii and then move onto Sorrento for 3 or 4 days to explore Capri and the AC? Or would you recommend sticking in one place the whole time? I have heard there is not as much to do in the town of Sorrento and by not having to do day trips to Naples and Pompeii from Sorrento could save some money on transportation?

Honestly we’re not much wine fans but I thought it was something we should try while we are there. Sounds like mixing all 3 locations into a tour in one day is the way to go!

If you think the time we have in AC is enough without adding more and 3 days in Rome is enough then it looks like I have an extra day to allocate somewhere. I’ll have to do some more thinking on where to place that extra day. Thanks for all your help so far!

Anytime, Edmond!

Sounds like a solid plan for Milan.

Personally I love both Naples and Sorrento, though they’re very different–just depends on what you’re looking for. You can day trip to Pompeii pretty easily from either, so I wouldn’t let that sway your decision. But the pizza, views, archaeological museum, underground, etc, in Naples are well worth your time if you can fit it in!

Great work on the site, it’s been super helpful.

Was wondering if you could gife me your opinion on an issue I am facing. My nieces wedding is in September so we are planning 16 days and wanted your thoughts if this is doable.

We are arriving before the wedding and have to end in Florence.

Arrive Rome – 3 nights Assisi – 1 night Bologna – 2 nights Venice – 3 nights Modena – 2 nights Florence – 5 nights

Would love your thoughts and thanks in advance!

Hi Michael,

Thank you so much!

The first thing that jumps out is that you have Bologna and Modena separated–I would definitely combine those! Modena is only a 15-25 minute train ride or so from Bologna, and virtually every train to it is going to require passing back through Bologna regardless.

Personally, I’d probably base yourself in either Bologna or Modena for one 3 or 4 night period, and take a day trip to the city you’re not staying in. It’ll be much more efficient and if you only stay 3 days, buy you an extra night to add to another city of your choice.

Bologna is the traditional choice for where to stay between those two: it’s bigger, there’s more to do, and as the capital and transportation hub of the Emilia-Romagna region, it’s easy to navigate to and from. However, Modena is beautiful and offers the benefits of being a more affordable and less crowded place to stay.

Other than that, your route looks wonderful and is very doable by train, so navigation should be very convenient. 🙂

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2 Weeks in Italy: 4 itineraries

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As one of the most visited tourist destinations in the world, Italy is home to some of the most breathtaking architectural features you could ever find. Along with gastronomic delights and cultural attractions, you can’t blame tourists as this country moves and inspires like no other. 

There is something to be discovered at every corner that will titillate your senses and fill your belly. Whether you are hungry for natural sights, culinary delights, or all things culture, Italy will not disappoint you.

If you have 2 weeks in Europe and have never been to the ancient country of Italy, well, you have to go. If you love the beach and wineries, you can also spend 14 days in Southern Europe .

That is why it is recommended that you spend at least 2 weeks in Italy to make the most out of your trip. You can also simply cover only a specific region and check out the other parts on your next visit.

THINGS TO KNOW BEFORE VISITING ITALY

Before you get ready for your trip to Italy, there are a few things that you need to know first. One is that taking public transport, such as the metro train, is convenient. The tips below will help you plan your travel to Italy.

ALSO READ: 2 weeks in France – choose between 3 different itineraries

When is the best time to go to Italy

The best time to travel to Italy is in spring (April to June) and fall (September and October). When you travel during these times of the year, you will get to enjoy perfect weather (not too hot or too cold, a little rain here and there). Plus, it is less crowded so you are more likely to find great deals on accommodation and airfare.

You might want to avoid the summer season (June to August) which is the busiest time of the year. During this time, it’s very crowded and prices in Italy that are related to tourism are usually at an all-time high making accommodations much more expensive.

If you want to go skiing and enjoy the Alps, go between December to February. December is also peak season because of the Christmas and New Year holidays.

Are 2 weeks enough for Italy

14 days might be a tight schedule for Italy, but if you decide to f ocus on a specific region or 2-3 cities, it can be a perfect amount of time.

For example, on this trip, visit northern Italy only. That means you can add Turin, Milan, and Genoa to your itinerary, especially if you love nature and history. But for those who are visiting northern Italy for the first time, you can go to Venice, Bologna, and Florence.

In southern Italy, you have Rome, Naples, and Bari or the island of Sicily plus Rome. Trying to see More than 2-3 cities will get your Italy itinerary really cramped and you’d feel like you’re chasing a bus, train, or flight most of the time than relaxing.

Average cost of 14 days in Italy

It’s undeniable that Italy has gotten more expensive in the last few decades. For a mid-range budget, a two-week trip to Italy could cost roughly $2,000-$3,500 per person . This includes staying in standard hotels, eating at mid-range restaurants, using public transportation, and participating in typical tourist activities.

If you’re on a tight budget, you could manage a two-week trip for about $1,000-$1,500 per person . This involves staying in budget accommodations like hostels or budget hotels, eating at inexpensive eateries or self-catering, using public transport, and focusing on free or cheap activities.

For a luxury trip, expect to spend anywhere from $6,000 to $10,000 or more per person for two weeks in Italy. This includes staying in luxury hotels or villas, dining at high-end restaurants, private tours, and premium experiences.

Getting around

Getting around in Italy as a visitor is very easy. Public transportation throughout the country is well-connected , especially the trains . Italy has a speed train which is a lot faster than driving. Although delay on the scheduled trip must be expected. You can also use buses to get from city to city.

Always be on the lookout for the local news. There are times when the train service is shut down due to labour strikes.

Renting a car will be an awesome ide a. You’ll be able to go and stop whenever you want and bus and train delays won’t affect your itinerary. You can also rely on domestic flights, however, only do this if the destination is further than a 6-hour drive.

If the distance is shorter than that, the flight will have to connect somewhere and will take more time. Just remember though, most cars in Italy are in manual transmission. You can reserve an automatic car if you do it in advance .

In the city, you can use city buses. Rome has a tramline that works great for tourists. You can also use taxis and ride-hailing apps. You can install MyTaxi and Uber on your phone to make booking easier. You can get an esim that works everywhere in Europe and has reliable data coverage.

What to pack

What you need to pack if you will be spending 2 weeks in Italy will depend on the season you plan to visit. In general, you’ll want to opt for lightweight and comfortable clothing. Since you will be doing a lot of walking and exploring, it would be easier on your part if you’re comfortable. 

A good pair of walking shoes is also ideal and actually recommended. And don’t forget to bring some form of a scarf to keep yourself covered when you enter churches and other sacred sites.

Due to Italy’s geographical shape, the weather throughout the country can be significantly different. It is also recommended that you research beforehand the climate for the specific region you are travelling to.

You don’t need to pack toiletries if you have limited space in your luggage. You can buy these when you land since most items, such as toothpaste and mouthwash, are heavy. But make sure you bring walking shoes or sandals that you already have broken into to avoid blisters.

We have a packing list for a 2-week trip which comes with a printable checklist that you can use for another trip too. We also have a packing list for a summer trip .

Language and currency

Italy’s official language is Italian. Most road signs are in Italian, and most locals speak this English. However, younger locals speak English and are happy to help especially in bigger cities. But it’s vital that you install a translation app on your phone to make things much easier.

Italy uses the Euro, and the ATMs will dispense this currency. The majority of the country is still a cash-based society. You can pay with your bank card in hotels, restaurants, and grocery stores. But for gas stations, food stalls, and entrance fees in parks – it’s best to use cash.

When you are dining, tipping is not required. But check the bill if it has a service charge included in your plan to give a tip for impeccable service.

Italy is a member of the EU and has the Schengen Area visa policy in place. For those who don’t qualify in a free visa, you must lodge your application in advance.

For US citizens, Canadians, New Zealanders, Australians, Japanese, South Koreans, Malaysians, and some countries in Latin America and the Middle East can travel to Italy without a visa for a maximum of 90 days stay (for both leisure and business travel).

You need to have a passport that is valid for at least 6 months by the end of your intended trip. For those who require a visa, the conditions vary according to your country of origin. 

Other basic travel tips

Pinned map of top things to see in italy.

Click the icon on the top right to enlarge the map. Credit: map data: Google

2 WEEKS IN ITALY ITINERARY

Choosing where to go in Italy seems like an impossible feat. Each destination or city has something unique to offer that makes it worth spending time in.

Notably, you have to consider what kind of attractions you can see. This will enable you to find the right destination that would match your interests or the places you want to explore.

Below are different travel itineraries for Italy if you plan to spend around 14 days. Take a look at which one suits you best. You can also mix and match the cities that you like and create your own travel itinerary .

Itinerary #1: North – Venice, Bologna, Florence, Milan

The north of Italy has so much to offer. From culture to traditions, historical sites to tasty food, and of course, amazing attractions.

This itinerary is great if you have been to Italy before but only got to see one or two cities. This time, you probably can skip Venice and visit Trento instead, skip Milan and go to Genoa or Lake Como.

This region is also a great place to explore, especially if you love history, literature, music, arts, fashion, and food, and even plan to spend a semester here or take your uni at the popular uni city of Bologna (the food capital of Italy) or Pisa.

You will still have to either land in Venice or Milan since most flights, especially international flights will arrive here. You can take a bus, train, or pick up your rental car at the airport to start your exciting trip.

If you’re going to Milan, I highly recommend you take a day trip to Lake Como, Genoa, and Turin. All those places are only less than 2 hours from Miland and offer incredible sights and experiences.

Venice for 3 days

As one of the most coveted tourist destinations in the world, Venice is punctuated by the charm of its ancient canals. It is known by many names, including “The Floating City” and “The City of Canals”. 

Venice is also a UNESCO World Heritage Site known for its architecture, artwork, and natural beauty. It is a sin to go to Italy and skip Venice. 

How to get here : Venice Marco Polo Airport is the main airport in the city. This is where you must fly if you are looking for flights from outside Italy. You can also get to Venice via train or cruise ship.

Bologna for 2 days

Bologna is known for many reasons, one of which is being a university city. Apart from that, this city also has impressive ancient churches and the location of a piano that Mozart used while he was studying in Italy.

Bologna is also the city you want to be in if you’re a foody. It’s the gastronomic capital of Italy, and many popular Italian dishes are hailed from this northern city.

How to get here : From Venice, you can take a 1.5-hour train south, Bolognia being the 4th stop. The service is run by Italo Treno and goes every 30-minutes. If you take the bus , that will take 2.5 hours (run by Flixbus). For those planning to drive, it’s a 1-2 hour journey.

Florence and Pisa for 4 days

As the capital city of the Tuscan region, Florence is one of the most romantic cities in Italy. This is mainly because of the abundance of Renaissance art and architecture .  It is the perfect place to go for those seeking cultural attractions.

You will be in awe of the awe-inspiring creations of Michaelangelo and Brunelleschi.

Four days is plenty of time in Florence . You can use one of the days by planning a day trip to Pisa, which is only an hour away and take a silly photo at the Learning Tower of Pisa.

If it’s been your dream to visit Cinque Terre, it’s only a 2 hours and 30 minutes drive from Florence. There are so many amazing photo spots in Cinque Terre for those into photography and of course, hiking.

How to get here : Florence is south of Bologna. The drive from Bologna to Florence is 1.5 hours, while the train will take about 40 minutes , and the bus is 1.5 hours.

There are two international airports in Tuscany that you can fly into to get to Florence: Galileo Galilei International Airport and Amerigo Vespucci Airport. You can also get to Florence via train from Italy or other parts of Europe. 

Milan for 5 days

As a city known for its “haute couture” image, Milan is showcased in the impressive architectural design in the cityscape. Indeed, the fashion week is held annually in this city, showcasing its style propensity. 

Milan is also considered an alpha global city as it is among the best in the fields of art, education, fashion, finance, design, and tourism. The city highlights include the Gothic Duomo.

How to get here : Milan is northwest of Florence. You can get there by your rented car, and the trip will take about 3-4 hours. There’s also a train which is only a 2-hour trip , and the bus is the longest, 4 hours. There is a direct 2-hour flight, the ticket usually costs $30-$50.

Malpensa Airport is the main hub for air transport to Milan. There are several flights daily from other parts of or outside Italy. There is also a train from Venice or Rome that travel daily to Milan. If the train is not an option, there are also coach services in Milan. 

Day trips from Milan : You have plenty of time in Milan, this means that you can easily take a day trip to many places. The most popular is to head to Lake Como. The other options that are less touristy are Turin and Genoa.

Turin is a less popular city an hour and a half away southwest of Milan. Here, you will see historical sites, and museums, and pretty much be in a metropolitan city that is the gateway to the Alps.

On the other hand, Genoa is a port city, about 2 hours south of Milan. If you have been to Marseille in France, some people would compare Genoa and Marseille and point out their similarities. This city has been a valuable maritime trade route for centuries. You can visit ancient sites, explore piazzas, and sign up for a boat tour.

Itinerary #2: South – Rome, Naples, Sicily

History lovers should definitely do this 2 weeks in Italy itinerary. It’s also perfect if you love the beach and plan to visit during summer to enjoy the famous Mediterranean Sea and the Tyrrhenian Sea.

This travel itinerary for 2 weeks in Italy is slower, giving you ample time to enjoy the trip and soak up the beauty of southern Italy. It’s recommended o book your flight to land in Rome, where you’ll be starting your escapade.

When you land in Rome, you can pick up a rental car at the airport or decide later. It’s much easier to traverse through Rome by foot or bus; it might be smarter to plan using a rented car once you’re ready to leave Rome.

Rome for 3 days

As the capital of Italy, Rome is known for its religion and art.  No visit to Italy would be complete without including Rome in your list of places to go . This is where you will find The Vatican City, the world’s smallest city-state. It is also home to many spectacular ancient ruins, such as the Colosseum and the Pantheon. 

How to get here: There are two major airports in Rome: Ciampino and Fiumicino. There are daily flights direct from major cities in Europe and the US. You can also take the train from other parts of Italy, such as Florence. And many of the visitors that come to Italy do so via a cruise ship. 

Naples for 4 days

Known as the birthplace of pizza, Naples is soul-stirring with its affection for art and undeniable elegance. When you visit the city, don’t forget to sample this famed culinary creation that is now popular all over the world.

Everywhere you look in this city, you’ll land your eye on cultural assets in the form of castles, cathedrals, palaces, and squares. It is bustling with energy and history that makes you feel like you are being transported back in time. 

It’s recommended to plan to stay in Naples for 4-5 days. During this time, not only can you cover Naples but also take a trip to Pompeii, Salerno, Capri, Sorrento, and the stunning Amalfi Coast.

How to get here : A high-speed train travels daily from Rome to Naples. The travel time can take just over an hour. For those planning to drive their own car, the distance between Rome and Naples is a little over 2 hours, and a bus will take 2-3 hours. If you are flying from outside Italy, you must book a flight to Naples Airport.

Catania for 3 days

It’s time to bid the beautiful Naples goodbye and continue your journey to Catania. This southern city is popular for its Baroque architecture and UNESCO status. But it’s popular for being the home to Mount Etna.

Catania is on the island of Sicily – rich in history, culture, and traditions that are very different from the north or even central part of Italy. Although Catania doesn’t get as much love as Palermo, there’s an upside to that. For people who wish to get away from big crowds, but still, learn about Sicilian culture – Catania is the place.

This is also the place you want to go if you don’t care much about the beach and are a hiker enthusiast.

How to get here : There is a great distance between Naples and Catania. A drive will take 7-8 hours and the train journey is 8-9 hours. It’s much better to take a flight which is only an hour flight and costs $20-$30. You can always rent another car once you arrive at Catania Airport.

Palermo for 4 days

Palermo is a metropolitan and busy harbour coastal city on the island of Sicily, and its capital. It’s the most sought-after destination in southern Italy for a good reason. Palermo has lots of historical and ancient sites dating all the way back to the 12th century.

This location has one of the most stunning architecture in the country, while opera performances are a must-do here. For food lovers, you might want to try out seafood, pasta alla norma, arancini, and cannoli.

If you prefer relaxing on the beach, pack your swimsuit and sunscreen, then head to Mondello Beach, Lido Valdesi, Magaggiari Beach, and La Praiola. But for a more serene environment, check out Alcamo Marina Beach during the weekdays.

How to get here: From Catania, it’s a 2 hours and 30 minutes drive, the same as taking the train. The bus is also possible, which will be cheaper, but probably takes 3 hours ro 3 hr and 30 mins.

Itinerary #3: Popular spots – Venice, Florence, Rome, Naples

Italy is such an amazing 2-week holiday destination . It has history, beach, hiking, and of course food. This 2 weeks in Italy itinerary is easily the one for first-time visitors. You’ll get to see and explore the top attractions and cities of the country.

This itinerary is suitable for pretty much everyone as it highlights Italy’s history, magnificent architecture, scenic landscape, and tasty food, which you can wash down with yummy and affordable wine.

With this itinerary, it’s also recommended to rent a car. You won’t have to drive longer than 3-4 hours unless you add stops along the way.

I don’t think Venice really need an introduction. We’ve heard the titles, praise, and every adjective that describes a magical city. Start your Italy trip by landing in Venice, renting out a gondola and visiting its waterway canals.

On land, you can pay a visit to its historical sites and simply admire its beauty. Don’t forget to sit down in one of the street restaurants and order a nice cup of coffee or pick up a delicious gelato.

You shouldn’t have a hard time getting to Venice. If you’re coming all the way from Latin America, Asia, or Africa, you might have to connect in Rome or other major cities in Europe, such as London, Paris, and Amsterdam.

Florence is the home of Renaissance art, architecture, and monuments. The Uffizi Gallery houses the famous “The Birth of Venus” by Sandro Botticelli, “Coronation of the Virgin” by Fra Angelico, and “Laocoon and his Sons” by Baccio Bandinelli.

Known for its iconic Leaning Tower, Pisa is a common day trip from Florence. It is a must-add to your 3-week itinerary in Italy.

It belongs to the region of Tuscany. Pisa is home to more than 20 historic churches, palaces, bridges, and other medieval structures. It is also known as a university town in the Tuscan region. 

How to get there : If you are travelling from within Italy, the train is the fastest way to get to Florence Pisa. It is only a 3-hour drive from Venice to Florence, the train will take 2-3 hours.

Unfortunately, there is no direct flight. In comparison, Pisa is only an hour away from Florence. The Pisa International Airport (also known as Galileo Galilei Airport) is the main airport to fly into to get to Pisa. 

The next destination is the glorious Rome! It’s the capital city of Italy and remains the most visited city in Italy. Spend your days wandering through the ancient yet well-preserved walls of the Colosseum, Pantheon, and Trevi Fountain.

Then find yourself a nice little restaurant or pick up a slice of pizza on the street and enjoy Rome’s unique atmosphere.

How to get here : Rome is only 1 hour and a 30-minute high-speed train ride from Florence. The drive will take 3 hours, and a direct flight is not available.

Naples is the lovely and ideal place to finish your 2 weeks in Italy trip. It’s located in the most admirable coastal region of the country. Have you heard of the names Capri, Amalfi Coast and Sorrento? These two small towns are Italy’s pride when it comes to splendid and romantic beaches.

Apart from Naples’ excellent beaches, it’s also a great location for hiking, which you don’t get the chance to do in the other Italian cities you have been to. The best hikes you can do in Naples are Punta Campanella, Pineta di San Costanzo, and of course, Vesuvio National Park.

How to get here : Driving from Rome to Naples will take a bit over 2 hours up to 2 hours and 30 minutes. The train will take a bit over an hour. Again, there are no direct flights between these two cities.

Naples is a very popular city in Italy. Finding a flight from here, either back home or to your next destination, should not be too hard. You can also easily fly from here to major European cities where intercontinental flights are available.

Itinerary #4: Away from tourists – Florence, Rimini, San Marino, Pescara, Viste

This final itinerary for 14 days in Italy is suitable for people who want to get away from tourists and most likely have been to Italy before. This travel plan highlights equally beautiful destinations and is worth exploring as other parts of the country.

You will get to visit cathedrals, archaeological sites, historical landmarks, beaches, vineyards, enjoy hiking, and do a day trip to San Marino. It is an independent country in the middle of Italy located in the northeast of the country.

I highly recommend renting a car for this travel plan since public transportation between less-touristic destinations can be unreliable.

Florence for 2-3 days

You will still have to arrive in a big city since these are the ones serviced by international airlines. You can either land in Florence or Rome, spend a few days gathering yourself, get local currency, and plan how to get to your next destination.

1-2 days would be ideal, especially if you are doing an intercontinental flight and want to catch up with sleep or arrange a rented car.

If you’ve never been to Florence, this city will surprise you in many ways. You can do incredible hikes around Florence, such as Palazzo Vecchio – Santa Croce Loop, Via Degli Dei, and Parco del Mensola. You can also simply walk downtown, explore quaint Italian alleys, and visit local markets.

Rimini and San Marino for 4 days

Rimini is situated in the Emilia-Romagna region, east of Florence. It’s a coastal city facing the Adriatic Sea. The beaches of Rimini are less busy than the ones in Naples. You can easily find a nice spot and just relax.

This place also has pretty interesting historical sites, such as the 15th-century Malatestiano Temple, located south of the city.

4 days is plenty, meaning you can afford a day trip and visit San Marino. It is an independent state that is landlocked in Italy. Wander through its city centre (San Marino), which is covered in cobbled stones and surrounded by traditional houses giving such a Medieval atmosphere.

This country is a favourite for professional cyclists due to its hilly roads and lack of flat ground. Many professional cyclists live here but also use this as an awesome training spot; it’s the equivalent of the country Andorra which is located on the border between France and Spain.

How to get here : Rimini is 237 km (147 miles) east of Florence, about a 2-3 hour drive; the train or bus will take about the same time. but you will be required to change carriage or bus in Bologna.

Pescara/Abruzzo for 3 days

Pescara is a nice and calming coast directly east of Rome, south of Rimini. It’s part of the magnificent region of Abruzzo. This region boasts rich vineyards, a church located on the hill that overviews snow-capped mountains, and a fantastic food culture.

Abruzzo produces olive oil, pasta sauce, pasta, and yummy jams. If you’re coming in summer, you might catch a food festival filled with local produce and artisan products.

There are also plenty of hike opportunities around Abruzzo, where you can visit ancient ruins, and beautiful national parks, and explore the walled city of L’Aquila, which was damaged in 2009 due to the earthquake.

How to get here: Pescara is 250 km (160 miles) south of Rimini. The drive will take about 2.5 hours, the same as the train.

Vieste for 4 days

To finish off your 2 weeks in Italy, you will be doing lots of hiking that are not too known to international visitors. You will get to hike, swim, and enjoy authentic Italian dishes for 4 glorious days. You will also visit a museum that displays unique shells and marine fossils downtown.

Gargano National Park is a wetland region with awe-inspiring valleys. It’s also located along the coast adding such a dramatic and stunning view of the Adriatic Sea. I recommend you base yourself at Vieste, a beach town and the most eastern point of the region and the location of the monolith reef of Pizzomunno.

But remember, during peak season, this area can still be busy due to local visitors and an influx of international tourists. But if you visit at the end of summer or just before it starts, you will be able to find tranquillity – an ideal way to end your trip.

How to get here : The distance between Pescara and Vieste is around 227 km (141 miles). The journey by car will take 3 hours; if you take the bus, it will be around 5-6 hours. Unfortunately, there are no train lines here.

THINGS TO SEE AND DO IN ITALY

Next is a list of the top attractions and sites you must visit in Italy. It’s arranged by the city to help your planning.

• Explore the city centre – do a walking tour or a guided e-bike tour
• Piazza Maggiore
• Torre degli Asinelli – get an entrance ticket and food tasting option
• Fountain of Neptune
• Sanctuary of the Madonna di San Luca
• Basilica di San Petronio
• Basilica of San Domenico
• Ferrari Lamborghini – visit the factory and museums
• Palazzo d’Accursio
• Pinacoteca Nazionale
• Certosa di Bologna
• It’s the food capital; don’t miss food tours such as home cooking class or self-guided food tasting or visit a Bologna food factory or do a walking food tour or a classic food tour with a local or Emilia Romagna food tour
• Castello Ursino
• Day trip to Sicily – and see The Godfather filming locations
• Villa Bellini/Chiosco Bellini
• Go on a sailing trip – read the tour reviews or Cyclops cruise and snorkelling
• Cattedrale di Sant’Agata
• Winery tour – 6-hour wine and food tasting or Mount Eta with wine and Alcantara tour
• Teatro Amssimo Bellini
• Food tour – do a cooking class
• Fountain of the Elephant
• Mount Etna – explore with 4×4 or do a morning Etna trip or Mount Etna and Taormina Village or Etna sunset tour or Mount Etna summit hike with cable car
• Riserva Naturale Oasi del Simeto
• Day trip to Syracuse – including Noto Culture tour
• Uffizi Gallery – buy an affordable skip-the-line tour in advance
• Cathedral of Santa Maria del Fiore
• Pallazo Vecchio
• David of Michaelangelo
• Pitti Palace
• Accademia Gallery and Brunelleschi Dome
• Piazzale Michaelangelo
• Forteza da Basso
• Chianti Wineries – vineyard and wine tasting tour
• Basilica of Santa Croce
• Cinque Terre hike from Florence
• Ponte Vecchio
• Join a handmade pasta and dessert cooking class
• Piazza del Duomo
• The Boboli Gardens
• Teatro Alla Scala
• Museo Nazionale della Scienza e della Tecnologia Leonardo da Vinci
• Duomo di Milano /Milan Cathedral – get a skip-the-line ticket
• Sempione Park
• Pinacoteca di Brera
• Sforzesco Castle /Sforza Castle
• Lake Maggiore
• Basilica di Sant’Ambrogio
• Santa Maria delle Grazie – Da Vinci’s Last Supper Tour
• Arco Della Pace
• Lake Como with Bellagio tour from Milan
• Aero Gravity – open from 10 AM – 10.30 PM
• All’Antico Vinaio – a great sandwich shop for a quick bite or join a Milan food tour
• Galleria Vittorio Emanuele II or Corso Garibaldi – streets for many dining options
• Best to use Milan 48-hour pass – free entrance to museums, discounts on restaurants, and transportation perks
• Milan hop-on hop-off bus tour

Naples and around

• Naples hop-on hop-off bus tour
• Naples National Archaeological
• Castel Nuovo
• Royal Palace of Naples
• Climbing Mount Vesuvius
• Piazza del Plebiscito
• Museo e Real Bosco di Capodimonte
• Anacapri/Capri Island
• Bourbon Tunnel tour
• Amalfi Coast
• Ruins of Pompeii – including the Casa del Fauno, the Temple of Apollo, the Amphitheater, and the Temple of Jupiter – book a combo tour
• Grotta dello Smeraldo
• Museo Correale di Terranova
• Bagni Regina Giovanna
• Veiled Christ – located in Cappella Sansevero
• Fiordo di Furore
• Visit Catacombe di San Gennaro
• Herculaneum
• Sorrento, Positano, and Amalfi full-day tour
• Castel dell Ovo is a sea-bound castle
• Naples Underground tour
• Spiaggia Marina Grande
• Villa Jovis
• Naples food tour
• Cattedrale di Palermo
• Spiaggia Vergine Maria
• Catacombe dei Cappuccini – catacomb and Monreale half-day tour
• Massimo Theater
• Quattro Canti
• Go sailing – join a half-day trip with snacks and drinks
• Santa Maria dell’Ammiraglio
• Fontana Pretoria
• Mafia tour – read the reviews
• Norman Palace
• Royal Palace and Palatine Chapel
• Vintage Fiat 500 – check the tour cost
• Castello della Zisa
• Riserva Naturale di Capo Gallo
• Day trip to Segesta, Erice, and Salt Pans – full-day excursion
• Baia di San Cataldo
• Explore the food scene – book a street food walking tour or a night food tour or a food tour with walking tour or pizza and gelato-making class or a pasta and tiramisu class
• Ponte del Mare
• Museo delle Genti d’Abruzzo
• Gabriele D’Annunzio’s Birthplace Musuem
• Piazza della Rinascita
• Nature REserve Pineta Dannuziana
• Museo Archeologico Nazionale d’Abruzzo
• Castle of Roccascalegna
• Monte Amaro/Maiella
• Spiaggia di Valle Grotte
• Leaning Tower of Pisa – get an entrance ticket
• Lungarno di Pisa
• Explore Pisa – get an all-inclusive guided tour or do a bike tour
• Santa Maria Della Spina
• Marina di Pisa
• Square or Miracles Monuments – check the tour cost
• Monte Pisano
• Day trip to Cinque Terre – check the itinerary
• Pisa Cathedral – do a guided tour
• Iglesia de Santa Maria della Spina
• Day trip to Chianti wine tour – read the reviews
• Book a food tour
• Borhese Gallery and Museum
• Piazza del Popolo
• Villa Borghese
• Colosseum, Roman Forum, and Palatine Hill – buy a combo ticket
• Piazza Navona
• Baths of Caracalla
• Vatican City, Vatican Museums – get yourself a skip-the-line ticket
• Altar of the Fatherland
• St. Peter’s Basilica – join a St. Peter’s Basilica to Underground Grotto tour
• Castle Saint Angelo or Mausoleum of Hadrian
• Spanish Steps
• Trevi Fountain
• Rome food tour
• Vatican and Rome City Pass with free use of transportation
• Venetian Arsenal
• Ca’ Rezzonico
• Basilica S.Maria Gloriosa dei Frari
• St Mark’s Basilica – buy a skip-the-line tour with terrace access
• St. Mark’s Square
• Venice Lido
• St. Mark’s Campanile
• Doge’s Palace
• Rialto Bridge
• San Marco Campanile
• San Giorgio Maggiore
• Venice’s Grand Canal Gondola tour
• Gallerie dell’ Accademia
• Don’t miss a Venice street food tour
• Spiaggia di San Lorenzo
• Scalinata dell’amore
• Monolite Pizzomunno
• Museo Malacologico Vieste
• Vieste Lighthouse
• Spiaggia di Scialmarino
• Riserva naturale Foresta Umbra
• Vicolo del Bacio
• Hike Coppa d’Incero

MUST-TRY ITALIAN DISHES, DRINKS, AND SNACKS

Food in Italy is like a great conquest. The challenge is being able to try all the must-eat foods within 2 weeks in Italy. Indeed, a country known for its culinary history requires you to taste as much as it can offer. 

Every region or city in Italy is known for its respective dishes. Thus, it is a must to sample them when you visit each city. Below is a list of the recommended dishes you cannot leave Italy without trying.

Probably the single dish that unifies and represents Italy as a country to the world, Pizza is easy, cheap, and very filling. This is probably why it easily grew in popularity in other parts of the world. 

Today, you will find a variety of pizza toppings. The classic Italian pizza is simply made with mozzarella cheese, tomato sauce, tomato slices, and basil leaves. 

Risotto originated in central-northern Italy and is now one of the most iconic Italian dishes, Risotto is made with short-grain rice that is slowly cooked with a creamy texture. Various ingredients are used for making risotto, including mushrooms, seafood, and saffron. 

Bruschetta Al Pomodoro

Bruschetta al Pomodoro (or tomato bruschetta) is one of many vegan options available in Italy . It is one of the must-try dishes in Italy because of the main ingredients representing the country – tomato and basil. The bread is char-grilled to give it that crunchy exterior to contrast the tomato and basil topping.

You simply cannot leave Italy without consuming their world-famous gelato. A scoop or two is perfect to relieve the heat during an Italian summer day. 

There are also a variety of gelatos to choose from, and you can find vegan options. The velvety texture of the gelato is smoother than regular ice cream. 

ACCOMMODATIONS (per city)

To help you plan your 2 weeks in Italy itinerary, here’s a list of recommended places you can stay depending on your budget arranged by city. Whether you’re a backpacker, an average traveller, or a luxury seeker, there’s something for everyone.

• Affordable: Casa Isolani Pizza Maggiore or Denise B&B
• Mid-range: Casa Isolani or A San Lazzaro Rooms
• Luxury: Art Hotel Commercianti or Hotel Corona d’Oro or NH Bologna De La Gare or Starhotels Excelsoir
• Affordable: Domoikos or Hotel Sofia
• Mid-range: B&B Stesicoro or Liberty Hotel
• Luxury: Palace Catania or B&B Palazzo Cerami or 81 Suite and Breakfast
• Mid-range: hu Firenze Camping in Town or B&B Home
• Luxury: Hotel De La Ville or Hotel della Signoria
• Affordable: Lion Hostel or Matteo Guest House
• Mid-range: Starhotel Business Palace pr Cesena3 Plus
• Luxury: Palazzo Cornalia or Hotel Manin
• Affordable: Los Mochileros Hostel or Naples Experience Hostel
• Mid-range: B&B Vesu or Raggio di Sole 2
• Luxury: Macchiato Suites or Relais della Porta
• Affordable: B&B Vivere Palermo or Teatro Del Sole Apartment or B&B Hotel Quattro Canti
• Mid-range: La Maison del Sole or Vittorio Emanuele Rooms or InCanto
• Luxury: Palazzo Santamarina or Duca di Villena or Quintocanto Hotel & Spa
• Affordable: B&B Hotel Pescara or Dimora Novecento
• Mid-range: Villa L’Aurora or Marini Bed&Breakfast or Aron Only Suites B&B or Corso 84 Suites
• Luxury: Wood Luxury House or Smartfit House or Villa Alba Luxury Resort
• Affordable: Ariminum Hotel or Card International Hotel
• Mid-range: Hotel Gabbiano or Hotel Baby
• Luxury: Savoia Hotel or Hotel Aria or Le Rose Suite Hotel or i-Suite Hotel
• Affordable: Residenza Laterano or Affittacamere de Barby
• Mid-range: Villa Paganini or Walker Guest House
• Luxury: Dimora ai Fori or Tree Charme Parliament Boutique
• Mid-range: Al Portico Guest House or Hotel Principe
• Luxury: Carnival Palace or Hotel Dell’Opera
• Affordable: Rocca Sul Mare Hotel or Quintessenza – Charme Rooms
• Mid-range: Agriturismo Posta Pastorella or La Duchessa e Il Contadino
• Luxury: Suite Mozart or B&B Armonia Vieste

SUMMARY OF 2 WEEKS IN ITALY

Italy is one of the most popular countries for tourism. But just when you think you know all there is to know about Italy, it surprises you. When you visit Italy, use the information above to help you plan for your trip.

But also come with an open mind because you will discover more hidden gems along the way, which isn’t always bad.

2 weeks in Italy might not sound like a lot, because it’s not. However, there are many ways to explore this country. I don’t recommend trying to overload your itinerary as you won’t have time to enjoy, slow down, and process everything you see.

It’s better to focus on one region or area and leave something for your next visit. Because after this trip, I’m sure you’ll be back.

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Two Weeks in Italy: A Complete Guide for First Timers

There’s a good reason why Italy tops the bucket list of countless travelers. It has a unique historical significance (even though Italy itself is actually one of the youngest countries in Europe) thanks to the Roman Empire’s escapades, it has a famous food culture (not to mention the wine), and it has gorgeous scenery.

Italy has spent hundreds of years building its brand which has millions of people dreaming of visiting Italy. 

But as we’ve learned over the course of our time in Italy over the past two years (almost two months in total), boiling the entirety of Italy down to just a handful of things it’s famous for means that you’re missing the things that really make Italy special.

Coming from an American perspective, we have a very specific view of what it means to be “Italian” that involves numerous stereotypes including some combination of chicken parmigiana, garlic bread, and talking with your hands (in our experience, only one of those is genuinely found in Italy – which one is it?).

However, after several trips where we’ve been able to go a level deeper than you usually do on that first trip, we’ve come to realize something important. 

Italy is a surprisingly diverse country. 

Not necessarily in terms of race or ethnicity, which is how the word “diversity” often gets translated, but in terms of regional differences that have been formed over thousands of years.  

The regional differences in culture, dialect, and cuisine that come from centuries spent as independent (and often warring) city states are what we love about Italy, and that diversity is what makes Italy a fascinating place to visit.

As you move between regions, you’ll notice that the food and wine menus change drastically, as do the accents and cultural norms. 

With so much to learn, see, eat, and drink in Italy, how do you even go about planning a two week trip to Italy?

In this guide, we’re going to go through what is, in our minds at least, a perfect 14 day Italy itinerary.

It covers Italy’s major cities – Rome, Florence, and Venice – along with some time spent in less heralded places like Bologna that most tourists miss, but we believe is well worth a stop. 

This guide is geared towards first-timers who want to see those main cities, but we also have an entire section below the main itinerary full of ideas on how to modify it, which you might find useful if you’ve done the whole Venice thing before and are looking for something new.

Either way, grab a cup of coffee (or a spritz?) and buckle in for a long one – here’s exactly (and we mean that) how we’d spend two weeks in Italy. 

Disclaimer: Some of the links in this post, like hotel links, are affiliate links, meaning at no additional cost to you, we make a little bit of money if you click through and book. That being said, we would never recommend something to you that we don’t stand behind 100%.

Is 14 Days Enough Time in Italy?

In short, no. Definitely not. However, we do think it’s a good amount of time to see a chunk of the country that will give you a nice overview and help you decide where you want to dive deeper on your next trip.

In this itinerary – which is primarily designed for first timers – we’re going to cover both the main cities (Rome, Florence, and Venice) and some of our favorite places that don’t usually make the list (Bologna and Verona).

P.S. If you have a shorter trip, make sure to check out our guide to 10 days in Italy , which focuses on Rome, Florence (and the surrounding area), and Venice, or our guide to spending a week in Italy , which has five ideas for a week in Italy that you can mix and match to build your own itinerary.

There are two places that you won’t find in this itinerary for various reasons.

First is southern Italy – specifically Napoli, Pompeii, and the Amalfi Coast.

The reason is not that they aren’t beautiful or worth seeing, but that we think your time is better spent in northern Italy, which is our favorite part of the country.

Getting between Napoli and northern Italy is going to take a lot of time that would be better spent exploring!

The second place is the Cinque Terre , and it’s for a similar reason. The Cinque Terre is gorgeous. But it’s not particularly easy to get to.

You’ll need to make multiple connections from Florence, and it’s going to take about three hours each way.

If you do want to add the Cinque Terre, you’ll need at least two full days. We have some ideas on how to add it below the main itinerary.

If you’re interested in visiting Cinque Terre, make sure to read our guides for Cinque Terre.

• The Best Things to Do in Cinque Terre: A Complete Guide
• How to Plan an Amazing 2 Day Cinque Terre Itinerary
• Where to Stay in Cinque Terre: The 4 Best Places to Stay (with Pros and Cons for Each)

Where to Fly In and Out Of?

If you follow the itinerary below as written, which takes you on a tour-de-Italy from Rome to Venice, you’ll want to fly into Rome–Fiumicino International Airport (FCO) and out of Venice Marco Polo Airport (VCE) .

An alternative would be to fly out of Milan (either LIN or MXP – we like LIN better because it’s closer to the city and a newer airport), which generally has more flight options than Venice, but it requires an extra day or two and a train.

Getting Around Italy

The best way to get around Italy is by train. At least for your purposes on the itinerary below It’s going to be cheaper, faster (once you include travel time and security at the airport), and better for the planet than hopping on a short flight.

There are a few things you should know about trains in Italy before we get any further.

First, there are (essentially) two types of trains in Italy – high speed and regional – and they operate differently.

High speed trains are more expensive, significantly faster, and less flexible. To save time since you’ve only got a limited amount of it in Italy, you’ll want to take the high speed trains between cities.

You’ll want to book your ticket as far in advance as possible, which usually will save you some money, but will be less flexible. If you want the flexibility, you’ll have to be prepared to pay a little extra.

Regional trains are slower, cheaper, and more flexible. They’re usually for connecting nearby smaller cities to each other (for example, there’s a regional train between Florence and Pisa).

You can buy these tickets when you arrive at the station, and they’re more flexible. You need to make sure you validate them before boarding.

The best way to book train tickets in Italy is directly through Trenitalia , the company that runs most of the trains in Italy. The only downside is that you’ll need to know the name of the station you want to travel to in Italian. 

We’d take high speed trains between Rome and Florence, Florence and Bologna, Bologna and Verona, and Verona and Venice . For day trips from Florence and Bologna, regional trains will do.

The Itinerary / Route

And now, the itinerary for spending two weeks in Italy. 

One quick note : In general, when you’re moving between cities, we’d recommend taking an afternoon train, which will give you some extra time to explore the city you’re leaving in the morning before heading to the train station.

Here’s how we would plan a trip to see the best of Italy in two weeks, starting in Rome and ending in Venice: 

• Day 1: Arrive in Rome
• Day 2: Rome
• Day 3: Rome
• Day 4: Rome + Train to Florence
• Day 5: Florence
• Day 6: Florence
• Day 7: Florence Day Trip
• Day 8: Train to Bologna
• Day 9: Bologna
• Day 10: Day Trip to Verona
• Day 11: Train to Venice
• Day 12: Venice
• Day 13: Venice
• Day 14: Venice + Fly Home

You’ll notice a couple of different things about the way we’ve structured this itinerary.

First , we’re big fans of spending at least 2-3 days in big cities to avoid feeling like you’re rushing around from sight to sight. That will give you some time to do some exploring to find a new favorite neighborhood, coffee shop, wine bar, or restaurant.

Second , we hate packing and moving accommodations. It sucks. Which is the reason we’re recommending you stay in a place like Florence or Bologna and use it as a home base for exploring the surrounding area.

Third , we’ve included a significant chunk of time in Bologna. Which is our favorite city in Italy not named Rome or Florence (Lucca and Verona are also in the running). 

Here’s why: Bologna is the capital of the best food region in Italy , home to the production of delicious things like Parmesan-Reggiano cheese (we LOVED touring a small producer of Parmigiano-Reggiano with Claudio on this tour ), prosciutto di Parma, mortadella, balsamic vinegar, Lambrusco (a sparkling red wine), tortellini, ragu, and plenty more. 

Not only is the food incredible, but the city – which feels noticeably younger and less “touristy” than most of the cities here – is a nice change of pace from places like Rome, Florence, and Venice.

Bologna also makes an excellent home base for day trips because it is so well connected.

Whatever you do, we’d implore you NOT to cut Bologna. It’s an amazing city, and you won’t regret spending a day or two there.

Fourth, it might seem like a lot of time in Venice at the end. However, it’s really only two and a half days if you take a midday train there, and have an early flight home.

If you have a full 14 days (you’re flying out on day 15, for example), we’d add an extra day either in Florence to do another day trip, or in Rome.

2 Weeks in Italy: A Perfect 14 Day Italy Itinerary for First Timers

And now, on to the detailed itinerary. 

Our intention here is to give you the information we think you need to know to plan an amazing trip to Italy.

We’ll go a little deeper than a short description of each place, giving you some of our favorite things to do, see, eat, and drink that come from our own experiences exploring Italy (and, equally crucially, what not to do – looking at you, Juliet’s House in Verona!). 

We believe those details – like specific wine bars, tours, and coffee shops we loved – are the difference between a good trip and an incredible trip, and hope you’ll find a few places that you wouldn’t have necessarily found on your own. 

The other intention here is to not just give you the same old itinerary that you’ll see in every guidebook.

Of course, we’re going to include Rome, Florence, and Venice, because those are places that are absolutely worth seeing on your first trip to Italy. 

However, we’re also going to include some of our favorite places (like Bologna) that don’t usually make the cut. Rick Steves (who Matt loves – he’s from Seattle too!) doesn’t even include Bologna in his Italy guidebook! What a miss.  

Rome: Days 1-3

I mean, if you’ve never been to Rome before, you’re in for a treat. Rome is one of our favorite cities in Europe, and there’s something special about walking past architecture from over a thousand years ago on your way to a hip natural wine bar in the evening. 

While Rome is famous for its historical sights, it’s also a great city for food and drinks (as we’ll cover below) and as I’m sitting here writing this, I literally made a Roman pasta dish (amatriciana) for dinner last night. 

We’d recommend three days in Rome, at a minimum, which will allow you enough time to see both of the main attractions, dive into the history of Italy’s capital city, and also indulge in some of Rome’s great food and drinks. 

What to Do in Rome

Look, there are two main attractions in Rome that, if it’s your first trip, you probably shouldn’t miss. 

They are, of course, the Vatican and the Colosseum and Roman Forum . They’re popular and “touristy,” but being touristy doesn’t necessarily mean it’s not worth doing. 

However, you should absolutely split them up and avoid doing them on the same day . It will simply be too much information if you try to knock them both out on the same day, and you will be exhausted, which means you won’t get the most out of them.

Do them on different days. Trust us. 

Let’s talk about those two first. However, this is going to be relatively brief.

For a more in-depth version of how we think you should experience them, head over to our guides to the best things to do in Rome , our guide to planning your Rome itinerary, and our review of the Colosseum and Forum tour we did (and, spoiler alert, loved). 

The Colosseum and Roman Forum are perhaps the best example in Rome of the grandeur that the Roman Empire was able to create nearly two millennia ago.

The Colosseum, in particular, is an architectural marvel to us.

The Forum is mostly just stones strewn about at this point, so it’s harder to visualize what it looked like roughly two thousand years ago at the height of Rome’s power. 

Which brings us to an important point: you should definitely do a guided tour of the Colosseum and Roman Forum .  

We have a strong opinion here, mostly informed by the fact that we did an amazing tour of the Colosseum with our favorite Italian tour company (you can read all about it here ) where we learned that some (really, most) of the things we thought we knew about the Colosseum were actually just fairy tales. 

We have personally done (and enjoyed) TakeWalks’ Skip the Line: Premium Colosseum Tour with Roman Forum & Palatine Hill – you can read about our experience here (spoiler: we loved it!). It is a great tour option that includes both the Colosseum and Forum.

Before or after your visit, there’s an excellent view of the Roman Forum from OUTSIDE the boundaries located here .

The Vatican is basically one of the greatest art museums on the planet. Sure, there’s St. Peter’s Basilica, but even that is very much about the art (which at the end of the day is just a way to show that you have money and power).

The Sistine Chapel, in particular, is incredibly moving, especially when you consider how long it took to finish, and how Michaelangelo had to paint it facing the ceiling. 

It’s worth a tour of the Vatican too, if you can afford it. We’d do the “Pristine Sistine” early access tour with Take Walks, which includes early access.

We haven’t done that specific tour ourselves, but we’ve done four separate Take Walks tours now, and all have been excellent because the guides are top notch experts in their fields. 

If you can only do one tour, we’d do the Colosseum and Forum because the added context and historical perspective from a guide is more useful when you’re looking at ruins. 

Since we’ve already rambled so much in this section, here’s a quick hit list of other things to do in Rome. 

The view from the Orange Garden (Giardino degli Aranci) . This is one of our favorite views in the city, and we’re not alone. Head up here around sunset for a treat, but it’s equally gorgeous in the early morning hours (perhaps better, because the sun is generally behind you), and there are far fewer people.

Trastevere in the evening . Our favorite neighborhood in Rome is Trastevere, and it’s not that close. It’s nice in the morning, especially if you visit the open air market that takes place at Piazza de’ Renzi, but the evening is when it comes alive. People spill out of the bars and restaurants into the streets, and the piazzas are full of people drinking and being merry. 

Wine! Enoteca il Piccolo in the Centro Storico ( here it is on Google Maps) is as great as it is popular. The owner came out to the terrace where I tried to explain in my bad Italian what kind of wine I wanted (dry white), and he walked away without a word, and returned with two excellent glasses of exactly what I asked for. If you’re looking for a bottle, Les Vignerons in Trastevere is the place to go (great beer and cider selection, too!). 

Roman cuisine . First, we make the four Roman pastas at home (carbonara, gricia, amatriciana, and cacio e pepe) all the time. Roman food is generally very simple, but delicious. The best way to learn about Roman food is taking a food tour with a local guide, where you’ll not only taste some delicious food, but learn about the history and context behind that food. Which is our favorite part about learning about food cultures of different places. We’d do this tour , which looks truly spectacular and includes a lot of cultural context along with tons of tastings. 

If you’re into good coffee, head straight to Pergamino Caffè near the Vatican, which is home to some of the best baristas in Rome who bring in a bunch of different Italian specialty coffee roasters to brew for you.

It’s my, Matt the coffee snob’s, favorite coffee in Rome. 

Of course, there are tons of other things in the Eternal City that are worth doing, seeing, and eating. For more, head over to our guide to the best things to do in Rome , which has a collection of our favorites. 

Where to Stay in Rome

While there are a bunch of areas you could stay in Rome, we have two strong recommendations for you to help you narrow it down.

We also have an entire, super detailed guide to where to stay in Rome if you want more details to make your decision.

Our overall recommendation is to stay in Trastevere , which is far and away our favorite part of the city.

We stayed there on our last trip, and it’s magical.

It’s a great place to eat and drink, and it really comes alive when the sun goes down, full of lively piazzas and small bars and restaurants that fill up on a nightly basis and spill out into the cobblestone streets.

We stayed at Horti 14 Borgo , a small boutique hotel in Trastevere, and absolutely loved it.

It’s a splurge compared to where we normally stay, but the stylish rooms, comfortable beds, and incredible breakfast buffet were worth it. 

A more affordable (but equally highly rated) option would be Ripagrande a Trastevere , which is essentially right on the River Tiber and within five minutes of everything in Trastevere. 

The only downside to Trastevere is the fact that it’s a little far from the train station, which doesn’t matter as much with three days, but is a little less convenient (you’ll need to take a taxi, most likely).

Which brings us to our second recommendation, which is Rome’s Historic Center (the Centro Storico). 

Stay here if you want to be right in the middle of all the action, within walking distance to just about everything in the city.

It’s the most convenient place to stay, though it will be crowded and potentially loud. Don’t miss an early morning walk from Piazza Navona to the Trevi Fountain and the Spanish Steps!

We stayed for five nights near Piazza Navona at these apartments , which were honestly a perfect location, especially if it’s your first time in Rome.

Coronari Palace and Casa Pietra are two hotels that were also on our list, though we decided we wanted more space and a kitchen for our time in Rome. 

Florence: Days 4-6

Historically, the city of Rome might be the crown jewel of the Roman Empire, but you could make a convincing argument that Florence is the second most important city in the history of the Italian peninsula because of its influence around the birth of the Renaissance. 

On a walking tour in Florence ( this one , which we recommend below because it’s a great introduction to the city), as we were walking through Piazza della Signoria, our guide made a point that I hadn’t really thought about before that moment. 

Florence was one of the richest cities in Europe (if not the world) in the 15th Century and through the Renaissance. 

A lot of people – myself included – might think that wealth came from the amazing art that was produced in Florence leading up to and during the Renaissance.

But the truth is that Florence was already a rich city thanks to silk production, and that wealth is what allowed it to become a cultural icon that thousands of people still flock to five centuries later. 

Walking the streets of Florence, it’s easy to see why so many people fall head over heels in love with it on their visit.

It’s charming. The Duomo is incredible, both because of how imposing it is, and the fact that it’s an architectural miracle. There are two world class museums.

The food and wine are both excellent (definitely get the wild boar if you see it on a menu – pappardelle al cinghiale – which was our favorite discovery on our Tuscany road trip itinerary ). 

I could go on and on about Florence – I’ve spent over a week in Florence between two trips in the past year (at the time of writing) – but let’s leave it there and get into how to make the most of your time in the Tuscan capital. 

In this itinerary, we have you spending two and a half days in Florence itself, and then using it as a home base for a day trip into Tuscany. 

What to Do in Florence

There are two main attractions in Florence that you’ve likely heard of before, and both are well worth your time.

They are the Uffizi Gallery , which is a chronological journey through Renaissance art in Florence, and the Galleria dell’accademia , which is where you’ll find Michaelangelo’s David . 

However, you should definitely try to do them on different days , because it’s too much information to process in a single day.

Believe me, my mom and I tried to do both in a day in Florence on my latest trip to Italy, and it was too much. 

The other thing I would say – and again, I’m speaking from experience here having done both museums with and without a guide – is that you should invest in a guided tour with an art historian if you can .  

After some truly great experiences recently, I’ve decided that I probably won’t do a huge art gallery like the Uffizi or the Louvre without a guide ever again.

The guide is able to add so much in terms of color, context, and storytelling that will give you a deeper connection to just about any museum visit. 

Otherwise, we’d look at the art, say “yeah, that looks pretty,” and move on without really understanding the context behind what we’re looking at.

If you only have the budget for one, make sure to do the guided tour of the Uffizi, where your guide will be able to explain exactly what you’re looking at, and what it says about the changing nature of society and culture during the Renaissance.

We did this guided tour of the Uffizi Gallery , and it was fantastic. 

For what it’s worth, I (Matt) also did this guided tour of the Galleria dell’Accademia on my last visit with my mom, and we also really enjoyed it.

However, like I said above, if you only have time or budget for one tour, you’ll get more out of the Uffizi. 

For more information, including on how to visit both galleries independently , head over to our guides to the best things to do in Florence and our guide to planning your Florence itinerary .  

As we said above, we’d split those two museums up and do one on each of your two full days in Florence. Which, obviously, leaves you with some extra time. Here’s what we’d do with that time. 

Take Andrea’s walking tour . We’re huge fans of walking tours as a way to get an introduction to a new city and connect with a local for tips on what (and where) to eat, drink, and shop. And we loved Andrea’s walking tour , which is a two hour crash course in Florence’s rich history, with all the salacious details about the Medici family (they were essentially royalty in Florence during the 1500’s). He also has a more in-depth version of the tour that adds an hour and includes crossing the river to Oltrarno. 

Climb to Piazzale Michelangelo . On the other side of the river from Florence’s Centro Storico, you’ll find what is arguably the best view of the city at Piazzale Michelangelo. You’ll have a view of the Arno River and Ponte Vecchio (the only bridge in Florence that wasn’t destroyed in World War 2), the Duomo, and the rest of the city. It’s nice at sunset, but it’s busy. Early in the morning is even better, because the sun is behind you and there are basically no crowds. 

Climb Brunneleschi’s Dome . The Duomo in Florence is massive. The best way to experience it, in our opinion, is to climb to the top. Along the way, you’ll get a view of the interior of the dome and the (somewhat creepy) artwork decorating it, then you’ll climb through the area between the interior and exterior dome (which gives you perspective on how it was built 600 years ago, which is mind-boggling) up to the top, where you’ll have a 360-degree view out over Florence. Try to do it first thing in the morning for the fewest people, and book in advance here . 

Dive into Tuscany’s food and drink offerings . We’d strongly encourage you to skip the pizza in Florence, and instead indulge in some of the local specialties. We love Pappardelle al ragu di cinghiale (a pasta with a wild boar sauce that my mom fell in love with), pappa al pomodoro (tomato and bread soup), and the Schiacciata (sort of like a focaccia sandwich, but slightly different). We liked the food at Trattoria da Garibardi . Most of the Florentine cuisine pairs well with the Tuscan reds like Chianti Classico and Brunello, which are a couple of the more prestigious red wines to look for. 

Where to Stay in Florence

Similar to Rome above, we have two recommendations for where to stay in Florence .

Also similar to Rome, your choice is going to be between the coolest neighborhood (in our opinions, anyway) and the most convenient area.

Convenience matters a little more here because you will be taking a day trip, which means you’ll be going to and from the train station.

Our favorite area in Florence is Santa Croce / Sant’Ambrogio , which is a five minute walk east of the Duomo. It has the best food (we think), fewer tourists, and is close to everything in the city.

We stayed at Pietrapiana Boutique Apartments for almost a week, and it was everything we wanted and more: access to a kitchen, a little more space to spread out, a quiet refuge from the hustle and bustle, and a comfortable place to sleep. Highly recommend! 

La Maison du Sage is another good option nearby – it’s more of a traditional hotel than serviced apartments.

The other option, which is best if you want to be super central to everything in Florence, is Florence’s Centro Storico , which is centered around the Piazza del Duomo and nearby Piazza della Signoria (home to the Uffizi Gallery).

It’s crowded, it’s loud, but it’s super convenient. It’s also closer to the train station for your day trip.

Day Trip from Florence (Choose Your Own Adventure): Day 7

Florence is the capital of Tuscany, which might be Italy’s most famous region for its wine and general dolce vita feeling. And, after spending a week in Tuscany, we can definitively say it delivers on both. 

Florence is an excellent base to explore Tuscany from, with most of the highlights accessible within 90 minutes by train. However, the main issue with Tuscany is that you really need a car to be able to see certain things properly.

Here are the three day trips from Florence we’d recommend, and which one you choose totally depends on what you’re interested in. 

If you’re looking to combine San Gimignano, Chianti, and Siena into one day, it’s going to be a long day, but this tour with Take Walks (which, as we’ve already mentioned a few times in this guide, is one of our favorite tour companies on earth), covers San Gimignano, Chianti, and Siena in one action-packed 10 hour day. 

Day Trip 1: Siena for the Cathedral (and the History) 

Siena is a popular day trip from Florence, and it’s a 90 minute train ride south in the heart of Tuscany.

There is, perhaps, no better example of a classic hilltop town than Siena, which is a red city perched on a hill overlooking a lush green valley. 

The cathedral in Siena is incredible, and we say that as people who usually don’t get all that excited about massive opulent churches.

The iconic dark green and white stripes of Siena’s Duomo are just the beginning of what makes it special.

The interior is where the real fun begins, particularly if you’re around when the floors are uncovered (usually in the summer), and the intricate art and tilework on the floors is on full display. 

We recommend climbing up to the Facciatone, which is a viewpoint inside the Museo del Duomo that has an excellent view of both the cathedral and the surrounding landscape. 

The other place not to miss in Siena is Piazza del Campo, which rivals Piazza Maggiore in Bologna (more on that in a second) as our favorite piazza in all of Italy. 

In terms of eating and drinking, head to Torrefazione Fiorella for a morning coffee at a stand-up bar (very Italian), Panificio Il Magnifico to try sweet Sienese specialties like ricciarelli, Du’ Cose Da Berna for traditional sandwiches at lunch (a recommendation from our friendly host at the agroturismo we stayed at outside of Siena), and Ristorante Gallo Nero , which was one of the best meals we had in Tuscany. 

How to get there : There are regional trains between Florence’s Santa Maria Novella (the main station in Florence) and Siena that take about an hour and a half. You can also take bus 131 (or the faster 131R) from the Florence bus station ( here on Google Maps – it’s right next to Santa Maria Novella), which is a similar amount of time. Both are very affordable options.  

Day Trip 2: Chianti for the Wine

Chianti is the place to go for wine. Chianti classico is the name of the game here, which is a Sangiovese-based red wine that follows strict production methods, and is one of the most famous wines that comes out of Italy.

If you don’t like red wine, I have some bad news for you – Tuscany is all about the red wines (except for vernaccia, which is a white wine that comes from San Gimignano!). 

Assuming you don’t have a car, your only option here is to do an organized tour because doing a self-guided tour of Chianti wineries would require both a rental car and a designated driver. 

In terms of guided tours, you have two options.

You can either choose a tour that goes deep on a single winery , usually including a cellar tour and detailed tasting (but you’ll have to make your way out to the winery), or a tour that takes you around to multiple wineries , which is going to be a little less personal, but give you more breadth where you’ll get to see multiple approaches AND usually includes transportation to and from Florence. 

We did this tour of a tiny organic winery and olive farm at the northern end of Chianti, and we loved it.

It was very personal and intimate, and we learned a ton about growing grapes (and olives) in Chianti.

We’d highly recommend it, and the nice part is that it’s easily accessible from Florence (and the hosts will help you figure out how to get there, including a bus station pickup). 

In terms of the other option where you get to visit multiple wineries with transportation to and from Florence, this is a highly rated tour with a sommelier that we considered.

You’ll get to visit three wineries, which are all closed for public visits, which is a good sign that it’s a unique experience because the host clearly has relationships with those specific wineries. 

If you want to see more of Chianti, including the super charming Badia a Passignano, we’d go with this tour . 

Day Trip 3: Lucca For the Views

You might have been expecting to see Pisa somewhere on this list of day trips from Florence, and we’re here to tell you that while, yes, the leaning tower is kind of cool, we would absolutely recommend skipping Pisa (which is crowded beyond belief with people wanting to see the aforementioned leaning tower) and heading to Lucca instead. 

There are a couple of reasons we love Lucca. 

First, the medieval walls are still intact, encircling the entire city. It’s well worth walking the full loop, where you’ll get some nice views of the city and the mountains beyond. 

Second is the tower. Climbing the Guinigi Tower will take you up to what might just be our favorite view in all of Italy.

On a day trip to Lucca, we’d spend your time walking the city walls, climbing the tower, and indulging in some Luccan cuisine for lunch (at Trattoria L’ Angolo Tondo , which is right on the Piazza dell’Anfiteatro where a Roman amphitheater used to be), which is slightly different than the food you’ll find in Florence because of its proximity to the coast, which means more fresh seafood. 

How to get there : There are regional trains between Florence’s Santa Maria Novella (the main station in Florence) and Lucca that take about an hour and a half. They come frequently, and they’re super affordable. 

Bologna: Days 8 & 9

You’re probably a little bit surprised to see Bologna on this itinerary, since it’s not exactly known as one of the “must-see” cities in Italy. However, we’re here to tell you that it absolutely should be on your list, particularly if you love food. 

One of the most interesting parts about traveling to Italy is having our expectations about “Italian” food completely shattered.

Here in the US, Italian food (we now know that Italian–American food is an entirely separate thing) consists of heavy sauces with lots of garlic, garlic bread, and chicken parmigiana. 

The truth is that Italian food culture is vastly different from region to region, and depends a lot on the fresh ingredients available in close proximity.

For example, in Sicily , you’ll find tons of fresh seafood because you’re on an island and are perpetually near the coast. In Tuscany, it’s olives, wild boar, and sheep cheese (pecorino) because those are the ingredients that are readily available. 

If you made us choose our favorite Italian food region, we’d choose Emilia-Romagna, which is where you’ll find Bologna. 

Here’s an exercise: write down your five favorite Italian ingredients (rather than dishes). If you’re anything like us, at least one of the things you wrote down comes from Bologna’s region, Emilia-Romagna. 

There’s a reason the city is known as “La Grassa” (“the fat one”). It’s about as close to heaven for foodies as you can get. 

There are, of course, other things we really like about Bologna. It’s a city of towers that overlook the distinctive red brick buildings (most of them are facades, though).

It’s a University town (one of its other nicknames is “La Dotta” which means “the learned one”) and it has a distinctly younger vibe than just about any other major city in Italy. There are far fewer tourists than any other city you’ll visit.

And it’s well connected to just about every corner of Italy. 

We think you should spend three nights in Bologna, using one of those nights to do a day trip up to Verona, which is another one of our favorite cities in Italy. 

What to Do in Bologna

Here are a few of our favorite things to do in Bologna. For more, head over to our guide to spending a day in Bologna . 

Climb the Asinelli Tower for Excellent Views . We have friends that live in Bologna, and when we visited them on our first ever visit to Bologna, this was the first thing they did with us. It’s a big climb, but you’ll eventually end up on the top of the taller of the Due Torre (“the two towers”), where you’ll have a commanding view out over Bologna. Book here in advance for a timeslot. 

Eat your heart out . Mortadella and filled pastas like tortelloni come from Bologna, but the broader region is home to just about every delicious food we associate with Italy. Parmesan, balsamic vinegar, prosciutto di Parma, lambrusco, and ragu alla bolognese. Go to any of the places in Quadrilatero, which is right off of Piazza Maggiore, to taste and shop. Specifically, we like Tamburini for tagliere (a plate of meats and cheeses) and a glass of wine (lambrusco!), Cremeria la Vecchia Stalla for excellent ice cream (which is NOT the same as gelato), and Vineria Favalli for their excellent Italian wine list.

Take a food tour with a local guide . While you can absolutely get a sense for Bologna’s food offerings on your own, a food tour is going to be the best way to dive a little deeper. This food tour in Bologna was on our list, but after learning they couldn’t accommodate gluten free diets (which, by the way, makes total sense), we decided to skip it. 

Take in Piazza Maggiore and Basilica di San Petronio . Piazza Maggiure is the beating heart of Bologna, and one of Italy’s best piazzas in our opinion (as we noted above, Siena’s Piazza del Campo is a close second). There are events nearly every afternoon and evening, from rallies to concerts, and even when there isn’t an official event, you’ll find some of Bologna’s best musicians out on the square (along with a crowd of admirers). The church is worth going into, but it’s only half finished after they tried to make it outshine the Vatican, who said “you can’t do that.” That’s why part of the church’s facade is exposed brick, which is the unfinished portion, while the other part is covered in marble.  

Make the climb to Santuario Madonna di San Luca . Bologna is known for porticoes, which are essentially just covered walkways, and you can walk through the 666 (someone has a sense of humor) to get up to this church on the hill. For what it’s worth, this the #1 recommendation from our friends that live in Bologna. 

Where to Stay in Bologna

There’s no doubt in our minds – you should stay near Piazza Maggiore while you’re in Bologna . It’s the beating heart of the city, and it’s going to be both the most convenient and the coolest place to stay.

I spent a few days in Bologna solo on my last trip to Italy, and stayed at Bibliò Rooms and Guesthouse . It’s essentially a small B&B that takes up one floor on a residential building about five minutes from Piazza Maggiore.

The rooms are fairly spacious with comfortable beds and private bathrooms, and it’s a good home base for a few nights in Bologna. 

I also stayed at the Social Hub in Bologna , which is a hip, young-feeling hotel in Bolognina up near Bologna Centrale.

While the location is further away from Bologna’s main attractions, it is a gorgeous hotel with all sorts of great amenities (a pool, a nice gym, a bar, an events calendar, and ping pong, to name a few). Plus, it’s about five minutes on foot from the train station, so it’s convenient in that sense. 

If you’re looking for an apartment, look at Canonica Suites , which is where I kind of wish we had stayed. 

We have an entire guide dedicated to helping you figure out where to stay in Bologna with FAR more detail, if you want more of an in-depth look at your options.

Day Trip to Verona: Day 10

On this day, we’d highly recommend leaving your stuff in Bologna and doing a day trip up to Verona, heading back to spend the night in Bologna.

Verona is famous for being the setting for Romeo and Juliet, but it tied with Bologna for our favorite discovery in Italy when we spent six weeks exploring Italy in 2021. 

You might be wondering why we’d do it this way, considering Verona is sort of on the way to Venice (the next stop in this itinerary).

The reason is that we don’t want you to have to worry about juggling your bags, and instead focus on getting an early train from Bologna without the worry of check in times and baggage storage. 

Take the high speed train, which takes about 45 minutes or so (book in advance for cheaper tickets!). 

Rather than go into the details of what to do and see with a day trip up to Verona, we’re going to direct you to a separate blog post where we go through exactly that. Here’s how we’d spend a day in Verona . 

Venice: Days 11-14

Venice is a place that we have mixed feelings about. We’ve both been to Venice, and as we’ve thought about it, we’re truly not sure if we need to go again. 

It’s true that Venice is the best-preserved example of a canal city in Italy, but it’s also true that it’s a beautiful disaster.

There are way, way too many people trying to see Venice for the infrastructure to handle, and cruise ships are a big part of the issue, with huge tour groups coming in for part of a day and contributing very little to the local economy while stressing Venice’s infrastructure. 

Remember in 2020 when the canals were all of a sudden empty and pristine, and the swans came back to Venice? It’s safe to say that’s over now. 

However, it’s not really fair to say that you shouldn’t get to see Venice because too many people go there. 

Instead, we’d recommend that you do go to Venice, but be deliberate about how you do it.

Spend multiple days there so you’re not stressed about the crowds and whether or not you’ll be able to do everything. Eat at local restaurants, and stay in Venice so that your money stays in the local economy. 

The best way to explore Venice is not to spend a day (or less) seeing the main sights and calling it a day.

Venice is at its best in the early morning and evening, when it’s notably less crowded. If you only spend a day in Venice, you’re likely going to miss out on that precious time spent exploring during those hours. 

That’s why we’d strongly recommend two and a half days in Venice, which gives you a couple of mornings and nights to really soak up the atmosphere of Venice when it’s not packed wall-to-wall with people. 

What to Do in Venice

There are a few main sights in Venice that you shouldn’t miss, and two days is more than enough time to see them. Like we said above, part of the fun of exploring Venice is wandering the canals in the early morning and evening. 

Piazza San Marco is the main piazza in Venice, and there are a couple of main sights right on the square. 

First is the Doge’s Palace , which is a big Gothic building (you know because of the pointed arches) on the lagoon. Over its long history, it served as a fort, a prison, and a residence for the most powerful person in Venice, the Doge. 

The version you see today was built in the 1100’s, and has been renovated a few times since as the needs of its inhabitants changed.

It housed the Doge of Venice (sort of like a Duke, but not quite the same) during the Republic of Venice, which lasted for more than 1,000 years starting in the 8th Century and was one of the most powerful city-states in modern day Italy for long stretches because of its position on the water.

The best part about the Doge’s Palace is that it’s an excellent place to learn about Venice’s history. For example, I had no idea that there was a Republic of Venice, let alone how powerful they were.  

You can buy your tickets in advance here . 

The second major attraction on San Marco Square is the church, St. Mark’s Basilica (Basilica di San Marco), which is the biggest church in Venice.

In a surprising (to no one) twist, the church is attached to the Doge’s Palace, showing the relationship between secular and religious power in Venice over the centuries. It’s set on the site of two older churches, which is a story that you hear over and over again at some of Italy’s biggest and most important churches.

Also similar to other churches in Italy, it was built over such a long stretch of time that it’s one big mish mash of architectural styles and art periods. 

It’s an impressive building from the outside, and the interior is special because of the mosaics that cover just about every surface. The Pala d’Oro, which is essentially a big golden altarpiece from the Byzantines, is also pretty cool. 

Information on tickets and opening hours here . 

If you want to see both with a guided tour, we’d (again) recommend doing the St. Mark’s and Doge’s Palace tour with Take Walks , who we’ve done multiple tours with in multiple Italian cities, and love. It’s three hours long, includes both the church and the palace, and will take you a level deeper than just visiting by yourself. 

The islands to the north of Venice – namely Burano and Murano – are well worth a visit, and the vast majority of visitors don’t make it out there.

These tiny islands are known for glassblowing, and they’re relatively easy to reach via water taxi from Venice. From this ferry terminal, it’s a quick 20 minute ride over to Murano, the closer of the two islands (it’s a significantly longer boat ride out to Burano). 

You can read more about what to do in Venice in our guide to spending 2 days in Venice . 

What to Do with More Time in Italy

If you’re blessed with more than 14 days in Italy, we have (lots of) thoughts on what to do with extra time. Whether it’s one or two days or a full extra week, we have ideas for you based on our own explorations. 

Keep in mind that this isn’t an exhaustive list – we haven’t been everywhere in Italy, and it’s hard to recommend something we haven’t experienced ourselves.

For example, the Dolomites and Lake Como are on our list, but we didn’t include them below. Once we make it there, we’ll definitely add them!

You’ll notice that there’s one very popular destination missing from this list that you might be expecting to see: Naples, Pompeii, and the Amalfi Coast.

We contemplated adding it because we know it’s a place that people have seen pictures of and want to visit, but we really wouldn’t do it ourselves due to insane crowds and associated overtourism. 

Just this last summer, we’ve seen about 30 pictures of friends on Instagram who all went to the Amalfi Coast within the same two month period. 

Which, when you take a second to think about it, is pretty crazy. 

We think there are better coastal destinations in Italy (like the Cinque Terre – which has its own over tourism issues – and Sicily ) that we’d recommend way before the Amalfi Coast. You’ll find both of those on the list below. 

Add Another Day Trip from Bologna 

The first thing we’d add if you only have an extra day or two is an extra night in Bologna to explore more of Emilia-Romagna.

Cities like Parma (famous for prosciutto and parmesan-reggiano) and Modena (famous for balsamic vinegar) are an easy train ride away, and are well worth your time. 

We’d highly recommend a day trip that starts with Claudio’s tour of a working parmesan-reggiano dairy, which of course includes a tasting of different ages of parmesan, and a vacuum packed chunk to bring home with you.

It was the highlight of our last trip, and Claudio is friendly, uber-charismatic, and an all around phenomenal host. 

That tour is a morning tour, going until roughly noon. 

We’d then spend the rest of the day in Modena, which is the capital of balsamic vinegar production and is an easy 20 minute ride from the train station in Reggio-Emilia (where you’ll get dropped off by Claudio). That’s what we did. 

We loved tasting small production balsamic vinegar at La Consorteria 1966 (you should know that the tasting costs money unless you buy a bottle afterwards, which are expensive because this is the good stuff). 

We also had multiple people recommend Osteria Francescana , which is a world-famous fine dining experience that you’ll need to book well in advance.

You can also try chef Massimo’s food at nearby Franceschetta58 , which is less expensive and more approachable (you still want a reservation, though!). 

Another great stop is the Mercato Storico Albinelli, which is Modena’s central market. 

Add Another Day Trip from Florence

The second thing we’d add is an additional day trip from Florence. We gave you three options above, and if you took our advice, you’ve already done one of them. Do a second (or third!) one if you have an extra day. 

Cinque Terre (2-3 Days)

For my mom’s 60 th birthday, we took her on a two week Italy trip. Her two must-do experiences were the Cinque Terre and seeing the Last Supper in Milan.

So, we spent a few days exploring the Cinque Terre, and we loved it.

However, we have a major caveat. We would absolutely NOT recommend a day trip to the Cinque Terre, which is what approximately 90% of people seemed to be doing.

The main reason is that it’s a long way from places like Florence and Milan, requiring three hours of travel time.

That means you won’t arrive until mid-morning, which is when all of the other day trippers arrive, and the streets and trails are packed wall-to-wall. It’s no wonder people say it’s too crowded!

The magic of the Cinque Terre is in the early morning and late evening, when the day trippers clear out and it becomes a tranquil, slow paced coastal retreat. That means you’ll need at least one night (two or more is better).

The Cinque Terre, which literally means “Five Towns,” is a series of charming towns tucked between the mountains and the coast in northern Italy.

It’s known for hiking, terraced vineyards, and colorful towns perched on rocky outcroppings above the sea.

You’ll definitely want to hike a section of the Blue Trail (we like the one from Corniglia to Vernazza the most), dive into the wines of Cinque Terre, take in some excellent sunset views, and explore all five towns.

We have a bunch of guides dedicated to helping you plan your Cinque Terre trip. Here are some links for you:

Milan (2 Days)

Milan is a really great city that offers something a little different from other major cities like Rome and Florence.

That’s not to say that it’s not a historic city, but it feels less “Italian” than Rome and Florence mostly because it has been trading hands between the Spanish, French, Italians, and Austrians for centuries.

There is a difference that you’ll notice right off the bat, probably when you exit the train station.

It looks and feels more modern, which is mostly a function of the fact that it’s a major financial hub and home to just about every high end fashion company in the country.

There are two world-class attractions in Milan – the Duomo di Milano which took 600 years to complete and is a mishmash of different styles that somehow still works, and Da Vinci’s Last Supper .

However, it’s worth lingering for an extra day to explore some of Milan’s less famous attractions and the hip food and drink scene.

Wander Parco Sempione and pop into Castelo Sforza, and experience aperitivo in the Navigli District, which is home to some of Milan’s last exposed canals (it used to look like Venice!). 

Where to add it : You could either do Milan after Bologna (there’s a high speed train connecting the two), or after Venice (and fly out of Milan).

We have a bunch of guides dedicated to helping you plan a trip to Milan. Here are some links for you:

• One Day in Milan: The Best of Milan in a Day
• 2 Days in Milan: How to Plan An Incredible Milan Itinerary
• Where to Stay in Milan: A Complete Guide
• The Best Things to Do in Milan
• Where to Find the Best Specialty Coffee in Milan
• Gluten Free Milan: A Complete Guide for Celiacs

Sicily (7 Days)

If you have about a full week of extra time, we’d highly recommend exploring Sicily.

We love Sicily (Alysha’s family is from a small town in southeast Sicily), and spent three weeks on the island in the fall (which somehow was still not enough time). 

However, you should know that Sicily is massive, and it’s impossible to do the entire island in a week.

For that reason, we’d focus on southeastern Sicily (Catania, Mount Etna, and Syracuse) . Unfortunately, that means you’ll miss Palermo, which is an amazing city in northwestern Sicily.

The other reason to focus on southeastern Sicily is that you don’t need to rent a car. The corridor from Taormina to Syracuse is connected by a regional train line, which is something that can’t necessarily be said for the rest of the island.

To get there, you’ll need to fly. The best place to fly into is Catania (Catania–Fontanarossa Airport) .

Definitely don’t miss a day trip from Catania up to Mount Etna, which was among the highlights of our trip (you can read about it in our guide to the best things to do in Catania ) and a trip to the amphitheater in Taormina, which has a spectacular view.

Oh, and eat all of the pistachio and almond granitas you can. 

We have an entire guide dedicated to helping you plan a Sicily itinerary , which has a couple of ideas for how to spend 7 days on the island (P.S. we recently wrote a specific guide for spending 7 days in Sicily , which is even more helpful and specific in this context).

Where to add it : We’d add it after Venice, flying from Venice to Catania (which might require a connection) and flying home from Catania.

What to Do with Less Time in Italy

We’re not going to dive deep into how to spend less time in Italy, mostly because we’ve already done exactly that in some of our other guides. 

We have a guide to 10 days in Italy that’s geared towards first-timers that focuses on Rome, Florence, and Venice, and how to make the most out of your time in those places. 

We also have a guide to spending 7 days in Italy , which is a little different because it gives a bunch of different ways to do a weeklong trip to Italy. 

If you’re looking for ideas for a shorter trip, definitely read those. 

When to Visit Italy

Having spent some time in Italy over two consecutive fall seasons, I’m here to tell you that it’s absolutely my favorite time to be in Italy.

Summer is oppressive for two reasons. One, it’s sweltering. My first ever visit to Italy was late July in Rome, and it was miserable. Two, it’s simultaneously crowded and empty. Crowded with tourists, empty of locals (who all go on vacation in August). Not a great combination. It’s also very expensive, relatively speaking.

Fall is more moderate in both respects. By the end of fall – late October and November – it gets a little chilly, especially further north. But, all in all, September and October are an incredibly pleasant time to be in Italy.

Winter is going to be cooler and grayer, but significantly cheaper. The other thing to watch out for is things – bars, restaurants, shops, tours – closing, especially in smaller, more tourist-centric places like the Cinque Terre and beach towns in Sicily.

Spring is just a hair behind fall in terms of the best time to be in Italy, and anytime between Easter and the end of May would also be an excellent balance of weather and crowds. 

Matt is the founder and main writer behind Wheatless Wanderlust, which he started back in 2018 as a way to share his gluten free travel guides with his fellow Celiac travelers.

Since then, Matt and his wife Alysha have visited 18 national parks, spent three months in Europe and six weeks in Colombia, and have explored every corner of the Pacific Northwest, which is where Matt grew up.

He writes super detailed guides to the places they visit, bringing together personal experience and historical context to help YOU plan an amazing trip.

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The Best of Italy: Ultimate Two Week Italy Itinerary (14 Days)

Ahh, the land of pizza, pasta, and gelato – what’s not to love about Italy? This boot-shaped country boasts so much to see, that it’s difficult to plan an itinerary for a limited amount of time. So, in an effort to take the guesswork out of it for others, I’ve put together this epic two week Italy itinerary for fourteen glorious days in Italy, now that I’ve visited multiple times. It hits all the main sights – Rome, Florence , and Venice – plus some extras so you can come back home seeing more than the bare minimum.

This guide (prices, links, and all other details!) was last updated in March/April 2024.

Now, I have to warn you. This two week Italy itinerary is super detailed . Like, how-the-hell-do-you-have-time-to-write-all-this detailed. And I did that on purpose. You can go to any old website to get a vague “two nights in here” and “one night here,” bare-bones itinerary for Italy. But those itineraries don’t tell you what to do in each place, or how to get from each city to city. You’d have to go look that up after. But not with this itinerary.

Basically, what I’m trying to say is: get ready for a long article! (About a 30 minute read.) You might definitely want to save this for later right now by bookmarking it or saving it on Pinterest, just in case you don’t finish all in one go . Then, grab a cuppa, sit back, and let’s get to it!

Pssst! Debating a shorter trip to Italy? Definitely skim through my detailed itineraries for ten days in Italy or one week in Italy .

The Perfect Two Week Itinerary

Let’s start off with an overview of this epic, fourteen day Italy itinerary, so you can have an idea what to expect.

If you’re the average traveler with limited vacation days, I suggest breaking it down like below. This way, you only need to use ten vacation days , but you get fourteen actual days in Italy.

What is the Best Time of Year to Visit Italy?

The absolute best time to visit Italy is definitely the shoulder seasons of April – May and September – October . This allows you to see everything in comfortable weather, but to avoid the extreme crowds (And heat! And prices!) of the summer. If you plan to swim, aim for September – October, so that the water has had all summer to get warm.

That being said, I’ve traveled to Italy in the middle of August and still had a wonderful time. So if July and August are the only time you have available, you’ll still have a great trip. Just come mentally prepared for the crowds.

Winter in Italy is generally warmer than winter in central Europe. However, I would avoid winter if possible for this itinerary. There are places that flood often during rain (Venice) and places that practically shut down out of peak season (Cinque Terre and the Amalfi Coast). If you can’t stand large crowds, I would also avoid Easter in Rome. Other than that, any time in Italy is a great time to visit Italy !

If you have more specific questions about your trip timing and what I think, definitely leave a comment at the bottom of this page. I’ll get back to you with my advice. Think of me like a free travel agent…!

Best Way to Get Around Italy?

One of my favorite things about Italy is how ridiculously easy it is to travel Italy without a car . This country gets a lot of slack for being inefficient and disorganized, but you have to admit, they do public transport just fine! This itinerary is completely car-free, relying solely on trains, buses, and ferries.

In my opinion, trains are the best way to travel Italy. This is especially true for your first time in the country. I do have dreams to one day complete a grand Italian road trip. But that is only because, after multiple trips, I now have places on my list that are remote and therefore easier to reach by car. All the more-typical destinations are much easier to visit without the hassle of Italian driving, filling up gas, finding and paying for parking, etc.

One very important tip for train travel in Italy is to always validate your ticket! Otherwise, you will be fined, and the fines ain’t cheap . (Like, truly. The fines are low-key high-key ridiculous.) How do you validate your train ticket in Italy? Simply stick the paper ticket into the machines before you enter the train. It’ll make a noise and time-stamp your ticket. These little validation machines are typically at the entrance to each platform. If you have trouble locating them, just ask a train station employee. If you buy your ticket online or via the mobile app – no need to stress!

In this itinerary, I include all the details and prices for each time you’ll use public transport to move around. I’ve got you covered!

Free Printable 2-Week Italy Itinerary E-Book

But once actually in Italy, you definitely don’t want to be walking around on your phone all trip trying to get to each next spot. So, I’ve made a printable, condensed version of this post with every important detail from this fourteen day Italy itinerary you’re about to read. Just download the PDF, print it double-sided (so four pages total), and you’re good to go for your trip. It even has a map! Click below to get it emailed to you.

(Finally) The Actual Two Week Itinerary for Italy

Beforehand, I just want to let you know you can do this itinerary in the order I have it or the reverse. Just look up flights and see which direction is cheaper. Also, at the very end of this page, I have a section on how to adjust this itinerary if you need to. Ready?!

Rome. The Eternal City. This place needs no introduction , since I’m sure you learned plenty about it in school. As the former capital of the Roman Empire and the current capital of Italy, Rome is a mix of old and new like you’ve never seen. Huge, crumbling ruins from 2000 years ago contrast against beeping Vespas zipping through the cobblestoned streets. Try to ignore the street vendors with no regard for personal space selling selfie sticks and whizzing gadgets, and I’m sure you’ll fall in love with Rome as I have.

How to Get to Rome

This is the start of your trip, so you’ll need to fly in. Rome has two airports, so be careful you fly into the correct one. The main international airport in Rome is Fiumicino (FCO) . This airport is the further out one. To get to the city center from FCO, you have two options.

• Option 1: Take the train. Follow signs in the airport to the train platform. From FCO, take the Leonardo Express train to Roma Termini train station. This costs €14 (or €40 if bought for a group of four!) and will take 30 minutes. The train departs every 15 minutes, so you shouldn’t need to wait too long. From Roma Termini, you can either walk to your accommodation, or use the Metro to take the subway if your accommodation is further away. Be very careful of pick-pocketers in this train station! Do not accept or ask help from anyone except official employees, and wear your backpack facing your front.
• Option 2: Take a taxi. Taxis from FCO into central Rome are a fixed fare of €50. Make sure you get into an official taxi (they’re white with a sign saying “TAXI” on top) at the taxi pickup line. They should accept card, and you can double check this as well as fare before getting in. This will take 30 minutes, just like the train.
• Option 3: Take a bus to Roma Termini train station. Terravision offers a €6 ticket, and the ride takes 45 minutes.

Rome’s other airport is Ciampino (CIA) . This smaller airport is actually slightly closer to central Rome. However, it is only used for budget airline flights within Europe, like RyanAir and EasyJet. If you’re flying here (or anywhere!) with RyanAir, definitely skim through my guide on how to not get ripped off ! Once again, you have two options on how to get to central Rome from CIA airport.

• Option 1: Take a bus to (right near) Roma Termini train station. There are multiple options you can explore here . Some include SITBusShuttle for €6 one-way, or Terravision for €6. This ride takes 40 minutes.
• Option 2: Take a taxi. Taxis from CIA into central Rome are a fixed fare of €31. Again, make sure you get into an official taxi at the taxi pickup line and confirm the fare before getting in. This ride takes 30 minutes.

What to Do in Rome (Three Days)

Three days in Rome is the minimum amount of time to “see everything.” Below is exactly how to see Rome in three days. Take it easy on day one , since it’s the day your flight gets in. But feel free to interchange days two and three as works best for you. If you get in way too late on day one, you can tack it onto day three.

Walking straight through this route as I have it below is 30 min (2km or 1.25 miles), just to give you an idea of total distance on day one. Start at whichever end is closer to you.

• Scalina Spagna: Otherwise known as the Spanish Steps, this beautiful staircase gets busy at night as a popular hang-out spot.
• Trevi Fountain: This is Rome’s largest and most-famous fountain. Prepare for major crowds, and start practicing major patience needed to get your perfect pic!
• Pantheon: Built in 120AD as a Roman (pagan) temple for all gods, it was transformed into a church in 609 AD. Still, everyone calls it the Pantheon, which means “honor all Gods” in Greek. Entry will set you back €5. You can purchase tickets in advance by visiting this site , typing “Pantheon” in the left-hand search bar, and clicking the result.
• Piazza Navona: I’m pretty sure this square is just popular because it’s beautiful! Lots of cafes line the edges of the piazza, which also has two impressive fountains, and a church in between them.
• Largo di Torre Argentina: This is where Roman senators assassinated Emperor Julius Caesar by stabbing him 23 times (dramatic much?) to death in 44 BC.
• Colosseum: Gladiators. Need I even say more?! Though it is now in ruins, back in its heyday, this thing sat 50,000 guests and even had retractable shades. Tickets are €16 for this plus the next two sites, plus €2 if purchased online from the official si te . This price quote is the highest price, but those 25 years and younger get discounts !
• Roman Forum: These are the ruins of numerous important government buildings during the ancient Roman Empire. It’s so cool walking around, seeing how huge the ruins are, and wondering how it must have been back then – almost 2000 years ago!
• Palatine Hill: This is where all the cool kids lived during the Roman Empire – the aristocrats and emperors and all that jazz.
• Arch of Constantine: This arc, built in 302 AD and the largest surviving one of its kind, is right outside the Colosseum.
• Via dei Fori Imeriali: This street is my favorite part of Rome, especially at dusk! You can look down on the Roman Forum from above on one side and view other incredible ruins on the other. It connects the Colosseum to the next attraction below.
• Vittoriano: This huge, marble building almost doesn’t fit in with its ancient surroundings.  But I love it, nevertheless. It is a memorial to Victor Emmanuel II, the first king of the united Italy as we know it today.
• Vatican City: Technically, this area isn’t Italy! It’s its own country – the smallest country in the world – and it’s ruled by the Catholic Pope. There are basically three things to see while here: St. Peter’s Square , St. Peter’s Basilica , and the Vatican Museums . St. Peter’s Basilica is free to enter, but dress code is very strict. Make sure your shoulders and knees are covered. This goes for all genders and ages. There is a slow moving-crowd-slash-line to get in, but I found it moved quickly enough when I went. Once in the basilica, you can climb up to the dome for iconic views. To the right from the entrance, there should be a “Cupola” sign. Follow the sign until at the ticket office, where you can purchase a ticket to either climb the whole way for €8 or one to take an elevator partway up for €10. As far as I know, you can only buy tickets (that aren’t with a guide) in person. The Vatican Museums house the world-famous Sistine Chapel. You’ll pay €20 for entry, plus a €5 online booking fee if you book in advance on the official site , which I highly recommend you do. Entry to the Museums is free on the last Sunday of every month. Seeing Vatican City should take up a whole morning.
• Castel Sant’Angelo: Emperor Hadrian originally commissioned this as a mausoleum for himself and his family, but it’s since been used as a fortress, castle, and currently a museum. I didn’t enter the museum, so I can’t recommend entering, but I think this castle over the river just looks so cool!
• Wander: Explore on your own! Get lost! You’ve checked off all the “can’t miss” things everyone else does, but who wants their trip to be just the same as everyone else’s? If you just run around ticking off attractions, I’m not sure you’ll like Rome. But wandering it’s less-crowded streets, strolling along the river, popping into a random church – these are the things that will leave you loving Rome.

What to Eat in Rome

Food in Italy is good just about everywhere. But each region is known for something different , so why not try all your favorite Italian dishes (and some new ones!) right in the specific regions or cities that they were invented? So throughout this guide, I will be listing and explaining some must-try foods from each place you will be overnight-ing. To start, here are some traditional Roman foods to keep an eye for while in Rome!

• Spaghetti alla Carbonara : This famous Roman dish actually arrived on the Italian scene relatively recently, in the mid-1900s. It is made by mixing whisked eggs and grated cheese into cooked spaghetti, then adding in cured pork, and topping with black pepper and, of course, some more cheese.
• Cacio e pepe : The name of this Roman dish translates literally into “cheese and pepper,” and that’s a pretty good description of what it is!
• Pizza al taglio : While pizza itself was not invented in Rome (don’t worry – you’ll stop by the city where it was born later on in this Italy itinerary!), pizza by the slice, or pizza al taglio, was. But it looks far different to the triangularly-sliced pizza you may be used to back home. Here, the slices are rectangular, and they often come piled high with meats and/or vegetables. It’s considered street food, so it makes the perfect quick lunch if you don’t have enough time for a sit-down meal as you explore the attractions in Rome.
• Supplì : These are another perfect Roman snack to grab while on the go! They are fried, breaded balls of seasoned rice with cheese and sometimes meat inside (essentially, croquettes).
• Bruschetta : This beloved Italian appetizer does not hail from Rome itself, but its origins date back to the Roman Empire, or perhaps even the Etruscans who preceded it. Regardless, as the capital of the Roman Empire, Rome makes a pretty good place to try some authentic bruschetta alla Romana, which is grilled bread rubbed with garlic and topped with olive oil. Of course, no one will blame you if you get the version with tomatoes as well!

Pompeii was an ancient Roman city, famous now for coming to its demise after a tragic volcano eruption . The city, along with nearby Herculaneum, was preserved under all the ash. It has since been excavated, which allows visitors to see a frozen-in-time snapshot of Roman civilization almost 2000 years back!

How to Get to Pompeii from Rome

First, take an early train from Roma Termini train station to Napoli Centrale train station . This takes either one, two, or three hours, depending on what type of train you take! Naturally, the costs are different, too. If you are buying a ticket for the next morning, you can expect to pay €13 for a 3-hour Regional train, €27 for a 2-hour Intercity train, or €48 for a 1-hour Frecciarossa train. If you are buying one month out, the prices for the faster trains drop to €20 for a 2-hour Intercity train, or €25 for a 1-hour Frecciarossa train. And if you buy three months out, the 2-hour Intercity train drops to €15.

Moral of the story? Always buy your long-distance train tickets online as soon as you know your schedule to save money in Italy! If you are taking regional trains, just buy them at the station on the day of, to allow flexibility in case plans change.

OK! So once you arrive at Napoli Centrale, follow signs to the connected underground station called Napoli Piazza Garibaldi . From here, take the Circumvesuviana train for 40 minutes to Pompeii Scavi Station for around €4. (This part was honestly very confusing for me! I accidently went to the Metro 2 area instead of the Circumvesuviana area. So my tip to you is to ignore the Metro 2 signs, and ask for help from staff if you need to.)

At Pompeii Scavi train station, there is a luggage storage service. Drop your bags off here for around €8 per bag. From here, it’s a 5-minute walk to the Pompeii site.

What to Do in Pompeii (Half Day)

The only thing to do in Pompeii is… tour Pompeii ! Entrance to this historical site costs €18, and you should plan to spend 2 – 3 hours here. You can buy tickets at the gate in person or online (for an additional €1 fee) at the official ticket site . Entry is free the first Sunday of every month. You can also check opening hours for the month you are visiting on the site.

If there is any place in all of Italy where you need a tour , it is Pompeii! Otherwise, you’re really just staring at a lot of old rocks with no idea why. There are a few options on how to actually know what’s going on in Pompeii.

• You can join a tour group by paying around €12 in cash on the day of. Guides hang out near the entrance, and the ones certified by the region of Campania have official ID badges. A private guided tour will, of course, cost more.
• You can buy an official audio guide set at the Porta Marina entrance for around €8 and tour at your own pace.
• You can get an audio tour for free by downloading Rick Steve’s audio guide for Pompeii. I did the live tour while in Pompeii, but I’ve used his guides for other Italian sites, and I was satisfied! It’s a great way to save money while still getting info.

While Pompeii is the more-popular site due to its much larger size, Herculaneum is actually the site that is better preserved. Personally, I only toured Pompeii, due to time constraints. But if you are a history buff and don’t mind a busy day, consider trying to squeeze both in!

Sorrento is a perfectly charming place, and it boasts seriously beautiful views over the Bay of Naples and Mt Vesuvius (that really destructive volcano way back when). However, its purpose in this itinerary is as a convenient jumping-off point for the Pompeii-Amalfi Coast-Capri area. I recommend using this as a base for the three nights to limit dragging your luggage around. However, if you prefer to be in the heart of the action, you can head straight to Positano (or Amalfi) after getting to Sorrento from Pompeii.

How to Get to Sorrento from Pompeii

Head back to Pompeii Scavi train station and pick up the bags you dropped off. Then, hop back on the same Circumvesuviana train route and ride for 30 minutes and around €3 to Sorrento. It’s the very last stop on the route , so don’t worry about missing it!

What to Do in Sorrento (Half Day)

If you decide to stay in Sorrento overnight or even use it as a base, I recommend simply walking around town at your leisure. It’s a super cute place to window shop (or actually shop), eat, and enjoy views of the Bay of Naples and Mt Vesuvius.

Amalfi Coast

I know all of Italy is stunning, but get ready for some insane beauty over the next few days exploring the Amalfi Coast! Unsurprisingly, this area is filled with lots of couples and is popular as a honeymoon destination. Though the area is named after the town of Amalfi, it is the town of Positano that truly steals the show. This area is a really special place, and it’s impressive to think about how the Italians built the curvy roads and quintesential houses into the steep cliffs.

How to Get to the Amalfi Coast from Sorrento

There are a few options on how to do this. Two of them include an insanely curvy and crowded two-lane road, so keep that in mind as you decide, especially if you’re prone to motion sickness.

• Option 1: Take the bus. This is the most budget-friendly option. Board the SITA bus 5070 from Sorrento (map below for exactly where). It takes either one hour to Positano or 1.5 – 2 hours to Amalfi. Unfortunately, this bus is crazy crowded , even in shoulder months. You’re not guaranteed a seat, so you might have to stand. I actually had to sit on the floor of the bus and couldn’t even enjoy the views approaching Positano *tear*. If you do snag a seat, sit on the right side for better views. Bus tickets cost €10 for 24 hours unlimited rides and are sold at “tabaccherie” (cigarette shops) or newspaper stands in every town on the route. They can’t be purchased on board the bus! I recommend buying yours in Sorrento at the ticket booth at the Circumvesuviana station, since you’ll already pass through here after Pompeii. You can buy them ahead, but the 24-hours starts once you board the bus and validate your ticket. Check out the bus schedule here .

• Option 2: Take the ferry. This is definitely the most beautiful way to pull up to each town. From Sorrento, this is 40 minutes and €18 one-way to Positano and 1 hour and €19 one-way to Amalfi. Though it won’t happen often, ferries get cancelled if sea conditions are too rough, so allow some flexibility in your plans. Below is a map of the ferry station in Sorrento. You can’t tell from the map, but it requires walking down a staircase . Check out the ferry schedules here .

• Option 3: Hire a private car. This is not a cheap option, but might be worth it with a large enough group. You’ll have to search for price quotes online depending on the car size, company, and pick up and drop off locations. But as an idea, a private transfer from Rome to Positano or Amalfi might cost around €500. If you do hire a private car, I recommend including a stop in Pompeii between Rome and the Amalfi Coast. That way, you’re saving a good amount of hassle between all the train transfers, luggage holding, and buses!

What to Do in the Amalfi Coast (Two Days)

These days are totally interchangeable however you please. There aren’t a lot of “attractions,” per se, in the Amalfi Coast. The main thing to do is to just take in the beauty, whether by shopping in the tourist-geared shops, eating with a view, or taking a swim. You really can’t go wrong! But, if you like to have a plan, I recommend you split two days in the Amalfi Coast like below.

• Positano:  This unreal village is the star of the whole area. You definitely want to get here earlier rather than later, if you can, to avoid midday crowds. For the best view, splurge on a meal at Le Sirenuse Hotel’s La Sponda Restaurant .
• The beach: After exploring during the morning, cool off from the midday heat by taking a swim. The easiest option would be the main beach right in front of the town, Marina Grande beach. If you have your own ride or are willing to bus back and forth 35 minutes each way, check out Fiordo di Furore beach. These two beaches are the most insta-famous ones in the area, but there are many more!
• Amalfi: This is the town after which the area is named. It boasts a beautiful church, the Amalfi Cathedral, which you can enter for €3. It’s actually pretty cool inside, but the exterior is the main show-stealer, in my opinion!
• The Path of the Gods: I didn’t get to do this, but I really wanted to and had planned to! This hike between Amalfi and Positano takes you along the very top of the cliffs and is supposed to be ahhhmazing. Just Google “Sentiero degli Dei” and follow the route. It starts in Bomerano, which you can reach by SITA bus 5080 from Amalfi. It ends in Nocelle, the upper part of Positano. I definitely recommend doing it this direction, since it’s all downhill, and you’ll get better views. Definitely check out the official page for more deets if you’re interested.

• Ravello: This tiny little village high up in the mountains has the area’s most famous villa – Villa Rufolo . Entry costs €8, and you can take the SITA bus 5110 from Amalfi. The ride takes 30 minutes.

What to Eat in the Amalfi Coast (and Nearby)

These are some traditional Italian foods from the Amalfi Coast and Naples.

• Mozzarella di Bufala : This famous Italian cheese is made from the milk of the Italian water buffalo, instead of milk from cows, like mozzarella without the “di bufala” is. It hails from the region of Campania (the region where Naples, the Amalfi Coast, and Capri are), but especially Salerno, a city just to the east of the Amalfi Coast. A great way to try this item would be in a caprese!
• Lemoncello : You will find this sweet, lemon liquor practically everywhere you look upon arriving in the Amalfi Coast.
• Pasta al Limone : With all the lemons in this area, it’s no surprise they found their way into the pasta dishes as well. This creamy dish with cheese and lemon is so unique and a must try when in the area.
• Anything Seafood : Since this area hugs the coast, get your fill of fresh seafood pasta dishes while in this region!
• Pizza : The birthplace of pizza is Naples, and while you won’t have time to stop for a bite when transferring from Rome to Pompeii, you might have time when transferring from Capri to Florence (covered in the next section of this itinerary). If not, the Amalfi Coast was part of the former Kingdom of Naples, so it’s the next best place to try the Italian staple. Authentic Neapolitan pizza is made in a wood oven (this part is crucial!) with only the simple ingredients of dough, tomatoes, mozzarella, olive oil, and a couple fresh basil leaves.

The celebrity-favorite island of Capri makes for the perfect final day in south Italy before your itinerary takes you up north. It’s known for yacht-studded waters, glowingly-blue grottos, and upscale shopping. Maybe just reading this hurt your bank account a little bit… but not to worry! I’ve got you covered with how to visit Capri on a reasonable budget.

How to Get to Capri from the Amalfi Coast

The only way to get to Capri is by boat (it’s an island – duh!). Ferries will be from Sorrento, from Positano, and from Amalfi. Expect €25.50 for a 50-minute ride from Amalfi, and less from the other two.

You’ll need to drop your bags off in storage while you explore.

You should be able to either near the main docks in Marina Grande on Via C. Colombo, to the left of Bar Grotta Azzurra, at a souvenir shop with a “deposito bagaglio left-luggage” sign above the door… or under the funicular station, past the signs for “toilette,” along the tunnel part of Via Acquaviva. This was my plan when I did this trip, but I couldn’t locate either storage place!

Luckily, an Italian waiter came to my rescue and offered to hold our bags in the restaurant all day if we ate at his place. Honestly, I’m sure you would have no trouble arranging the same.

But if you want to be more prepared, another baggage storage option (which I haven’t tried) includes Bounce . You can book in advance online for €5 a day. Just search “Marina Grande, Capri” and select an available location in the Marina Grande harbor.

What to Do in Capri (Half Day)

There is so much to do in Capri that you’d have trouble fitting it all into a single day, let alone a half day. So you’ll have to pick and choose what interests you most from the below . The island’s official site actually has a pretty good itinerary you can follow, too.

• Marina Grande: No need to even add this to your list. You’ll inevitably walk by this colorful harbor-front area after disembarking the ferry.
• Boat tour around the island: This is the best way to truly appreciate Capri’s magnificent cliffs. You’ll also go past Faragolioni , that ultra-iconic arch in the water. Boat tours can also include an add-on of the Blue Grotto. Without the Blue Grotto, expect €21 for an hour-long tour.
• Blue Grotto: This cave is probably the most famous attraction in Capri! Unfortunately though, it’s a bit of a time-suck because of that. We were told we would have to wait on a small, bobbing rowboat for an hour before our turn to enter, so we skipped the grotto, even though our boat tour included it. The only way to avoid the long wait is to be the first ones out, but the best time for viewing is noon – 2pm, so it’s quite the dilemma. Tours departing from Marina Grande cost €18.
• Piazzetta: This is the island’s most famous square. Be sure to stroll down the Via Camerelle while in the area.
• Anacapri: The island of Capri actually has two towns; Capri and Anacapri. Anacapri is less crowded than Capri, and it has more artisanal shops, rather than just high-end boutiques. While here, definitely pass Piazza Vittoria , the main square. You can also ride the chairlift 12 minutes to Mount Solaro for a view (€12), or walk there in 30 minutes.
• Villa San Michele: Entry costs €10 for some spectacular views.
• Gardens of Augustus: From here, you get that classic Capri viewpoint of the Faraglioni . Entry only costs €1.50!
• Marina Picola: If you’d rather spend your half-day relaxing at the beach instead of running around the island, this beach is a classic.

As the birthplace of the European Renaissance , Florence is known for all things art. It houses world-famous masterpieces, such as the David statue by Michelangelo and The Birth of Venus painting by Botticelli. Personally, I was expecting a bit more from Florence than I got, since everyone and their mothers raaave about it in comparison to Rome. (For the record, I’m staunchly team Rome!) But maybe I’m just not into art enough? That being said, though, it’s definitely still a can’t-miss Italian destination with plenty to do.

How to Get to Florence from Capri

(Psst: You’ll actually be doing this transfer from Capri to Florence on the same day that you visited Capri. Then, the next day, you’ll wake up in Florence to start your two full days there. Just scroll back up to the itinerary summary at the top of this page if you’re confused!)

First, get back to Napopli Centrale from Capri . I recommend taking the ferry directly to Naples from Capri. This will be 1 hour 25 minutes for €12.30 or around an hour for €20 – €25. Then, take a taxi from the ferry station in Naples to Napoli Centrale. When I did this, the taxi cost me €20. I also stopped and picked up a pizza to go while in central Naples. After all, Naples is the exact birthplace of pizza! How could I not?!

Alternatively, you can take a ferry from Capri to Sorrento. This takes 20 or 30 minutes minutes and costs around €21. Then, go up those stairs to the Sorrento Circumvesuviana station, and ride the Circumvesuviana train to Napoli Piazza Garibaldi for 70 minutes and around €4. From there, walk the underground connection to Napoli Centrale. This is a little more hassle – hence why I recommend the ferry straight to Naples – but it’s cheaper.

Either way, once in Napoli Centrale train station, take a direct, 3-hour train to Firenze S. M. Novella train station . Since this is a long distance, don’t even think about taking one of the Regional or Intercity trains ! These will set you back 2 – 4.5 hours. Trust me – just book the Frecciarossa train for this route as soon as you have your dates to get the cheapest price you can. As an idea, it will cost €86 if you buy the day before, €35 – €55 (depending on departure time) if you buy two weeks in advance.

What to Do in Florence (Two Days)

Many people recommend considering the Firenze Card , which covers a lot of attractions in the city. For two days in Florence (or even three days in Florence), the card is not worth it. Instead, I recommend purchasing the Brunelleschi Pass . This grants entry into the Duomo, a climb to the dome of the Duomo (the Cupola), a climb to the bell tower (the Campanile), entry into the baptistery, entry into the Duomo museum, and entry into the crypt beneath the church. It costs €30 if bought on the official website .

Now that that bit’s out of the way, here’s everything to do in Florence in two days! I haven’t split it out into separate days here, because I think it’s better if you decide . Do you like to visit one museum a day, or have one single day devoted to all the museums? Do you want to avoid climbing stairs twice in the same day, or do you not care? Do you prefer a viewpoint for sunset, sunrise, or can’t be bothered? These are the things that will determine what you do each day, so I can’t recommend that for you. But don’t worry – most sights in Florence are rather compactly located, so planning a route shouldn’t be an issue!

* Items with an asterisk are totally skip-able if you’re not interested, but I’ve included them since they’re included in the ticket I recommended above. If you want a more-detailed breakdown of the below, plus pictures, check out my full guide on everything to do in Florence .

• Basilica di Santa Maria del Fiore (aka, the Duomo): It’s the third largest church in the world, was instrumental in the Renaissance, and is the symbol of Florence. Entry is free, but prepare for a massive line at least an hour long.
• Cupola: Bruneschelli’s Dome, named after the architect who designed it, is actually the most impressive part of the entire church. Architecturally, it was the first of its kind. He literally had to invent new tools and architectural systems to do it! Definitely climb up the steps for the view from the top. You’ll have to select a specific time slot, though, when you buy your ticket! Otherwise, you will be turned away and asked to return.
• Campanile di Giotto: Yes you already climbed up the cupola, but there’s another viewpoint! This time, the view is the cupola itself.
• Battistero di San Giovanni: This is the building right across the main cathedral. The Byzantine-like mosaic inside was actually pretty cool in contrast to all the typical-Renaissance paintings. Everyone will be snapping pics of the gold doors outside, but those are copies. The real ones are in the Duomo Museum!
• Duomo Museum*: Since you already paid, it might be worth a quick visit. It will help you understand why all this Duomo stuff in Florence is such a big deal!
• Crypt of Santa Reparata*: This is included in the Duomo combo ticket, which was the only reason I saw it. But once I got there, it was actually much more than I expected! It’s basically church ruins from 405AD inside the main church. The unfortunate thing about the crypt is that you have to wait in the same line as for the free Duomo entry. So definitely time these two activities together!
• Piazza della Repubblica: One of the main squares in Florence.
• Piazza della Signoria: This square has a lot going on! The best part is definitely the Loggia dei Lanzi . It’s basically a free, open-air museum of dramatic sculptures that really should be in one of the museums. (Like really though, I’m super surprised these are just out there!) Also in this square is a copy of the David statue , for those of you who don’t pay to see the real thang.
• Palazzo Vecchio: I didn’t enter except for the free courtyard. But apparently it’s supposed to have a great view of the Duomo.
• Ponte Vecchio: This iconic bridge has become synonymous with Florence itself! It was originally a passageway so the Medicis (a super rich family that basically made Florence….well, Florence) didn’t have to walk with the commoners on their commutes from their palace. Since then, shops have been added and create the look it has today. Prepare for major crowds!
• Piazzale Michelangelo: The best viewpoint in all of Florence – hands down! I recommend trying to time your visit with sunset, but it’s gorgeous anytime. (I went three times in my visit….so I would know.) It requires an uphill walk and is the furthest out you’ll get from the city center. So make the trek worth it! Bring some snacks and hangout for a while like everyone else does.
• Accademia Gallery: Unfortunately, the only reason to enter this gallery is for one piece of art. The David. Don’t at me, art fanatics. You decide if that’s worth it for you, but y’all know me! I have such FOMO that I had to pay €16 and see for myself. Pro-tip: avoid the lines AND the €4 online skip-the-line fee to book by visiting on one of the days they allow night visits! I got in lickety-split! No one really knows about it, which is why it’s so empty, so let’s try not to tell too many people? *wink* Confirm the night time hours, or book online, here .
• Uffizi Gallery: Uffizi actually means “offices” in Italian, which makes sense, because this building used to be the Medici’s offices. Now, it’s a museum, and a world-famous one at that! Its most-famous art piece is the Birth of Venus painting. Entry costs €25, plus €4 for the skip-the-line online booking fee on the official site . Everything I read beforehand swore up and down that wait times are upwards of three hours. But when I went (mid September, early afternoon) there was no line in sight.
• San Lorenzo Market: This is Florence’s most-famous market. Stop by here to shop leather and eat in the indoor food stalls.
• Santa Croce: I didn’t enter this church, since admission was not free, but I do think it’s in a picturesque area and warrants passing by!
• Palazzo Pitti: Normally, palace equals royalty…not in Florence! This palace belonged to the Medicis (shocker). I personally have seen way too many European palaces at this point. So I forwent paying the €16 entry fee (€22 if seeing the gardens as well) and only observed from outside. But I did regret maybe not having arrived earlier in the day than I did, to buy just a Boboli Gardens ticket (€10)! You can purchase online in advance from the official site (the same site as for the Uffizi) for an additional €3 fee, but it was not very crowded at all when I was there.

What to Eat in Florence

These are some Florentine and general Tuscan traditional dishes to try while in Florence.

• Bistecca alla Fiorentina : You will have no trouble finding Florentine-style beefsteak to try in a restaurant in Florence. Keep in mind that since it’s a pretty thick cut, getting the inside well done would be difficult without ruining the outside of the steak!
• Gelato : Yep – everyone’s favorite frozen Italian dessert made from milk, cream, and sugar is from the city of Florence! Now, that absolutely does not mean you should wait until arriving in Florence to try authentic gelato (after all, if you’re not having gelato at least once a day, are you really even on vacation in Italy?). But, maybe it does mean taking a gelato making class at the Carpigiani Gelato Museum ?
• Biscotti : These dry, crunchy, oblong-shaped almond cookies are traditionally called cantucci. They originally come from the Tuscan city of Prato, which sits just north of Florence.
• Crostini Neri : Also known by the names of crostini di fegatini and crostini Toscani, this typical Tuscan appetizer is toasted bread with a chicken liver paste spread atop.

Is there anything more quintessential Italy than the image of the leaning tower of Pisa? It’s funny how such a famous Italian landmark is from the most random of Italian cities! Luckily, Pisa is a necessary transfer station on the route between Florence and the Cinque Terre, so you lose almost no time making a couple-hour stop to get out of the station, snap your cliché photographs, and get right back on your way .

How to Get to Pisa from Florence

Take a regional train from Firenze S. M. Novella train station to Pisa Centrale train station . This is a 1.25 hour ride and costs €9.30. Once at the train station, head to the luggage storage in the station, and drop off your things for €5 per bag. Check out the storage website . Two other storage options near (but not inside) the station include this and this .

What to Do in Pisa (Half Day)

Personally, because this two week Italy itinerary is so jam packed, I recommend you head straight to the leaning tower, snap your pics, and head back to the train . The walk is about 30 minutes each way, plus I expect you’ll spend about 20 – 30 minutes trying to get that perfect leaning picture. So budget 1.5 – 2 hours for your stop in Pisa. The reason I recommend this is so that you can have as much time as possible in Cinque Terre.

But , if you want more than just a photo, there actually are a decent amount of things to do in Pisa.

• Climb the leaning tower: It’ll cost you €20 and you’ll need to choose a time-slot! The line looked long as I passed by.
• Go inside the Duomo (for free!): You still have to get a ticket, though, and time slots do book out. Do this at the building with all the signs, right by the leaning tower.
• Visit the Baptistery: I didn’t enter, but pictures do look very pretty! This alone will set you back €7, or you can pay €10 or €27 for a four or five-monument combo, respectively. See the official website to understand!
• Chiesa di Santa Maria della Spina: I actually know nothing interesting about this church, but I think it looks super cool. Try to walk by it by using Ponte Solferino bridge on your way back to the train.

Also, Pisa is a really pretty Tuscan city! So there’s absolutely no harm in sticking around longer and actually seeing the city of Pisa. You can just budget extra time to walk around before heading back on the train, or even stop for a meal.

Cinque Terre

Cinque Terre translates literally into the “five lands” in Italian, representing the five villages that make it up. The villages are Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore . I highly recommend not choosing Corniglia as a base, only because there is a 350+ step staircase from its train station to the actual village. (Psst: Check out my guide on alternative, cheaper Cinque Terre bases .)

How to Get to Cinque Terre from Pisa

Take a regional train from Pisa Centrale train station to your preferred Cinque Terre village of choice. All journeys will require a train transfer at La Spezia Cenrale station. You might consider using La Spezia as your base, since it might be cheaper, saves some train hassle , and is included in the Cinque Terre Rail Pass (more on the pass later on – don’t worry!). Train times and prices are below.

• Pisa to La Spezia: 75 minutes and €8.40
• Pisa to Riomaggiore (the southern-most village): 1.5 – 2 hours, because it requires a transfer at La Spezia, and €9.45
• Pisa to Monterosso (the northern-most village): 1.5 – 2 hours, because it requires a transfer at La Spezia, and €10 – €12, depending on the time

What to Do in Cinque Terre (One & a Half days)

The main things to do in Cinque Terre are visit all five villages and hike between them. Unfortunately, more than half of the famous trail is closed for reconstruction after an avalanche. Currently, the only open part of this specific trail is from Monterosso to Vernazza and from Vernazza to Corniglia, but you can check here for updates.

To hike it, you’ll need to pay (unless it’s winter when there’s apparently no one checking). For this itinerary, get the two-day €33 tr ails and train card . This grants you unlimited access to the paid trails and unlimited train travel between Levanto and La Spezia. It also allows you free public toilet usage in the villages and free WiFi at the village train stations. You can buy in person at any train station or information desk.

Besides the hikes, there is no real to-do list of attractions for each village, so just stroll around at your leisure, swim when you feel like it, and enjoy the beauty! If you’re looking to get off the beaten path (literally), I wrote about the free Cinque Terre hikes you can do instead of the paid ones. The views are better, too, in my opinion!

Day One (Half Day)

Riomaggiore and Manarola: After settling in from Pisa, I recommend splitting the remainder of this day relaxing and hanging out in Riomaggiore and Manarola. Try to be in Manarola for sunset , to get that cliché Instagram view. That café you see everyone take their pics at? It’s called Nessun Dorma .

Hike Monterosso to Vernazza to Corniglia: Finish up the last three villages, and get some hiking in! You can do the hike either direction you please. I highly recommend hiking with your swimsuit underneath , because there is nothing you’ll want to do more after a hike, than jump into that water!

What to Eat in the Cinque Terre

These are some yummy traditional foods to try while exploring the Cinque Terre.

• Pesto alla Genovese : This beloved pasta sauce made from crushed garlic, pine nuts, salt, basil leaves, olive oil, and cheese hails from the region of Liguria (the region where the Cinque Terre are located). More specifically, it comes from Genoa, as the name implies. But anywhere in Liguria is an authentic place to try a pesto dish!
• Focaccia : A warm slice of this fluffy, oily goodness makes for the perfect snack while zipping from village to village, or even a quick breakfast alongside some coffee before heading out for the day. It is made from flour, water, olive oil, salt, and rosemary, so it’s a great option for vegans as well.
• Farinata : Another delicious vegan food to try, farinata is a flat pancake-or-crepe-like food made from chickpea flour. You can pick up a slice as a snack on the go.
• White wine : Especially if you hike the trails between the Cinque Terre, you’ll notice a lot of white grape vineyards scaling the cliffs of this area. So it’s no surprise Liguria is known for its white wines!

Milan is known as fashion capital of Italy …and honestly not much else! It’s a city many aren’t enthused by, and I wouldn’t recommend it if you only have one week in Italy . But for a two week Italy itinerary, I really do think it’s appropriate. It’s home to the world-famous Last Supper painting, an iconic Duomo…and not a whole lot else! Which, in my opinion, makes a perfect, not-too-hectic stop towards the end of your epic, two week tour di Italia.

How to Get to Milan from Cinque Terre

Take a train from La Spezia Centrale to Milano Centrale . I recommend taking the direct, 3.5 hour InterCity train. Expect to pay around €20 if you book a month out, around €25 if you book two weeks out, and around €29 the day of.

What to Do in Milan (One Day)

• See the Last Supper : Book this is as soon as you can! Tickets to see Leonardo Da Vinci’s masterpiece are available on the official site three-ish months in advance. They cost €15, plus a €2 online fee, and allow you a 15-minute viewing of the famous painting in the Santa Maria delle Grazie church . On the first Sunday of every month, tickets are free, so all you would pay is the online booking fee. Unfortunately, official tickets tend to get scooped up on the first day they’re available by tour operators. So if you don’t get a ticket yourself, the only other way is to book a guided tour. These run for around €40 and above.
• Go to the Roof of the Duomo: Entrance to the roof costs €14 on foot or €16 by elevator, but €20 and €25 respectively if you add entry into the church itself. You can purchase tickets in advance on the official site . Remember to be dressed modestly to be able to enter!
• Galleria Vittorio Emanuele II: It’s to the left of the Duomo, and it’s just way too glamorous not to walk through! It’s also Italy’s oldest active shopping gallery. If you fancy a rooftop view of the Duomo, apparently you can take a €12 elevator up to the top.
• Navigli Lombardi: This area of a couple canals is super cute to walk around or eat in the evening!
• Starbucks Reserve Roastery: I’m not even a coffee fanatic, but I just had to pop my head into the first Starbucks in Italy. Definitely the bougiest Starbucks I’ve ever seen.

What to Eat in Milan

• Risotto alla Milanese : No trip to Milan is complete without trying this famous dish! Its yellow color comes from the saffron used, which just so happens to be the world’s most expensive spice – more expensive than gold.
• Cotoletta alla Milanese : This veal cutlet is similar to the Wiener Schnitzel you might be familiar with from Austria, but it is cooked and served with the bone in.
• Panettone : This world-famous Italian sweet bread dotted with candied fruits and raisins hails from the city of Milan. It is especially popular during Christmas and New Years.

I was worried before getting to Venice that I would hate it. So many people complain about its crowds, its mosquitos, its flooding… The list of negatives seems endless! But after just my first hours in Venice, I really felt like people give it a bad rep. Yes it is way too crowded in the center. But honestly, the crowds are completely justified.

I would describe Venice as: so beautiful, it’s unreal . And can you really blame crowds for flocking to something like that? Try to knock out all the main sights at less-crowded hours. Then spend the middle of the day exploring the rest of the city, where it’s much, much less crowded, but just as beautiful. Do that, and you might just end up liking it!

How to Get to Venice from Milan

Take a train from Milano Centrale to Venezia Santa Lucia . I recommend taking the direct, 2.5 hour Frecciarosssa train if you book a month in advance, when it’s around €29 for the morning train. If you buy closer to the departure date, it’ll be €52. Otherwise, the regional train (the type that costs the same no matter when you buy it) is €21.95, and the transfer in Verona only adds an hour more to your journey.

Once in Venice, you’ll want a vaporetto pass . Trust me – you don’t want to be lugging bags up and down those bridges! If you are 29 years-old or under, I highly recommend buying the Rolling Venice Pass . I wish I knew about it earlier! It costs €6, but in order to buy it, you must also purchase (at minimum) an unlimited three-day vaporetto pass for €27. With the pass, you also get discounts on many attractions , like a €12 discount entrance to the Doge’s Palace! The one-day transport pass alone costs €20, and the two-day pass costs €30, so getting the Rolling Pass quickly pays for itself. You can buy these passes online or in person once in Venice.

What to Do in Venice (Two Days)

Assuming you take a reasonably-timed morning train from Milan, you can get to Venice in the late morning. Add some time for navigating the canals to locate your accommodation, and you basically have a little under two days in Venice. (If that sounds like too little, you can remove the Burano and Murano day trip from the suggested itinerary below. But honestly, you’ll be fine!) If you want a more detailed walkthrough plus photographs of each of the below, check out my article on best things to do in Venice .

• Piazza San Marco: This main square is where most of the (tourist) action is. Firstly, there’s the Basilica San Marco . It’s €3 to enter, but there can be a very long line most hours of the day, so be careful what time you go. I went in the middle of the day when I saw it was shorter, and was in and out in 10 minutes! If you’d rather not risk it, you can book your time slot online during high season for a €3 booking fee. Large bags are not allowed inside, but there’s luggage storage nearby that the basilica will tell you to use. Across from the basilica is the Campanile (the bell tower). You can take the elevator up it for €10 if purchasing in person, or pay a €2 booking fee to reserve online in advance . If you want to skip the line, it’s the same website as the basilica. There’s also the Doge’s Palace . Entry is €25 if booked over 30 days prior, but only €13 with the 29-year-old Venice Rolling Card I mentioned above. See the official site for more deets.
• Bridge of Sighs: Walk around the Doge’s Palace, making a left turn around the corner along the water. From the first bridge, you’ll see the famous Bridge of Sighs. It’s named so because it connects to the prisons, and prisoners sighed while taking one last look over beautiful Venice as they walked through the bridge to their dooms.
• Rialto Bridge: If you haven’t figured out by now, Venice has a lot of cool bridges!
• Accademia Bridge: This was my favorite bridge , because it has such an amazing view.
• Take a half-day trip to Burano and Murano: Honestly, I did find this a little overrated, but maybe I’m just bitter because I got bad weather? I have an in-depth guide on how to visit the islands from Venice , as well as what each island is all about.
• Fondaco dei Tedeschi: This shopping center has free rooftop views of Venice, but you’ll need to book in advance (I recommend at least a day or two prior to get your ideal time slot). It’s located right at the edge of the Rialto Bridge on Calle del Fontego .
• The Grand Canal: The obvious way to float around Venice is on a Gondola. This will set you back €80 per gondola (six people max) in the daytime, or €100 sunset and later. Prices are fixed, so check current gondola prices , and don’t let anyone overcharge you. Alternatively, you can ride the vaporetto between San Marco and the train station, which is free since the vaporetto pass for the Burano and Murano day trip is still valid! I reeeeally recommend timing this during sunset. It’s SO pretty (and a lot less hectic).

What to Eat in Venice

These are some Italian favorites to try that come right from either Venice itself or the Veneto region.

• Tiramisu : This beloved Italian dessert made from coffee-dipped ladyfingers, whip, sugar, mascarpone cheese, and cocoa is not from Venice itself, but rather from the nearby city of Treviso to its north. Nevertheless, anywhere in the region of Veneto is an “authentic” place to try this yummy sweet.
• Risotto al nero di seppia : Some may find the black color intriguing, while others may find it offputting. Either way, squid ink risotto is a must try while in Venice!
• Aperol Spritz : Also called a Spritz Veneziano, you’re sure to spot this bright orange drink all throughout your two week Italy vacation. But this cocktail made from prosecco wine, Aperol, and soda water was actually invented in the Veneto region.
• Belini : Another famous Italian cocktail invented in Veneto – but this time from the exact city of Venice itself. In fact, you can have it right in the very bar where it was invented, Harry’s Bar, in San Marco Square. (But be warned – this is a very expensive way to have it if you sit down at one of the tables there!) This cocktail is made with Prosecco wine and peach purée or nectar.
• NOT PIZZA : If you are looking for an “authentic” Italian pizza, Venice is not the place to have it. As I mentioned above when explaining where you should try authentic pizza (Naples), pizza as it was first invented must be made in a wood burning oven. And Venice has none! Venice is built out of wood, and apparently wood burning ovens were banned after a pretty bad fire in the past. So if you fancy a pizza while in Venice, that’s fine, but know that it’s very far from “authentic” pizza!

How to Get Out of Venice

Alas, your epic two week Italy trip has come to an end! You’ll need to get out of Venice. Venice’s international airport is Venice Marco Polo Airport (VCE) . There are a few ways you can get from Venice’s city center to VCE.

• Option 1: By bus . From the Venice Piazzale Roma ATVO bus stop, ride the bus for €10. The ride takes 30 minutes. Purchase tickets at the ATVO ticket office in Piazzale Roma, from the automated ticket machine outside that ticket office, or online .
• Option 2: By water bus . From any of Venice’s Alilaguna water bus stops at San Marco, Rialto, Fondamenta Nuove, or Guglie, ride the water bus for €15. The ride takes up to 1.25 hours. Purchase tickets onboard the water bus or online for a €1 discount. Private water bus rides are also an option.
• Option 3: By taxi . The fare for this 30 minute ride from Venice Piazzale Roma is around €40. Make sure you get into an official taxi. They should accept card, and you can double check this as well as fare before getting in. You can also purchase online in advance (select “Town > Venice (P.Roma)” for Venice city center).

Adjustments to this 14 Day Italy Itinerary

• Starting in Venice instead of Rome: You can totally do this two week itinerary in reverse order. However, when you get to Florence and head to the Amalfi Coast, keep the Amalfi Coast portion in the same order. That is, still start at Pompeii and end in Capri. Then, head from Capri to Rome to end the trip.
• Flying in or out of Milan instead of Venice: Venice and Milan can easily be reversed in the itinerary, in case you find a good Venice flight. You’ll just train between Venice and the Cinque Terre instead of Milan and the Cinque Terre. This will, however, add about 1.5 hours to the train journey.
• Visiting Siena instead of Milan: If you already know you have no interest in Milan, consider replacing that day with adding an extra night in Florence. From there, you can make an easy day trip into Siena (or any other town in Tuscany!).
• Visiting Lake Como from Milan: If you can add just one extra night in Milan to this fourteen day Italy itinerary, you can squeeze in a lovely day trip to Lake Como from Milan . I detail exactly how to do it without a tour group and on a budget here .
• Skipping Capri if it seems too hectic: If the half-day in Capri and evening train to Florence sounds too hectic, I don’t blame you. It might be more enjoyable to save Capri for a return trip to Italy. Use the extra day as another day in either the Amalfi Coast, or add an extra night in Florence or Milan for one of the day trips I mention above.

Any Questions on These 2 Weeks in Italy?

I know that was A LOT! If you’re planning your own two week itinerary for Italy soon and want some personalized advice, drop a comment below with your questions . Whether it’s a two week Italy honeymoon or you’re backpacking Italy two weeks, I love playing travel agent for people!

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163 comments.

Hi, Thank you so much for the detailed plan. My family of 4 are planning to go to Italy for 2 weeks starting August 1st and coming back on the 15th or 16th. I have two kids that are 2 and 4 so I would like to hear more details on strollers, walking distances. Is amalfi good destination for my situation or should we focus on the north side of Italy. Any tips and tricks would be much appreciated. Thank you

That Travelista

I’m glad this itinerary has helped you!

I’ve never traveled with strollers in Italy. But it could be annoying in places like Positano, Amalfi, and Capri, due to how steep the villages are built into cliffs. You could remove the Amalfi Coast portion of this itinerary and use those days to add on some extra days in Cinque Terre if you don’t want to lose time on the coast. In Cinque Terre, the town of Monterosso is flat (the rest are not, especially Corniglia) and has a proper beach, so that town might be of interest to you as a family with kids.

You could also add an extra night to Venice, as it might take longer to get around with a stroller due to all the bridges, even though it is rather compact.

Rome is probably the least compact of all the main cities in terms of attractions. So you might want to add an extra night or two there too, to be able to go slower and allow time for naps.

So in summery, I’d remove Amalfi Coast and tack on the extra nights to the other stops in order to go slower. In Cinque Terre, I would focus on Monterosso.

I hope some of that helps!

Hi Em!!! I love this article!! I’m getting married this August and my future husband and I want to travel to Italy next year for our official honeymoon!! based on your article we would want to go in early September, this is when we usually like to travel anyways to avoid crowds lol. It has always been my dream to travel to Italy and we are planning on going for about 2 weeks. Where do you recommend we start?? A must for us is definitely Rome and definitely the coast as I love the beach; but we would like instead of staying overnight in multiple places, we want to maybe stay in 2 or 3 main cities and then take day trips from there. Anywhere from 2-3 hr tops train rides. Any recommendations as to how we should do this? I look forward to hearing from you!!!

Hi Cristina,

Thanks for letting me know that you love my itinerary! Congrats on your engagement! Italy will make for a lovely honeymoon destination.

I would consider visiting Venice/Florence/Rome in one week and then Amalfi Coast (based in Positano) the next week. The Amalfi Coast is very much honeymoon vibes (I even mention in this article that there were many couples). The way I have it in this itinerary is the bare minimum time to see the highlights, but you could spend a whole week there and it would be much more enjoyable. You could do it in either direction: Venice > Florence > Rome/Amalfi Coast > Amalfi Coast/Rome (whichever you didn’t see after Florence) OR the exact reverse. You can fly into/out of Venice and Naples if you find good flights, or Rome instead of Naples if not.

That would be 4 bases. If you really want 3 bases or less, you could visit Florence as two round-trip day trips from Rome on the fast train. It’s 1.5 hrs each way.

I hope that helps!

Claudia Mandish

Please can you clarify the order of cities if arriving and departing in Milan for 2 weeks covering Milan / como / Venice / positano .

Hi Claudia,

For those destinations, I would recommend Milan > Lake Como > Venice > Positano > Milan OR the exact reverse.

Hi Em, thank you so much for taking the time to respond . Italy is such a hot destination and I’m sure a lot of people find this infos useful . I know I have and pretty much read all the comments . I bookmarked you as well so its easy to find you for my next destination . We are arriving in Milan July 18 at 9 am, I’m not sure if I should make Milan my base and just do day trip to COMO /Bellagio/Varenna or stay in Milan for one night and move to Como for 2 nights . Im also hoping to stay one night in Venice- Cinque Terre/ Florence /PISA just for the picture bec my 10 year old son requested this / Tuscany (just to visit the Terre di Saturnia – Rome- Positano/Amalfi . we are flying out of Rome and we have exactly 2 weeks (excluding flights).. Is this the “correct ” sequence of cities location wise .. Your recommendation is much appreciated .. thank you so much .. Best travel blog and happy to find you !

Thanks for your kind feedback! I’m glad my site has been helpful. 🙂

With regards to Lake Como, it’s really up to you and how much time you want to spend there. There is definitely enough to see to spend several days on the lake. The one day Lake Como itinerary I have is packed to the brim and just includes the highlights. Two days would allow you to better fit in Como city, if that is what you mean by “COMO” in your comment. So it’s really up to your personal preference and your time constraints.

The sequence you have listed out seems fine. I would consider making Pisa a stop between CT and Florence as I have in this post (or as a day trip from Florence) as opposed to spending the night. I can’t comment on Terre di Saturnia because it’s complicated to reach without private transport, so I haven’t visited it myself.

Hope that helps!

I am so overwhelmed planning this trip for my family and so thankful I found your blog. Family of 4 travelling with my 20 year old daughter and 11 year old son, flying out of BWI to Milan July 17 – Aug 1, 2024. My daughter wants to spend time on the beach/lake , my son wants to see the leaning tower. I am going to print your guide , thank you of being so detailed ! What can I omit or add ? We are traveling light with hand carry and personal item each . If we go with private transport , do we just arrange them with the hotel or is there a website I can check and book in advance. We did London/amsterdam /paris/germany last summer and we are so spoiled with the convenience of uber for transportation. From your post and some of the comments, I guess Uber is not widely used but just find taxi stand, do they do meter or you set and agree on a price before hopping in .. Just curious if you have ideas on this

I’m glad to know that my post has helped you in your planning!

This itinerary as I have it has 2-4 days on the sea (1 day in Cinque Terre, up to 2 days in the Amalfi Coast, and up to 1 day in Capri. The only problem, though, is that it is a lot of moving around. So if you want to spend more time in a single beach place, you can remove 1-2 of the three destinations to add those days to the one that interests you most. So for example, cut out Capri and use that half day trip as an extra half day to just lay on the beach in the Amalfi Coast. Or cut out Cinque Terre and use that day as an extra day in the Amalfi Coast, etc.

The leaning tower, as you will have read in this itinerary, can be a day trip from Florence. If you cut out Cinque Terre, you can just do Pisa as a round-trip from Florence or as part of an organized tour group from Florence, rather than as a stop en route to Cinque Terre, as I have it in this itinerary.

If you would like to see a lake, there is also the option of doing a day trip to Lake Como from Milan , which I have a guide on. That would require one day taken from elsewhere.

Everything I recommend in this guide is kind of the minimum amount of time I deem appropriate for each destination, so it’s hard for me to tell you what to cut since you have exactly 14 days, just like my itinerary. So just decide what interests you and your family least.

That’s great that you are traveling carry-on only. I think that’s a great idea for a trip of this length and in warm weather!

As for transport, you can reach out to your accommodation to schedule private transport for you, but there are also options you can look at online to book yourself for a fixed price in advance (I’ve used such things in other countries, but never in Italy, so I can’t provide much personal recommendation. Just check the reviews that company has.). Uber does exist in Italy, though I’ve personally never used it. Italy has a really good train network between all the major tourist stops, and the train between major cities is MUCH faster than going by car. Private transfer around the Amalfi Coast might be worth it, though, especially splitting the cost as a group. For cabs, prices are set fares between city centers and their respective airports (I quote some of those prices in this itinerary), but it will be metered otherwise.

Greetings, Em!

Thank you for your superb itinerary. My fiancée and I will be spending sixteen days in Italy for our honeymoon next year, during April-May. If we count air travel, then it’s really fourteen days to enjoy the country. We’ll arrive in Rome on April 23rd, 2025 at 12:50 p.m. and depart from Venice on May 8th at 7:10 p.m. Here’s our planned itinerary:

April 23rd: Arrive in Rome at noon-ish and already start the itinerary. April 26th: Leave Rome (later in the day) and arrive at Pompeii, Positano and the Almafi Coast (PPA.) April 29th or 30th: Leave PPA and arrive at Capri. May 1st: Leave Capri (early) and arrive at Florence. May 3rd: Leave Florence (early) and arrive at Pisa. May 3rd/May 4th: Leave Pisa and arrive at Milan. We decided to skip the Cinque Terre and go straight to Milan. May 5th/May 6th: Leave Milan and arrive at Venice. May 8th: Leave Venice at 7:10 pm flight.

I think we should skip either Capri or Pisa so that we add an extra day to either Florence, PPA or even Venice. Or, maybe take one of the two days in Milan and add it to Capri, Florence or PPA.

What would you recommend? I don’t think there’s much to do in Milan. Capri sounds more interesting. Or maybe Florence deserves a third day? Or Venice a fourth day? I believe Rome already has enough. Maybe we can even cut half a day from Rome.

Hi Murillo,

I’m glad to know you like my itinerary!

I would recommend adding one night to Florence. This is because the journey from Capri will be around 5 hours, between the ferry to Naples, the cab to the station, and the train ride to Florence. So if you depart from Capri at 8am, for example, you’d arrive in Florence around 1pm, then check in to your hotel, and then have closer to 1.5 days in Florence instead of 2 full days, which I recommend. If you do add one night to Florence, you could instead leave Capri in the late afternoon, say 4pm, and arrive in Florence around 9pm. So it gives you a good chunk of extra time in Capri as well and thus kind of kills two birds with one stone.

But Capri can also be a round-trip day trip from Positano or Amalfi or Sorrento. So incase you do remove overnight-ing there, you can still decide last minute from within Italy to tack it on as a full day trip from the Amalfi Coast, if you feel like it.

I personally think one full day in Milan is enough to see its main draws, because, as I say in the itinerary, they are the painting, the church, and the galleria. So I would take the extra night to give to Florence from Milan.

If you’re not too bothered about missing the photo opportunity in Pisa, I think you’re find to remove it as well. It’s a necessary transfer between Florence and CT, which is why I feel it’s worth it in my itinerary. But since you would go from there to Milan, the Pisa visit becomes a bigger detour, since there aren’t direct or fast trains to Milan from Pisa. Another option would be to add yet another night to Florence, but use it for a day to do tour group day trip to the Tuscan countryside for some wine tasting that also includes a couple hour stop in Pisa. Then, you just take the fast train from Florence to Milan the morning after the day trip.

Four days in Venice for me would be a lot. It’s quite a small city, which is why I only devote 2 days to it in my itinerary. So with 3 days, I do think you guys will have enough time to enjoy it, but it of course depends on your interests.

I hope some of that helps you decide!

How about this then:

April 23rd: Arrive in Rome at noon-ish and already start the itinerary. April 26th: Leave Rome (later in the day) and arrive at Pompeii, Positano and the Almafi Coast (PPA.) April 29th or 30th: Leave PPA and arrive at Florence. (We decided to leave Capri for another time). May 3rd: Do the Tuscan countryside and Pisa combo, then return to Florence. May 3rd/May 4th: Leave Florence and arrive at Milan. May 6th: Leave Milan and arrive at Venice. May 8th: Leave Venice at 7:10 pm flight.

I think that looks quite nice! The only thing I would add is that it looks like you might have 2 full days in Milan if you go with the option of arriving there May 3rd and leaving May 6th. I do think one full day in Milan is enough for a trip of limited time where each day is precious time, so I wanted to mention that, in case you would prefer to allocate that as an extra day anywhere else in your itinerary. For example, I (personally) think 3 days in Venice or 3 days in Florence is better than 2 days in Milan.

But another option would be to stay in Milan two nights with the intent of using one day as a day trip to Lake Como from Milan . In case you don’t like the idea of checking in and out of hotels so quickly.

Have a great trip!

Hey Em! Thank you very much for your help! I’ll definitely keep that in mind. Have a wonderful day! =)

You’re welcome!

Hi Em… We have a 12 day summer trip planned in and out of Rome. I like the look of your 14 day itinerary. So plan to cut a few things to make it work. For whatever reason I would really love to see the Amalfi coast. Which is why we are adjusting your 14 day itinerary instead of adding days to your 10 day one that doesn’t include the Amalfi coast. Also milan isn’t as important to me. So if we are heading straight from Florence to Venice on day 9, What train logistics would change from what you have listed? Also if my kids really want to see Pisa, is this possible without doing cinque Terre, like a pit stop on the way to Venice? My other question, is taking the train back to Rome from Venice on the 12th day in the evening ok if our flight is in the am on the 13th day? Or should we devote a whole day to getting back to Rome?

I think all that is perfectly doable.

From Florence to Venice, just take the two respective train stations from my itinerary (Firenze S. M. Novella and Venezia Santa Lucia), and copy and paste them into the TrenItalia website to book the high speed, direct train in advance.

You can do Pisa as a round-trip day trip from Florence one day, or you can head from Florence to Pisa and then Pisa to Venice on the day of your first night in Venice, like you suggest. The train journey from Pisa Centrale to Venezia Santa Lucia would require a transfer at Firenze S. M. Novella and take 3.5 to 4 hours. (You could leave your bags at your Florence hotel reception after check out and return to your Florence hotel to pick them up before continuing on to Venice, if you prefer that to bringing them to Pisa and leaving them at luggage storage in Pisa Centrale station. But it would be faster to leave them at the Pisa station and not have to exit the station once back in Florence.)

Venice back to Rome on your final evening/night would be ideal. The journey on the fast/direct train will take 4 hours.

That helps a ton. Thanks for taking the time to reply to all these unique questions.

You’re welcome! 🙂

Actually one more question…. we are doing the following main stops: Rome, Amalfi Coast, Florence and then Venice. We chose this order as it follows thus itinerary but wanted to get your opinion because we eliminated CT and Milan… Thought we should ask if you would still do the stops in this order if not going to CT or Milan

Also thinking of taking the overnight train from Venice to Rome on the last evening, mostly for the experience. We will arrive at the main terminal 4hrs before our flight. Do you think this is wise?

The order doesn’t matter much! I would have mentioned it to you if it would have been better in another order 🙂 . The only difference would be that if you do it the other way around (Rome (0 nights) > Venice > Florence > Pisa > Rome (3 nights) > Amalfi Coast > Capri > Rome (1 night, same day as Capri)), you would have the option of direct trains between Pisa and Rome at certain times of day, whereas between Pisa and Venice will always require that transfer in Florence, as I already mentioned.

The overnight train sounds fine. I assume by “main terminal” you mean Rome’s main train station, Roma Termini? If so, you can of course go from there to the airport in 30 min, plus maybe 20 min wait time for the next train if you arrive right after one leaves. So let’s just say 1 hr. That’d give you 3 hours at the airport before your flight, which is what is recommended by airlines for international flights these days. The only thing would just be if you are one of those people who would be less relaxed due to not being in your departure city the night before. But if not, I think your plan sounds totally fine.

Just want to thank you again for all your work. I’m down to just restaurant reservations to plan for our peak season trip. The time I have put into this is next level, but I can not imagine where I would be without your guides. Thank you! Thank you!

You’re welcome! 🙂 I know you will have a lovely time and that you will appreciate all your hard work planning once you are there!

Hello! What would you recommend if I wanted to replace Pompeii with Sorrento? What would be the order from Rome -> Capri (Keeping everything after the same. Could you explain the trains/ boats for it too?

It would literally be the exact same as this itinerary, but instead of going to Naples to Pompeii, and then Pompeii to Sorrento, you just go from Naples straight to Sorrento. It’s not replacing anything, but rather skipping something. Because this itinerary already has you heading to Sorrento. Pompeii is just a stop on the route between Naples and Sorrento. So just skip the Pompeii stop and stay on the train until Sorrento.

I’ve read over this post and love how detailed it is. I am travelling to Italy in 2 weeks and haven’t planned anything yet. We are going for 2 weeks aswell but would like more of a relaxed holiday but still want to see the main sights. Where would you suggest to spend most of our time?

I’m glad to know you like the post!

The most lounge-y destination on this itinerary is the Amalfi Coast portion. So you could cut out other parts (Cinque Terre and Milan are what I would recommend, since you say you want to see the main things, and I’d define that as Rome, Florence, and Venice) to add more days in the Amalfi Coast.

Alternatively, you could just focus on the main three cities and maybe Milan, and go slower by staying in each one longer.

I hope those suggestions help!

I wanted to let you know that your itinerary has been extremely helpful. I’ve visited your page more than 100 times while finalizing my plans. My travel companion and I are not big fans of museums, so instead of spending a day at the museum in Florence, we’re considering doing a day trip to Tuscany, the Sienna Region, or maybe even scheduling a winery tour. Do you have any tips for a day trip itinerary or traveling without organized tours? Also, which winery would you recommend visiting? Thanks in advance!

Thanks for letting me know how helpful my itinerary has been! I love to know that. 🙂

I’m not big on wine, so I unfortunately don’t have too much to recommend on DIY wine tasting or tours in the region. 🙁 I see lots of group tours you can book that take you to parts of the Tuscan countryside that aren’t reachable by public transport and include wine tastings. But if you prefer to DIY (which, if you can’t tell already by my site lol, I would totally understand!), I would maybe google “best wineries in Tuscany,” jot them down on a list, and one by one, search in Google maps how to get to each from Florence. That way you can see if any are simple to reach by train or bus.

I can say that Siena is a very easy DIY day trip from Florence. There is a bus that leaves from near the main train station in Florence. There is also a train, but the bus takes you to the city center of Siena, whereas the train leaves you further out, so I recommend the bus for that reason. I don’t have a guide on this day trip because I didn’t take good enough notes while doing it myself. But I think you can find the schedule at this site by using the Trip Planner section. I bought my ticket in person the day of at the bus station, but I was there in late Sept, so depending on your time of year, you might want to book online or at least a day or two in advance if in person.

I hope some of that helps! Sorry to not be of more help on the wine!

Thank you so much, Em, for taking the time to reply!

You’re welcome! Enjoy your trip! 🙂

I have one more question. I’ve read some negative reviews about traveling from Naples to Sorrento via the Circumvesuviana train and the Campania Express, which I’ve heard is overpriced with poor service. We are a family of 4 traveling from Naples to Sorrento and planning to stop over to see Pompeii. We will be storing our luggage at Pompeii and then heading to Sorrento. What would you recommend other than the train? Is there a reliable bus service that we can take? Also, on our return trip from Sorrento to Naples, do you recommend taking a ferry or a bus instead of the train?

What kind of negative reviews are you seeing for the Circumvesuviana train? I ask because, it’s been some years since I did the exact journey that I recommend in this itinerary of going from Naples to Sorrento with the stop in Pompeii, but I don’t recall the ride being anything out of the ordinary! And my travel companion was a bit complain-y that trip lol, but she didn’t say anything about that ride either. So I wonder if it’s one of those situations where the only people who are taking the time to share a review are the few who had an extraordinarily bad experience? Because I believe that train is the sort of default way for tourists to get to Pompeii from Naples/Rome, if not on a tour or using private transport. The only bad thing, which I mention in my post, was that the platform was a little confusing for me to locate, because it’s kind of in the same station as Naples Centrale, and there is also the city’s metro in that same building, too. So that’s why I recommend to ask the staff for help if needed.

All that being said, there does seem to be a bus from Naples to Sorrento with a stop at Pompeii. You can check the timetable here . You will have to exit the station to find the bus stop. (I can’t find that line on Google maps, otherwise I’d link it.) Also, based on my experience with other buses in Italy, you will likely need to stop at a tobacco shop to purchase the bus tickets. The bus seems to take the same travel time as the train. I have no experience taking that bus, so I can’t share too much more than that, unfortunately!

There is also the option of a private transfer or a cab. Since you will be a group of 4, it might be worth the per person cost.

I wouldn’t recommend taking the ferry just to get from Sorrento to Naples, because the Naples ferry port is not a reasonable walking distance from the train station. You would have to get a cab to the station. The train (or the bus) will take you right to the building with Napoli Centrale.

Thank you, Em, for taking the time to respond! I’ve read some negative reviews on Tripadvisor about trains not being punctual, getting canceled at the last minute, and being so overcrowded that there’s no room to stand, among other issues. But I appreciate you sharing your experience with me. I will look into the private transfer option. Appreciate your insight!

Ah, I see. I think those are all valid possibilities. I definitely had to sit on the floor of the bus between Sorrento and Amalfi because we were let on rushedly and didn’t get a chance to realize how crowded it was inside until the bus already started moving.

A private transfer would be most comfortable, and it’s honestly the way I’d probably choose to travel from Naples into the Amalfi Coast if I had a party of 4 to split the cost with.

Your itinerary is such a gem and full of wonderful practical logistical detail. I am helping my adult daughter plan a high school graduation trip to Italy for her and granddaughter next June. I look forward to the accommodation list you say you will soon provide to help fill in that part. How can I ensure that I receive?

I’m glad the itinerary is helpful! I can respond back to this comment you’ve posted when it’s live. 🙂

On my homepage you can also always see my latest posts, so it’ll be visible there once it’s up.

Thank you so much for this itinerary. We are planning a trip to Italy next year, to celebrate becoming empty nesters and I wasn’t sure where to begin. This is a life saver. I can’t wait to see what accommodations you recommend. Do you know when you will share that? 🙂

I’m glad this itinerary has been helpful in your planning! I love the idea of your celebration trip. 🙂

I hope that the accommodation guide to match this itinerary will be live in the next month, or two months max if not!

I really like your itinerary and was wondering if you could suggest places to stay in the cities marked Overnight. Definitely looking for more affordable options as a solo female traveler. I am guessing you will obviously consider convenience of travel when making recommendations. I will be using public transportation for all my travels. Also, I have never been to Italy before. Thanks a lot in advance.

Hi Madhurima,

I’m glad to know you like the itinerary!

I unfortunately don’t have specific options I’d recommend for each spot. 🙁 I usually end up booking the most budget-friendly decent option that is reasonable distance from the train/bus station, since I tend to travel solo and more slowly, but it’s not what I’d always recommend to others. But I am working on a guide to provide this, since I get asked it so much! I’m not sure when your trip is, but I can let you know when the post goes live if your trip isn’t super soon.

Thanks so much for this great Itenerary! We’re planning a 18 day trip into and out of Rome with our 15 year old Sona nd 12 year old daughter. We’re an active family that loves hiking and swimming/ snorkeling. Any major modifications you’d make/ places you’d cut out that would be less interesting/ fun for teens/ preteens?

Also any advice for the bags? Would you do standard luggage or better off with a backpack? Thanks!

I’m glad you like the itinerary!

If we use one of your days as a travel day back to Rome from Venice (it won’t take a whole day), let’s say you have 17 full days, so 3 more days than in my itinerary. Based on your family’s interests, I’d add 2 more days to the Amalfi Coast (so that you definitely have time to do the Walk of the Gods hike, plus more time on beaches, and then can do a full day trip to Capri round trip and then head up to Florence the next morn, unlike the half-day trip I have here) and 1 more day to Cinque Terre (so that you have time to either add in the free Cinque Terre hikes (which I liked more than the paid ones) and/or rent a kayak from one village and kayak up/down the coast, finding little coves along the way). Or you could do the opposite, 1 more day in Amalfi Coast and 2 in Cinque Terre, if you think you’d like that more from what you’ve read.

If your kids don’t like history, you might consider whether Pompeii would be enjoyable for them or not. And if they don’t care for art, you might consider if they will like Milan (the main draw is the Last Supper painting and maybe the Duomo). You could use the extra days to do some cooking classes if the kids would like, or just move slower.

For luggage, it sounds like you are going in warm weather, since you mention swimming and snorkeling. So I would pack light. For a trip of that length, I would personally see if it’d be possible to not check in a bag and just take carry-on (so one “under the seat” sized backpack plus one carry-on luggage, for each person). I prefer suitcases to backpacks because they are easier to open/dig around/repack during the trip and also are healthier for your back. But it’s personal preference. If you guys have liquids or some other reason that you need a check-in bag, I would consider taking one large check in per 2 people (so maybe your partner and you split one and the kids split the other) and one carry-on per 2 people, plus one “under the seat” sized backpack per person.

Victoria Stasichin

I’m eloping to Italy in September and trying to plan it all out. I wanted go fly into Venice and travel south but it seems like the flights are not affordable for that so it looks like I would have to do round trip to Rome. I want to visit Rome, Florence/Tuscany, Venice, Positano, Amalfi, and Capri but I’m having trouble figuring out the trains and best order to do this in considering some are north and some are south! I’m worried about wasting a lot of my trip on trains.

Hi Victoria,

Congrats on your engagement!

I would recommend a figure-8-ish shaped itinerary with Rome as the center: Rome > Amalfi Coast (I would choose one base town and day trip form there) > Florence via train from Naples, like I explain in the “how to get to Florence” portion of this itinerary (Florence can be a base for other Tuscan day trips) > Venice > Rome. OR the exact opposite.

Brittney Vaughn

Thank you for sharing such an awesome itinerary, this is extremely helpful! My bestfriend and I are visiting Italy – landing in Rome on November 1st (arrive at 9 AM) and departing from Venice on November 14th (leave mid-day). I’ve read various recommendations and it seems like it’s not recommended to visit Cinque Terre in November. My best friend and I would like to visit Rome (& Pompeii), Siena, Florence, Pisa, Cinque Terre, and Venice. I would love to do the amalfi coast but knowing the weather won’t be the best, I am honestly ok with skipping it unless you’ve heard otherwise.

I am wondering if you can provide suggestions in terms of how many days I should stay in each town, and if you have any additional recommendations, knowing the time frame we are visiting.

Thank you so much for your help!

– Brittney

Hi Brittney,

I’m glad the itinerary is helpful for you!

It sounds like you have ~13 full days. To hit all the locations you’ve listed in 13 days, I would recommend: Rome (4 nights – 1 of those days as a day trip to Pompeii, can include some time in Naples if you want) > Florence (3 nights – 1 of those days as day trip to Sienna, better if done by bus rather than by train) > Cinque Terre (3 nights – stop at Pisa on the way from Florence, keep in mind that the trails might be closed due to mud and that many shops/eateries will be too due to the time of year) > Venice (3 nights, it’s prone to flooding in rain so bring appropriate shoes based on the forecast closer to your trip).

Hi Em We are visiting Italy for 17 days during early Dec and it’s our first Europe trip with our 2 teenage boys.

We heard a lot that it’s wet season and many places to avoid (Tuscany, Cinque Terre etc). We are flying in to Rome and departing from Venice. Not a fan of Milan. We were originally think of Rome> Naples/Amalfi Coast> Florence/Pisa > Cinque Terre > Venice…… though we have yet to think thr the detail itinerary. What do u think of this for Dec?

How exciting that you’re taking your sons to Europe for the first time!

I think that itinerary as you have it sounds fine! Just a heads up though that from Cinque Terre (from La Spezia) to Venice is going to be two train transfers (one at Pisa and one at Florence) and will be around 5 hours (including waiting for transfers). It’s doable, but I just wanted to give that heads up.

You might have read in this post and/or in some comments here below that I don’t recommend this itinerary in winter. This isn’t due to the temperatures themselves (I personally hate cold/gloomy weather, but not everyone else does lol and Italy’s winter is milder than many other places in the world), but rather because Venice is prone to flooding in rain, and because places like Cinque Terre and Amalfi Coast pretty much shut down in the off season. The CT trails might be closed due to mud, ferries in the Amalfi Coast will run with less frequency, and in both places, many shops/eateries will be closed until next season.

If none of that bothers you, then you can definitely visit those places in December!

Hi Em Thanks for replying so swiftly! Yeah totally get you on the flooding and shut down as I read it on some other travel blogs. Would you have alternatives to recommend us so that we can fill up our itinerary:)

One alternative would be to just go slower than I have in this itinerary, because it is pretty jam packed. So you could add one night each to Rome, Florence, and Venice (if you are going to be in Italy anyways, it might be worth it just to go and bring rain boots just in case or depending on the forecast closer to your trip), just to enjoy them more slowly/thoroughly.

Then I would add some day/side trips for the extra days. Pompeii + a bit of Naples could be an easy day trip from Rome. Or you could overnight in Naples if you want to see more of it, climb the volcano, etc. From Florence, you can day trip to Siena (better by bus than by train), San Gimignano (I haven’t been but I’ve bumped into so many travelers that liked it), Bologna (the main city in the region of Emilia-Romagna, which is home to many of Italy’s most famous foods like bolognese sauce, parmesan cheese, balsamic vinegar, etc.). You could also overnight in Bologna between Florence and Venice, and use it as a base to visit Parma (parmesan) and Modena (balsamic vinager) and do some tasting tours there. You could also add in Verona , which is day trip-able from Venice or from Bologna. And you can always use the extra time to do some experiences, like organized tours to the Tuscan countryside from Florence, cooking classes, etc.

I hope some of those ideas help!

Thanks loads Em! Much appreciated

Hi That Travelista, I think this post is very helpful but only a little suggestion about Cinque Terre: the really gem of Cinque Terre National Park is located in Prevo, a little hamlet of Vernazza, right on the Blue Path in halfway between Corniglia and Vernazza, in the hisghest spot at 208 meter a.s.l. There is only a little bar, a Farm Shop of Azienda Agricola Sentiero Azzurro and some beautiful houses for rent totally sea view: theheartofcinqueterre.com

Hi Pierpaolo,

I do recommend in this itinerary to walk the Blue Path from Vernazza to Corniglia on the second day in Cinque Terre, so people who do follow my recommendation will already be passing by the homes in Prevo. 🙂

Kurt Schneider

Thanks so much for this helpful article! Sorry if someone already asked you this, but I’m curious as to why you reccomend starting in Rome vs starting in Naples. It seems like with starting in Naples and working your way up you could avoid any backtracking. I’m sure you have a reason. Just curious!

Thanks so much!

I’m glad the article is helpful!

Starting at Naples would be better! But most readers of this article are visiting Italy from outside of Europe, so their airport options will likely be Rome, Milan, and Venice, since Naples is a smaller airport. But if you find a flight to Naples, that’d be better as a start/end point instead of Rome. You would then switch the order of Rome and Amalfi Coast in this itinerary.

Hi Em! I LOVE this itinerary so much! Thank you for sharing it 🙂

My husband and I are planning on using this itinerary but tweaking it a bit to fit in attending the Formula 1 race Aug 29-Sept 1 at the Autodromo Nazionale di Monza. We are planning for an 18 day trip (2 of which we’ll be flying) and since the race will be a 4 day event, we will need to cut out a few things or condense it quite a bit. Any tips?

I’m glad to know you love the itinerary! 🙂

I would cut out whatever interests you least. It sounds like you have 12 days (18 – 2 for flying – 4 for the race). So you would need to cut two days from this itinerary. Monza is close to Milan so that seems easy to keep in. You could cut out the 2 days for Cinque Terre and Pisa. Or cut out 2 days from the Amalfi Coast (cut out the Capri day trip and combine Positano and Amalfi into one day trip from Sorrento, or only visit Positano and not Amalfi). Or you could cut out all 4 days in the Amalfi Coast since there’s enough there for a week-long trip in the future. And then have 2 extra days to add elsewhere to not move around as fast. Maybe an extra day in Cinque Terre and an extra day in Milan to do a day trip to Lake Como from Milan .

Hope some of those ideas help!

Hi! Your very detailed itinerary is really a welcome! Am planning about a 12 days visit in mid to end June. What are your thoughts on visiting during this time?

Like I say in the post, I believe that anytime outside of winter is a good time to do this itinerary! You’ll have a great time. 🙂

Thanks for the response! Need your input on this! Am considering your itinerary for my visit. The issue here is I made a mistake in booking my return flight! I’m flying in to Rome and will be ending my tour in Venice but my return flight is from Rome! Any suggestion?

Not a huge problem! Just take the fast train from Venice to Rome on your final evening if your departure is in the morning, or on your final morning if your departure is in the late afternoon or evening. It takes around 4 hours.

Hey Em! My husband and I are going to Italy May 19-June 2nd! We are flying in and out of Rome, and I’m having a hard time trying to figure out the best trajectory! We will spend the first 3 nights in Rome, then from there I’d like to see a few places and I’d love your thoughts on direction!

We’d love to see:

Almalfi Coast Tuscany Florence Modena Cinque Terre Maybe Venice.. too much?

I just can’t figure out the best way to make the best use of our time. I’d love to hear your thoughts!

It sounds like you have 13 full days in Italy? In order to hit everything on your list in 13 days, I’d suggest:

Days 1 – 3: Rome Days 4 – 6: Amalfi Coast Days 7 – 11: Florence (2 days for Florence itself, 1 day for Cinque Terre day trip, 1 day for a day trip somewhere else in Tuscany (bc you list “Tuscany” and also list “Florence,” but Florence is already in Tuscany, so I assume you mean the Tuscan countryside or a smaller village), and 1 day for Modena day trip) Days 12 – 13: Venice

From Venice, take the fast train back to Rome.

If you want more time in Cinque Terre, you can remove 1 day from Amalfi Coast and move it there.

Alexis Pratt

This is incredible! Thank you for all the research and real travel experience. And taking the time to write it all out! My only question thus far.. do you know how much this all cost? I want to get an estimate to know what to start saving for! Thank you so much.

I’m glad it’s helpful for you!

The biggest cost is going to be housing, and that is going to depend on your personal preferences, your party size, and how far in advance you book. So it’s hard for me to ballpark it for you. I would just look at some places on a booking site to get an idea for a per night rate for the type of accommodation that you personally will be ok with.

Besides that, I’ve tried to put all the prices of attractions and transport in this guide, so you can just add up all the attractions you would enter (for example, not everyone will do a gondola ride or enter every attraction) and the transport you would take (for example, using a cab is different than using a bus or ferry).

If you plan to have a restaurant meal 3 times a day, I’d budget around €60 per day to be super safe. But I personally usually spend less than €25 a day on food in Italy, because I have pastries for breakfast and simpler meals for lunch and dinner.

Sorry to not be of more help!

Thank you for the detailed itinerary. We are planning a 12-day trip to Italy (not including the travel time), starting from Venice and ending in Rome. Amalfi Coast/Capri is at the top of our list. We are debating whether or not to add Lake Como and skip Cinque Terra since we are planning to go to Amalfi Coast anyway.

I’m glad the itinerary is helpful!

I think that sounds like a fine plan! The debate between Cinque Terre and Amalfi Coast is a common one! Both are full of pretty, colorful villages along the water. Cinque Terre is easier to get to/around and fun for hiking and then jumping in the sea afterwards. It’s also cheaper. But I think the nature/scenery in the Amalfi Coast is more impressive.

You could do Venice (2 nights) > Milan (2 nights, one day for Milan and second for a Lake Como day trip from Milan ) > Florence (2 nights) > Amalfi Coast via Naples (3 nights) > Rome (3 nights).

Thank you so much for reply!

Hi, Do you have recommendations on accommodations in all the cities you have included to visit over the 2 week period? We’re looking to go in September. Thanks, Gemma

Not yet, but I am actually currently working on a guide that will be just that! It will definitely be published before September, but not for a while still. I can let you know through this comment thread when it’s up, in case you still haven’t booked your accommodation by then.

Hi, Is it advisable to rent a car in Venice and make a day trip to Either Dolomite or Lake Como?

I’ve replied to your other comment. 🙂

I’ve never done it, so I can’t speak from personal expensive. But from what I’ve seen/read, I would definitely recommend renting a car to travel around the Dolomites. I can’t speak to whether it’s worth the drive for just one day though, since I haven’t been.

For Lake Como, it’s quite a bit further out (3 hours one way to the best part of the lake). Lake Garda is also popular and is closer, so you might consider that, too.

Thank you so much!!

I’ve responded to your other comment. 🙂

This was a lifesaver! I may ( 99.9%) have more questions as I finalize my trip, however, I have 2 I thought of now. Following your list and ending in Venice, we than are heading to Sicily… Can you provide the best route? Also if I wanted to add 1 additional ( 2 night stop) between Venice and Sicily, what you would reccomend with the travel details as well please.

Hi Jacqueline,

I’m glad this itinerary has been so helpful!

If it were me, I would probably fly to Sicily from Venice, because Sicily is quite far by train from anywhere on this itinerary.

If you do want to go by train, I would probably reverse this itinerary, so that you train to Sicily via either Rome or the Amalfi Coast (or ferry, if from Naples). They are still far, but closer to Sicily than Venice. Puglia might be an interesting stop to break up the long train journey. I haven’t visited it yet, though, so I can’t speak to it personally.

But like I said, if it were me and I had limited time, I would fly. If you are looking to add one more place to your trip, maybe you can add a night or two in Lake Como from Milan, before heading to Venice. Or visit Lake Garda from Venice. I have an itinerary on a day trip to Lake Como from Milan , if you are interested. You could also add extra nights to rushed parts of the itinerary, like Amalfi Coast or Cinque Terre.

Thank you for this detailed itinerary. It’s the best 🙂

We decided to not go to Cinque Terre. We are still planning on going to Pisa after Florence. How would we go from Pisa to Venice? The different train systems confuse me and we want to get there as soon as possible. Also, how did you feel about the luggage storage in some of the trains? We plan to bring a 28 inch luggage to hold everything for 2 weeks.

Hi Jennifer,

I’m glad the itinerary is helpful!

If you see the directions from how to get to Venice from Cinque Terre in this itinerary, you’ll see that there is a transfer at Pisa. So you will do the same journey, just minus the part from Cinque Terre to Pisa, saving one transfer. You will go Pisa>Florence>Venice (but just purchase one ticket with a transfer, not two tickets).

The luggage storage has been fine for me. I traveled with one those medium sized check-in luggages for 5 weeks, and I usually had room to keep it in front of me. One day it was crowded and someone offered to lift it to the racks overhead for me, because it was way too heavy to lift myself, so that he could sit in the seat front of me. There also should be space for large bags at the end of each train carriage, but I’ve never used that before in Italy.

This is a great itinerary. I am planning on taking my three daughters to Italy for 2 weeks in May 2025. This looks just what I was wanting. I am wondering if you could recommend hotels (2 rooms) for each stop. I do not want 5*. We want quaint boutique hotels that give a flavour of the region. I would love to be able to book this trip myself using expedia or similar companies. Thoughts? I would appreciate your feedback.

Hi Elizabeth,

I’ve responded to your email, but to answer your question publicly for anyone else who might be reading, it’s definitely doable to book this trip yourself! 🙂

Hello! I’d love to go visit Dolomites when i go to Italy next year. Do you have any advices on where to put this destination during the trip? And which city can i skip for exchange of Dolomites?? Thanks a lot!

Ah and I love to go to Sicily as well! I plan to arrive in Rome and depart from Milan. 🙂

I haven’t visited neither the Dolomites nor Sicily yet, but both are on my list!

From what I’ve researched on the Dolomites, it’s easier with a car rental. I’m not sure if you plan to rent a car. Without a car, I do think you can see some things, but you might not be as time efficient (i.e. it might require more days). So what cities you can cut out is going to depend on how many days you want to spend in the Dolomites.

Sicily is quite far from the rest of the itinerary, so it will be either a long train ride (from Rome, Naples, or Salerno at the eastern edge of the Amalfi Coast) or a flight. It’s a decently sized island, so again what cities to cut out will depend on if you are satisfied to just see one city and get a taste of the island or if you want to see more of the island.

I would recommend axing Milan, the Amalfi Coast/Pompeii/Capri leg, and/or the Cinque Terre/Pisa leg because they are less “must see” than Rome, Venice, and Florence. The Dolomites are going to be closest to Venice. So I would add them from there. Sicily is very south, but you might need to take a domestic flight to not waste time, so it might not matter where you add it in. But probably from Venice or Rome airports (or Naples if you decide to not remove the Amalfi Coast bit of the itinerary).

I hope that helps a bit!

Hi Em we will be travelling to Italy in late September from Australia, spending several days cycling in the Dolomites and then using your itinerary as a broad guide for the rest of our trip. If we have a couple of extra days spare (we have three weeks in total) would you recommend Puglia? Or somewhere else as a higher priority?

I haven’t been south of the Amalfi Coast area yet, but Puglia looks beautiful, less touristy, and is on my list! That and also Sicily, but I think Puglia would be easier in 2 or 3 days than Sicily, from what I’ve read/seen.

Another option is one of the northern lakes, Lake Como and Lake Garda being two of the most popular. I haven’t been to Garda, but Lake Como was stunning and easy to move around. But quite touristy.

Just some other options to consider, but (keeping in mind that I haven’t been there myself) Puglia sounds like a great addition! With the 2 week itinerary I’ve written out, you’re already going to see all the most “priority” stops in the country, from a touristic point of view, so anything else on top of that is going to be a bonus and just based on your interests!!

My fiancé and I are arriving in FCO on 4/1/24. We have two weeks in Italy, in theory. I wouldn’t mind hitting Croatia for a couple of days, if that is doable. I’ve been to Italy numerous times, and he has not, but is happy just going where I want to visit. Croatia is high on both of our lists, so, if we’re there, why not? Any thoughts or insights about that?

I LOVE Croatia and think it’ll pair perfectly with Italy!

If I were making an itinerary for just your fiance alone, who hasn’t been to Italy nor Croatia, I would recommend combining my one week Italy itinerary and my one week Croatia itinerary to make a two week trip. Each itinerary is what I would recommend for a first timer in each country (so Rome, Florence, Venice for Italy, and Dubrovnik, Split area, Plitvice Lakes for Croatia).

BUT since you’ve already been to Italy, and many times at that, I’d have to ask what you’re hoping to get out of both countries this visit. What places are you interested to see in Italy? Do they have to be new, or are you willing to repeat things for your fiance to see? Do you want to see “all” of Croatia, or just Split and Dubrovnik? If so, Split and Dubrovnik both have airports with flights to/from Italy, so you can even just tack that portion of my Croatia itinerary somewhere in your Italy trip. I’m happy to give more specific recommendations/thoughts if you let me know! 🙂

I think you submitted two comments, so I’ve responded to the other one. 🙂

Hello Em, really enjoyed reading your 14 day Italy itinerary for first timers. My darling wife and I are considering a trip to Italy this fall. We are in our sixties, and while we can walk, we cannot “hike”, so do be gentle, haha. While we would love to cover as much as possible, we do like to take it easy and travel in a leisurely manner.

Based on your itinerary in reverse, here is what we have come up with: Fly into Venice early afternoon. Stay in Venice for 3 nights, (one extra night) as we would need to get over the jetlag from an overnight flight from North America. Florence for 2 or 3 nights. Cinque Terre/Pisa for 2 or 3 nights. (As suggested by you, thinking of staying in La Spezia for ease of train travel to the 5 village and budget as well.) Rome for 5 nights. This would include a day trip to Amalfi Coast and or Naples if possible.

Seeking your guidance to set up the itinerary along with details of places to visit. So this would be a 13 or 15 nights itinerary, depending on your valuable input. Also we cannot decide if we should begin the Italy trip mid September, late September or early October, keeping in mind weather and crowds.

Thanking you in advance and best wishes

I think that sounds like a really nice itinerary!

If you are not going to be staying overnight in the Amalfi Coast, I would recommend switching the order of Florence and Cinque Terre around to save an hour of train travel time. So Venice > Florence > Cinque Terre > Rome.

The later you go, the lower accommodation prices will be and the lesser the crowds will be (especially in Venice, because of cruise ships, though I believe they have limited the sizes ships can be now). But also, the cooler the weather should be (but you never know what weather you will get, of course!). If it were me, I would opt for mid or late September. This is because I’m really affected by weather, unfortunately lol! If you don’t mind the weather being cooler, October might be fine for you.

There are tours on sites like Get Your Guide and Viator for Pompeii and Amalfi Coast day trips from Rome that run around $100 – $150, so that might be an option to consider if you want to see them both in one day.

All my recommendations on what to visit or extra day trips to add are basically what I’ve put in this post, so if there is any question in specific, let me know! I think having more time in each city will just allow you to enjoy it more by not being rushed or having to wake up early to fit everything in, and allowing you free time to meander and discover things on your own. There’s no reason to rush if you don’t have to! 🙂

Hello Em Thank you so much for your time and input for our trip. Noted your suggestion about the routing, CT to Rome. A few questions: 1. Taking the train from Florence to CT, should we stop in Pisa. Is the Tower a thing not to miss. 2. What is best train route from Florence to CT. 3. We decided to spend two nights instead of 3 at CT. Question, should we stay in La Spezia or in one of the towns, maybe Monterosso. Any thoughts. 4. What is the best train route from CT to Rome. I guess we should plan to arrive at Roma Termini station. Thanks once again. Best wishes

1. It’s totally up to you if the tower is worth missing or not! It’s not as impressive as the buildings you will see on the rest of your trip (the Colosseum, Venice’s buildings coming out of the water, the Duomo in Florence which literally had new tools invented to build it). It’s just a very cliche symbol of the country for whatever reason, and not worth visiting on it’s own, so that’s why I’ve put it as a quick photo stop in this itinerary, since you already have to exit the train at Pisa station to make a transfer between CT and Florence anyways.

2. I have the train route from Florence to CT in this itinerary. If you don’t want to see the Leaning Tower of Pisa, you can just skip that and can continue the transfer to La Spezia at Pisa station. From there, you can continue to CT proper if you want, or stay in La Spezia as your base, like I recommend in the itinerary. The only reason I mentioned the switch to you is because you are doing my itinerary from Venice to Rome, so backwards. So I didn’t want you to do Venice > CT > Florence, because since you aren’t doing Amalfi. Then to get to Rome from CT, it will be from La Spezia Centrale to Roma Termini (direct train as fast as 3 hours in the morning, closer to 4 hours later in the day). For all other train journeys, just do the exact reverse of what I have detailed out in this post.

3. I answered this slightly in the previous bullet, but in the itinerary I recommend La Spezia for just two nights. I explain a bit why in the itinerary.

4. I answered this in the second bullet, but I’ll add that when looking for tickets to a city, you can type just the name (in Italian, so Roma, Firenze, Venezia, etc.) and then select “Tutti Le Stazioni” if that option is there in the drop-down. This will include all stations for that city in the search. But yes, for this journey in particular, it’ll be Roma Termini. 🙂

Thank you so much Em You are the best.

Glad to be of help! 🙂

Hi Em! Thank you so much for this detailed itinerary, very helpful! I’m planning on visiting Italy in September for 2 weeks, perhaps a little longer. It’ll be my first solo holiday! I’m really keen to explore Sicily as well as the destinations set out in your article. I’ll be flying from Bristol and planned to begin in Milan and make my way down the country, flying home from Sicily but flights are either a lot more expensive or hours long! Do you think it would be okay to follow your itinerary, ending in Sicily and then flying from Sicily back to Milan so that I can book a return flight from there? Thank you again for your help! ☺️

You can definitely tack on Sicily to this itinerary, and I think a domestic flight to save money/time makes a lot of sense.

I’m not sure if you are planning to connect my itinerary to Sicily by train or do two domestic flights. If you are wanting to use the trains to get to Sicily and just the flight to get home, there are direct trains from Roma Termini and Salerno to Messina Centrale, Palermo Centrale, and Siracusa. Salerno will save you about 2 hours compared to Rome, and it is at the eastern end of the Amalfi Coast. So if you decide to go that route, I would recommend moving my itinerary around to end in Amalfi Coast rather than in Rome. That would also make me recommend moving Florence and Cinque Terre around, to save an hour of train time there.

So Milan > Venice > Florence > Cinque Terre > Rome > Amalfi Coast > Salerno (reached either by train with connection in Torre Annunziata or Naples, or by ferry) > Sicily > flight to Milan.

You could also fly from Naples to Sicily. The train journey is so long that it might be worth looking into.

I hope that helps!! Your trip sounds like it’s going to be amazing!!

Hi Em, Thank you so much for your reply! I ended up missing out Sicily and decided to do it another time. Instead I have tweaked things slightly and planned it Venice – Florence – Pisa – Clique Terre – Rome – Pompeii – Sorrento – Matera – Milan – Lake Como. Thank you so much! ☺️

That sounds like it is going to be an amazing trip! Have the best time!

My husband and I will be visiting Italy in June. I would love to visit EVERY place on the itinerary, but my husband is not looking forward to packing up and jumping on a train every 2 days. I read that you recommended cutting out Capri, but that’s high on my list. Can you tell me if cutting out Cinq Terre is a good alternative?

Hi Camille,

I think that’s a great alternative. If Capri is high on your list, that settles it, in my opinion! My itinerary only allocates a half day to Capri, but by removing Cinque Terre, you can either overnight in Capri with those two nights originally meant for La Spezia/Cinque Terre, or add two nights to the Amalfi Coast, allowing you to do a longer day trip to Capri than you would be able to do if you were going to Florence afterwards, like in my itinerary.

The reason I recommended cutting out Capri in another comment is because (1) it only occupies half a day of my itinerary, so it’s one of the smallest things to cut out, and (2) it added the most inconvenience to the itinerary. But now, the train journey between Cinque Terre and Venice has also gotten about an hour longer than it used to be for some reason. I’m not sure if it is because of work on the route or if it’s a permanent change. But now the inconvenience is kind of similar between the two.

And lastly, I think Cinque Terre on its own is easier to return to on a future trip than Capri on its own is.

I hope that helps you make your decision! Enjoy your trip!

Kelley Strutton

Thanks for this wonderful guide – it paints such a beautiful picture of Italy and all the details are really helpful. We are seniors and looking for info to ease the logistics of things. Specifically: Would it make sense to take a train from Rome to Sorrento, using Sorrento as your base for a few days. Then, on one of the days take a train back to Pompeii for the day to see the ruins – trying to avoid the luggage and train transfer hassles. Also, can you tell me how luggage is handled and where it is stored on the trains? Will there be any assistance available for this? Quick impressions of the best area to stay in Rome, Florence and Venice for convenience to attractions and trains would be helpful. Thanks so much.

I’m glad my guide is helpful!

You can totally day trip to Pompeii from Sorrento if you prefer. You could technically even do it on the same day as you leave Rome, if you don’t mind doubling back on the same day. The train ride is around and hour each way, and it will be the same train you take from Naples to Sorrento, so you’ll already have experience with it.

I’ve always put my luggage above me, if the carriage is so full that I cannot keep it near my seat. I’ve never traveled Italy with anything larger than the medium-sized check-in bag, though. (I mean the kind that are definitely too large to be check-in, but not the standard check-in sized luggage.) There is usually also a designated area for luggage at the end of each carriage. There isn’t impromptu service that I have witnessed. I’ve only ever seen train staff give directions and answer questions. But TrenItalia does have this service to deliver luggage to your hotel. So maybe that will interest you.

I personally always try to stay walking distance from the train stations. In Rome, this area visually seems a little dodgy, so you might want to keep that in mind. You can try to find something still walking distance from the train, but in the direction of the attractions (northeast of the station). But in Florence, I found the area near the train to be fine. In Venice, I would definitely recommend to be near the train, because it is annoying transporting luggage over all the bridges, and it can be confusing to navigate the water taxis right upon arriving and with luggage in hand. Florence and Venice are both rather compact.

I usually use Booking.com to search, because I like that their interface allows you to filter criteria and then move to a map view, which allows me to see where the accommodation is relative to the train and attractions. I’m not currently affiliated with Booking.com.

I hope some of that helps!!

So, do you have to change trains to get from Rome to Sorrento? Or is there a direct train?

As my itinerary details in the section about how to get to Pompeii, you have to transfer at Naples. There are two Naples stations. You go from Rome to one. Then, you walk to the other one and head on a second train towards Sorrento. My itinerary has you getting off this second train at Pompeii on the way to Sorrento, but you can of course just keep on the train and head to Sorrento. 🙂

I see. Thanks for the good info

Shani Damodaran

HI, Planning to do a trip of Italy plus Malta starting in first week of April 24 for 17 days. We are a family of 3 (2 adults and a 15 years old child) Landing in Milan and flyout from Rome Can you advice a complete itinerary with an option of flying in and out of Malta in between this 17 days. Malta can be 2 nights only. We would like to spend some quality time in Rome for sure. (if less also, give an option).

That trip sounds like it will be a dream! I think Malta can be squeezed into this Italy itinerary quite nicely.

What I recommend is to do my itinerary backwards then find a way to squeeze Malta in using the airports of Naples, Bologna, or Pisa.

This could yield something like:

April 24: land in Milan April 25: travel to Venice in afternoon or evening (depending on how much time you had in Milan on day 1) April 26: Venice April 27: travel to Florence in evening April 28: Florence April 29: Florence April 30: travel to Cinque Terre (La Spezia) in morning, stopping in Pisa if interested May 1: Cinque Terre May 2: travel to Pisa Airport (9am flight) and fly to Malta May 3: Malta May 4: fly to Naples Airport, travel to Amalfi Coast (Sorrento), stopping in Pompeii if interested May 5: Amalfi Coast May 6: Amalfi Coast May 7: travel to Rome in morning, stopping in Capri if interested May 8: Rome May 9: Rome May 10: fly home

The flights I reference are all through RyanAir. So be sure to read my guide on flying with RyanAir without getting ripped off before purchasing.

Hope that helps, and have a great trip!

Planning to go to Italy for 2 weeks 15-17 days. I was planning to add Malta too.. do u think I can add Sicily and then Malta after Naples ? and miss Milan from the trip. Please let me know your thoughts on these places. If they all look and feel the same in June then may be I could skip them.

Hi Archana!

There are direct flights between the three places (Naples, Sicily, and Malta), so you definitely can tack those onto the itinerary if you’d like. In that case, I would probably make the trip Venice > Florence > Cinque Terre > Rome > Naples/Amalfi Coast > Malta + Sicily. Or the exact reverse. The only thing is that removing Milan only saves one day, so if you are following the rest of my itinerary, your trip will be longer than 17 days if you tack on Sicily (which is a large island) and Malta. So you might have to cut a bit more out from my itinerary, if that is what you are following.

I haven’t been to Sicily or Malta yet, so I can’t advise on them from personal experience. I’ve heard that Sicily is a bit of a different vibe from the rest of the country. And Malta of course is a separate country. But the three places are going to seem similar compared to, say, Norway. They are all in the Mediterranean, they are all southern Europe, they all have been part of the Roman Empire, etc. So it depends on your definition of “the same.” My own opinion is that I absolutely plan to visit both Sicily and Malta in the future!

Jessica Cloutier

Thank you so much for all the valuable information! We’re doing a bit of a shorter trip as we are staying a few days in Paris as well as Switzerland. We plan to have 11 -12 days in Italy. I am wondering how you would reconfigure the itinerary. I have been to Italy on a school trip and was planning on skipping Rome this time around (been to Florence as well but would like to go back). I also wanted to check out lake como. Any suggestions are greatly appreciated.

Hi Jessica,

I’m glad the information is helpful!

Since the itinerary is 14 days and the Rome portion is 3 days, I would just remove those 3 days and have an 11 day itinerary. That would have you starting in Naples (which has an airport) and ending in Milan, or the reverse – whichever works out better for you.

If you want to see Lake Como on a day trip, it’s possible and would keep the itinerary within 12 days. I detail how in my Lake Como day trip itinerary from Milan . If you want to overnight in Lake Como, I would cut some days out from whatever interests you least and tack on those days to Lake Como. Maybe the half day in Capri because it’s a little complicated, or maybe Milan because it’s not as beloved, or maybe a night from Florence since it’s a repeat for you, etc.

I hope that helps!!

This post is amazing! Would love your input on 14 days flights to and from FCO – Rome (Wednesday arrive, Tuesday depart). We hope to hit Rome, Pescara, Roccamorice, Naples, Pompeii, Sorento, Pompeii, Amalfi, the hike you mention, and maybe Capri. We dont mind paying for some accommodations, but we also have a friend in Naples where we can stay for free. Any tips on itinerary and how to get around?

Hi Ken! I’m so glad to know the post was helpful! 🙂

That’s so awesome you have free housing in Naples!

The bulk of everything you listed is day-trip-able from Naples – just Rome, Pescara, and Roccamorice aren’t. I haven’t been to Pescara or Roccamorice, but based off a quick Google Maps search of public transport, it seems there are trains and buses between Rome and Pescara. It seems that there is a long (5hr) Flixbus between Naples and Pescara, but that a train trip between the two has to transfer at Rome. I didn’t see any way to get to Roccamorice with public transport from Pescara, Rome, or Naples.

Off the top of my head, I would say to combine Rome, Pescara, and Roccamorice as one leg of the trip. Let’s call it Leg A.

Leg A: Day 1: land in Rome, explore if you have time/energy, sleep in Rome Day 2: Rome, sleep in Rome Day 3: Rome, sleep in Rome Day 4: travel (probably train) to Pescara, explore, sleep in Pescara Day 5: day trip to Roccamorice (I imagine there must be some way to get there by local bus? I’d look more into that!), sleep in Pescara Day 6: travel to Rome (or to Naples by Flixbus, depending on the day)

Sorrento, Pompeii, a hike up Mt Vesuvius (if that interests you), and Capri are all super-duper easy day trips from Naples. So, if you’re wanting to save budget, I’d plan all those as day trips (and maybe overnight in Capri if you want, to experience it without the day-trippers) from your friend’s place. And Naples itself also has things to see!

I think it’s worth spending a night or two in either Positano or Amalfi to spend one day in each and do the Walk of the Gods hike. But you technicallyyy can day trip to them from Naples as well. If you do, I’d recommend by ferry, because doing the train from Naples to Sorrento, then the bus from Sorrento to Positano/Amalfi, and then returning…all in the same day…multiples days…just sounds terrible to me! But the ferry would be €30 – €40 ish round trip each time, so multiply that by multiple people and two or three days, and I feel like you can just put some of that money towards accommodation instead, spending more time exploring and less time commuting!

Either way, I’d say to combine Naples, Pompeii, Sorrento, Positano, Amalfi, the hike, and Capri into another leg of the trip. Let’s call this next bit of the trip Leg B.

Leg B: Day 1: travel to Naples from Rome by train (or from Pescara by Flixbus), explore depending on time, sleep at friend’s place Day 2: day trip to Pompeii + Sorrento, sleep at friend’s place Day 3: travel to Positano in morning (probably ferry), explore, sleep in Positano (or Amalfi if you decide) Day 4: take bus/cab to Amalfi, explore, take bus/cab to start of hike, hike to Positano, sleep in Positano (or rearrange this if you decided Amalfi for Day 3) Day 5: take ferry to Capri, explore, take ferry to Naples, sleep at friend’s place (or overnight in Capri, taking ferry to Naples the next day)

So all that puts you at about 10 – 13 days, depending on if you add extra nights to Capri or the Amalfi Coast or Naples, and whether you combine day 6 of Leg A with Day 1 of Leg B.

If you have an extra 2 – 4 days, you can add a Leg C of Naples/Rome-Florence-(+ Pisa if you want)-Rome, or Naples/Rome-Florence-Venice-Rome, or Naples/Rome-Venice-Rome, etc. by fast train. Know that Venice is going to be a long train ride from Naples, though!

And you can rearrange any of the Legs A – C into whatever order fits best with your flights or your friends’ schedule, etc. since Rome is kind of the focal point of them all.

Hope some of that is helpful!! I think it all depends on how much you care to “fit everything in!” If that’s not a concern and you can return to Italy later on to tour the north, I’d say spending all 14 days in the areas you listed and taking it more slowly sounds the most enjoyable! (Renting a car is also an option, but as I’ve never done that in Italy and my itinerary was all public transport, I’ve stuck to public transport in this response.)

I’m sure you’ll love your trip whatever you decide. 🙂

Is it best to book the air first and then find the accommodations? I’m wanting to go to Italy this May…in a few weeks.

Hi Ruth! Italy in May sounds like the perfect time!

I’m a huge planner, so I like to plan a rough itinerary (which includes looking at any train schedules/prices, skimming housing options, flight options, etc.) before booking anything.

Sometimes I book free-cancelation accommodation first before booking my flight/transport. But if I am staying in an Airbnb or something not fully-refundable, or if the flight price is very good, then I tend to book the flight before the accommodation. So there really is no correct order! 🙂

But since your trip is coming up soon, maybe it’d be a good idea to at least look at accommodation first to make sure there are enough options for your destination within your budget before you put down money on a flight.

disfruta2vidagmailcom

So, I’ve decided to change my trip to 21 day in and out of Milan…how would you restructure the itinerary?

How exciting!

With seven extra days I would use one day to travel back to Milan from Rome at the end of the trip (Roma Termini to Milano Centrale, fast train takes 3 hrs) and for the remaining six days, choose what interests you the most from the below options:

– one extra night in Milan to do a day trip to Lake Como (or spend a couple nights on Lake Como) – one extra night in Milan or Venice to do a day trip to Verona (or spend one night in Verona in between traveling between Milan and Venice, or spend two nights in Verona to see Verona one day and day trip to Sirmione on Lake Garda the second day – I meant to go to Sirmione from Verona myself but didn’t because of rain) – one or two extra nights in Cinque Terre to rush less or do a day trip to Portofino ( this guide is from Genoa but is just as doable from Cinque Terre) and/or Portovenere – one extra night in Florence to do a day trip to Siena – one extra night in Florence to do some sort of organized day trip that includes Val d’Orcia and/or Tuscan countryside wine tour (I haven’t done either of these) – one extra night in Florence to do a day trip to San Gimignano (I haven’t been but have heard nice things) – one extra night in Amalfi Coast to rush less (and/or add a night to Capri to spend a full day there and not just a few hours) – a couple nights in the Emilia Romagna region (in between Venice and Florence – main city is Bologna) I only recommend this if you love the food from here (bolognese sauce, parmesan cheese, prosciutto di parma, and balsamic vinegar are a few famous ones) and plan to do food tours, as it’s known as a foodie haven

The above options allow you to stay in the same area and get to know it better/less rushed. But you could also add an entirely different region to your trip if that is what you prefer. You could rent a car and explore the Dolomites in the north, you could travel alllll the way south and see some of Sicily or Puglia (but that would be a very long travel day back to Milan or require a domestic flight), you could spend time on the island of Sardinia, etc. I haven’t done any of these things (yet!) so I can’t give much advice on them. If it were me, I would stick to the first options I listed and save further-away things for return trips to Italy. 🙂

Hope some of that helps!! 🙂

I have a 2 week vacation coming up in May and I’m thinking about going to Italy but have to idea how to plan it; where to go or where to stay!

Hi Stephanie! How exciting! I think May is a perfect time to see Italy (that and September) because the weather is warm but it’s not high season. You’re going to have an amazing time. 🙂

If it were me and my first time in Italy, I would follow this two week itinerary exactly as I have it laid out. I like to maximize places I’m seeing while still having enough time to “see everything” in each place, and the itinerary as I have it laid out does that. It hits the three main, can’t-miss Italy destinations (Rome, Venice, and Florence) plus fits in the next tier of popular destinations (Cinque Terre, Pisa, Milan, Amalfi Coast/Capri, and Pompeii).

The only additional planning you would need to do is your accommodation. I like to use Booking.com because I like its interface and app, that many properties listed allow free cancelation, and that it lists hostels (I’m not doing hostels at the moment though, due to the virus). But other sites you can use include Hotels.com, Airbnb, or HostelWorld. It depends on your budget and style. 🙂 Also, I always check the walking distance from the train station to the accommodation on Google Maps before I book.

If the itinerary as I have it laid out seems too jam-packed for you and you like to travel slower, you can let me know what you’re looking for (beaches/relaxing, focusing on one region and returning to the country later for other regions, art/history/museums), and I can give my thoughts on what to add and take out! 🙂

Karan Sachan

My wife & I are heading to our 2 weeks Italy adventure next week. After Rome, we were thinking of renting a car until the end. Do you know what is the parking situation? Would hotels/airbnbs provide accessible parking options overnight? Is parking fare like insane expensive?

Hi Karan! How exciting!!

I’ve never driven a car in Italy, so I can’t say much from personal experience. But the answer depends on what places you are visiting. 🙂 If you are seeing just the places on this itinerary, for me, a car isn’t worth the hassle because it’s so easy to travel between the main tourist destinations by train. The only parts of this itinerary that I think could be easier to get to with a car would be Positano and Amalfi, so just 2 out of 14 days. But maybe you will be exploring smaller towns of the Tuscan countryside, or heading to Sicily, or something like that, which then would have a different (easier) parking situation than the major tourist cities/spots! So the answer depends a lot on your specific itinerary.

Airbnbs sometimes do have parking and they list it on their Airbnb page if they do. Same with hotels. But if it’s not listed on their page, I wouldn’t expect parking. In my experience driving in other European cities, parking is expensive, but like I said, I can’t speak from experience on Italy.

If you do go with a car because you prefer to not be on a train schedule, I would suggest to plan where you will be parking in advance (Google search or see what others on TripAdvisor have shared). You might be able to find the costs in advance and then decide for yourself if it is too expensive vs the trains or worth it. 🙂

My wife and I are planning a trip to Italy in late May. Your itinerary has been of great help in coming up with our plan – thanks very much for taking the time to write such a detailed travel plan. The following is our draft itinerary:

17-Mar Arrive Milan 2:30 PM 18-Mar Milan sightseeing 19-Mar Lake Como 20-Mar Morning train to Venice 21-Mar Venice, Train to Florence in the evening 22-Mar Florence 23-Mar Florence, Pick up rental car drive to Tuscany in the afternoon 24-Mar Tuscany (includes Pisa and Cinque Terre among other places) 25-Mar Tuscany 26-Mar Tuscany 27-Mar Drive back to Florence, drop rental car, take train to Rome 28-Mar Rome 29-Mar Rome 30-Mar Vatican 31-Mar Train back to Milan, flight out at 2 PM

We will be meeting my sister and brother-in-law in Florence and will be with them for the Florence and Tuscany leg of the trip. The dates and days for this leg of the trip are kind of fixed so we are going with their plan and will be sharing the AirBnB they booked in Tuscany. We intend to cover Pisa and Cinque Terre while we are there. We intend to rent a car to drive to Tuscany, only place on this trip where we plan to do that.

Initially I had Amalfi Coast in there but reading your comments, I took that out for a later trip that could combine that and potentially Sicily (always wanted to visit Palermo/Bagheria – The Godfather effect!).

Would appreciate your insights on the overall itinerary. A couple of doubts that we have are are we budgeting too little time in Venice and is 3 days too much for Rome/Vatican? Thanks a lot in advance.

Hi Kam! I’m so glad to know my post and comments have been helpful to you. 🙂

What you have looks like an awesome itinerary! You are going to have a great time leaving it just as is. Personally, I liked Rome most between Rome/Venice/Florence, so I may be a little biased in saying that 3 days would never be “too much” for Rome. 🙂 That being said, my own itinerary only allots 2.5 days to Rome, so if you wanted to arrive in Rome one day later so that you take the train from Florence the following morning, arrive in Rome by or even past noon, and have 2.5 days instead of 3, I think you can still see everything in Rome that you would have seen. That would allow you to either have more time in Florence or maybe arrive in Florence from Venice the next morning and have one more night in Venice. (Not sure if that part is already fixed though?)

I think, make your decision on what interests you and your wife most between ancient history (Rome), renaissance art (Florence), and a visually stunning city (Venice). I think you’ll be able to “see everything” in Venice with your current itinerary because it’s a pretty small place, especially the touristic center. So the decision is more if you think you want to “hang out” longer in a visually pleasing city rather than about if you will miss seeing something touristic. As for the Vatican, some people allot a whole day to it. Others half a day. (This also depends on if you are buying skip-the-line tickets in advance.) I personally am not interested enough to spend more than half a day (I love Rome’s ancient Rome stuff more than the Vatican stuff), but maybe you and your wife love art and museums more than I do. 🙂

So to answer your question, I think the itinerary as you have it looks good and you’ll “see everything.” But if you are nervous, I think you can remove 0.5 days from Rome and add it elsewhere without seeing any less of touristic Rome. And I think Amalfi + Sicily for a future trip sounds like a dream!

Many thanks for taking the time for writing a detailed reply and apologies for my late response. We have made one change to our original plan: the more Youtube videos I saw of the Amalfi coast the more it felt like we should get at least a glimpse of it on this trip. So I have gone in the opposite direction and added one more night to Rome (stealing a day from Tuscany)!. In addition to giving more time for the historical sites, we plan to do a quick day trip of the Amalfi run by Walk Tours of Italy which should gives us a glimpse of its wonder and hopefully tempt us for a return trip! Once again many thanks for your help and all the best.

An organized day trip is a great way to quickly see the Amalfi Coast from Rome! It’s very stunning/unreal place, and I know you’ll love it! I would love to know how the whole trip went after you return. 🙂 Have the best time!!

Thanks for your help again and will be sure to write after we return from the trip.

Hi. We are planning on arriving in Naples March 26th or so and want to spend two weeks in Italy. Our final destination will be Marseilles France. We will arrive in Naples from Sicily. What do you recommend for an itinerary for those 2 weeks. Thanks

Hello! I’d recommend this exact itinerary, just in a different order. Since you are arriving in Naples instead of Rome, that’s actually less backtracking. 🙂

I’d say to start with the Pompeii/Amalfi Coast/Capri leg. If you wanted to be based in Naples, it is technically possible to do Positano, Amalfi, Capri, and of course Pompeii each as day trips from Naples. So you would either rent a car, join tour groups, hire a driver, or DIY it by using the buses/ferries I mention. It would just be more time in transit each day vs being based in, for example, Sorrento.

After that, I would take the train up to Rome and do the Rome portion of this itinerary. Then, from Rome take the train to Florence and continue with this itinerary exactly as is for Florence > Pisa/Cinque Terre > Venice > Milan. RyanAir has direct flights from “Milan” (the BGY airport in Bergamo, not the MXP airport) to Marseilles. But remember that they are a budget airline and very strict on baggage size/weight!

Hope that helps! Feel free to respond back 🙂 Sounds like it will be such a lovely trip!!

Thank you for such GREAT information!! We plan to be in Italy in November…Hubby is teaching in Milan & Lithuania the first week of Nov & I will meet him in Rome when he’s finished. We should have 15 days, not including our travel days and I’m thinking Rome, Florence & Venice for sure. We like to be leisurely when we travel 😉 Are there any of the destinations you listed that we should omit due to it being November? Leslie

Hi Leslie! So glad you found the info useful 🙂

As a Californian who’s pretty much only known the drought years, weather (including rain) really impacts where I want to travel! So keep in mind that bias in my response LOL.

Like I mentioned towards the beginning of this post, Venice is prone to flooding during rain. So if it’s raining heavily there on your visit, it might not be enjoyable, but you won’t really know the forecast until closer to the date. I wouldn’t go as far as to say omit it, but just keep that in mind, and maybe you can pack or plan to purchase rain boots worst case.

Personally my own interest in beach-y places (which in this itinerary would be Cinque Terre, Amalfi Coast area, and Capri) is entirely dependent on warm weather. So those would be the ones I personally omit and save for another visit. The order of omission for me would be: Capri, Amalfi Coast, Cinque Terre. Cinque Terre would be last to go for me because it’s all connected by train, so I imagine it would still be just as easy to visit. And apparently no one checks for the ticket to the paid hiking trail in winter, so assuming it is not rainy or just rained (muddy trail would not be fun) that might be a plus to going in winter. Amalfi Coast should still be doable, but I imagine the ferry schedules would be heavily reduced in low season, and potentially more canceled due to sea conditions, so getting to Capri might be annoying. All three of these destinations’ villages/towns are filled with souvenir shops, boutiques, and restaurants, so I would imagine some might be closed in winter, but not all.

Since you like to be leisurely and the itinerary as I have it is very jam packed, * I would omit the entire Amalfi Coast and Capri leg of the itinerary. It’s a lot of moving around in a short time frame, and I don’t know that it’s worth it in cold weather. You can keep the Pompeii portion of the itinerary by just adding 1 more night in Rome and making Pompeii a day trip. So in the end, that would net save you 3 days. * I think Cinque Terre will be worth it if you just wanted to SEE the pretty towns (they’ll look exactly the same in winter as summer, and will be much less crowded!) but not worth it if you’d be very upset if the trails are closed do to mud from rain. If you omit this, that would save you 1.5 days. I’ll assume you don’t omit this for the following bullet. * With the 3 extra days, I would choose the 3 of the following that interest you most: ~ Day trip to Siena from Florence (add 1 night to Florence) ~ Day trip to San Gimignano from Florence (add 1 night to Florence) – I have not been, but have heard nice things ~ Day trip to Bologna from Florence or Milan (add 1 night to Florence or Milan) – I only recommend this if you love the food from here and plan to do a food tour, as it’s known as a foodie haven and is in the region where a LOT of the Italian dishes Americans love/know are from ~ Day trip to Verona from Venice or Milan (add 1 night to either Venice or Milan) – where Romeo and Juliet was set ~ If it happens to be a nice day, day trip from Milan to Lake Como (add 1 night to Milan)

This would be a lot less moving around, so a lot more leisurely. If you want to save moving accommodation from Florence to Cinque Terre, you can also just do Cinque Terre as a day trip from Florence, especially if you do not plan to hike. I detail how I’d recommend fitting all villages (plus the main hikes) into one day here . This way, you would only be based in Rome, Venice, Florence, and Milan for the entire 2 weeks.

Hope some of that helps! Feel free to respond back 🙂

Thank you, thank you, thank you! Your reply is very helpful 🙂 We’re less about the beaches so omitting the Amalfi Coast & Capri makes sense. I hadn’t considered the Bologna region and that idea intrigues me as we do like food 😉 Is it a crazy idea to think that we can plan just our Rome leg from the States & then figure out the rest while we’re over there, according to the weather forecast at the time? That would give us flexibility as to whether we begin or end in Venice before heading back to Rome for our flight home. Again, I appreciate all the time & effort you’ve put into your blog & responses! Leslie

I don’t think that’s crazy at all! You will just have to pay some more for any long distance train tickets due to purchasing them closer to the date of travel vs weeks or months out (which I mention some price examples of in the post as well). November will be off season, and on top of that, we have the lovely pandemic which doesn’t seem to be going away any time soon, so I do imagine you would be able to get accommodation just fine.

One thing I personally would do though is to still plan out what you want to do in each of the non-Rome legs of your trip in advance (at least roughly), and then just mix and match the order of the non-Rome legs later on. So plan what you want to do in Florence, how many nights there, roughly how to do any day trips from there, and then same for Venice and any other base cities, but then don’t book until getting to Rome if you like. That way, you don’t waste your vacation time in Rome searching the internet to plan time-consuming details. You can just spend a few minutes searching the weather, deciding the best order, and booking 🙂

Awesome, that’s good to hear. Thank you again!!

You’re welcome! I’m sure you’ll love your trip 🙂

Hi, my husband and I are planning a 14-day honeymoon this October. I am worried we will spend most of our time on trains if we try to visit too many places. We fly in and out of Rome. Would you recommend skipping out on Amalfi Coast and heading north (Rome-Florence-Cinque Terre-Milan-Venice-Rome) instead? We don’t want to miss out on anything!

Hi Ashley! I definitely understand that sentiment!

If there was any portion of this itinerary to take out, in my opinion, the Amalfi Coast/Capri/Pompeii leg would be the one to go. The main reason for that is that it is a rather high ratio of travel time to non-travel time compared to the other legs of this itinerary, AND it easily could make up its own entire week+ Italy trip if you are able to return. A third reason would be that since you mention you don’t want to miss out anything, I think all the other destinations rank above Amalfi Coast/Capri/Pompeii in terms of what is considered most “must see.”

So yes, what you said is what I would recommend. 🙂 Especially for a honeymoon, slowing down would be a lot more romantic!

Hi, this itinerary sounds amazing. My husband and I would like to travel from the US to Italy for the first time next May. Do you have lodging accommodation recommendations and how to book them?

Hi Jennifer! May is a lovely and comfortable time to travel to Italy. You will love it!

I can’t say I have specific lodging recommendations for each destination, but I pretty much always use Booking.com to look for and book my accommodation. I just really like the interface of their website for searching as well as how it lists your bookings out in chronological order, so it’s easy to keep track of where you are headed next. Plus, a lot of their listings offer free cancelation so that (1) I feel comfortable booking something earlier than I’m totally certain on it and (2) things are easy if plans change. And I find this to be true of both their desktop site and mobile app. They also have a large range, from five star hotels to hostels to guest homes, so I really like it as a one stop shop. (I’m not affiliated with them at all, they just happen to be the site that I almost always use for several years now.)

One tip with them and with any hotel listing site is to check TripAdvisor after you have settled on the hotel but before you book. The photos on those booking sites are always provided by the hotel itself, so I often just do a quick skim of the traveler uploaded photos on TripAdvisor, especially if it is more of a budget accommodation.

A lot of people of course love apartment rentals, so if you and your husband like that experience more, definitely look at AirBnB and Vrbo. I just personally prefer not having to coordinate check in and check out time with each host in an itinerary like this where you are moving around every few nights. I like that at hotels/hostels I can drop off my bag with reception if I arrive before check in or leave it there after check out if I’m sticking around. But the plus side is that you have the whole place to yourself, feel a bit more “like a local,” and can save money on food by grocery shopping and using the kitchen, packing lunches, etc. So kind of just depends on your style!

I hope some of that helps! I just haven’t revisited each destination on this itinerary enough to try out enough different accommodations to be able to give strong recommendations 🙂

This is the most amazing, detailed, helpful itinerary I have seen. Thank you for putting this together, it was SO helpful!

Thank you so much for your kind feedback! 🙂 I’m glad to know it was helpful. I hope you love your time in Italy!

Hello there! Your itinerary is so helpful! My husband and I are a planning a hopeful trip to Italy this summer and since we are coming from the states we will have two less days than your itinerary permits. Do you have any advice when it comes to narrowing it down? Also, we are flying in and out of Rome. Thank you!!

Hi Jenny! I’m so excited for your hopeful trip!!

This itinerary is for 14 full days in Italy, so with two less days I understand you will have 12 full days instead. I would recommend you remove the Pompeii/Amalfi Coast/Capri and head straight from Rome to Florence instead.

This is for three reasons:

-Firstly, this part of the trip is the trickiest logistically (unless you hire a private car the whole way), so crowding it into the 14 day itinerary was already pushing it.

-Secondly, this part of the trip is a little less “must-see” than the other destinations in my opinion. I define the “main” Italy spots as Rome, Florence, Venice, Milan, and in recent years, Cinque Terre.

-Thirdly, this region would make/justify a nice one-week trip on a return visit to Italy.

This would bring you down to 10 full days (which I happen to map out here: https://thattravelista.com/italy-ten-day-itinerary/ ). I would save one day as a travel day back to Rome at the end. That brings you to 11 full days.

I would use the last full day as an extra night in either Cinque Terre, Florence, or Rome. I’d reco Cinque Terre so you don’t have to rush through it as quickly as I have in the itinerary. But you could also see more of Tuscany via a day trip from Florence if that region interests you more (Siena and San Gimignano are two popular ones, or perhaps a wine tasting excursion!). Or if you or your husband love the history of Pompeii, you can do a day trip there from Rome.

Hope that helps! Feel free to respond back if any more questions/thoughts!

I can’t believe how detailed and helpful this is! I will definitely use this when my long-awaited trip happens. ❤️

So glad to hear it’s helpful, Rachel 🙂 <3 I seriously wish I was (safely) traveling Italy right now! But at least we can plan now so everything's ready once we can go later 🙂

Since Italy is my “neighbour” country I’ve been there numerous times and visited majority of the places you included in the itinerary – and I must say you did a great job! Thorough & interesting – definitely super helpful for anybody who is planning their trip to Italy!

Thanks so much, Sandra! Jealous that Italy is so close for you! 😉

Disha Smith

You post has me missing Italy so much! I love how detailed you are in this itinerary. I definitely missed out on quite a few gems in Italy.

The best part about missing something is it’s an excuse for a return trip 😉

Snazzytrips

I love all the detail here. Will use this to plan my next trip to Italy. Amalfi Coast and Capri definitely on my list, including the Blue Grotto, but not sure now if I can do it.

If Blue Grotto is top of your list, definitely don’t rule it out! Just budget enough time and skip out on some other Capri sights 🙂

Melissa Roos

The detal in this post is amazing! I’ve been looking to visit Italy for a few days so these tips are very helpful.

I hope you love your trip! I’m sure you will 🙂

This is such a wonderful and detailed blog, so much useful info. And your photos are beautiful, thanks for sharing!

Thanks, Emma! 🙂

wow!! the detail on this post is beautiful!! 🙂 this is inspiring me to go back to Italy ASAP 😀

Thank you, Daniela!

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How to Day Trip to Burano, Murano, & Torcello from Venice

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Delightfully Italy

The insider's Italy travel guide for independent travelers

Italy in two weeks: the perfect 14 days Italy travel itinerary

Discover Italy in 2 weeks. Visit classical destinations such as Venice, Florence, Tuscany, Rome, Cinque Terre and the Amalfi coast. 

Two weeks in Italy are probably the minimum time needed to give you a fair view and feeling about this wonderful country: you should be able to see many of Italy highlights and spend a decent time in each one of them.

This Italy in 2 weeks itinerary is based on my experience, personal tastes and on a tight 2 weeks schedule (reasonable days in brackets). I’m assuming you will purchase  an “open jaws” ticket (meaning: landing and departing in two different airports),  to save valuable time. A round trip would imply at least half a day more.

I tried to use train / public transportation as far as possible, and showed (in brackets) average transfer times.

However, you may wish to rent a car, especially to explore Tuscany at your own pace, and to discover beautiful hamlets off the beaten path. If this is the case, I recommend you have a look at   www.rentalcar.com , and book your car as early as possible , to ensure availability and to get the best rates. It’s an aggregator, and allows you to compare offers from the main car rental companies.

These are just ideas, with optimized logistics. Days to be spent in the different places can be modified based on your tastes and interests. Feel free to mix everything up, it’s your Italy in 2 weeks very personal trip!

Would you like some help on your Italian trip planning? Then have a look at my Italy Travel Consultant page!

Destination 1:   Venice  – (2-3 days)

Ferry Boat in Venice + a lot of walking (and maybe a romantic gondola ride  ). Of course Rialto, San Marco and Palazzo dei Dogi, but also fancy Museums like Punta della Dogana . If you are travelling with kids, have  a look at a  child oriented itinerary . On the third day visit Murano, Burano and Torcello (1 day, by ferry).

Venice main highlights, and especially San Marco church, suffer from very long queues. To skip the line and to know more about its masterpieces, a guided tour could be a clever option. Click here for a good San Marco guided tour .

Where to stay in Venice:

• The Foscari Palace : enjoy a room on the Canal Grande, just in front of Rialto market
• The Hotel Pausania : a charming hotel in the off the beaten path Dorsoduro Neighborhood.

Want more choice? Click here to find the best places to stay in Venice

Destination 2: Florence (1-2 days)

The length of your stay in Florence will depend on how much time you wantto dedicate to Florence Museums.

Key highlights are Uffizi, Michelangelo’s David (in Galleria dell’Accademia, the one in front of Palazzo Vecchio is a copy) , Palazzo Vecchio, Santa Croce, San Miniato, piazzale Michelangiolo, Via Tornabuoni, Palazzo Pitti, Boboli, Fiesole (20-30’ out of town). Have a look here for a one day walking itinerary. 

You may consider a guided tour, to better appreciate Florence history and culture. If you would be interested in taking a g uided tour, or to skip the line in the main museums , just follow the link.

Where to stay in Florence:

The Grand Hotel Cavour : lots of atmosphere and history for this fascinating hotel located between Santa Maria del Fiore and Palazzo Vecchio. The roof bar will seduce you with its fantastic views over the Santa Maria del Fiore cathedral.

Want more choice? Click here to find the best places to stay in Florence

Destination 3:  Florence >> Pisa  (Lucca) >> Cinque Terre (1 day) .

It takes a little less than 3 hours to go by train from Florence to the Cinque Terre area, via Pisa. Lucca is half an hour from Pisa by train. If you decide to visit also Lucca, you could consider spending the night in one of the two towns (I personally prefer Lucca).

Destination 4:  Cinque Terre .

It’s worth spending 1-2 days at Cinque Terre, but should also visit Portofino and San Fruttuoso (convenient boat services/tour available). Sestri Levante, lovely little town located between Portofino and the Cinque Terre could be a good Base. Don’t use a car, parking is a nightmare. (2 days).

Destination 5: Cinque Terre – Siena / Tuscany country side .

Here you could consider renting a car,  to provide you with all the freedom you want to explore this fascinating countryside. Tuscany country side >>> Rome. Chianti, Monteriggioni, Siena, Montalcino, Val d’Orcia, Pienza, Montepulciano >>> Rome. (1-2 days, even more if you like the countryside and the good food).

This itinerary assumes you rent a car, by far my suggested option. In case you didn’t feel comfortable driving on Tuscany country roads, then you can use Florence as a hub and join Tuscany country side guided tours. Here are my recommended ones .

Where to stay in Tuscany: Monteriggioni (Siena)

• The Hotel Monteriggioni : a charming and romantic hotel, located in a fortified medieval village
• The Castel Pietraio , a true medieval castle, now four star hotel, to treat yourself like a king

Destination 6:   Rome (3-4 days or more) .

You don’t want to have a car in Rome; walk + hop on – hop off buses ( follow this link to reserve on line, no need to print the receipt ). Bicycles or scooters, if you dare, are fantastic solutions!  Spanish steps , Piazza Navona, Panteon, Fontana di Trevi, Campo dei Fiori, Old Ghetto,  Trastevere . St Peter (consider  climbing on the Cupola ) + Vatican Museum ( RESERVE! queues are terrible – click here if you wish to reserve your visit with Ticketbar ).

Mercati di Traiano, Fori Imperiali (including Orti Farnesiani), Colosseum, Palatino are unmissable destinations, and for this reason may be crowded. Purchasing the ticket in advance is a clever way to skip the line and to save time .

Don’t miss Trastevere + Isola Tiberina (very lively area in summer time, funny & crowded). Appia antica + Catacombs (best by bike, you can rent one in via Appia),  medieval Rome and its underground treasures .   If you are a running fanatic, don’t miss Villa Borghese and the awesome  Borghese Gallery .   Villa Adriana and Villa D’Este , both in Tivoli (30 km from Rome) make a pleasant day trip out of town .

Where to stay in Rome:

• The  Hotel la Lumiere , a delightful hotel hidden a few blocks away from the Spanish steps, in posh via Condotti. Great roof top, have your breakfast while admiring Rome century old roofs!

Want more choice? Click here to find the best places to stay in Rome

Destination 7: Rome >>Naples/Sorrento (2/3 days) .

You can sleep in Naples or, better, in Sorrento. Visit Pompei, Sorrento, Positano , Ravello, Capri. Naples is also worth a visit. You can use public transports: boat service between Sorrento and Positano is very convenient, while buses, especially to Ravello, could be extremely crowded (consider sharing a taxi with fellow travelers). Renting a car could be an option in high season, but car parks are very expensive (and driving on the costiera is an experience on its own!).

Looking for a hotel? Click here to find the best places to stay in Sorrento

For more info about Amalfi coast visit my posts: Capri: breathtaking Faraglioni and Natural Arch walking tour and Best of Amalfi coast

Enjoy your Italy in two weeks itinerary!

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If you wish to  visit Italy  for the first time, or if you already discovered Venice, Rome, Florence, the Amalfi coast, but still want more, delightfullyitaly.com is here to disclose to you  Italian Must See  as well as  Italian hidden treasures .

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27 Replies to “Italy in two weeks: the perfect 14 days Italy travel itinerary”

Thank you for the post and a wonderful blog! I am using your itinerary for our first trip to Italy.

Tks Phoenx, enjoy Italy!

I must state that yours is a very well written blog. We spent two weeks in Italy’16 and very much followed an itinerary similar to what you have proposed. However we added Milan as our flight out was from there. We did not include CT as we had read that cramming CT to a 2 week trip in Italy would have been rather hectic. We are middle aged and wanted to take things rather laid back. Mine was a complete DIY trip and I thought I should share my experience with other first- time would be travellers to Italy. So I have started a very hands- on kind of travel blog which is almost 75% complete.diytravelexperiences.wordpress.com. Glad if you can critique the same and hope that others will visit my blog and benefit. Regards. Dhiraj

Hi, nice blog. I particularly liked the hands on tips and the “myths about Italy”!

Hi grateful for visiting my blog and thanks a ton for your comments. Good luck. Regards. Dhiraj

Hi- we are taking our 2 boys in 2018. My favorite is Venice and my husband loves the Amalfi coast. Is this doable in 2 weeks adding CT, Pisa, Pomeii and Rome?

How old are your boys? Children have their own pace, and need time to relax and play, on top of visiting. By the way, you are not mentioning Florence and Tuscany, unless you have already seen them you may probably wish to spend some time there. So, coming back to your question: yes, you can do it: Day 1: getting to Venice, check in, relax Day 2-3: Venice and the lagoon (Murano, Burano) Day 4: Venice >> CT (this will take close to one day, change train in Milan) Day: 5-6 CT Day 7: CT >> Pisa (visit the leaning tower, reserve in advance!!!) Sleep in Florence Day 8: Florence >> Rome (1,5 hours) >> Check in, city center walk (look for my post for detailed itinerary) Day 9-10: Explore Rome Day 11> Rome – Sorrento Check in, relax (yu may squeeze Pompei in day 11 if you leave early) Day 12: Visit Pompei (or Capri if you already seen Pompei on day 11) Day 13: Visit Amalfi coast: Positano, Ravello, Amalfi (renting a car could be a good idea) Day 14: Back to Rome & fly home

In my opinion, this is doable if your children are at least 8-9 and used to travel, otherwise too tiring.

Hi, thank you so much for this. It looks like your first flight coming in drops you off in Venice, but tell me at what point do you take another flight other than back home, is there one needed at all other than home?

Hi Arlene, you don’t need any additional plane for this itinerary, you can just use trains. I’m available in case you need any help for your Italy trip planning. You can also follow delightfully Italy Facebook page for additional travel inspiration https://www.facebook.com/delightfullyitaly/

Enjoy Italy!

Hi, we are headed back to Italy for our second trip. We will have 2 weeks and starting from London. We would like to spend a few days in Amalfi Coast and also Tuscany. Maybe Milan, CT, Lake Como, Naples. Not sure how to plan this. We will not be going to Venice or Pompeii or Pisa as we already did this. Would appreciate any help.

Sure Lydia, with pleasure. I will send you an e-mail with some suggestions.

Would love to see this itinerary!

Hello. We are planning trip to Italy beginning of June this year. I was thinking 2 weeks and would like to visit the following places Venice, Milan, Florence, Amalfi Coast, CT, Pompeii and Vatican. Is this doable in 2 weeks. I am flying from Tampa, FL and was thinking of arriving in Milan or Venice and then come back home from Rome or Naples. Or do it the other way around arrive to Naples or Rome and come back from Venice or Milan. Any thoughts?

Hi Ana, would fly to Venice and come back from Rome, or the other way round, depending on the air rates. Will send you additional details on your mail.

thank you for your blog it is very helpful. few questions, what is the best way for transportation between the 7 destinations? is renting a car for the whole trip possible or you recommend taking the train? also flying back the last day from Naples or Rome what you suggest. thank you!

Hi, I recommend to use the train, and hire a car only to visit specific areas such as Tuscany. The reason is taht trains are much faster and taht you are not allowed to use private cars in city centers such as Rome or Florence (and of course you don’t need a car in Venice!). If you can find a suitable flight from Naples (meaning: good time slot and not too expensive) then a flight from Naples makes a lot of sense.

Hi Jean, thank you for the blog – very helpful!! Would love to get your recommendation on a 14 day travel with 2 kids, 3 & 11 in July. We love the beaches and would like to visit few historical sites. We are flying into Milan. I was thinking about renting a car, driving down to CT, Pisa, Florence, train to Rome/Naples/Amalfi Coast. Any recommendations? Kids love train rides. I thought a car would be convenient to do things at your own pace. Thanks!

Hi Brian, thanks for your appreciation! I’ll send you a separate mail with my views and suggestions

Hi Jean, I wish to also have the same trip plan exactly like Brian. Flying into Milan and flying out from Rome for a 14 days travel, but in December. Appreciate your advice as well. Thanks.

Hi, I just answered to Brian specific points, I didn’t design a bespoke plan. For a 2 weeks itinerary you can get inspiration from my “Italy in 2 weeks” post or subscribe to my Italy Trip Planning” service.

Hi Jean love your Blog , I’m flying in to Rome with my Husband and meeting my Brothers . We have 4 days booked in Rome and then 10 days who knows , I really like to be organised my Brothers want to wing it . What’s your thoughts on this and best places to go .. thank you Karen

Hi Karen, the needed level of organization and pre-booking depends on three factors: A) when you are planning your trip: if you are planning to come in low season (ie, winter), not much need to plan ahead, in July and August you may hardly find decent accommodation and trains availability B) Were you are planning to stay, mainstream destinations: Venice, Rome, Florence, Cinque Terre, Amalfi coast get overbooked long ahead, while off the beaten regions (Apulia,marche, …) are less crowded C) Your visiting ambitions: if you want to limit your visit, say, to Rome, Tuscany and Umbria, then you have a reasonable amount of time to decide day by day where to go and stay, also based on availability. On the other side, if your plan is to squeeze the mainstream destinations in 14 days (Rome, Amalfi Coast, Florence, Tuscany, Cinque Terre, Venice, …), then you need to design an optimized itinarary and make sure the logistics is fixed much ahead.

Hope this is useful. Enjoy your visit and don’t hesitate to contact me should you need some help on your trip planning.

We are planing for three weeks in Italy in either may or September. Starting in Milan and ending in Sorrento and fly to back to the US from either Naples or Rome . the second week of our trip we plan on staying in Greve in Tuscany for a week and travel from there. Any suggestions.. Thanks.

Hi Mike, I would rather choose September, weather should be nicer and it’s a better period to visit the vineyards. Milano deserves 1, max 2 days, from tehre you can get to Como Lake in one hour by train (train to Varenna, then ferry to Bellagio) You may want to have a look at my post about Chianti, there’s lots of information about what to do, where to sleep…and where to wine taste! Once you are finished with Tuscany, take a high speed train to Naples, and start your Amalfi coast exploration from there. Try to dedicate one day to visit Naples, it really deserves it. Do spend a night in Capri (avoiding the week end), it’s a magical place and for a real off the beaten path experience the island of Procida will seduce you (no tourists there, just colored housed and a lost in time feeling). Even though Sorrento is a perfect hub to visit the area, in my view it’s not the most beautiful place to stay, I would rather select Positano.

These are the first things that come to my mind. If you wish help on your Italy trip planning (select best accommodations, optimize logistics, select the unmissable experiences) don’t hesitate to contact me, I’ll be more than happy to help.

Thank you for your quick response. We travel to Italy almost every year and rent an apartment in a small town just south of Florence. (Qurco)..The name of the place is Le Torri. This coming trip we are going to rent a car and drive from Milan down south and visit friends in Rome and Lake Bomba In Abruso.. then on to Sant Agata del golfi near Sorrento. then depart either from Naples or Rome depending on the flights. I would like to know if you know a good route and any good bed and breakfast places on the way. We come there to visit the people and and and enjoy your beautiful country and try not to stay at large hotels. Thanks again. Mike

Thanks for a great itinerary, am using it as a foundation for our first trip to Italy!

Hi Douglas, apologies for the late reply. I’m glad you liked my suggested itinerary. In case you need any further help for your trip planning don’t hesitate to contact me.

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2 Weeks in Italy – A 14-Day Itinerary for First-Timers

A trip to Italy has something for everyone: artistic masterpieces, ancient history, amazing food, fabulous landscapes and local folklore.

A 14-day itinerary allows you to discover all the facets of this unique country, from its main cities to some of its most fascinating villages.

Are you ready to spend 2 weeks in Italy?

There are two ways to travel, by car a do an Italy road trip or by train as described below.

Don’t forget to check: my Italy packing list .

Disclaimer: This post contains affiliate links. This means that should you click on certain links, and then subsequently purchase a product, I will receive a small commission.

Table of Contents

How to Spend 14 Days in Italy – 2 Week Itinerary

Day 1: Flight to Rome and Transfer To Naples

Fly to Rome, which is not only the Italian capital but also one of its main transportation hubs allowing you to easily reach any other large city.

To find the cheapest flight options from your city, you can use the search form below

Catch a high-speed train to reach Naples in about 1h. Try to be there around lunchtime to be able to spend a few hours visiting the city.

But first, enjoy a real Neapolitan pizza and a well-deserved lunchbreak!

In the afternoon, you can choose between:

• A visit to the National Archeological Museum (if you’re not too tired!) for a real blast from the past. Book your skip the line tickets for the museum here.

• a visit to the mystic Sansevero Chapel to admire the famous Veiled Christ. Click here to book a small group guided tour to the Old Town and the Veiled Christ.
• In the evening, take a stroll in the trendy Chiaia neighborhood and have a drink outdoor like a local

Where to stay in Naples

Check out my guide on where to stay in Naples here. 

Renaissance Naples Hotel Mediterraneo : This 4-star hotel, a member of the Marriott Group, is located centrally close to the main attractions of Naples and the ferry terminal. Rooms are comfortable and modern while the rooftop where breakfast is served has lovely views of the Bay, Castel Nuovo, and Mount Vesuvius. Click here for more information and to check the latest prices. Grand Hotel Europa – Sea Hotels Group : Located near the main station, this hotel is an excellent choice for those thinking about visiting Pompeii or the Amalfi Coast. It provides excellent 3-star value with comfortable rooms including Wi-Fi, satellite TV, air-con, and safe. Click here for more information and to book the Grand Hotel Europa.

You might be interested in: 3 days in Naples.

Day 2 Pompeii & Sorrento

Visiting Pompei is a must and you cannot miss this stop during your 2week stay in Italy! You can easily reach Pompei by train and it will surely be an emotional visit making you feel like an ancient inhabitant of these places. To see the main points of interest and make the best of your time, join a guided tour ( Pompeii: Small-Group Tour with an Archeologist ). As an alternative, get a fast-track ticket ( Pompeii Fast Track Entry Ticket ).

An organized tour will take around 2- 3 hours, but armed with the knowledge already gained, you may want to spend more time there on your own before returning moving on.

No matter how you choose to visit the site, know that it is very busy especially from May to October. Bring a hat and sunscreen, wear comfortable shoes and drink plenty of water.

In the afternoon, head to the lovely town of Sorrento . How can you spend a few hours?

• take a stroll in the picturesque alleyways of the Old Town
• visit the beautiful S. Francesco Cloister
• linger in a café in Piazza Tasso

• meet local fishermen in Marina Grande village
• watch the sunset from the panoramic terrace of Villa Comunale

As an alternative, you can join a walking tour. If you are looking for an organised skip the line guided tour starting from Naples I suggest this full day guided tour that combines a visit to the Pompeii ruins and the mount Vesuvious .

Day 3 Amalfi Coast

Option 1 : rent a car and spend your day driving around to explore all the picturesque villages along the coast. A few tips?

• Positano : winding alleys, a medieval flair, and some wonderful views. If you feel like being active, don’t miss the Path of the Gods.
• Amalfi: the main and largest town on the coast, full of historical buildings and monuments. Visit at least S. Andrea Cathedral and the Cloister of Paradise .

• Ravello : up in the Lattari Mountains and overlooking the Mediterranean Sea. Visit the Gardens of Villa Cimbrone to take the most amazing pictures!
• Cetara: a lovely fisherman village where you can taste a local gastronomic specialty named “colatura di alici” (anchovy extract)

Option 2 : a guided tour from Naples to the Amalfi Coast.

Option 3: It is very easy to do this day trip on your own as well. You just need to catch a train to Sorrento from Naples. There are about 3 trains per hour depending on the season and the journey is about an hour depending on the type of train. As soon as you exit the train station there is a kiosk where you can buy a bus ticket to either Positano or Amalfi. The buses are in front of the station and tickets cost 2-3 euros one way.

It takes around an hour to get to Positano by bus as the road is small and there is huge traffic especially during the summer and you need even more time to get to the Amalfi village because it is further away. Also, during the high season, the queues to take the bus are huge and you might have to ride standing. Also, the road is very curvy and a lot of people get sick.

Option 4: There is an alternative way to get to the villages, which is by ferry from Sorrento. You can get the ferry from the port. It is a 10- minute walk from the train station. From Sorrento to Amalfi it is one hour by ferry and the ticket was 16 euros in September that I visited. The ferry makes also a stop in Positano before arriving in Amalfi. There are many small boats connecting Positano with Amalfi and the other villages of the Amalfi Coast. Tickets can be bought at each port.

You might also be interested in: 11 Amalfi towns to visit. An Amalfi Coast itinerary and a guide on where to stay in the Amalfi Coast. A guide to Positano

Day 4 Capri

Take a ferry from Naples to reach Capri island in about 40 minutes. The fast ferry takes 50 minutes to Capri from Naples and tickets cost around 21,50 euros one way.

Start your visit with a boat tour taking you to the wonderful Blue Grotto ( Capri Boat Tour With Stop by the Blue Grotto )

Catch a bus and reach the village of Anacapri . Its highlight is the beautiful S. Michele Arcangelo church with its precious majolica floor ( Chiesa di San Michele (chiesa-san-michele.com) )

Now you can either take the chairlift and reach the top of Mount Solaro ( The Chair Lift Monte Solaro (capriseggiovia.it) ) or go back to Capri to visit its Old Town and the medieval Certosa di San Giacomo

Don’t miss a visit to the Gardens of Augustus to enjoy some local nature

If you still have some time to spend on Capri island, reach Villa Jovis on Mount Tiberius

Alternatively, you can book a full-day tour to Capri from Naples.

Click here for my post: Things to do in Capri

Day 5 Naples to Rome

Spend your last hours in Naples taking the Underground Tour to learn more about some important archeological findings ( Naples Underground (napolisotterranea.org) )

Catch a high-speed train to reach the second stop of your 14day itinerary in Italy: Rome !

Spend the afternoon walking around the city center. Start from Piazza Navona and take a moment to admire the Fountain of the Four Rivers by Bernini

Reach Piazza di Spagna and climb its iconic stairs to reach the panoramic terrace in front of the church of Trinità dei Monti

Admire the neoclassical beauty of Piazza del Popolo with its Egyptian obelisk and its twin churches

Reach the Trevi Fountain and wait in line to throw a coin into the basin!

If you still have some time, enjoy some shopping in via Condotti and via del Corso

Where to stay in Rome

Royal Rooms – Via Del Corso : The Royal Rooms are just 200 meters from Via Margutta and many amenities are in the immediate vicinity. They include shopping, piazzas, and cafes. Within the Royal Rooms, you will find everything you need for comfortable accommodation. Click here for more information and to check the latest prices. Palazzo Medusa : Palazzo Medusa is regularly selected by its guests as one of the best in the whole city. Comfortable accommodation includes a large TV, an en-suite bathroom, and a hairdryer. You can even rent a bike if you wish. Palazzo Medusa has gained a reputation for its fine cuisine; enjoy it! Click here for more information and to check the latest prices. Navona Colors Hotel : Located less than 200 meters from Piazza Navona, its situation is ideal for visitors wanting to walk or cycle around. The food is good and the bedrooms are comfortable in this beautiful Baroque building. Click here for more information and to check the latest prices. Piazza Del Gesu Luxury Suites : Situated on the Piazza Navona, a 5-minute walk from one of Rome’s highlights, the Pantheon. Facilities you will enjoy include free WI-FI, lovely furnishings, and a modern bathroom. The views over the City are stunning. Click here for more information and to check the latest prices.

You can also check a local’s guide on where to stay in Rome .

What’s best than starting off the day with a visit to the Colosseum ?

Dive into ancient times by also visiting the Roman Forum and the Palatine Hill . You can also take a guided tour with skip the line tickets to make the best of your time as lines are huge .

In the afternoon, head to the Pantheon and watch the light entering from the hole in its dome.

Enjoy some nature in Villa Borghese Park , but not before taking a tour of the beautiful Villa Borghese Gallery housing some famous statues by Canova. Book your skip the line tickets here to avoid the queues.

Tonight, taste some typical Roman dishes in Trastevere !

You might also be interested in: 5 days in Rome .

During your 2week stay in Italy, you should absolutely spend a whole day visiting the Vatican . Start from the Vatican Museums and save enough time for the Sistine Chapel, the Galleries, and Raffaello’s Room.

Tip: Visiting the Vatican is an essential Rome experience, and it will be quite overwhelming! Before anything, you should know that the queues are huge. No matter how much you think you can wait, you can’t. The queues go on for seemingly forever, so I recommend a skip a line tour. Another way to enjoy the Vatican if you don’t have much time is by this Pristine Sistine, early entrance small group Vatican tour . The reason I like this tour is that you get inside the Vatican one hour before it opens, the group is small and you get to see the Vatican in under 4 hours. All 3 times I’ve been there were with the skip-the-line guided tour, and it added to the overall comfort and convenience of my entire visit there.

Visit St. Peter’s Basilica and get lost among its many artistic masterpieces and stunning architectural features like the dome.

Leave the Vatican by walking along the majestic via della Conciliazione and take one last picture of the Basilica

Reach S. Angelo Castle and watch the Tevere river from the homonymous bridge lined with huge stone Angels. Book here your fast-track ticket to Castel San Angelo or a guided tour.

Spend a romantic evening walking along the Tiber river .

Day 8 Rome to Florence

Get up early and catch a high-speed train to reach Florence in about 1h30.

Start your tour from the Duomo Complex , the beating heart of Florence. It consists of: Santa Maria del Fiore (Cathedral), Brunelleschi Dome (belonging to the cathedral), Baptistery , and Giotto Tower . A guided tour of the Cathedral is always a great idea.

Tip: There is a dress code to enter the church. Women must wear clothes covering their knees and their elbows. Men must wear long trousers. Tip: The queues to enter the Duomo and to climb the Cupola are long and you might have to wait for hours to enter. A great way to skip the lines is by taking a guided tour or if you are using the Firenze Card (The Firenze Card works like a three-day fast pass to your favorite attractions. This is a great option for visitors trying to pack as much sightseeing into a Florence vacation as it lets them skip the long queue lines at most of the most popular sites. It is a great buy if you are staying in Firenze for 3 days). Here are some recommended tours of the Duomo: Duomo skip the line guided tour. Guided Tour of the Duomo Including the Rooftop and View the Terraces

Head to the elegant Piazza della Repubblica with its beautiful Triumphal Arch and the ancient Column of Abundance

Now reach Piazza della Signoria with the iconic Palazzo Vecchio and the famous Loggia dei Lanzi .

Cross the picturesque Ponte Vecchio , but not before having touched the nose of the wild boar decorating a small fountain nearby (it brings good luck!)

Your last stop will be Santa Croce Basilica , with its marble façade, its frescoes, and the tombs of some famous people like Galileo Galilei and Michelangelo.

Taste the famous Fiorentina Steak for dinner!

Where to stay in Florence

Tourist House Battistero : This accommodation in a 15 th Century building is close to the Ponte Vecchio and the Scudieri Café. You will get a comfortable room with lovely views over the City. Click here for more information and to check the latest prices. C-Hotels Ambasciatori : You will be close to Florence’s main attractions if you stay at this 4-star hotel. It is a chic, modern hotel surrounded by a wonderful history. Click here for more information and to check the latest prices. Plaza Hotel Lucchesi : Built in 1860, this is 4-star accommodation situated close to the Arno River. You will have lovely views of Florence during your stay. Click here for more information and to check the latest prices.

Day 9 Florence

Spend the whole day admiring some of the most famous artistic masterpieces in the world! An example? The iconic David by Michelangelo! Where to find it? In the Galleria Dell’ Accademia .

Tip: There are usually long queues for the Accademia. To save time you can either buy a timed entrance ticket beforehand or book a guided tour. Skip the line entrance ticket to the Accademia Another great option is to book a skip-the-line half-day tour to both the Accademia and Uffizi.

Another iconic museum is waiting for you: the Uffizi . Skipping the endless line at the entrance is a must, but a guided tour is what you really need to see everything without spending the whole day wandering around and getting lost!

Tip: The queues for the Uffizi are long. To save time you can either buy a timed entrance ticket beforehand or book a guided tour. Here are some great options: Skip the line Ticket to the Uffizi Skip the long queue with a guided tour of the Uffizi

As an alternative, you can replace one of these visits with Palazzo Pitti , especially if you love Renaissance art. If you go there, step outside and visit the beautiful Boboli Gardens !

Don’t miss the sunset from Piazzale Michelangelo and remember to take a picture of the iconic city’s skyline

The Piazzale Michelangelo has become famous because of its wonderful views of Florence and the neighbouring areas. It is equally impressive by night with its flickering lights or as the sunsets.

Check out here my 2 day Florence itinerary. 

Day 10 Tuscany Tour or Cinque Terre

There are interesting day trips from Florence to see the larger region. The choice is yours from a few alternatives:

• San Gimignano and Siena and Chianti are medieval towns within a famous wine region of Italy. It is a lovely region of rolling hills so even the journeys there and back are fun.
• Pisa with tickets to the leaning tower, another alternative especially if you want to see the Leaning Tower of Pisa.
• Cinque Terre is a region of lovely small villages that can be done by train from Florence or with an organized group.

You might like: How to spend one day in Cinque Terre . How to get from Florence to Cinque Terre. The most beautiful hilltop village in Tuscany.

Day 11 Florence to Venice

Get up early and take a high-speed train to reach the third stop of your 14day itinerary in Italy: Venice ! Try to be there as early as you can to be able to spend the whole day exploring the city.

Start from Piazza San Marco . Enter the majestic San Marco Basilica and enjoy its golden decorations and its byzantine vibes. It’s always extremely crowded, so it’s best to skip the line .

Visit also Palazzo Ducale (Doge’s Palace) and learn who the famous Doge was

Recommended: Skip the line tour to Doge’s Palace & St Mark’s Basilica.

Learn something more about the other two landmarks of San Marco Square: San Marco Tower and the Clock Tower . You can enjoy a complete visit to the Square and its monuments by taking a guided tour .

In the afternoon, relax and slowly stroll along the canals . Cross Rialto Bridge and don’t forget to take a picture of the Canal Grande !

Your first night out in Venice shall involve some “cicchetti” and an “ombra” in a local “bacaro” (meaning tasting some local tapas and a glass of wine in one of the typical taverns of Venice!)

Where to stay in Venice

Hotel Al Codega : This comfortable hotel has regularly received positive reviews from its guests. That is because of its location close to some of Venice’s top attractions as well as the facilities they have found within their accommodation. Click here for more information and to check the latest prices. Hotel Rio : Hotel Rio is central within Venice so that you will find attractions close by including the Rialto Bridge. The Venezia Santa Lucia Train Station is near and so it is convenient for arrivals and departures. You can expect every modern amenity including satellite TV and Wi-Fi. Click here for more information and to check the latest prices. Hotel Ai Reali – Small Luxury Hotels of the World : An eclectic mix of Baroque and Neoclassical architecture with plenty of marble, this hotel is among the top tourist selections in Venice.  St. Mark’s Basilica is just a short walk away; perhaps the first major attraction you will see in Venice if you book here? Click here for more information and to check the latest prices.

Day 12 Venice

Start your day with some Venetian art at the Accademia Galleries . Save at least 2h30 for this visit!

If you love modern and contemporary art, replace this visit with a tour of the Peggy Guggenheim Collection. Click here to book your skip-the-line tickets.

Spend the afternoon visiting the smaller islands of the Venetian Lagoon: Murano, Burano, and Torcello . They are well connected to Venice by water taxi, but you can also choose a combined tour Find here more information and book a cruise to Murano, Burano , and Torcello islands.

The perfect Venetian night? It shall start with a romantic gondola ride . Find here more information and book a 30-minute gondola ride.

Check out my detailed post about 2 days in Venice .

Day 13 Venice to Milan

Today, you’ll reach the last stop of your14day itinerary: Milan ! You can reach it in about 3h by high-speed train

Since you only have 1 day left, focus on the city center and start with the symbol of the city: the Cathedral in Piazza Duomo . This gothic masterpiece deserves a thorough visit and you should absolutely climb up to the rooftop to take in a breathtaking view of the Alps and to see the golden Madonnina (a golden statue of the Virgin Mary protecting the city).

To make the best of your time, choose a fast-track Milan Cathedral and Terraces Guided Tour .

You won’t probably have enough time for a visit, but you should spend a moment to watch the medieval Sforza Castle .

Take a moment to also enjoy some nature and get out of Milan’s crazy traffic in the lovely Sempione Park !

How to spend your last night in Italy? At La Scala Theater of course! It doesn’t need to be super expensive, just have a look at the discounted shows offered by ScalAperta – Teatro alla Scala . Check the regular schedule at Teatro alla Scala

Where to stay in Milan

NYX Hotel Milan : This 299-room hotel near the Central Station is close to a number of the City’s attractions; “La Scala” Opera House, the Sforzesco Castle and”Golden Triangle” (Quadrilatero Della Moda). There is a bar, restaurant, gym, and Wi-Fi. Click here for more information and to check the latest prices. Mandarin Oriental Milano : This 104-room hotel takes up four 18 th Century buildings in Quadrilatero della Moda. Its elegant décor, spa, pool and gym, and excellent service combine with a Michelin-starred restaurant, one of two in the hotel, to provide a memorable stay in Milan, no matter how brief. Click here for more information and to check the latest prices.

You can also check my one day Milan itinerary.

Day 14 Fly Home

Book your flight in the afternoon to be able to enjoy an unmissable artistic masterpiece also included in the UNESCO’s World Heritage List: The Last Supper by Leonardo da Vinci . It is kept in the Cenacolo Vinciano, which is part of the monastery of Santa Maria delle Grazie. Visitors are admitted a few days a week and in small groups, so plan your visit in advance ( Last Supper, Leonardo Da Vinci | Cenacolo Vinciano Official Website ). As an alternative, take a guided tour .

Time to fly home!  Reach Malpensa international airport by bus ( By Coach | Milan Malpensa Airport (milanomalpensa-airport.com) ) or by train ( By Train | Milan Malpensa Airport (milanomalpensa-airport.com) ) and say bye to Italy…or better, see you soon!

TRAVEL TIPS

🚗 Rent your car in advance

with Rentalcars and make your trip as convenient as possible

✈️ Book your flight in advance

To find the cheapest flights and most suitable option, use WayAway

🧾 Get your tickets and tours

with Viator and get the most out of your journey

Looking to extend your trip to Italy? Check out the following 20 Northern Italy cities you should visit. One day in Verona. Best Towns on Lake Como. Things to do in Lake Garda. Best towns in Lake Garda.

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2 Weeks In Italy: An Epic 14 Day Italy Itinerary

August 30, 2022 //  by  Follow Me Away //   4 Comments

Are you dreaming of the perfect 2 weeks in Italy itinerary? If so, this article is for you!

Planning your Italy itinerary should be fun and exciting, not stressful, which is why there’s this detailed post to show you how to spend 14 days in Italy!

This itinerary includes some of Italy’s most popular things to do as well as some lesser-known suggestions that may not be recommended by others.

Planning your trip to Italy last minute?

Make sure to book your hotels and tours in Italy in advance to ensure availability! Here are my top picks for your trip!

Tickets you MUST book in advance:

• Vatican Museums And Sistine Chapel (A MUST in advance)
• Colosseum Entry Tickets (Another MUST! Book online in advance!)
• Michelangelo’s David Tickets (Often sells out in Florence)
• Skip-The-Line Uffizi Gallery Tickets (Buy online to save time!)
• Doge’s Palace Entry Ticket (Very busy, can sell out)
• Milan Cathedral And Rooftop Tickets (Sells out and a must-see!)

Top picks for places to stay in Italy:

• Rome: Hotel Relais Dei Papi (Amazing Vatican location)
• Florence: Relais Pizza Signoria (City center location)
• Venice: Hotel Carlton Grand Canal (Grand Canal views!)
• Dolomites: Parkhotel Laurin (Central location with pool!)
• Cinque Terre: Affittacamere Casa Dane’ (Affordable location)
• Milan: Collini Rooms (Just 10 min from Milan airport!)

If you follow this itinerary, you will see the best of what Italy has to offer on your trip. That includes visiting the highlights as well as seeing some seaside villages.

For this 14 days in Italy itinerary, you will be provided with a breakdown of some recommended stops and the best sites to see at each.

There is also a recommendation for how long to stay in each area. Since everyone is different, though, feel free to change this to fit what you would like to see!

Instead of planning out every moment of every day of your 14-day Italy vacation, this itinerary provides you with a structured yet flexible plan to follow for your first trip to Italy itinerary!

If you’re not sure what to pack, check out this list of 10 things to include on your Italy packing list .

Keep reading to learn how to plan a trip to Italy for two weeks!

Read next: 10 Days In Italy Itinerary

Begin Your 2 Weeks in Italy Itinerary by Flying into Naples

When planning an Italy itinerary, most tourists decide on flying into Rome or Milan, as those are the more popular airports. However, it is very possible to fly into smaller airports throughout Italy.

This is great for your 2 week Italy itinerary. To begin your vacation to Italy, you can fly into Naples Capodichino Airport (NAP).

This airport is very convenient, as it is only four miles away from the city center, and is the perfect place to start your 14 days in Italy!

When booking your flight to Naples, an easy way to save money is checking to see if you can switch to a smaller airline.

You will most likely already have a transfer on your way to Italy, so see if switching to a budget airline might make it a lower price tag.

Once you have arrived at Naples Capodichino Airport, it is easy to catch a bus to Napoli Centrale Railway Station or take a taxi to the city center.

Getting Around During Your 2 Weeks In Italy Itinerary

When deciding how to get around during your 14 days in Italy, you have a few options.

The first is by using public transportation during your trip. Italy has some amazing high-speed trains that can get you from city to city quickly and easily.

This is the recommended use of transportation for this Italy sample itinerary, as it will get you to your destinations quicker, leaving more time for sightseeing!

You could also rent a car or a Vespa for this two-week Italian trip. This will definitely be the more expensive option, though.

On top of the normal rental price, you will also be dropping off the vehicle at a different location, which can really drive up the price.

The tolls in Italy can also be pretty high, averaging about $25 a toll. This can add up pretty quickly, so you’ll need to budget at least $200 just for tolls.

Parking can also be hard to find in some of the bigger cities.

Having a car does give you a lot of freedom, though, and you can get from one town to another as quickly or slowly as you would like

There is also the option of hiring a private driver for your 14 days in Italy, but only if it works for your financial position.

Whether you go by car or train, you will love your 2-week Italy road trip!

Read more:  Pros And Cons Of Renting A Car In Italy

Days 1-2: Naples

Whether you want to spend your first couple of days in Italy eating pizza, exploring, or both, Naples is an excellent spot to start your two-week Italian trip!

How long you have in Naples depends on your flight and what time you plan on heading to your next destination.

There is so much to do, so pick what sounds the most interesting to you, and get to exploring!

You will probably be tired once you arrive, but once you take the time to rest, make sure you explore Naples during your 2 weeks in Italy itinerary.

Noteworthy Things To Do In Naples:

Find art at the national archaeological museum of naples.

If you want to see all of the relics from Pompeii and Herculaneum, make sure to stop by the National Archaeological Museum of Naples.

This museum is home to one of the most impressive selections of Roman art and artifacts in the world.

Unfortunately, this museum can be confusing, so it is best to visit with a tour group or a self-guided walking tour from a guidebook.

You don’t want to miss out on any of the artifacts from Pompeii and Herculaneum.

Discover the Church of San Francesco di Paola

Located on the west side of Piazza del Plebiscito is this beautiful 19th-century church.

It is one of the most important pieces of neoclassical architecture in Italy.

This church is actually inspired by the Pantheon in Rome, but you won’t find all of the crowds here.

Tour Palazzo Reale (Royal Palace)

Palazzo Reale is a genuinely spectacular palace that is located in Naples. You should definitely try to make it here during your 2 weeks in Italy!

The palace was initially built in the 1600s as a residence for a Spanish King, who never ended up going to Italy.

It wasn’t used until the 1700s when it became the palace for a Bourbon King.

Since it is also close to the Church of San Francesco di Paola, you can easily see both of them while exploring.

It might not seem like eating pizza should be on this list of what to do in Naples, but it most definitely deserves its spot!

After all, you are in the birthplace of pizza, so finding a restaurant serving up Naple’s signature dish is a must.

If you want to find an authentic Neapolitan pizza, look for a place serving “pizza vera Napoletana.”

If you are interested in trying a more “street food” pizza, then be on the lookout for pizza frittata. It’s fried pizza dough stuffed with cheese and/or meat.

See an Opera at San Carlo Theater

If you can grab a ticket to see the opera at the San Carlo Theater, it is highly suggested.

San Carlo is the oldest theater in Europe and the largest theater in Italy, so it definitely worth seeing during your 14 days in Italy.

If you are not able to snag a ticket to the opera, then take a guided tour so that you can still marvel at the interior.

Buy A Ticket To The Opera

Admire The Veiled Christ

A truly spectacular sight, the Veiled Christ is a must while you are in Naples!

Even if art and sculptures aren’t typically your thing, you will definitely appreciate the Veiled Christ during your 2 weeks in Italy.

The Veiled Christ, which is located in the center of the Sansevero Chapel, was carved in 1753. You should definitely check out the Veiled Christ while in Naples!

Skip The Line By Getting Your Tickets Online

Visit Il Duomo (The Cathedral) 

While you are in Naples, you must visit this 14th-century Cathedral!

This Cathedral is a wonderful mix of periods and art styles, making it fascinating to explore.

It was initially built in the 14th century but was destroyed by an earthquake in the 15th century. There were many repairs and additions made, including the neo-Gothic Facade that was only completed in 1905.

Where To Stay In Naples:

There are so many options for where to stay in Naples.

Whether you’re looking for budget, luxury, or something in the middle, there is an option for you.

The area you want to stay in depends on what you want to do during your time in Naples.

If you want to stay somewhere close to the airport where you still have relatively convenient access to some of the sights, you should stay in the Historic Center.

If you would like to be closer to some of the popular attractions in Naples, you should try to find a hotel in Chiaia. No matter what you’re looking for during your 2 weeks in Italy, Naples will have something for you!

Stay Near Piazza del Plebiscito: Chiaja Hotel de Charm e Check Rates: Booking.com

Mid-Range: Culture Hotel Centro Storico Check Rates: Booking.com

Stay In The historical Center: M Gallery Palazzo Caracciolo Check Rates: Booking.com

Luxury: Grand Hotel Vesuvio Check Rates: Booking.com

How Long To Spend In Naples During Your Italy Itinerary:

How long you spend in Naples will depend on what time your flight arrives and what time you are leaving.

Whatever your schedule, we suggest that you spend at least one night in Naples.

Since it is the beginning of your 14 days in Italy, you will most likely be tired, so this gives you some time to rest before starting to travel again.

While you are in Naples, you should also try to get some sightseeing in, as there are so many incredible places to see!

Days 3-4: Amalfi Coast

The Amalfi Coast is made up of multiple towns set along the mountainous coast of Italy.

It is one of the most popular areas of Italy, and for excellent reasons. It is absolutely stunning and will leave you only wanting more.

There are so many options for which towns to visit during your time at the Amalfi Coast.

Whether you’re looking for the perfect Amalfi beaches , a more authentic (less touristy) town, or the best place for photos, there is a place for you!

Once you decide on which area you want to stay in, then there’s the decision of where to stay. There are so many different hotels and bed and breakfasts to choose from, no matter your budget!

The Amalfi Coast is the perfect place to relax during your 2 weeks in Italy!

You have multiple options for how to get from Naples to the Amalfi Coast.

If you are driving, then it’s a pretty easy drive that should only take you around an hour.

If you are using public transportation, then you have two main options. The first is the train between Naples and Sorrento , as of summer 2019 though, this option is having many delays and cancellations. It is still an option that is very cheap, but recently the service has not been consistent.

Then you have the option of taking the ferry from Naples to Sorrento, which is called Metro del Mare . Taking the ferry is an excellent option for a couple of reasons.

The first is that you have control over which towns you go to. The second is that even if you don’t stop at some of the popular coastal towns, you can still see them and photograph them to your heart’s content!

What To Do At The Amalfi Coast:

Visit the lovely town of sorrento.

This well-known town on the Amalfi Coast is definitely worth a visit during your 2 weeks in Italy.

It’s located in the northern section of the Amalfi Coast and is most popular for its beautiful scenery and the lovely buildings situated along the coast.

While in Sorrento, make sure to check out the gorgeous cathedral that was built in the 11th century.

There are also two different ports in Sorrento that hold fishing and sailing boats.

If you find yourself interested in the history of Sorrento, you can go to two different museums during your time in Sorrento.

Head Out on the Water With This Boat Tour!

Admire The Colorful Positano

Positano is considered one of the most picturesque towns in Italy, and it’s not hard to see why. It is full of colorful houses that are set against the mountainside

If you want an extra-pretty view of Positano, take a boat out so that you can see all of this lovely town.

Full of pretty beaches, cute cafes, and bright buildings, Positano is the perfect spot to relax during your 14 days in Italy.

See Praiano’s Gorgeous Sights

Praiano is located between Positano and Amalfi and is the perfect spot to take in some gorgeous views with fewer crowds.

This town is not as well known as some of its neighbors, but that doesn’t mean that you should skip over Praiano.

It doesn’t matter if you want to stroll through the quiet streets, take a dip in the ocean, or relax on the beach, you will find each to be incredibly enjoyable.

See The Popular Town Of Amalfi

Amalfi is the most popular of all of these coastal towns and is generally packed with tourists.

Don’t be scared of the number of tourists though, Amalfi is still a gorgeous town to visit.

Amalfi even has its own cathedral, which is absolutely magnificent. There are also plenty of shops for you to spend an afternoon exploring.

For The Best Views On The Amalfi Coast, Visit Ravello

While the Amalfi Coast is known for its spectacular views, go to Ravello to see something rather extraordinary.

Unlike the other towns on the Amalfi Coast that are built into the mountainside, Ravello is located at the top of the mountains, giving some breathtaking views.

It is also much more relaxed than some of the other tourist destinations along the coast.

There are also plenty of outdoor terraces where you can enjoy your evening meal taking in the ocean.

Head To Cetara For An Authentic Italian Town

If you want a more authentic experience, head to the town of Cetara.

Unlike most other towns along the Amalfi coast, Cetara remains relatively unspoiled by tourism. It is a great place to head to for a day of relaxing.

Cetara also has the only fishing fleet in this region that is still in operation, so you can see all of the fishermen going about their work.

Tour The Emerald Grotto

If you are feeling up for a bit of an adventure and want to leave the coast, take a tour to the Emerald Grotto, a genuinely spectacular natural occurrence.

The Emerald Grotto is a collection of caves that are bathed in green light. They are only accessible by boat, so I hope you don’t get seasick!

You can take either a car or a bus to get to the facilities along the road, then take an elevator down to the point of departure; it is open from 9:30 a.m. – 4 p.m.

Where To Stay On The Amalfi Coast:

There are so many options for where to stay along the Amalfi Coast, whether or not you are looking for budget or luxury.

Depending on how much you are willing to spend, there are certain areas that will be best for you.

We have an entire post devoted to Where to Stay On The Amalfi Coast in case you are looking for our suggestions in detail! 

Positano and Amalfi are definitely going to be more expensive, so if you are traveling on a budget, these probably aren’t the towns you should spend the night.

Ravello and Cetara would be much more budget-friendly options. If you are planning on staying in luxury though, you will have no lack of gorgeous and unique hotels offering first-class treatment!

Budget In Cetara: Cetara Albergo Diffuso Check Rates: Booking.com

Mid-Range In Ravello: Hotel Parsifal Check Rates: Booking.com

Private Beach In Amalfi: Hotel Miramalfi Check Rates: Booking.com

Luxury In Positano: Hotel Villa Gabrisa Check Rates: Booking.com

How Long To Spend At The Amalfi Coast During Your 14 Days In Italy:

You will probably want to spend 1-2 nights at the Amalfi Coast in order to have a chance to explore or relax.

Because it is more expensive, you might want to spend 2 nights in Naples, then leave early in the morning to head to the Amalfi Coast.

It’s around a 40-minute ferry ride to the Amalfi Coast, so you can spend the day exploring.

This way you only spend one night on the coast but get 2 days of exploring.

If you have found an awesome deal in Naples though, you might even consider staying at a hotel in Naples and taking the ferry both days. I would only deal with this though if you get an awesome hotel in Naples.

Days 5-6: Rome

Next up on your 2 weeks in Italy itinerary is one of the most popular cities in Italy: Rome.

Rome is full of history, art, shopping, and some excellent restaurants! You will have no shortage of things to do during your time in Rome.

Spend time exploring some of Rome’s historical sights, like the Colosseum or Vatican City, or strolling through the picturesque streets and stopping at some of the wonderful little cafes!

You can even find some little hidden gems in Rome !

Driving from the Amalfi Coast to Rome will take you around 4 hours depending on the traffic, and be aware that the traffic in Rome can be pretty awful.

You can also pay for a private driver, but this will come with a higher price tag than some of your other options.

For public transportation, you can take the ferry or train back to Naples, and from there take a train to Rome .

Top Things To Do In Rome:

Throw a coin in the fontana di trevi.

While in Rome during your 14 days in Italy, make sure to stop by the Trevi Fountain and drop a coin in.

Dropping in a coin means that you will return to Rome one day (why not throw in a few more coins for some extra luck on getting back to Rome?).

This is one of the most famous landmarks in Rome, so get there early to beat the crowds!

Explore The Colosseum

No trip to Rome is complete without visiting the Colosseum, so make sure you make it there during your two weeks in Italy!

It is one of the most popular places in Rome, and it will be an experience you’ll never forget!

You won’t be the only one planning on seeing the Colosseum though, so you should look into booking a tour. This way you can skip the lines and guarantee your entrance! 

Skip The Line With This Colosseum Tour!

Explore The Roman Forum

Although not as popular as the Colosseum, the Roman Forum is still an impressive sight, and it’s so close to the Colosseum!

You only have to walk a few steps from the Colosseum, and you’ll be able to imagine how the Roman people used to live.

Book Your Tour For The Colosseum And The Roman Forum Here!

Visit Piazza Navona

If you are looking for a place to spend your afternoon shopping and eating at delicious cafes, head to Piazza Navona!

It is one of Rome’s most popular squares, and for good reason! This square was built in the 15th century and is a beautiful area to explore.

Admire Basilica Di Santa Maria Maggiore

Basilica di Santa Maria Maggiore is known as a Basilica Major, which means it is one of the largest churches in Rome.

It is a truly magnificent structure and is well worth a visit during your 14-day Italy vacation!

The interior is intricately designed with gold, frescos, and detailed paintings on the walls and ceilings.

This is a great place to go during winter in Rome to get out of the cold.

Skip The Line With This Basilica di Santa Maria Maggiore Tour!

Climb The Spanish Steps

What would a visit to Rome be without seeing the famous Spanish Steps?

You’ve probably seen them in a movie or two, as they are one of Rome’s famous landmarks.

If you want to climb the steps (which is highly recommended) make sure to bring your walking shoes, as there are 135 steps.

Gaze Upon Castle Saint Angelo

Castle Saint Angelo, also known as the Mausoleum of Hadrian, is a circular castle that was once the tallest building in Rome!

It was built in 129 AD and was originally intended to be a Mausoleum for the Emporer.

It has now been connected to St. Peter’s Basilica, and if you climb to the top of the castle ramparts, you can see a stunning view of Rome.

Visit The Pantheon

The Pantheon is a former Roman temple that is now a church.

Not only is it one of Rome’s most popular landmarks, but it is also full of interesting history. You should add it to your 2 weeks in Italy itinerary.

Reserve An Affordable Audio Guide To The Pantheon Here!

Wander Through The Vatican City

There is so much to do in Vatican City, that you could easily spend one of your days in Rome just exploring this area.

You’ll definitely want to explore other parts of Rome though, so you should decide on what you really want to do in Vatican City.

The two main things to do in Vatican City are St. Peter’s Basilica and the Vatican Museums.

If you are deciding between the two, we highly suggest touring St. Peter’s Basilica. It will be one of the most memorable experiences of your life!

There are also the Vatican Museums that hold tons of history, and it’s where you will find the famous Sistine Chapel.

The Vatican Museums will take about 3 hours to explore, and St. Peter’s Basilica will take around 1 to 3 hours, depending on how long you want to spend.

Vatican Museum And Sistine Chapel Fast Track Entry

St. Peter’s Basilica: Tour with Dome Climb

Sistine Chapel, Vatican Museums, And St. Peter’s Guided Tour

Where To Stay In Rome:

Staying near Vatican City while in Rome will be your best option, especially when you’re only going to be in Rome for two days during your two weeks in Italy.

This way, you can walk to Vatican Square at night when it is all lit up and it is a peaceful getaway from the hustle and bustle of the city.

We highly recommend taking a look at our detailed guide on Exactly Where To Stay In Rome!  There are also lots of shops around!

If you want to stay at an Airbnb, there are plenty of Airbnb options in Rome from budget to affordable depending on your funds for your best itinerary for Italy. 

Near the Vatican: Vatican Style Suite . Check Rates: Booking.com

Budget: Bed In Roma . Check Rates: Booking.com

Mid-Range: Casa Montani . Check Rates: Booking.com

Upscale:  The Westin Excelsior Rome . Check Rates:  Booking.com

How Long To Spend In Rome During Your 2 Weeks In Italy Itinerary:

For this 2 weeks in Italy Itinerary, we recommend spending 2 days in Rome .

This gives you time to explore Rome, but still gives you plenty of opportunity for the other areas of Italy that you will be visiting.

You can, of course, alter this however you need to. Try not to stay for more than four days though, as this is plenty of time to explore Rome.

If you do choose to stay longer, there are plenty of lovely day trips from Rome to explore!

Days 7-9: Florence and Tuscany

Next up on your 2 weeks in Italy itinerary is Tuscany, specifically its capital: Florence.

Florence is a much more laid-back city than Rome, so it’s a great place to take your time while seeing what Florence has to offer.

It’s also a very walkable city, so you will only need to use public transportation if you want to explore other villages.

There are so many things to do in the Tuscany region !

Getting from Rome to Florence is very easy to do by train, and it will only take you about 1 hour and 30 minutes.

For the best option, take the high-speed train from Roma Termini station to Firenze S M Novella in Florence. This will take 1 hour and 30 minutes. If you choose to drive, it will take you around 3 hours.

Top things to do in Florence:

Explore boboli gardens.

If gardens are your thing, plan a visit to Boboli Gardens !

Whether you want the perfect place for a photo op, or just want to admire the beautiful surroundings, this 16th-century garden is the place for you.

Bring some sturdy shoes though, as Boboli Gardens is up a steep hill.

You should plan on spending around 1-2 hours here, though you could spend less or more depending on your interest.

Boboli Gardens Skip The Line Tour

Visit The Duomo

While in Florence during your 14 days in Italy, make sure to stop by the Duomo. Even if you only set aside one day in Florence, this is a must-see stop!

This Catholic Church towers over Florence and is pretty difficult to miss.

If you plan on going in though, know there is a dress code for women and men; your knees and shoulders must be covered.

You also must be completely silent when visiting the Duomo in Florence .

It is usually very crowded, but you can skip the line by taking a tour.

Skip The Line At The Duomo With This Tour!

Walk Across The Ponte Vecchio

If you are looking for a picture-perfect bridge during your Italy in 2 weeks trip, Florence has you covered!

Ponte Vecchio is a beautiful bridge, and it’s the perfect spot to watch the sunset. You can also enjoy a leisurely stroll and some delicious gelato if you choose!

It is one of the best free things to do in Florence during your trip! 

See David At Galleria dell’Accademia During Your Italy Itinerary

If you are a lover of art, then you definitely want to explore Galleria dell’Accademia.

This museum is home to some of Michaelangelo’s greatest works, including the famous “David” statue.

The museum gets very crowded, and since you don’t want to waste any of your 14 days in Italy, you should consider buying a timed ticket or booking a tour.

Timed Entrance Ticket For Michaelangelo’s David

Marvel At Renaissance Artwork At Palazzo Pitti

Palazzo Pitti is another museum to see if you are an art lover. It’s Florence’s largest art museum, and is full of Renaissance works of art!

There are so many stunning works of art to admire, and it is a wonderful way to spend an afternoon.

Admire The Church Of Santa Maria Novella

If you are arriving in Florence on the train, then you will have no struggle in seeing the Church of Santa Maria Novella, as it is located right in front of the main railway station.

It is a stunning church and is a wonderful example of Renaissance architecture.

Skip The Line And Audio Guide Ticket For The Church Of Santa Maria Novella

Explore The Countryside Of Tuscany

Florence is the capital of Italy’s Tuscany region, but that doesn’t mean there’s nothing else to do.

Tuscany is known for its beautiful countryside full of rolling hills and vineyards. But that isn’t all!

There are many things in Tuscany such as hot springs and magical castles that you are going to want to see, if possible!

Exploring the countryside will be easiest if you are driving, but is possible to take public transportation to some of the villages.

For ideas on what to do in Tuscany, check out this Tuscany road trip .

Where To Stay In Florence:

Florence is much smaller than Rome so if you are staying in the city center there really are no bad places to stay!

We even have an entire post on where to stay in Tuscany which includes Florence!

We also have a complete breakdown of where to stay in Florence .

Hotels in Florence range from affordable to luxury options. You can get a really nice hotel in the city center of Florence for a very reasonable price. 

Affordable:  Hotel Bavaria .  Check Rates:  Booking.com  

Mid-Range:  Globus Urban Hotel .   Check Rates:  Booking.com

Upscale:  Hotel Garibaldi Blu  Check Rates:  Booking.com

How Long To Spend In Florence During Your 14 Days In Italy:

When deciding how long to spend in Florence, it’s important to think about how you want to see Florence.

If you want to wake up early, maybe stay out a little late, and rush through some of the sights, it’s completely possible to see the highlights that Florence has to offer in a day.

If you want to take your time, then two days is the perfect amount of time to stay in Florence.

Days 10-11: Venice

Venice, known as one of the most romantic cities in the world, is next up on your 2 weeks in Italy itinerary.

Venice is the capital of Italy’s Vento Region, and it is made up of over 100 tiny islands!

There is plenty to explore during your 2 days in Venice , and you won’t be disappointed!

If you want to rearrange this itinerary and only spend one day in Venice , that is okay too!

It is so easy to get to Venice from Florence, all you have to do is hop on a train and enjoy the ride!

We even have a full Northern Italy itinerary if you are interested in exploring this region in more detail. We highly suggest it as it is one of the most beautiful spots in Italy! 

Here is a post we wrote on Exactly How To Get From Florence To Venice which explains all of your transport options! 

The best route to go from Florence to Venice is to get on the train at Santa Maria Novela station in Florence and head to Venezia Santa LuciaIf in Venice.

This train trip takes a little over 2 hours and is a nice easy ride. Driving will take you around 3 hours, though this will depend a lot on Rome’s traffic.

What To Do In Venice During Your 2-Week Italy Itinerary

Explore the popular piazza san marco.

Piazza San Marco, also known as Saint Mark’s Square, is the most popular square in Venice, and maybe all of Italy!

It was built during the 12th century and is in the center of the square at St. Mark’s Basilica, which you can tour.

If you are looking to do some bird feeding during your 14 days in Italy, this is the square where everyone feeds the pigeons.

It is also one of the best photo spots in Venice if you are looking for something new for your Instagram! 

St. Mark’s Basilica: Tour with Terrace Access

Climb The Campanile di San Marco Bell Tower

While at St. Mark’s Square, why not climb up the bell tower?

When you reach the top you will have one of the most beautiful views in Venice. The tower itself rises high above the square.

It’s very popular, and you’ve probably seen it in many photos or the replica at Walt Disney World.

This is one of the best things to do in Venice !

Walk Across The Bridge Of Sighs

Legend has it that when criminals were taken away from the palace, over the bridge, they would gaze at Venice for the last time and sigh as they thought about their upcoming punishment, hence the name the Bridge of Sighs.

Who knows how true this is, but it’s something to think about as you cross the bridge on your way to Doge’s Palace.

Go On A Gondola Ride

One of the most popular things to do in Venice is to go for a gondola ride.

Though it will require a bit of a splurge, what could be more fun than riding a gondola through the canals of Venice?

This experience is unlike anything else that you will do on your Italy in 2 weeks itinerary.

Venice: Private Gondola Ride along Canal Grande

Admire The Architecture Of Doge’s Palace

Doge’s Palace is an ornate gothic palace right on the canals of Venice!

It is not only a museum but a showroom, and it is one of the most impressive palaces you will see during your Italy in 14 days itinerary.

Doge’s Palace holds lacework, paintings, sculptures, and more and is a real treat for architecture lovers!

You will definitely enjoy exploring this wonderful palace. If you are visiting Venice during the winter, museums such as this one are the perfect way to stay warm.

Timed Admissions Ticket To Doge’s Palace

Take A Tour Of The Venetian Islands

If you are struggling with deciding which of the Venetian Islands to visit during your two weeks in Italy, why not take a tour?

You will visit the small towns of Murano, Burano, and Torcello, depending on what tour you take.

Since Venice isn’t exactly a walkable city, the best way to see these islands and the lagoon is to take a guided tour.

You will also learn lots of great information about Venice!

Boat Trip: Glimpse of Murano, Torcello & Burano Islands

Walk Over The Rialto Bridge

The Rialto Bridge is an iconic sight that you must see during your two weeks in Italy!

While walking across the bridge is incredible, it is also absolutely beautiful to view it from afar.

It’s the perfect place to get some great photos and is one of the best things to do in Italy during your trip!

Where To Stay In Venice:

When staying in Venice during your 14-day Italy itinerary, we highly recommend staying in the city center!

There is a variety of hotel and Airbnb options in Venice ranging from the budget $70 a night places to luxury $300 a night hotels.

There are plenty of cute, boutique hotels in Venice too if you are looking for something special.

Please don’t forget to check out our VERY detailed guide on Exactly Where To Stay In Venice Italy!

There is something for everyone when planning your stay during your Italy in 14 days trip so choose the accommodation that feels right for you.

We recommend staying near Saint Mark’s Basilica or the Rialto Bridge.

No matter where you decide to stay, you are in Venice and that is something to celebrate!

City Center:  Hotel Casanova . Check Rates:  Booking.com

Affordable: Alberghiera Venezia . Check Rates: Booking.com

4-Star:  Royal San Marco Hotel .   Check Rates:  Booking.com  

How Long To Stay In Venice During Your Italy Itinerary:

Spending 1-2 days in Venice during your 2 weeks in Italy Itinerary should be enough time to experience what the city offers.

The amount of time that you should spend in Venice really depends on how much you want to see, and this Italy itinerary can be easily changed to fit what you desire for your 14 days in Italy.

Days 12-13: Cinque Terre

Cinque Terre is a popular destination for travelers, and it definitely deserves to be explored during your 2 weeks in Italy.

Cinque Terre is split into 5 villages or towns, and that is what the name translates to as “cinque” means 5 and “Terre” means village.

Each of these towns is beautiful and unique, and you should aim to explore each of them during your 14 days in Italy!

Once you have made it to Cinque Terre, getting between the villages is incredibly easy, as there is a train that connects all five.

The journey between villages only lasts a few minutes, so you’ll have plenty of time to explore!

The drive from Venice to Cinque Terre will be around 4 1/2 hours, and you will probably want to use public transportation once you get there, as it can be crazy and expensive to park.

You can also take the train from Venice to Monterosso , which will place you in the perfect spot to explore the surrounding villages.

Top Things To Do In Cinque Terre During Your 14-Day Italy Itinerary

Hike the monterosso footpath.

The Monterosso footpath connects the towns of Monterosso and Vernazza and provides stunning views of the towns!

This hike is a bit challenging as you are going up the coastal cliffs, so plan on at least 1-2 hours to complete it.

The views are worth the effort, but bring plenty of water, especially if you visit during the summer!

Explore The Church of San Francesco

Overlooking the Mediterranean Sea, the Church of San Francesco provides some pretty remarkable views of the dazzling blue water below.

The church was built in the 17th century and is a great place to stop while exploring Cinque Terre during your 2 weeks in Italy.

Visit Parco Nazionale Cinque Terre

This National Park is one of the smallest in Italy at only 15 square miles but it is also one of the most popular and most beautiful!

Parco Nazionale Cinque Terre is one of the most heavily inhabited national parks in Italy and it is easy to see why!

A one-day pass costs $9 per person to enter the National Park. Parco Nazionale Cinque Terre is also a UNESCO World Heritage Site.

Take A Boat Tour Of Cinque Terre During Your Italy Itinerary

If you are short on time during your Italy in 14 days trip, consider taking a boat tour of the Cinque Terre villages.

A boat tour will allow you to see all of the towns with ease and speed and you won’t feel like you missed a thing!

A boat tour is an easy and affordable way to add Cinque Terre to your Italy itinerary even if you are short on time because you can see everything by water!

Cinque Terre: Riomaggiore, Monterosso, Vernazza Boat Cruise

Watch The Sun Set

It doesn’t matter where you do this, but while you are in Cinque Terre you must watch the sunset one evening.

It is absolutely breathtaking, and you won’t regret taking the time to relax and take it in.

This can and should be done from any of the 5 towns in Cinque Terre, so it doesn’t matter where you are staying for the night.

One of the Cinque Terre Beaches is the perfect place for watching the sunset during your trip!

Cinque Terre Sunset Boat Tour 

Where To Stay In Cinque Terre

Which of the 5 towns you decide to stay in during your time in Cinque Terre really depends on what you’re looking for.

Here’s a complete guide to where to stay in Cinque Terre !

You have so many options when staying in Cinque Terre. The hard part will be deciding between all of the beautiful hotels!

Enjoy The Nightlife In Riomaggiore: Locanda Ca Da Iride Check Rates: Booking.com

Stay In Manarola For The Best Views: Olimpo Affittacamere Check Rater: Booking.com

Corniglia Is Where To Stay To Escape The Crowds: Arbanella Check Rates: Booking.com

Stay in Vernazza Near the Beach: Appartamento Margherita . Check Rates: Booking.com

A Room with a View in Monterosso : I Tibei Guesthouse . Check Rates: Booking.com

How Long To Spend In Cinque Terre During Your 14 Days In Italy

Even though there are 5 villages that you can explore during your 14 days in Italy, the simple and quick transportation makes it possible to visit all of them within 1-2 days, depending on how long you spend in each village.

You can adjust this, of course, but try to give yourself enough time to enjoy all Cinque Terre has to offer.

Day 14: Milan And Fly Home

Your final stop on your 14 days in Italy is Milan, and it is where you will fly out.

Milan is home to a very large international airport and many affordable flight options fly in from all over the world.

Beginning your trip in Naples and ending it in Milan is perfect, especially if you want to spend the majority of your Italy itinerary exploring!

For this 2 week Italy itinerary,  you will get the most of your time by buying two one-way tickets.

However, it would be rather easy if you needed to get back to Naples for a roundtrip flight.

All you have to do is book a train or a flight. This could also be done the other way, by flying into Milan and then heading to Naples.

Just because you have only one day in Milan doesn’t mean there aren’t plenty of exciting things to see and do! 

Milan: Bergamo Airport Transfer

Suggested Things To Do In Milan To End Your Italy Itinerary:

Take in the breathtaking milan cathedral.

Even if you are short on time in Milan, you must visit the Milan Cathedral to admire the stunning architecture, even if it’s just for a moment.

You’ve most likely seen pictures of the Milan Cathedral, but it is so much larger and magnificent in person.

Try to make it a priority to see it during your Italian itinerary in 2 weeks!

Milan Cathedral And Rooftop Entrance Tickets

Go Shopping At Galleria Vittorio Emanuele II

If you want to get some shopping done during your 14 days in Italy, you must visit Galleria Vittorio Emanuele II.

It is Italy’s oldest shopping mall, and a very popular place to spend time browsing through all of the fantastic stores.

Even if you don’t want to shop, Galleria Vittorio Emanuele II is incredibly beautiful and deserves a visit just for the 19th-century glass-covered arcade that houses the mall.

Visit Sforza Castle In Milan

Sforza Castle in Milan is a 15th-century castle located right in the city.

It is also home to various artistic works, including those from Leonardo Da Vinci!

If you are looking to add another museum and art gallery to your Italy itinerary, make sure to put Sforza Castle on your list of things to do in Milan.

Explore The City On A Bus Tour

An easy way to explore Milan when you’re short on time is by doing a hop-on-hop-off bus tour!

Even if you aren’t into doing super touristy things, you will still enjoy this bus tour of Milan.

It will provide insider information about some of the most famous sites in Milan and you will easily be able to get off the bus should you want to explore more!

This is perfect if you only have one day to tour Milan.

Milan: 1, 2, or 3-Day Hop-On Hop-Off Bus Ticket

Where To Stay In Milan:

If you are catching your flight out of Milan Airport the next day, we highly recommend spending your last night in Italy somewhere close to Milan Airport.

This will allow you to explore on the last day of your 14-day Italy itinerary without worrying about waking up early and taking a long transfer taxi or bus to the airport to catch your flight the next day.

That being said, we put together this post on exactly where to stay in Milan where we break down the areas so that you can get a feel for what is best for you!

Mid-Range:  Sheraton Milan Airport Hotel.  Check Rates:  Booking.com

Affordable:  First Hotel Malpensa .  Check Rates:  Booking.com

How Long To Spend In Milan On Your 2 Weeks In Italy Itinerary:

You really only need one day in Milan during your 14 days In Italy itinerary at the most.

Compared to other Italian cities on this itinerary, the highlights of Milan can be done very quickly.

If you are looking for how to save time and budget days elsewhere in this 2-week itinerary for Italy, you can shorten the length of your stay in Milan as you can see the city in a short period of time.

Use Milan as your gateway to the airport, stop off and see a thing or two, and then be on your way home!

There is so much to see and do in Italy, that it can be hard to narrow down what you should do during your best itinerary for Italy in 2 weeks.

This itinerary gives you some structure to make some of the big decisions a bit easier.

It is also completely flexible, so you can easily change what it is that you see during your 14 day Italy vacation.

Since not everything has made it onto this list, what are some of your favorite things to do in Italy?

Reader Interactions

August 31, 2019 at 9:28 am

Please send me more info, can we choose our travel dates and expenses. Thank you Andra Cook

June 17, 2022 at 11:23 pm

I am interested in your itinerary. do you have it in a downloadable option?

August 28, 2022 at 1:52 pm

This is a very very nice itinerary. There is no right or wrong answer on where to stay for the 2 weeks. If I was taking my family/friends who have never been to Italy for 2 weeks it would be the following: Fly into Naples early morning and go to Sorrento: 3 nights Sorrento 4 nights Rome 3 nights Tuscany town like Montepulciano 3 nights Florence Fly into Naples and out of Florence. I am in the minority in saying Venice is so over rated and expensive and too far out of the way for an optimal 14 day trip. I think you suggest going all the way North and east to Venice then backtracking from one side to the other to get back to Cinque T. In Sorrento day boat trip to Capri, Day tour Amalfi towns like Positano. Then get a car and stay inside a town such as Montepulciano and drive to see all the towns while coming back to experience spending the evenings/nights in a hillside town. From Florence day trip to Cinque Terre and if yo missed Siena and San Gim. you do that in a Day trip that also includes Pisa. Least amount of backtracking and luggage hauls and checking in/out of hotels. But there is no right itinerary and how did we leave out Sicily or Lake Como, or Dolomites or…..LOL too much to see.

August 28, 2022 at 3:32 pm

Thank you for sharing this!! It sure is hard right!! so many epic things to see!

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Two-Week Itinerary

Two Weeks in Italy: The Perfect Itinerary

Matteo Colombo/Getty Images

Ah, Italia! It's one of the world's favorite destinations in Europe. And one where you could go in a hundred tempting directions. So how do you design a dream vacation there? By focusing on places that capture essential elements of Italy: the magnificent architecture, the people and their romantic nature, the culture, the singular food, and wine.

You can do it in just two weeks with the following once-in-a-lifetime travel itinerary: three or four days in Rome, a week in the hill towns and countryside of Tuscany or Umbria, and three or so days in romantic Venice.

As for booking your plane tickets, hotel and tickets to sought-after tourist attractions, you should do this well in advance from home. Allow up to six months in advance: For example, you're likely to find better prices and availability in mid-winter for a trip you plan to take in June.

If you like warm weather but want to avoid the high tourist season, the optimal times to visit Italy are May–June and September–October. Also, prices tend to be lower in these months than at the height of summer. Try to book your apartment or hotel room when you book your plane ticket. If you plan on visiting a major attraction like the Uffizi Gallery in Venice, which has 10,000 visitors a day, book that early, too.

Traveling between destinations is best by car or train. If you choose to drive , check with your car rental company for the optimal time to book, but earlier is always better for Italy. Traveling by train in easy; just buy the tickets for your next destination when you arrive in a place so that you're all set when it's time to leave. Traveling inside cities can be done by public transportation or taxi. In the countryside, you'll likely need a car to shop and explore.

Start in Rome: Day 1

TripSavvy / Christopher Larson

Rome is a fantastic starting point for this trip. For one thing, you can easily fly there from most places and you may not need (or want) a car. Plan to spend at least three or four days in Rome. Consider consulting a three-day Rome travel itinerary for ideas.

Choose a hotel that's near public transportation. Use our guide to  places to stay in Rome , which includes recommendations, from budget-conscious to luxurious accommodations. If this is your first visit, you might want to choose a small hotel or bed-and-breakfast offering personalized service. A favorite is the ​Daphne Inn, which is especially good for your first visit to Rome. The helpful, English-speaking staff will map out your days, make restaurant recommendations and even give you a cell phone so you can call them if you get lost or need advice. 

On your first day, take some time to just wander around, get used to Rome and recover from your jet lag. Choose an area near your hotel and just wander—don't worry about seeing all the tourist sites. For an overview of Rome, you can hop aboard bus number 110 (the touristic circuit) at Termini Station.

Rome: Days 2–3

Plan to spend one day touring ancient Roman archaeological sites.

Allot another day for the Piazza Navona, Campo de Fiori, Pantheon, Trevi fountain and Spanish steps (all free) and for visiting museums. You might want to walk through some interesting districts such as Trestevere , the Jewish quarter and the up-and-coming Testaccio , where you can dine on authentic Roman food. 

Rome: Day 4

 You'll also need one more day if you want to visit  Vatican City , including the Vatican Museums, St. Peter's Basilica, Sistine Chapel, and Castel Saint Angelo. If you want to see the Pope, go on Wednesday and get tickets far in advance. You can even  request an audience with the Pope .

Tuscany or Umbria: Days 5–11

For the next part of your vacation, you'll rent a vacation house or an  agriturismo   (renovated farmhouse) in Tuscany or Umbria , where you can visit some great Renaissance and medieval towns, drive through beautiful countryside and experience Italian life as more than just a tourist in a hotel. Here are some resources to help you plan this leg of the journey and make reservations for a place to stay, learn how to get around and figure out what to visit.

By staying in a house for a week, you can usually save money, shop and eat where the locals do and spend time relaxing. Look for a house with a washing machine, so that you can pack light and wash clothes in the middle of the trip. You'll enjoy shopping at Italian farmers' markets and specialty food shops, and you'll be able to cook what you buy and eat at home.

You'll need to arrange your house a few months before you go. You can choose a house in a small village, in a city or out in the countryside in an agriturismo (renovated ​farmhouse). If there are certain cities you want to visit, be sure the house is within easy driving distance so you can get there and back in one day. In Tuscany, Le Torri vacation apartments are in a prime location between Florence and Siena. If you want to visit both Tuscany and Umbria, the holiday houses at Il Fontanaro Organic Farm in Umbria near the border of Tuscany make a good choice.

Italy's train system is inexpensive and fairly efficient. Consider taking the train from Rome to a city near where you have arranged your lodging. Then pick up your rental car, which you have also pre-arranged, and drive to your house. Consider booking a car through  Auto Europe  because there are no hidden (extra) charges. If you're renting a vacation apartment in a town, you may not need a car.

Most house rentals run from Saturday afternoon to the following Saturday morning. Since Italian shops are generally closed on Sundays, you will want to do a little shopping when you arrive to stock up for the weekend and at least have bottles of water and wine. Then spend a little time walking in your neighborhood.

Sightseeing

Tuscany and Umbria are both beautiful and fairly compact, so you will be able to visit a number of places easily. If you want to visit Florence or some of the other larger cities, save yourself a little trouble by driving to a nearby train station, parking and taking the train into Florence.

Popular Tuscan destinations include Siena, Pisa, San Gimignano, Lucca, the wine towns of Montepulciano and Montalcino, the Chianti wine region, and Cortona (made famous by "Under the Tuscan Sun").

In Umbria, you can visit Assisi, Perugia, Orvieto, Spoleto, and other medieval hill towns as well as Lake Trasimeno and a few Roman ruins.

Venice: Days 12–14

After a week in your rented country house, drop off your car, and take the train to Venice. This city on Italy's eastern, Adriatic shores is a treasure, with much to see and do.

In Venice, you'll get around by walking or taking a  vaporetto , a large passenger boat that functions like a city bus. 

You'll want to spend at least two or three days here. Months before you leave, take a look at a  Venice sestiere map and guide  to choose the neighborhood where you want to stay. If you stay longer than two or three days, you may want to rent an apartment for a week in a sestiere ,  or local neighborhood. 

While in Venice, visit  San Marco square , the  Rialto Bridge , and the Grand Canal. Give yourself some time to get away from the tourists and wander the back streets and small canals to get a real feel for Venetian life. Before lunch, stop in a bar and order some cicchetti (little Venetian snacks) and a glass of wine. Try a ride in a  gondola .

From Venice, you can fly back to Rome or take the train to Milan and fly home from Malpensa Airport, after spending a night or two in Milan, Lake Como or Lake Garda. From here, it's easy to fly back home to the United States.

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How To Spend 2 Weeks in Italy: Itinerary Advice From An Italian

Posted on Last updated: February 2, 2024

Need help planning your Italy 2-week itinerary? You’ve come to the right place!

Italy is located in the middle of the Mediterranean Sea and is home to some of the most beautiful views and experiences (and no, I’m not just saying it just because I’m Italian).

Being Italian I get asked a million times for Italy travel advice, so I decided to put together this ultimate Italy 2-week itinerary that covers all the major sights and cities.  

This Italy two week itinerary starts with the history and beauty of the Eternal City, Rome, to then head over to Tuscany for a bit of exploration in Florence and Pisa, before heading to Cinque Terre for an amazing hiking experience.

Exploring Piazza del Duomo in Milan, Italy

After that this Italy travel itinerary continues on to the city of fashion, which also happens to be my hometown, Milan, and then ends in Venice, the city of lovers.

Two weeks in Italy aren’t enough to see the whole country, I’ve lived here for 18 years and there are regions I still haven’t been to either!

But it’s a great start and a good enough amount of time to travel comfortably around Italy and see all the main tourist hotspots.

I’ll also go over useful travel information like how to get around Italy, where to stay, what to pack and more. Ready to discover how to spend 2 weeks in Italy?

• 1 Do you need travel insurance for 2 weeks in Italy?
• 2.1 Day 1: Arrive in Rome – Colosseum & Trevi Fountain
• 2.2 Day 2: Rome – Visit the Vatican
• 2.3 Day 3: Rome – Pantheon & Fori Romani
• 2.4 Day 4: Travel from Rome to Florence
• 2.5 Day 5: Florence – Gallery and Gardens
• 2.6 Day 6: Explore the Old Town of Siena
• 2.7 Day 7: Travel to Pisa & explore Piazza dei Miracoli
• 2.8 Day 8: Pisa to Cinque Terre
• 2.9 Day 9: Hike the Sentiero Azzurro in Cinque Terre
• 2.10 Day 10: Cinque Terre to Milan
• 2.11 Day 11: Explore Piazza del Duomo in Milan
• 2.12 Day 12: Travel from Milan to Venice
• 2.13 Day 13: Explore Venice
• 2.14 Day 14: Fly home from Venice or extend your trip
• 3 How to travel around Italy
• 4 What to pack for 2 weeks in Italy

Admiring the colourful houses of Manarola, one of the five towns along the Sentiero Azzurro in Cinque Terre, Italy

Do you need travel insurance for 2 weeks in Italy?

After my personal experience spending two nights in a private hospital in Tenerife, and having to pay for it out of pocket (it wasn’t cheap), I always recommend getting travel insurance.

You might not end up needing it, but for a small fee you can travel without worries. Personally, I suggest getting your Italy travel insurance with  Heymondo .

Heymondo offers tailor made travel insurance, providing the best value for money for your specific trip. You can also buy it once you’re already abroad and have forgotten about it before flying (which, if you’re anything like me, is quite likely).

Besides the usual cancellation, medical expenses, luggage coverage and general travel insurance services, Heymondo also has a 24/7 doctor chat and instant assistance through their app.

As a Greta’s Travels reader, you get 5% off your Heymondo travel insurance !

Click here to get your 5% off Heymondo travel insurance!

Exploring the Golfo di Orosei and Cala Luna by kayak in Sardinia, Italy

Italy Itinerary: 14 days of exploring

Let’s dive right in to our 2-week Italy itinerary ! If you want to do this itinerary, without having to worry about booking hotels, tours and transfers yourself, you can book my customised Italy itinerary by Designer Journeys here !

Day 1: Arrive in Rome – Colosseum & Trevi Fountain

You should start your 2 week trip to Italy in Rome . After all it’s the capital of Italy, the Eternal City and it’s home to some of the worlds most ancient and beautiful history and art.

You’re only going to spend three days in Rome , so you’ll need to hit all the major attractions on your first day.

Plan your flight strategically, so that you land in Rome in the early morning. This gives you the ability to see a decent amount of the gorgeous ancient city right on day one. 

The first stop on your Italy route will be the ancient Colosseum!

There are many guided tours of the Colosseum , which will provide you with the knowledge about the brave gladiators, and the bloodthirsty entertainment that took place in Rome’s most famous monument.

The queue to go inside the Colosseum can get pretty huge so make sure to book online beforehand , or check out this guide to skipping the line at the Colosseum on a budget . 

Another way to skip the queue, is to join a night tour of the Colosseum . That way you’ll skip the crowds, and see this iconic attraction lit up at night. It’s one of the most popular Rome by night tours , and it’s easy to see why.

Click here to book your Colosseum skip the line tour!

Or click below to see prices & availability for your chosen date!

Enjoying the beauty of the Colosseum in Rome, Italy

Next, you’ll want to visit Trevi Fountain. It’s a beautiful monument decorated with sculptures and is a must-see when in Rome . I recommend walking there from the Colosseum, as this will take you past the famous Fori Romani.

These are a series of public areas that are centred around a monument. These were an integral part of Roman culture, and each served a different purpose in ancient times.

With its beautiful statues and white marble, the Trevi Fountain is without a doubt one of the most Instagrammable places in Rome .

They say if you throw a coin in the Trevi Fountain, you’ll get the chance to visit Rome again. I do it every time I go to Rome, just to be sure (and so far I’ve always gone back so I think it’s working)!

From the Trevi Fountain you can walk onwards to Piazza del Popolo and Piazza di Spagna, to see the famous Spanish steps and enjoy the view from Villa Borghese over the rooftops of Rome.

I love this part of Rome in spring , when all the trees are green and the flowers in bloom.

The Trevi Fountain in Rome, Italy

You can end your first day in Rome with a dinner out in Trastevere. Trastevere is one of my favourite areas in Rome, with lots of osterie and trattorie to choose from for your aperitivo or dinner options.

It’s a beautiful area of Rome at night , when the warm lights of the trattorie overflow into the cobbled streets, and especially so if you’re in Rome in summer , when locals and tourists alike mill around the streets and enjoy the long days and warm evenings of Italian summers .

I’ve eaten before at Osteria Cacio & Pepe and loved it, but most restaurants there will be good. It’s also a fun area to go bar hopping after dinner.

Eating spaghetti carbonara in Rome

Where to stay in Rome

My ex-boyfriend is from Rome so we tried our fair number of bnb and apartment rentals in Rome . That said, my personal favourite are places close to the Colosseum or Pantheon , as they’re in a great position to explore Rome.

If you want to save a little, here are some great places to stay in Rome for every budget. 

Budget: Palladini Hostel :Budget option for the backpackers or hostel lovers; this hostel is super central, close to the train station and all the action of Rome, with spacious dorms and a lively atmosphere

Mid-range: Tridente Rooms : Mid-range option, the rooms are simple but spacious and it’s right next to Villa Borghese, in the heart of all the Rome attractions

Luxury: Hotel Eden – Dorchester Collection : If you can squeeze it in your Italy trip budget , this beautifully decorated hotel is very conveniently located in the centre of Rome

Click here to book your accommodation in Rome!

Castel Sant’Angelo & Ponte Sant’Angelo in Rome, Italy

Day 2: Rome – Visit the Vatican

On the second day of your Italy travels, I recommend paying a visit to the famed Vatican museum. It’s one of the most popular tourist attractions in Rome, and it’s not hard to see why.

The best Italian trips include something ancient and something beautiful. This attraction just happens to include both!  Especially if you visit Rome in winter , it gives you an excuse to be indoors and out of the rain and cold for a while!

You can take a guided tour of the Vatican Museum and the Sistine Chapel , where you can ogle at masterpieces done by the great Michael Angelo, admire the incredible architecture, as well as learn about the cities fascinating past.

V isiting the Vatican Museum will easily take up a whole half-day, if not more depending on how long you want to spend in the museum. You can also go to the top of the dome and see an epic view over Rome .

I recommend buying your tickets online beforehand or you might end up queueing for hours just to get in.

Click here to book your Vatican Museum & Sistine Chapel skip the line tickets!

The Basilica di San Pietro and main square of the Vatican in Rome

In the late afternoon and early evening you can grab dinner and drinks around Campo Dei Fiori, where all the students and young people in Rome go out in evenings.

Once it’s properly dark you can also wander around the Fori Romani, where they play projections and light shows that aim to teach the public about these areas that played such an important part in Roman history.

You’ll see what the Fori Romanis looked like when they were built, which is an interesting insight into the past of this wonderful city.

| READ MORE: THE ULTIMATE ITALY BUCKET LIST |

Lost somewhere in the side streets of Rome

Day 3: Rome – Pantheon & Fori Romani

Start your third day in Italy off the right way by visiting the Pantheon ! It’s an ancient Roman temple that was later converted into a church, and holds great cultural significance within the Italian community.  

The architecture is absolutely stunning! This circular building is beautiful both inside and out, and it is also free to visit.

However, with free attractions comes queues, so I recommend you head to the Pantheon as soon as it opens to make sure you miss the crowds.

Alternatively, you can take a guided tour of the Pantheon , which allows you to skip the line, and learn the history of the Pantheon from a knowledgeable guide.

Close to the Pantheon is Gelateria 100 Palme, an ice cream shop that sells over 100 different flavours. Needless to say every time I go to Rome I try a different flavour.

Click here to book your Pantheon skip the line tour!

Or click below to see prices & availability!

The Pantheon in Rome, Italy

Best tours in Rome

These highly rated tours are a must during your time in Rome!

Vatican Museums & Sistine Chapel Skip-the-Ticket-Line Entry   – Like I already said, if you only have two days in Rome you don’t want to waste part of that time queuing up for things! 

Rome: Colosseum, Roman Forum, Palatine Hill Priority Tickets   – Same goes for the Colosseum, don’t waste time and don’t miss out on this awesome Italian attraction!

Rome: Street Food Tour with Local Guide   – Italians take food very seriously, the best way to discover true Roman cuisine is with a local!

Exploring Piazza Navona in Rome

Day 4: Travel from Rome to Florence

On your 4th day in Italy, you’ll travel from Rome to Florence. You can get to Florence either by plane or train. I personally recommend the train.

The flight might be one hour, but you still have to factor in travel time to and from the airport, and you usually have to be at the airport at least one hour before.

If you get the fast train from Rome to Florence this takes you from the centre of Rome straight to the centre of Florence in roughly the same amount of time as the total flying travel time.

Once you arrive in Tuscany , you’ll have plenty more activities to take part in and areas to explore. No matter how many days in Florence you have, you’re sure to fill up your Italy itinerary with a multitude of awesome things to do.

Your first stop in Florence should be the grand Florence Cathedral . It’s possibly the most celebrated cathedral in the world, making it one you don’t want to miss!

Known as Duomo or the jewel of the city, the incredible building was built in 1436 but wasn’t finished being built until the 19th century. 

The architecture is amazing and is an absolute must-see if you’re looking for Italian vacation ideas!

Click here to book your skip the line guided tour of the Florence Cathedral!

Getting up close to the majestic Duomo of Florence

Next, you should visit Ponte Vecchio, which is a historically significant bridge that stretches across the river Arno. The bridge is enclosed and has become famous for the many quaint shops built into its sides.

The earliest recordings of the bridge date back to 996, but nobody really knows its true origins. Take a meander along the bridge as you browse the shop windows.

| READ MORE: HOW TO SPEND 2 DAYS IN FLORENCE |

Light reflections at the Ponte Vecchio in Florence

You can end your first day in Florence at Piazzale Michelangelo. This is a park with a beautiful view over Florence. The huge dome of the cahedral towers over the rooftops of the houses, and makes for a stunning sunset spot.

When I visited Florence with my mum we stayed at Palazzo Riblet .

This hotel is a family-run business with only a few room within a historical building, with beautiful decorated bedrooms and original Renaissance affrescos on the ceilings.

It’s a great place to stay in Florence also thanks to its convenient position, close to both the train station and centre of Florence. 

Check out the latest prices and  availability at Residenza d’Epoca Palazzo Riblet here!

Sunset over Florence from Piazzale Michelangelo

Day 5: Florence – Gallery and Gardens

On your second day in Florence, you should aim to fill your day with as many beautiful Florence sights as possible.

Galleria dell’Accademia is a wonderful gallery that houses some of the most incredible sculptures from the Renaissance period. 

You can expect to see original sculptures from Michelangelo, as well as masterpieces from a multitude of other incredible artists. 

After a visit to the wonderful gallery, spend the afternoon exploring the Boboli Gardens! The gardens cover an area of 45 000 square metres, making them the largest gardens in Florence.

If you love being out in nature, this is the perfect Italy vacation idea. The gardens were created in the 16th century and feature rolling lawns with a scattering of beautiful sculptures to admire.

A stroll through these gardens is the perfect escape from the hustle and bustle of the city!

The Duomo of Florence and Battistero of San Giovanni in front of it

Best tours in Florence

Here are some tours with awesome reviews to check out for your time in Florence.

Florence: Uffizi Gallery Timed Entrance Ticket  – Skip the queue for your visit to the Uffizi!

Florence: City Walking Tours with entry to Accademia  – Discover Florence on foot with a local guide, and then explore the Accademia with them!

Florence: Small-Group Tour on E-Bike  – Try something a little different and discover Florence by bike!

Aerial view of Florence – Photo by Garrit Wes Anderson on Scopio

Where to stay in Florence

Besides Palazzo Riblet, I wanted to suggest a few places to stay for every budget.

Budget:  Plus Florence   – This hostel has spacious dorms, a sociable atmosphere and a spectacular rooftop with views over the Florence skyline.

Mid-range:  Palazzo Riblet   – I stayed here when I visited Florence with my mum and can highly recommend it. This family run hotel is situated in a historical building, with affrescos on the ceiling and in a great location.

Luxury:  Firenze Rentals Corso 12  – This lovely apartment has a balcony directly overlooking the Duomo of Florence. It doesn’t really get any better than this!

The view from the top of the dome of the Duomo of Florence – Photo by Giuseppe Trimarchi on Scopio

Day 6: Explore the Old Town of Siena

But Tuscany isn’t just about Florence, so travel on to Siena on day 6. In Siena you’ll discover a different side of Italy, as you explore the well preserved medieval city. 

There are plenty of things to see and places to explore in this wonderful town in the middle of the Tuscany region.

Start your tour of Siena at the central square, called Piazza del Campo, and learn about its great historical significance before paying a visit to the Gothic town hall.

Every year they run an important horseriding competition in this square, called Palio di Siena, and it’s a huge event much loved by the local people of Siena.  

Visiting the Cathedral of Santa Maria Assunta is an absolute must when you’re in the beautiful town.

It was constructed in the 13th century, and just like many of the other wonderful buildings in Italy, it has incredible architecture that rivals the worlds best.  

You can take a guided tour that will take you to both the Piazza del Campo and the Siena cathedral.

Click here to book your Siena highlights guided tour!

Piazza del Campo in Siena

You’ll also want to visit the Siena national gallery, which is housed in a former palace, making for a wonderful destination to tour.

Inside the gallery, you’ll find wonderful artworks from famed artists between the 12th and 16th centuries.

If you don’t feel like being indoors, spend some time wandering around the streets of Siena. Siena has one of the best preserved medieval old town centres and even just getting lost in its quaint streets will be a fun experience. 

We only spent one night in Siena and we stayed at Hotel Athena , within the old town walls.

The rooms were spacious and they included a tasty breakfast, but the highlight for me was by far the stunning view they had from the rooftop restaurant of the Tuscan countryside.

Click here to see the latest prices and availability at Hotel Athena

View over the Tuscan countryside from our hotel in Siena

Best tours in Siena

Here are some tours in Siena with excellent reviews.

Siena: Guided City Tour with Cathedral Skip-the-Line Entry – Discover the beauties of Siena with a local guide and without wasting time in a queue.

From Siena: San Gimignano, Montalcino & Wine Tasting – Explore the surroundings of Siena and taste delicious local wine!

From Siena: Vespa & Chianti Tour in the Tuscan Hills – Live your Italian travel movie dreams and zoom around the Tuscan countryside in a traditional Italian vespa!

View over the rooftops of Siena, Italy – photo by Roberto Destarac on Scopio

Where to stay in Siena

Besides Hotel Athena, I wanted to include a few accommodation options for every budget.

Budget: Camping Siena Colleverde – For something a little different, you can stay in this unique camping with epic views of Siena!

Mid-range: Hotel Athena   – The hotel I stayed at, it has cozy rooms and great views of the Tuscan countryside.

Luxury: Grand Hotel Continental Siena  – If you want to treat yourself, this is the place to do so!

Sunset views in Siena – Photo by Giuseppe Trimarchi on Scopio

Day 7: Travel to Pisa & explore Piazza dei Miracoli

After a week in Italy, you’re sure to have fallen in love with the beautiful country! However, there’s still plenty more to see if you’re feeling up for it!

On your 7th day in Italy, I recommend you travel from Siena to the wonderful town of Pisa. 

As soon as you arrive you should head straight for the famous Leaning Tower of Pisa, which was completed in 1372, and yes, it was leaning then too.

It’s incredible that this tower has managed to stand for hundreds of years at what seems to be a dangerous angle.

The Leaning Tower of Pisa is located in Piazza Dei Miracoli, which houses also the Baptistery and Duomo of Pisa. With one visit you can tick off all the main landmarks and attractions of Pisa.

| READ MORE: ONE PERFECT DAY IN PISA |

The Leaning Tower of Pisa

These aren’t as famous as the tower (nothing crooked or unusual about their architecture after all) but they’re still important parts of Italian history.

You can do a guided tour of Piazza Dei Miracoli where they will take you into both the Leaning Tower, the Baptistery and the Duomo, so that you can learn everything about this stunning city. 

You should then head to Borgo Stretto, a street that combines magnificent architecture and high-end shopping.

The street is located in the heart of the city and features many branded stores, boutique shops, designer clothing labels and quaint cafes that offer the perfect break from your shopping experience.  

A fter an incredibly scenic shopping experience, head to the Mezzo bridge that spans over the river Arno. It’s a great place to take pictures during sunset and it provides beautiful views of the sleepy town.

Click here to book your Pisa guided tour!

The baptistery of Pisa in Piazza dei Miracoli, Italy

The Duomo of Pisa with the Leaning tower in the back

Where to stay in Pisa

I haven’t slept in Pisa myself but here are some suggestions for places to stay.

Budget – Hotel Cecile : A good budget option, with finely decorated rooms and conveniently located in Pisa

Mid-range – Grand Hotel Duomo : This mid-range hotel is in an amazing location, with a rooftop terrace with a stunning view over the rooftops of Pisa and you can also get a glimpse of the Leaning Tower of Pisa. The rooms are also spacious and finely decorated

Luxury – Allegroitalia Pisa Tower Plaza : This luxury hotel is a bit outside Pisa but has a beautiful swimming pool, for those searching for a quiet place to take a break in the middle of this busy Italy itinerary

Click here to see the latest prices and availability for accommodation in Pisa

Exploring the off the beaten track courtyards of Pisa

Day 8: Pisa to Cinque Terre

After spending a wonderful night in Pisa, it’s time to move on to another wonderful part of Italy! Cinque Terre is a string of ancient sea-side villages that stretch along the Italian Riviera coastline.

Travelling from Pisa to Cinque Terre by train will take you between 1 – 2 hours, and gives you the chance to enjoy spectacular views along the way.

If you want to stay in Cinque Terre I recommend staying in either Monterosso or Riomaggiore. These are the two towns at the two ends of the Sentiero Azzurro, and as such are great starting points for your hike tomorrow.

It’s cheaper to stay outside Cinque Terre and travel in, but these towns really are beautiful and if you’re only going to spend 2 weeks in Italy, I get it if you want to absorb more of their atmosphere. 

The First – La Vista di Marina in Riomaggiore is a lovely apartment with absolutely gorgeous views. They’re right on the sea front and have epic views both of the sea and the colourful houses of Riomaggiore.

Click here to see the latest prices and availability at The First – La Vista di Marina!

Admiring the colourful houses of Riomaggiore in Cinque Terre, Italy

Many travellers only do a day trip to Cinque Terre , but in my opinion, they don’t realise how much they’re missing. It’s better to plan a longer Cinque Terre itinerary , so you can relax a bit too.

By day 8 I imagine you’ll be pretty knackered with all this intense sightseeing, so I suggest that after your train journey to Cinque Terre you take some time to relax.

Riomaggiore seemingly rises out of the ocean, leaving the entire town with exquisite views! You can spend some time exploring the town, wandering around the harbour or basking in the sun.

The coastline in Cinque Terre is rugged, but there are a few beaches in Riomaggiore worth exploring. Batteria beach is one of them. 

Fegina Beach in Monterosso al Mare, Cinque Terre

Hiking along the Sentiero Azzurro in Cinque Terre

Day 9: Hike the Sentiero Azzurro in Cinque Terre

You should spend a full day in Cinque Terre hiking the Sentiero Azzurro , a wonderfully scenic hike.

The trail passes passes through Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore, giving you the option to explore each town individually.

The trail is 12 kilometres long, but if you’re not up for the entire hike, you can do segments of it instead. You can start at either end of the trail, depending on where you’re staying, and then take a train back.

All the towns are connected via train. Access to the Cinque Terre national park and the Sentiero Azzurro hike costs 8 EUR for just entry, or 15 EUR for a combined park plus hop-on hop-off ticket to the trains.

Wineries somewhere along the Sentiero Azzurro in Cinque Terre, with Monterosso in the distance

Admiring the colourful houses of Vernazza, one of the five towns along the Sentiero Azzurro in Cinque Terre, Italy

If you can handle 12km in a day, I highly recommend doing the hike. While the colourful houses of Cinque Terre are the highlight of this trail, there are stunning views all throughout.

Along the way, you’ll enjoy the beautiful scenic views of the ocean and sheer rock faces that rise up out of the sea. It’s a wonderful hike for photographers or Instagrammers looking for the perfect shot. 

Be sure to find a great spot to watch the sunset in the evening, as the views from the trail are absolutely exquisite. Although it’s easy enough to head down to a seaside restaurant and watch the beautiful views from there.

The beautiful streets of Manarola in Cinque Terre, Italy

View over Vernazza from the start of the Sentiero Azzurro, enroute to Corniglia

Best tours in Cinque Terre

You can explore Cinque Terre on foot by hiking the Sentiero Azzurro, but these highly rated tours can add a special something to your holiday!

Cinque Terre Sunset Boat Tour   – Admire the coloured houses of Cinque Terre as the sun goes down and the sky turns golden!

From Monterosso: Cinque Terre Kayak Tour  – Combine a workout with a unique experience, and see Cinque Terre from a completely different angle!

From La Spezia: Cinque Terre Full-Day Boat Tour   – Spend a whole day sailing along the beautiful Ligurian coastline.

Sunset over the perched colourful houses of Riomaggiore in Cinque Terre, Italy

Where to stay in Cinque Terre

I’ve already given you my opinion on the best place to stay in Cinque Terre, but here are some optons for every budget.

Budget:  Grand Hostel Manin   – This hostel has spacious dorms, a friendly atmosphere and is located in the heart of La Spezia. It’s the perfect place to use as base to explore Cinque Terre on a budget!

Mid-range:  ALTIDO Villa Monterosso Apartment Bellavista   – This modern villa is tastefully decorated, with gorgeous views of the Ligurian coastline and sea. It’s also in an excellent position in Monterosso.

Luxury:  La Vista di Marina by The First   – This apartment combines modern furnishing with exposed bricks for a rustic vibe, plus spacious rooms and white décor for an airy feel. It also has a spectacular terrace with view over the sea and iconic perched houses of Riomaggiore.

The harbour and colourful houses of Porto Venere

Day 10: Cinque Terre to Milan

After your hiking and seaside break it’s time to take the train from Cinque Terre to Milan (my hometown)!

By now you’ll be very familiar with taking the train in Italy, and learning to enjoy the journey as the views are usually spectacular!

The slight delays that often happen on Italian railways are just part of the journey.

The train trip should take you around 3 hours, leaving you with plenty of time in the afternoon and evening to explore the wonderful city of Milan and its nightlife .

Piazza del Duomo in Milan, Italy

This city is one of the fashion capitals of the world, so you can be sure its a creative city with loads to explore!

The best way to start a trip to Milan is by visiting the Brera District. You can walk through the charming cobbled streets, admiring the architecture and taking in all the wonderful sights and smells.

Sit down for a meal at one of the charming cafes or restaurants before exploring some of the amazing art galleries in the area.

Especially if you’re visiting Milan in winter , it gives you an excuse to be indoors while still discovering the culture. 

And, if you need a little retail therapy, there’s plenty of high-end shops that can provide you with just that!

Galleria Vittorio Emanuele seen from across Piazza del Duomo in Milan, Italy

Where to stay in Milan

Wondering where to stay in Milan ? Being from Milan I’ve never had any need to stay in a hotel there, however there are a couple thatI’ve had friends stay at before that I can recommend:

Budget – Ostello Bello : There are two hostels of this chain around Milan and both are good budget options, with a lively atmosphere, spacious dorms and convenient central locations

Mid-range – Ibis Milano Centro : Part of the Ibis chain this is a good mid-range hotel, with a guaranteed standard of room set up and a great central location

Luxury – Galleria Vik Milano : If you’re looking to splurge a bit, this is the place to do so. Located in Galleria Vittorio Emanuele this luxury hotel couldn’t get any more central than this, with stunning views over the galleria just outside your window

Click here to see the latest prices and availability for accommodation in Milan!

The inside courtyard of the Accademia di Brera, Milan

Day 11: Explore Piazza del Duomo in Milan

You should spend your full day in Milan  around Piazza del Duomo, this is the central square in Milan and all the main tourist attractions are located around it. It’s a great meeting place amongst locals and tourists alike.

You’ll see unbelievable architecture, intricate sculptures and the wonderful Duomo itself.

You can start with a guided tour of the cathedral which is very informative, however the highlight of the tour for me is the rooftop tour that comes along with it. 

It allows you to enjoy a view over the city while seeing the spires and architectural intricacies of the rooftop sculptures and designs.

This is also a great place to take photos, especially as the sun is rising or setting in the background!

Book your fast track tour of the Milan Duomo here!

Exploring the rooftop of the Duomo cathedral in Milan, Italy

Sunset over Milan from the rooftop of the Duomo, Italy

After exploring the wonderful interior of the Duomo, it’s time to head outdoors and enjoy the scenery that Milan has to offer!

From Piazza del Duomo you can easily visit Galleria Vittorio Emanuele, the Teatro della Scala and Castello Sforzesco, two must-sees that are close in the area.

Some of my favourite food places can also be found close to he Duomo; Luini for panzerotti (these are tiny fried calzone) and Spontini for pizza.

You can end the day by going for a stroll around the navigli. Not many people realise that Milan has canals (yes like Venice!) even if it only has two.

The Naviglio Grande canal was built in 1177 and has been expanded since then. This is one of the hip areas to hang out in evenings, where you can have a lovely aperitivo or dinner out amongst locals.

Admiring the perfect symmetry of Galleria Vittorio Emanuele in Milan, Italy

Best tours in Milan

Here are some of the best tours you can’t miss during your time in Milan.

Milan: Fast-Track Milan Cathedral and Terraces Guided Tour  –  Discover the beautiful Duomo and its stunning rooftop, without having to waste time queuing!

Best of Milan Tour with Skip-the-Line to Duomo & Last Supper   – For the art lovers, no visit to Milan would be complete without seeing the Last Supper!

Milan: Grand City Highlights E-Bike Tour  –  Discover all the highlights of Milan on bike!

Castello Sforzesco in Milan, Italy

Day 12: Travel from Milan to Venice

Travelling by train from Milan to Venice offers some amazing views along the way.

The trip should take just over 2 hours, if you set off in the morning it will give you plenty of time to start getting your bearings around the famed city of Venice.

As soon as you get to Venice, after you drop off your bags, you should visit San Marco square, where you’ll find some some of the most beautiful basilicas in Venice.

If you love exploring old churches, why not take a tour of the basilica and the palace ? This will give you a chance to learn a great deal about Venetian history and the culture of the city.  

Click here to book your skip the line tour of St Mark’s Basilica and the Doge’s Palace!

Piazza San Marco in the early evening

On the way back from San Marco square you will come across Ponte di Rialto, which is the most famous of the 400 bridges that are scattered throughout Venice.

The bridge offers magnificent views over the romantic city and it’s a wonderful spot to enjoy the sunset.

I spent one night in Venice with my mum and we slept at Hotel alle Guglie . This was ideal since it was located just outside the main touristy area of Venice, but was still within short walking distance of all the attractions.

The rooms were a bit small but they made up for it with an abundant breakfast, good price for value and great location.

Click here to book your stay at Hotel all Guglie!

Sunset on the grand canal in Venice from Ponte di Rialto

Day 13: Explore Venice

Seeing as you only have one full day in Venice , you need to make the most of it by doing as many sightseeing activities as possible.

You can start the day with a gondola ride through the canals of Venice. These are a bit expensive but it’s such a traditional Venetian experience, how could you possibly miss it?

It will give you a unique and lovely view from the waterways, since you can see the ancient buildings that seemingly rise up out of the water.

I recommend starting your gondola cruise by Rialto Bridge, as it offers the best views and calmest waters.

There’s no need to book beforehand, since there are plenty of gondolas all over Venice waiting to take tourists around (kind of like taxi stands in any other city) and the price is standardised.

However if you want to be sure to have your experience confirmed you can also book online .

Click here to book your private gondola cruise in Venice!

Enjoying my gondola cruise around Venice

Our gondola ride took us close to Rialto Bridge

After your gondola cruise you should visit the Bridge of Sighs or Ponte dei Sospiri, which is a very famous bridge in Venice. Despite popular stories, the name isn’t inspired by love stories.

The bridge connects the interrogation room to the prison, and it’s said that prisoners would sigh while crossing the bridge, as they took in their very last sight of Venice.

Not as romantic as you’d think right? But it’s still a beautiful spot in Venice and definitely worth a visit.

The Ponte dei Sospiri in Venice

From here you can take a tour of the Basilica di Santa Maria Della Salute . It’s a beautiful church with some of the best architecture you’ll ever find in the city (which is really saying something).

You can explore it yourself, or take a guided tour if you’d like to learn a little more about its history. Just across from the Basilica there’s also a killer sunset spot so you can sit here and enjoy the end of your Italy itinerary.

Best tours in Venice

Book one of these highly rated tours for your time in Venice!

Venice: Private Gondola Ride to Rialto Bridge   – Go for a private gondola ride amongst the most beautiful canals of Venice!

Venice: Doge’s Palace Priority Admission Ticket   – Skip the queue and visit this iconic site in Venice!

Venice: Small Group Wine Tasting and Food Tour with a Local   – Go for a guided tour of all the best places to eat and drink in Venice with a local guide!

Sunset at the Basilica di Santa Maria della Salute in Venice

Where to stay in Venice

I’ve already mentioned my great stay at Hotel alle Guglie, but I wanted to include some more accommodation options in Venice for every budget.

Budget:  Combo Venezia   – This hostel has a combination of modern dorms and a traditional courtyard. It’s also in a great location and has a very sociable atmosphere.

Mid-range:  Hotel alle Guglie  – I stayed here with my mum and found it a perfect compromise for those looking for a comfortable room, great location and affordable price.

Luxury:  Ai Patrizi di Venezia   – These luxury apartments are the perfect place to treat yourself during your Venice stay.

Cruising the canals of Venice in our gondola

Day 14: Fly home from Venice or extend your trip

It’s the 14 th and final day of your Italy trip! The time has sadly come to fly home. However, if you manage to get a few extra days in, there is still so much more of Italy to see!

Want to do this Italy trip without the hassle of booking all the tours, transfers and hotels yourself? Book this itinerary on Designer Journeys !

Click here to book your customised Italy 2-week itinerary on Designer Journeys!

Exploring the Greek amphitheatre of Taormina at sunset

Alternatively, after hitting all the main cities and tourist landmarks of Italy, I imagine you’ll be ready to head out off the beaten track!

If you’re not ready to leave Venice just yet you can go on some awesome day trips from Venice . You can easily get to beautiful cities like Verona , Bologna and more.

If you want to see a completely different side to Italy, it’s time for a nature escape!

If you’re looking for beautiful beaches, I recommend you head to Sardinia for a boat trip  (one of the best beach destinations near Milan ), where you’ll get the chance to explore the beautiful archipelago and see a more tropical side to my wonderful country.

I’ve seen a lot of beaches all over the world, but I’m yet to see beaches that are better than the ones in Sardinia . If you’re looking for a mixture of sea and culture, you can also head to   Sicily .

Here you can spend your afternoons with the sunshine warming your skin and your toes in the sand, before cooling off in the turquoise waters, but also exploring the food scenario and wandering around the cute towns. 

A relaxing boat trip day in Sardinia, Italy

If you’re not a beach bum, or you’re visiting Italy in winter , you can head to Trentino for an adventurous escape.

In summer in Trentino you can entertain yourself with some magnificent hikes and epic views over alpine lakes , whilst over Christmas you can ski in world famous slopes .

Either way, you’ll get your heart pumping and your blood flowing. I’ve visited Trentino loads of times as a kid in winter, but only recently in summer and I can honestly say this region is stunning at any time of year.

It’s the perfect place for a nature escape after 2 weeks of city sightseeing in Italy.

Hiking at Rolle Pass in Trentino

Another beautiful place in Italy, which I haven’t included in this Italy 2-week itinerary is Lake Como. Lake Como is one of the most popular tourist spots in Italy.

With its stunning natural landscapes, picturesque towns and relaxed vibe, it’s easy to see why. Many travellers only do a day trip to Lake Como from Milan , but I always say it’s well worth spending at least three days in Lake Como .

If you stay in Lake Como overnight you can go on a beautiful Lake Como boat tour , discover the towns of Bellagio and Varenna, go on a scenic hike and much more!

The picturesque streets and views of Bellagio in Lake Como, Italy

You could also head to the south and visit the Sassi of Matera . This city went from being considered the “Shame of Italy” to being the European Capital of Culture in 2019. 

Also in the south of Italy, is the famous Amalfi Coast . I recently spent five days in Amalfi Coast , hiking the Path of the Gods , going on boat trips to Capri , exploring Positano and discovering the ruins of Pompeii .

I didn’t include Amalfi Coast in this video since there’s just too much to do in the area. Even if you only do day trips to Pompeii and Capri , and skip the Positano boat tour , it would take up too much for your two weeks in Italy, leaving little time for other destinations.

Don’t have two weeks to travel around Italy? Check out this Italy 10-day itinerary or my 7 days in Italy itinerary instead.

Wondering how much all this would cost? Check out my Italy 2-week trip budget to find out!

Enjoying the view over the Sassi of Matera in Italy

How to travel around Italy

Travelling within Italy is fairly easy.

We have a pretty decent railway system (Trenitalia is often late but it always gets you where you need to go), lots of bus companies, internal flights that connect most major and minor cities to each other, and pretty good roads for driving.

My personal favourite way to get around, as you may have guessed from this itinerary, is by train.

On long distances the Frecciarossa (the high speed train here in Italy) is often faster than flying, if you were to factor in also travel time to the airport, airport faff time and then travel time from the airport to home.

Driving in Italy is also great if you have a licence and friends to share the journey with, as it gives you more flexibility than the trains.

What to pack for 2 weeks in Italy

I’ve written a full Italy packing list  with all the essential items you might need in Italy, however if you don’t want to open a new tab (I get it, it’s the end of the article, you’re tired and excited to start planning your trip) here’s a couple absolute must haves you don’t want to forget.

International adaptor  – depends on where you come from but I like to always carry with me an international adaptor just to be sure.

It’s a bit more expensive than the one country adaptors but at least I only need one that I can take everywhere

Power bank  – you don’t want to be wandering around the medieval streets of Siena and then all of a sudden your phone dies! You want to always be charged both for Google Maps and let’s be real, photo opportunities!

Steel water bottle  – In Italy we’re not as ahead as other countries with water dispensers in restaurants and other public places, but generally speaking the tap water is drinkable everywhere, so if you want to cut down on your plastic consumption and save some cash in the process, don’t forget your own water bottle!

Exploring the side streets, canals and bridges of Venice, Italy

Final thoughts on the best Italy itinerary

If you’re looking for the best way to visit Italy in 2 weeks, you’ve just found it! I’ve made sure that this Italy itinerary is jam-packed full of exciting entertainment, sightseeing opportunities and adventures you’ll treasure forever.

Yes it’s a bit of a touristy itinerary, but after all tourist places are so for a reason, usually because they’re beautiful! 

Travelling to all the major cities and tourist destinations is a must during your 14 days in Italy trip. However that doesn’t mean you shouldn’t venture a little off the beaten track to find the hidden gems that will keep you coming back. 

If quaint cities, beautiful architecture and ancient history all sound right up your ally, then Italy is the place for you to roam. I hope you find this 2-week Italy itinerary useful in planning your own trip.

From an Italian point of view, I tried my best to include all the most beautiful cities that I would want any new traveller to visit. I hope you’ll fall in love with my country as much as me! 

I f you’re still looking for more Italy inspiration, check out my guide on the 10 things to know before travelling to Italy , or these 60+ inspiring quotes about Italy .

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• Travel Planning Guide

The Best 2-Week (14-Day) Tours in Italy

Looking for the perfect 14-day getaway to Italy with a fantastic guided tour? We've carefully analyzed all of the possible two-week tour options to Italy based on price, comfort, service, guest ratings, cuisine, and activities in order to find the absolute best multi-day organized tour options available. Whether you're seeking a relaxing getaway or an action-packed expedition, these guided tours offer the perfect length to indulge in the best of both worlds. From captivating excursions to tantalizing cuisine, get ready to experience the ultimate 2-week escape to Italy that will leave you with unforgettable memories and a renewed sense of wanderlust. Great for museums & attractions, food, nightlife, and beaches, Italy is a terrific destination. So, check out our curated list of tours below to get started!

• Mediterranean Flavors 14 Days, $2649.00
• Italy's Best 14 Days, $2839.00
• Splendours of Italy (13 Days) 13 Days, $2725.00

Which 14-day tour options are available in Italy?

Here are the important factors:

• 29 trip options analyzed
• $317 average price per day (USD)
• 13 to 14 days in length
• 4.69 of 5 average rating
• 33 people or less on average

Curious about the diverse range of tours lasting 2 weeks? Prepare to be amazed by the array of options available to suit every traveler's preferences. It comes as no surprise that visitors adore these tours, given their exceptional average guest rating of 4.69 out of 5 stars. When it comes to group sizes, the average maximum capacity stands at 33 people, allowing for a comfortable and sociable experience. The shortest tour is 13 days, while the longest is 14 days. As for physical activity options, the tours are thoughtfully categorized as easy and moderate, with the most being easy. For transportation , the tours are marked as coach / bus, train & rail, and ocean cruise, with a prevalent number on coach / bus tours. With a comprehensive analysis encompassing 29 tours lasting 2 weeks, you can rest assured that Italy has something tailored to your interests and preferences, promising an unforgettable experience for all.

(All tour prices are in US Dollars before taxes, and come from a base price that is reported by TourRadar. Peak season prices can vary significantly, particularly in destinations where seasonal travel fluctuates dramatically.)

So, let's get to it and see...

The 10 Best 2-Week Tours in Italy

Mediterranean flavors.

• Great Value: the daily price is lower than average for tours lasting 2 weeks.
• High Quality: guest ratings are higher than average.

This exceptional trip offering by Cosmos has received a 4.9 out of 5 rating. On this 14-day trip, visiting Spain, France, and Italy, you can unwind while also making new memories. Along the way, this journey encompasses 15 destinations, including Cuenca, Valencia, Peniscola, and Barcelona. Madrid will mark the start of your journey, while Rome will serve as its final destination. With a group size of 50 people, it's suitable for travelers from 5 and up. This extraordinary adventure also revolves around local culture and family-friendly activities. This remarkable trip is priced at an unbeatable $189 per day.

• Coach / Bus
• In-depth Cultural

Italy's Best

Check out this voyage that has received rave reviews, earning a stellar 4.9 out of 5 rating. This itinerary covers 17 captivating destinations, with stops in Sorrento, Pisa, Montecatini, and Florence, among others. Rome will be both the start and end of your journey. This terrific trip also highights local culture and family-friendly activities. Spanning across 14 unforgettable days, this voyage offers an intimate group experience with 50 participants, and it's great for travelers from 5 and up. Brought to you by the renowned Cosmos , this exceptional opportunity is priced at an incredible $192 per day - an unbeatable value.

Splendours of Italy (13 Days)

This 13-day voyage, visiting Italy and Vatican City (Holy See), is ideal for travelers from 5 to 80 years old. And priced at only $188 per day, it's a great value, too. Immerse yourself in a travel experience that includes 12 destinations, featuring Verona, Lugano, Saronno, and Pisa. Your adventure starts and ends in Rome. It's offered by Costsaver , a very popular company with rave reviews and knowledgeable guides.

Highlights of Sicily & Southern Italy

Priced at just $254 per day, this terrific 14-day voyage is ideal for travelers from 5 to 80 years old. Uncover the beauty of 13 destinations on this itinerary, with highlights such as Lecce, Alberobello, Matera, and Reggio Calabria. Rome will mark the start of your journey, while Palermo will serve as its final destination. Organized by the reputable Globus , this is one of the best tours on this list.

Italian Glory (13 Days)

Check out this incredible journey that has received a 4.6 out of 5 rating from previous guests. With an emphasis on local culture and family-friendly activities, you know you'll have an amazing adventure. With a duration of 13 days, this journey ensures an intimate group size of 50 people, and is good for travelers from 5 and up. Traverse through 9 enchanting destinations, with Florence, Maiori, Amalfi, and Pompeii among the must-see stops along the route. Milan marks the starting point, while Rome stands as the final stop on your incredible journey. This fantastic option, organized by Trafalgar , presents an unbeatable value at just $291 per day.

Best of Italy (Summer, 13 Days)

Spanning over 13 days, this journey has a maximum size of 50 individuals. Welcoming travelers from 5 and up, it is organized by Trafalgar , a very popular company with plenty of great reviews. This trip visits 12 destinations, including Pisa, Florence, Pompeii, and Sorrento along the way. You'll start and end your journey in beautiful Rome. And since the priority is on local culture and family-friendly activities, this tour is a great choice. Available at an unbeatable price of only $296 per day, this option also has a rating of 4.6 out of 5 stars from previous guests.

A Taste of Italy: 14 Days

Here's your chance to take off on an exceptional journey, visiting Italy and Vatican City (Holy See), that has garnered a 4 out of 5 rating. With a duration of 14 days, this jouney will have 45 participants, and it warmly welcomes travelers from 8 and up. Expertly organized by Omega Tours , this amazing trip is an incredible value at just $276 per day.

Italian Mosaic

This memorable trip, visiting Italy and Switzerland, is offered by Globus which has received plenty of positive reviews. The trip itself has a guest rating of 5 out of 5 stars, and is priced affordably at $377 per day. Explore 13 incredible locations on this trip, including Sorrento, Capri, Pisa, and Florence. You'll start and end this amazing trip in Rome. This extraordinary adventure also revolves around local culture and family-friendly activities. The maximum group size is 46 people, welcoming travelers from 5 to 80 years old.

Best of Italy

Set off on an extraordinary journey that has been awarded a 4.3 out of 5 stars by previous guests. With a duration of 14 days, this trip offers an intimate group setting, accommodating 12 individuals, while extending a warm welcome to travelers from 15 and up. Discover a journey that spans 11 destinations, with notable stops in La Spezia, Cinque Terre, Portofino, and Asti. Beginning in beautiful Rome, you'll have a terrific journey that ends in Venice. Brought to you by Intrepid Travel , this exceptional deal is an incredible steal at a mere $246 per day.

Best of Italy (Winter, 13 Days)

With this option you can experience an unparalleled journey for 13 unforgettable days. It ensures an intimate group setting with 50 participants at most. This trip takes you on an adventure to 13 destinations, including Pompeii, Sorrento, Capri, and Cassino. Your adventure starts and ends in Rome. Trafalgar , the organizer of this journey, extends a warm invitation to guests travelers from 5 and up. You're in for an epic adventure with a strong emphasis on local culture and family-friendly activities. This extraordinary opportunity offers exceptional value at only $266 per day.

See also The Best Family-Friendly Tours to Italy , The Best Hiking & Trekking Tours in Italy , The Best Historical Tours in Italy , The Best 10-Day Tours in Italy , The Best One Week (7-Day) Tours in Italy , The Best 3-Day Tours in Italy , The Best Bicycle Tours in Italy , Tours for Outdoor and Nature Lovers in Italy , The Best Christmas & New Years Tours in Italy , The Best Coach Bus Tours in Italy , The Best Adventure Tours to Italy , The Best Eco Tours in Italy , The Best Train & Rail Tours in Italy , The Best Thrill-Seeking Tours in Italy , The Best Sightseeing Tours in Italy , The Best Cultural Tours in Italy , The Best Vineyard & Wine Tours in Italy , The Best Food and Culinary Tours in Italy , The Best Music Tours in Italy , The Best Romantic Tours for Couples in Italy , The Best Self Drive Tours in Italy , The Best Walking Tours in Italy , The Best Tours Under $1000 in Italy , The Best Luxury Tours to Italy , The Best Budget Tours to Italy , The Best Tours for Seniors to Italy , The Best Contiki Tours to Italy , or The Best G Adventures Tours to Italy for more tour ideas. With so many options, there's a guided tour or vacation package for every type of traveler.

Also, if you're departing from a specific destination, see The Best 3-Day Tours from Rome , The Best 3-Day Tours from Florence , The Best One-Week (7-Day) Tours from Rome , The Best One-Week (7-Day) Tours from Venice , The Best One-Week (7-Day) Tours from Catania , The Best One-Week (7-Day) Tours from Naples , The Best One-Week (7-Day) Tours from Florence , The Best One-Week (7-Day) Tours from Milan , The Best One-Week (7-Day) Tours from Bari , The Best One-Week (7-Day) Tours from Palermo , The Best One-Week (7-Day) Tours from Pisa , The Best One-Week (7-Day) Tours from Bolzano , The Best One-Week (7-Day) Tours from Olbia , The Best One-Week (7-Day) Tours from Bologna , The Best One-Week (7-Day) Tours from Merano , The Best One-Week (7-Day) Tours from Cagliari , The Best One-Week (7-Day) Tours from Alberobello , The Best One-Week (7-Day) Tours from Como , The Best One-Week (7-Day) Tours from Montecatini , The Best One-Week (7-Day) Tours from Siena , The Best One-Week (7-Day) Tours from Lucca , The Best One-Week (7-Day) Tours from Turin , The Best 10-Day Tours from Rome , The Best 10-Day Tours from Venice , The Best 10-Day Tours from Palermo , The Best 10-Day Tours from Catania , The Best 10-Day Tours from Milan , The Best 10-Day Tours from Naples , The Best 2-Week Tours from Rome , The Best 2-Week Tours from Milan , The Best 2-Week Tours from Venice , or The Best 2-Week Tours from Palermo for more package tour options.

How much do 14-day tours to Italy cost?

After analyzing 29 tours lasting 2 weeks in Italy, we found the average price to be a remarkably economical $317 per day. Naturally, this region has many fantastic options for tours lasting 2 weeks with a variety of prices. The individual costs will vary by the destinations, travel style, available dates, and other factors. If you're interested in more information about tours here, see our guide to tour prices in Italy .

And for more information on Italy, see Italy Travel Costs and Italy Hotel Costs .

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2 Weeks In Italy Itinerary, The Ultimate Italy Road Trip

Planning a trip to Italy for 2 weeks? You are at the right spot! I’ve been exploring Italy for decades. So I have all the hands on experience and tips to give you the best 2 weeks in Italy itinerary. 

Italy is located in the middle of the Mediterranean Sea and is home to some of the most beautiful towns, cities, and experiences on offer in Europe.

Italy is probably my favorite country to travel in. You’re engulfed in history, can admire some of the world’s best art, and eat some of the world’s best food. What could be better?

Overview Of 2 Weeks In Italy Itinerary

This 2 week Italy road trip itinerary starts in Venice and ends in Naples. It’s a perfect itinerary for first time visitors to Italy.

Venice’s airport is terrific and typically inexpensive to fly into. The city’s Santa Lucia and Mestre train stations connect to just about everything south with high speed service. 

You can pick up your car leaving Venice or leaving Bologna. Alternatively, you can also do the entire 2 weeks in Italy by train.

With this Italy itinerary, you’ll have 5 bases: (1) Venice; (2) Bologna; (3) Florence; (4) Rome; and (5) Naples.

If you need a break from the city, instead of staying in Naples, you can base yourself on the Amalfi coast for 3 days and day trip from there.

The cliff top town of Sorrento makes a perfect springboard for visiting the Amalfi Coast. From there, you can day trip to Pompeii, Positano, Capri, and even Naples.

• Day 1 : Venice
• Day 2 : Venice
• Day 3 : Bologna
• Day 4 : Bologna, day trip to Parma or Modena
• Day 5 : Florence
• Day 6 : Florence
• Day 7 : Florence, day trip to Siena
• Day 8 : Rome
• Day 9 : Rome
• Day 10 : Rome, Vatican City
• Day 11 : Rome, day trip to Orvieto
• Day 12 : Naples
• Day 13 : Naples, day trip to Pompeii
• Day 14 : Naples, day trip to Amalfi Coast

Where To Stay With 2 Weeks In Italy

Here are my hotel recommendations for the cities listed as bases.

Venice : Gritti Palace , Hotel Danieli , St. Regis , Aman Venice (my favorite), Bauer Palazzo

Bologna : Grand Hotel Majestic Gia Baglioni (my pick) Il Portici , Art Hotel Orologio

Florence : Il Touranbouni ,  Hotel Brunelleschi , Portrait Firenze , Palazzo Vecchietti , Villa Cora (my favorite in the Oltrarno)

Rome : Li b ert y Boutique Hotel ,  H o t el  M aalat ,  De co  Ro ma ,  Hotel H a s s ler Roma , Pa lazzo Man fr edi  (my favorite)

Naples : Grand Hotel Vesuvio , Romeo Hotel , Hotel San Francesco al Monte (my pick)

2 Weeks In Italy Itinerary: 14 Days Of Exploring

Ok, let’s dive right into this 2 week Italy itinerary. If you’re landing in Venice, the easiest way to get to the city is via a private water taxi transfer .

Day 1: Venice

Kick off your 2 weeks in Italy in the magical floating city of Venice. Even though Venice is very touristy, there’s a reason for its popularity.

Venice is a natural film set. It’s like no other city in the world.

Start your day in Piazza San Marco. Visit the pink marble Doge’s Palace, which is the very symbol of Venice.

You can traipse up the famed Scala d’Oro, the world’s fanciest staircase, admire the Doge’s apartments, and see the world’s largest painting by Titian.

Click   here  to book a skip the line ticket to avoid a long queue. I also loved the Secret Itineraries Tour , which take you to secret spots in the palace you can’t see on a regular tour.

Then, move on to one of the world’s most unique and stunning churches, St. Mark’s Basilica. It’s absolutely essential to book a skip the queue ticket . You can also purchase an  after hours ticket  for fewer crowds and to get access to some places you can’t see during the day.

The basilica is famous for its almost blinding golden mosaics from the 5th century B.C. They blanket the walls, covering 90,000 square feet.

Then, take a ride along the Grand Canal. It’s one of the most iconic things to do in Venice. You can also hop on and off the Vaporetto yourself.

Along the way, you can check out Ca’Rezzonico, Ca’ Foscari, and Ca’ d’Oro. In addition to housing some great art, the palaces offer up great views of Venice.

You can book a  1 hour guided boat tour . You can also book a  3 hour guided tour   of the St. Mark’s area that comes with a boat cruise.

Day 2: Venice

On day 2 in Venice, take a stroll through the Rialto neighborhood. Snap a classic shot on the Rialto Bridge, check out the Fish Market, and myriad shops. You can also take a  lunchtime tour of the Rialto Market and other foodie hot spots .

Next, head to the Dorsoduro neighborhood. Stroll around the pretty streets, check out the shops and eateries, and then go to one of the neighborhood museums.

The two I love are the Peggy Guggenheim Collection and the Galleria Accademia .

The Guggenheim is for people who want to see some of the greatest works of modern art from the 20th century. It’s a star studded lineup compiled by the eccentric American heiress, who helped launch Jackson Pollock’s career.

This museum will be packed. Click  here  to purchase a skip the line ticket. Click  here  to book a private guided tour of this extraordinary collection of art.

The Galleria Academia is for travelers who love old masters. It houses the world’s best collection of pre-19th century Venetian painting. You’ll find works by luminaries such as Veronese, Titian, Tintoretto, Tiepolo, Bellini, Canaletto, and Giorgione. 

The museum is not usually crowded, so you won’t have to worry about buying tickets in advance. But, if you’re a fan of Renaissance art, you may want to book a 2 hour  guided tour of the museum .

If you want to see the “Sistine Chapel of Venice,” head to the San Polo district to the Scuola Grande di San Rocco. It’s decorated wall to walk with dramatic paintings by Titian.

Then, spend some time in the Cannaregio district. you can escape the crowds, poke in and out of cute lanes, and grab some cicchetti , Venice’s version of tapas.

Cannaregio is an excellent neighborhood to sign up for a   f ood and  wine  tour . You can also book an  evening food tour and gondola ride .

For more information, you can check out my 2 days in Venice itinerary . It has detailed information on gondola rides, how to use the vaporetto, and how to get to the other Venetian islands in the lagoon.

Day 3: Bologna

On day 3, head to beautiful Bologna. This food-loving city is underrated and absolutely deserving of a spot on your 2 weeks in Italy itinerary. It’s sandwiched between 3 major cities — Venice, Florence, and Milan — and is often skipped.

Don’t skip it! To me, Bologna just oozes old world medieval charm.

It has all of the charm of Italy with none of the tourists! Bologna is filled with striking architecture, beautiful piazzas, endlessly photogenic streets, porticos, and a swathe of palaces and towers.

Most of the must see attractions are clustered in or around the city’s main square, Piazza Maggiore. On one end of the piazza is the massive Basilica of San Petronio, honoring Bologna’s patron saint. On the other is the swishy Palazzo dei Rei Enzo.

You can also climb Bologna’s leaning tower, Asinelli Tower, for views. Since it’s a rickety 500 steps to the top, you’ll deserve a gelato afterward.

Be sure to meander through shops in Bologna’s medieval Quadrilatero neighborhood. You can also visit FICO Eataly World . It’s part farm and part theme park, with 20 acres of food and livestock stalls, restaurants, grocery stores, and food labs.

There are lots of fun tours to take in Bologna. Naturally, most of them food related:

• classic food tour
• 3 hour FICO Eataly food and wine tour
• food tour with factory visits and a gourmet lunch
• history tour and learn food secrets
• e-bike tour with cheese and wine

Day 4: Bologna, Day Trip To Parma & Modena

On day 4, take a day trip from Bologna to either Parma or Modena. Both are foodie towns that are pretty and un-touristy.

Underrated Parma is just too cute for words. It’s one of Italy’s most beautiful cities , a foodie haven, and home to the greatest works of the famed Renaissance artist Correggio.

Parma has a gorgeous Romanesque cathedral and pretty pink octagonal Baptistery. The entire town is dotted with red, pink, and yellow walls. Purple flowers decorate the Ponte Verdi.

Parma is tailor made for art lovers. The town was home to Correggio, the opera composer Giuseppe Verdi, and the conductor Toscanini. In 2022, Parma was chosen as Italy’s Capital of Culture.

Precious frescos by Correggio literally blanket the city. There are art-filled palaces, a famous opera house, and a world class museum.

Parma will also appeal to traveling foodies. It’s home to some of Italy’s best known culinary products — parmesan cheese, prosciutto, fresh pasta, and other delicacies. All this goodness has led the town to be dubbed the heart of the “Italian Food Valley.”

You can easily spend one day in Parma just popping in and out of food shops, taking a food tour, and having some memorable meals. Check out these cool food tours in Parma:

• 5 hour prosciutto and parmesan tour
• 7 hour cheese, ham, and balsamic tour
• 3.5 hour traditional food tour
• 2 hour tour of parmesan cheese factory
• 2 hour tour of dairy and prosciutto factory

Modena is a hidden gem in Italy , an elegant little city that’s well worth a visit.

If you’ve heard of Modena, it’s probably because of its food. Modena is a foodie haven. It’s famous for hams, cheeses, and barrel aged balsamic vinegar. You can sample the dark elixir in shops around the town. 

But Modena isn’t just about food. Modena is beautiful and immaculate.

Piazza Grande is its eye catching main square. It’s home to several monuments, including a Duomo, town hall, a picturesque 15th century clock tower, and medieval relics.

The 12th century Duomo is one of the finest examples of Romanesque architecture. It comes complete with a slightly leaning bell tower called the “Ghirlandina.”

Modena was also the birthplace of Luciano Pavarotti. His titular museum,  Luciano Pavarotti Museum ,  is located about 20 minutes from city center on the estate where the famous tenor lived.

Since Modena is for foodies, you may want to book a  guided food tour , do a  balsamic vinegar tasting , or  tour Italy’s most famous cheese factory .

Modena is just a 45 minute drive from Bologna. You can also visit on an 8 hour guided day tour from Bologna.

Day 5: Florence

Ah Florence . It may be Italy’s most beloved city, even over Venice. The “Cradle of the Renaissance” is beautiful from every angle.

You can content yourself with just absorbing the beauty and street life. But there are so many amazing attractions in Florence, you won’t be able to resist them.

Start your day at one of Florence’s hotspots, the Galleria Academia . It’s home to the world’s most famous statue, Michelangelo’s David , and his prisoners.

The lines are epic here, so you should definitely pre-book a  skip the line timed entry ticket .You can also opt for a  1.5 hour guided tour with fast track ticket .

For even more Michelangelo, head to the Medici Chapels. Inside, you’ll see the over-the-top Prince’s Chapel and the New Sacristy with 7 Michelangelo sculptures.

You’ll need to  pre-book a ticket  with a time slot reservation. These fill up fast, so don’t delay. You can also book a  guided tour of the chapels . This isn’t a bad idea because there’s not much explanatory signage.

After lunch, it’s time to tackle the Florence Cathedral complex . This consists of 5 separate sites: Florence Cathedral, Brunelleschi’s dome, the Baptistery, the Duomo Museum, and the Giotto Bell Tower. 

If you buy the  Brunelleschi ticket , you have entry to all the sites. You can only enter each attraction once, but you have 3 days to use the pass. I suggest you visit them all this afternoon. 

There’s a lot to absorb at these wonderful attractions. You may want to  book a guided tour  to get the full scoop.

Go the Duomo Museum first. It’s the best cathedral museum I’ve ever visited. It’s chock full of stunning statues by Donatello and will give you a primer on how Brunelleschi built the iconic dome of the cathedral.

I would climb either Brunelleschi’s dome or the Giotto bell tower. It might be a bit much to do both in one day.

Giotto’s bell tower might offer slightly better views. But, if you climb Brunelleschi’s dome, you can admire the Giorgio Vasari frescos on the way up.

In the evening, take a stroll through Piazza della Signoria and admire the statues in the piazza.

If you want, you can visit the Palazzo Vecchio (right in the square) in the evening because it’s open late. Inside, you’ll find Medici apartments, a Michelangelo sculpture, and room after room of Vasari frescos.

>>> Click here to book a skip the line ticket for Palazzo Vecchio

Day 6: Florence

On day 6 of you 2 weeks in Italy itinerary, begin with a visit to the Basilica of Santa Croce . It’s Florence’s most stunning church and a mausoleum for its most famous citizens.

The basilica opens at 9:30. You should arrive with a pre-purchased  skip the line ticket . You’ll have to dress modestly with knees and shoulders covered or you won’t be let in. They’re very strict on this score.

Click  here  to book a skip the line ticket for the basilica. You’ll need one in high season unless you can brave the lines. There’s so much to see that you may want to  book a guided tour of Santa Croce .

After Santa Croce, head to the  Uffizi Gallery . The gallery is Florence’s premiere museum and one of the best museums in the world. This is where you come to admire Botticelli, Leonardo da Vinci, and Michelangelo.

The museum is huge and just stuffed with world famous masterpieces. You could spend hours there. The most popular rooms are the two Botticelli Rooms and the Raphael and Michelangelo Room.

You won’t be able to visit the Uffizi, almost in any season, without pre-booking a  skip the line timed entry ticket . Once inside, keep the ticket with you because they ask for it at several checkpoints.

You may want to book a guided tour of the museum. The last time I was there, I booked a  2+ hour private guided tour . My husband, who’s not an art lover necessarily, loved it!

After admiring the fine art, take a stroll through the Piazza della Repubblica and stroll over the iconic Ponte Vecchio. The bridge takes you to the Oltrarno neighborhood , which is a more authentic and less touristy part of Florence.

The main attraction here is the Pitti Palace . It’s another Medici palace stuffed with world class art. You’ll need to book a skip the line ticket in high season.

You should also hit one of Florence’s viewpoints for panoramic views of the city — Piazzale Michelangelo (or 10 minutes further uphill) San Miniato al Monte . I would opt for San Miniato. It’s less crowded and one of Florence’s most ancient buildings.

Have apertivo and dinner in the Oltrarno. I thought this neighborhood had some of Florence’s best restaurants. Check out my one day in Oltrarno itinerary for more details and restaurant ideas.

Day 7: Florence, Day Trip To Siena

It’s tough to leave Florence, I know, but Siena is also fabulous. It’s one of the most beautiful medieval cities in Italy and is effectively an open air museum.

Plus, Siena is full of first rate art and stunning architecture. It central square, Il Campo , is one of the most beautiful squares in Italy. This is where the annual Palio horse race is held.

You can admire the city’s art-laden  Siena Cathedral , gaze at a famous fresco cycle in the  Palazzo Pubblico , and stroll the vibrant streets full of artisan shops and boutiques.

You should  book a ticket to the Siena Cathedral complex . Then, I would add on a  ticket to the Palazzo Pubblico . It’s worth it just to see the stunning  Allegory of Good and Bad Government  frescos.

If you can, try to stay for dinner in the evening. The day trippers will be gone and you can stroll the pretty lanes in peace.

Siena is just a one hour drive from Florence. You can also  book a guided day tour   to save you the hassle of arranging transportation. This tour also takes you to the gorgeous medieval town of San Gimignano .

Day 8: Rome

From Florence, it’s time to move on to Rome, the Eternal City, where you’ll stay for 4 nights. I’ve been to Rome many times and written dozens of articles on the city, which you can check out on my Rome page .

On your first day, I would tour the imperial ruins. That includes the Colosseum , the Roman Forum , and Palatine Hill . I’ve linked my article on each place, which describe everything you can see at each stop.

You can’t really visit these sites without a skip the line ticket . You’ll also need to make a separate timed entry reservation for the Colosseum. There are plenty of tour options as well.

• 3 hour guided tour and entry to all 3 sites
• tickets & tour of all 3 sites + underground Colosseum access
• 4 hour private day tour of Ancient Rome
• skip the line private guided tour with an art historian
• skip the line private tour of all 3 sites + the underground Colosseum

When you’re done touring the ruins, head to the nearby Monti neighborhood for a stroll and lunch. You can also pop into the beautiful Basilica of Santa Maria Maggiore .

Then, head to Piazza Venetia. You can admire the Vittorio Emanuele Monument and take an elevator up for views.

Don’t miss the Capitoline Museums . It’s surely one of Rome’s ancient art museums . It boasts a vast repository of ancient sculpture that’s just incredible.

>>> Click here to book a ticket to the Capitoline Museums

In the evening take a stroll in Trastevere, Rome’s most beautiful neighborhood. You can admire the ochre colored buildings and ivy clad facades. This is also a great place to book a food and wine tour .

Day 9: Rome

On you next day in Rome, take a classic  walk through central Rome . You might consider booking a  3 hour walking tour  or  private walking tour to get the full historical backdrop on all the sites.

Start at Campo de’ Fiori and end at the Spanish steps. Along the way, you can stop to admire some of Rome’s most iconic monuments — Piazza Navona, the Pantheon, Piazza Colonna, and the Trevi Fountain.

Grab some lunch and then head to Rome’s best museums, the Borghese Gallery. It’s one of the world’s greatest small museums. You’ll find the most famous sculptures of the Baroque artist Bernini and paintings by Caravaggio, Raphael, Titian, and Correggio.

Here’s my  complete guide  to the Borghese Gallery . You’ve got to  pre-book a timed entry skip the line ticket  to visit this magnificent museum.

When you’re done admiring the art, I recommend heading over to the west side of the Borghese Gardens, towards the Piazza del Popolo. The view from the Pincio Terrace is quite beautiful, particularly at sunset.

Consider ending your day with a food tour. There are a bunch of great options:

• a  food tour of the trendy Testaccio district
• a  food tour in the off the beaten path Pratti district
• a   food tour in the beautiful Trastevere district
• a  market food tour and pizza class
• a   food and wine tour in the historic center

Day 10: Rome, Vatican City

On day 10 of 2 weeks in Italy, it’s time to explore Vatican City. I’ve written a detailed one day in Vatican City itinerary . So won’t repeat myself too much here.

St. Peter’s Basilica and the Vatican Museums are heart and headquarters of the Roman Catholic Church.

St. Peter’s Basilica is the most famous church in Christendom. Designed by Bramante, Raphael and Michelangelo, it’s a true Renaissance masterpiece.

The basilica is the burial place of St. Peter and past popes. It houses the famous Bernini Baldachine altar, scads of sculptures, and Michelangelo’s tragically beautiful  Pieta .

For a panoramic view of St. Peter’s Square and Rome, you should climb the dome. Here’s my complete  guide to St. Peter’s Basilica , with tips for visiting. You can take a  guided tour  of St. Peters. You can only visit the  underground grottos on a guided tour .

The Vatican Museums hold one of the world’s greatest art collections. Some of the most famous art works on the planet are there, including Michelangelo’s frescos in the Sistine Chapel .

You absolutely must pre-book a  skip the line ticket  for the Vatican. Or else you’ll be stuck in line for hours unless it’s the dead of winter.

Here are some sample Vatican tours you might consider taking:

• a  2.5 hour overview on a skip the line small group guided tour
• a  3 hour no  w ait tour that also includes the Raphael Rooms
• a  3.5 hour tour Vatican visit with a guided tour of St. Peter’s Basilica
• a  3 hour Friday night tour of the Vatican
• a  Vatican tour that includes a climb of the dome of St. Peter’s Basilica

Day 11: Rome, Day Trip To Orvieto

Day 11 sees you day tripping to Orvieto, a hill town in southern Umbria . I personally just loved Orvieto and you can check out my one day in Orvieto itinerary for the full scoop.

Orvieto’s most famous attraction is its glamorous Duomo, Orvieto Cathedral . It has one of the most colorful and art-filled facades of any church in Italy. Inside, you’ll find one of the most famous fresco cycles in Italy by Luca Signorelli.

You’ll also want to take a stroll through Piazza della Repubblica and climb the Torre del Morro.

But part of the charm of Orvieto is just aimless strolling. Wherever you look in Orvieto, there’s a picturesque lane, quaint shop, or terrific displays of flowers.

Every once in awhile the medieval lanes part and you can glimpse a brilliant slice of the Umbrian countryside.

Last time I was in Orvieto, I booked a  2.5 hour guided private walking tour . My guide was Emma and she was excellent, making the cathedral and its beautiful art works come to life. 

You can also book a  3 hour small group walking tour  that includes the cathedral, the old town, and Orvieto’s underground.

Day 12: Naples

From Rome, venture on to Naples. It’s about 2.5 hours by car or 1:10 by train.

This Mediterranean capital is lorded over by the still-kicking Vesuvius volcano. Naples is unpretentious with chaotic streets, Baroque excess, and layers upon layers of history.

The historic center is brimming with striking architecture, fascinating museums, and lively piazzas.

Naples Cathedral has a 13th century Gothic church with Baroque frescos. The Santa Chiara Cloisters are simply gorgeous, with hand-painted Majorca tiles covering benches and columns. The Basilica of San Lorenzo Maggiore is chock full of Greco-Roman ruins.

Art lovers will want to take the shuttle to the Capodimonte Museum , which is one of Italy’s best museum s . It features works by Caravaggio, Correggio, Masaccio, Titian, Raphael, El Greco, Bruegel, and Sebastiano del Piombo.

History buffs should head to the Museo Archeologico Nazionale , which is truly one of the world’s best archaeological museums. 

You can see original mosaics and frescoes from Pompeii and Herculaneum. The most famous piece is the  Farnese Bull , which once decorated Rome’s Baths of Caracalla . In high season, you’ll definitely need a skip the line ticket .

Naples is famous for its cafe culture and as the inventor of pizza. One of the most exquisite cafes is Caffe Gambrinus. For pizza, the two most famous spots are Gino Sorbillo and Antica Pizzeria da Michele.

Naturally, in Naples, you can go on a street food tour , take a walking tour of the street markets , or take a pizza making class .

As an alternative to basing yourself in Naples, you could stay in the Amalfi Coast instead and day trip into Naples to see the museums and sample the pizza.

READ : One Day In Naples Itinerary

Day 13: Naples, Day Trip To Pompeii

On day 13 of your 2 weeks in Italy, head to Pompeii. The site is Italy’s most famous archaeological treasure. It’s a 2,000 year old living museum.

In 79 A.D., Mount Vesuvius erupted and buried the city in 60 feet of ash. The city was entombed and preserved for many centuries. Beginning in 1748, archaeologists began painstakingly excavating the ruins.

Today, you can see dazzling frescos in ancient abodes. The House of the Vet just opened to the public in January 2023 and the frescos in the Villa of Mysteries are newly restored.

It’s definitely easiest to visit Pompeii on guided day tour from Naples . I recommend this  guided walking tour with an archaeologist  to learn everything abut Pompeii. But if you can do it yourself, you’ll at least need to book a skip the line ticket .

I advise getting the longest and best tour possible so that you can see everything at Pompeii (the new frescos) and not just walk down the main drag, as some tours do.

For the complete scoop, here’s my complete guide to visiting Pompeii .

Day 14: Naples, Day Trip To Amalfi Coast

On your last day of 2 weeks in Italy, head to the Amalfi Coast. It’s a stunning 30 mile stretch of the Italian coast where cliffs tower above pebbly coves and villages cling to steep slopes.

One day isn’t much time to explore this area. And it isn’t easy to get to. You will drive down a precarious road and take ferries and buses.

With one day, if you take a guided day tour from Naples, you can more efficiently get a quick peak at Positano, Amalfi, and or Ravello.

Positano comes complete with sherbet colored cliffside homes, stunning beaches, and tiny cobbled lanes. It’s considered Amalfi’s most picturesque town, cut into a cliff with views galore.

Called the “mountain pearl,” Ravello is suspended between the sky and sea. Ravello is known for its stunning views. You can get them at the town’s two stunning medieval villas Villa Cimbrone and Villa Rufolo.

Amalfi town is a lively port city. It’s known for the stunning Amalfi Cathedral , which is one of the most beautiful churches in Italy. You can visit the cloister, church, and the Diocesan Museum.

Positano and Sorrento are the most touristy towns. If you’d like to avoid crowds, you can try the towns of Ravello, Praiano, Maiori, or Minori.

Alternatively, you could visit the island of Capri from Naples. Capri is one of the most dazzling and seductive islands in the Mediterranean.

Capri is known for its soaring cliffs, shimmering emerald water, whitewashed towns, and historic landmarks. It’s a great place to hike. And it’s known for its natural wonder, the Blue Grotto.

You can take the ferry or get to Capri on a guided day tour from Naples .

Alternative 2 Weeks In Italy Itinerary

For a slightly different spin, here’s an alternative two weeks in Italy itinerary. This itinerary drops Bologna and gives you more time in southern Italy.

• Day 3 : Florence
• Day 4 : Florence
• Day 5 : Florence, day trip to Siena & San Gimignano
• Day 6 : Rome
• Day 7 : Rome
• Day 8 : Vatican City
• Day 9 : Rome, day trip to Orvieto & Civita di Bagnoregio
• Day 10 : Naples
• Day 11 : Naples, day trip to Pompeii
• Day 12 : Amalfi Coast
• Day 13 : Amalfi Coast, day trip to Capri
• Day 14 : Matera

Tips For Spending 2 Weeks In Italy

If you need tips for visiting Italy, you should check out some of my relevant articles:

• 40 tips for visiting Italy
• Tips for visiting Rome
• Tips for visiting Florence
• Tips for visiting Venice
• Tips for renting and driving a car in Europe

I hope you’ve enjoyed my 2 weeks in Italy itinerary. You may enjoy these other Italy travel guides and resources.

• 12 Ways To Spend 1 Week in Italy
• 5 Ways To Spend 1 Week In Sicily
• 10 Days in Southern Italy Itinerary
• 10 Day Tuscany Itinerary
• Tips For Visiting Italy
• 7 Day Road Trip From Venice To Milan
• 130+ Bucket List Experiences in Italy
• Historic Landmarks in Italy
• Most Beautiful Towns in Italy
• Best Museums in Rome
• Hidden Gems in Rome
• Best Museums in Florence

If you want to spend 2 weeks in Italy, pin it for later.

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Last Updated on October 17, 2023 by Leslie Livingston

2 Weeks in Italy Itinerary: Italian Highlights 14 Day Travel Guide

By: Author Sophie Nadeau

Posted on Last updated: 20th February 2024

Categories Italy , Itineraries

Last Updated on 20th February 2024 by Sophie Nadeau

At 19, I took my first trip to Italy. And from the moment I step foot in the boot-shaped country, I was enthralled by the land of pizza, pasta, and plenty of wine. I loved the monuments, the history, the architecture. I loved the beautiful weather. And of course, I loved the people! Here’s your ultimate 2 weeks in Italy itinerary and travel guide!

Things to know before visiting Italy for two weeks

Venice/ venezia, milan/ milano, cinque terre, florence/ firenze, naples/ napoli & pompeii, amalfi coast, enjoyed reading this 2 weeks in italy itinerary: italian highlights 14 day travel guide pin it now, read it again later:.

This 14 day travel guide encompasses a lot of distance, and so if you prefer travelling more slowly, you may well want to miss out on a few of the smaller towns and spend longer amounts of time getting to know the larger cities on a more local level.

The easiest, quickest, as well as undoubtedly cheapest way to take this trip is to voyage by train or bus. Italian transport is largely fast and affordable, meaning that it’s easy to travel between all the places mentioned in this itinerary.

When you reach the Amalfi Coast, however, you may well want to rent a scooter or small car ( check here for the best car rental comparison prices ) to transport yourself via all the small towns and cliff side villages this beautiful stretch of Italian coastline has to offer!

If you’re looking for even more inspiration about the boot-shaped country, then be sure to check out our best travel  quotes about Italy . And if you need to know more information before heading to the South of Europe, check out our  top Italy travel tips.

When it comes to the best time to travel to Italy, the choice is really up to you! In the summer months, the crowds and heat are at their highest, meaning that if you prefer exploring in a cooler climate with fewer people around, then heading to Italy in the European shoulder seasons (late spring/ early autumn) is probably your best best.

Finally, you’ll soon discover that everyone speaks great English, especially in the tourism industry. However, it’s only polite to learn some basic Italian . I personally recommend learning how to say ‘please,’ ‘thank you,’ ‘hello,’ and ‘sorry’ to get you started.

Otherwise, you might want to bring along an Italian phrasebook like this one . For travelling around Europe, a universal adaptor like this one is a must, so you can keep your essentials (phone, kindle, tablet) charged as you travel.

Suggested itinerary for 2 weeks in Italy

Stay: 1 night

Where to stay: Hotel Moresco

Ah, the picture-perfect canals and waterways of Venice! The meandering cobbled lanes of Venice are the ultimate starting point for an Italian adventure. Though it’s better to spend 3 or 4 days in Venice, here’s a guide on how to spend one perfect day in Venice .

Nearby international airports mean that budget airlines fly into the city from all across Europe and beyond and rail connections away from the city mean that Venice is the perfect location for reaching other Italian cities.

If you truly want to make the most of the Venetian scene, you’ll want to stay at least one night, either in the city or close by. This way, you’ll be able to experience the city without the crowds of day trippers who only come to the floating city during daylight hours.

Once there, Venice offers oodles of small bars, little museums and endless streets in which to get lost. In order to make the most of your budget, avoid eating in the tourist areas (and never eat or drink anything in Piazza San Marco). 

Essential tour: Doge’s Palace & St. Mark’s Basilica 2-Hour Tour

Home to world-famous fated lovers Romeo and Juliet, Verona is not only a city for lovers, but a city to fall in love with. This is a particularly popular destination among those planning a honeymoon in Italy but is regardless a must-see for any first timer to the country.

Head to Verona if you’re a literary lover or history buff- the city offers plenty of things to do whether you want to see Roman remains or wander the streets which have since become intertwined with the story of Juliet. For even more inspiration, be sure to check out our suggestions for one day in Verona .

Essential tour: Verona Food Tour with Wine Tasting

The hidden gem of the Lombardy region, beautiful Bergamo is a beautiful settlement characterised by its many ancient churches and small off the beaten path eateries.

Best seen in the spring, summer or early autumn when green blankets the slopes and it’s possible to dine outside into the early hours of the morning, the city has plenty of museums, and even more traditional trattorias where you can sample local Lombardian cuisine!

While many tourists miss out on a trip to Milan in favour of other more iconic tourist hotspots, if you love design, art, and fashion, you certainly don’t want to miss Milan!

Highlights of the city include the impressive Duomo dedicated to Saint Mary of the Nativity (a gothic-renaissance masterpiece) and the Galleria Vittorio Emanuele II (Italy’s oldest shopping mall).

Other Milanese pastimes include wandering the colourful streets of the Brera district, picnicing in one of the city’s expansive parks, and consuming countless coffees in small Italian cafés, as well as a bar designed by Wes Anderson.

Essential tour: Milan: Last Supper Guided Tour

Where to stay: Le Stanze del Cardinale

The stunning university town of Pavia is not necessarily a must-see when it comes to Italy, but it’s one of those small, secluded, and not-yet-overrun-with-tourists kind of city that gives you a real feel for authentic Italian life.

After all, Pavia was once capital of the Lombardy Kingdom and was where both Barbarossa and Charlemagne were crowned kings of the area.

The town is complete with a Duomo designed by the hand of Da Vinci himself, as well as plenty of ancient buildings which form part of one of the oldest universities in Italy.

Elsewhere in the city, an easy 8km north day trip via train means that you can visit one of the most beautiful Renaissance buildings in Italy in the form of the Certosa di Pavia .

Stay: 2 nights

Otherwise known in English as the ‘five lands’, Cinque Terre is a magical place where the pillow-soft bread of focaccia was invented. Cinque Terre gained its name as it is a collection of five towns and villages, each with a different vibe.

Many are not accessible by car; only by sea, rail or on foot! Monterosso Al Mare is best-known as being the commercial tourist village, whereas Riomaggiore is the most southern, and therefore most remote.

Before visiting the five lands of Italy, make sure you read extensively about each settlement, so as to choose where you want to stay; do you want great food? Or would you prefer perfect views when you awaken each morning?

It is also here in Liguria where a sea-inspired cuisine draws tens of thousands of culinary lovers on an annual basis, and excellent hiking trails set against an azure blue sea attract countless other Italian enthusiasts to return again and again. Make some space on your Cinque Terre within your two weeks in Italy itinerary and you certainly won’t regret it!

Essential tour: Cinque Terre Wine Tour  

Stay: Don’t! Visit Pisa as a day trip en route to Florence from Cinque Terre. 

Best-known for its iconic leaning tower of Pisa, this small Italian city doesn’t necessarily merit a nights stay, especially if you’re looking to pack as many Italian adventures as possible into this 2 weeks in Italy itinerary! As such, I recommend visiting Pisa en route to Florence from Cinque Terre.

Essential tour: Reserved Entrance to Leaning Tower of Pisa & Cathedral

Where to stay: The Moon Boutique

Birthplace of Dante Alighieri (you know, author of the Divine Comedy and the Inferno!) , Florence is a magical city and probably my favourite place in all of Italy.

Filled with secret passages, off-the-beaten-tourist-track coffee shops, and countless museums, you could spend ten lifetimes trying to decode the secrets of Florence, and still never uncover them all.

Florentine highlights include the domed Duomo Santa Maria del Fiore and its countless artworks and architecture dating back to the time when Florence shot to fame as the place of the Cradle of Renaissance (la culla del Rinascimento) .

To really make the most of Firenze, you’ll definitely want to dedicate at least two nights staying in the city! For more inspiration on planning a trip to Florence, be sure not to miss out on the wine windows in Florence and here’s our Florence suggested itinerary .

Essential tour: Florence Dome Climb

Where to stay: G-Rough

As the capital of Italy, you’ll want to spend at least two nights in Rome during this two weeks in Italy itinerary! While you could spend just one day in Rome , this definitely won’t allow you to even scratch the surface of what the Eternal City has to offer.

If possible, you may well want to dedicate a little longer to uncover even more of the secrets of this ancient city. After all, Rome was once at the heart of the Roman Empire and has seen over three millennia worth of human inhabitation.

Highlights of Rome include throwing a coin or two in the Trevi Fountain (one to return to Italy, two to return to Rome, and three if you want to meet an Italian lover!) and entering the gigantic Colosseum.

When in Rome do as the Romans do, and make sure to dedicate at least half a day to exploring Vatican City, as well as all of its treasures. The smallest City State in the world is home to treasures such as the Sistine Chapel and St Peter’s Basilica.

Essential tour: Vatican Museum, Sistine Chapel & Saint Peter’s Guided Tour

Where to stay: La Ciliegina Lifestyle Hotel

Lovers of pizza simply must head to Naples for the best pizza in all of Italy! Though a little rougher round the edges than some other Italian destinations, this gritty city has plenty of Baroque architecture to enjoy and an impressive labyrinthine underground to explore. For even more inspiration, here’s our suggested one day in Naples itinerary .

Nearby, the Roman ruined towns of Herculaneum and Pompeii give an insight into what life would have been like for ordinary people living and working within the Roman Empire almost two millennia ago.

Essential tour: Pompeii Skip-The-Line 2-Hour Private Guided Tour

To end your Italian adventure, you’ll want to spend a little bit of time soaking up some Italian sunshine along the Italian coastline.

Stay in a pretty port town such as Positano or Sorrento to ensure that you wake up each morning basking in the sunshine and within easy reach of many of the day trips the region has to offer. If you have time, then I recommend spending at least one day of your two weeks in Italy to exploring the stunning Island of Capri!

Essential tour: Day cruise to Capri

Sophie Nadeau loves dogs, books, travel, pizza, and history. A Francophile at heart, she runs solosophie.com when she’s not chasing after the next sunset shot or consuming something sweet. She splits her time between Paris and London and travels as much as she can! Subscribe to Sophie’s YouTube Channel.

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• Europe Tours
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Italy 2-Week Tours and Itineraries

Discover the best 2-Week multi-day tours in Italy with Bookmundi. We offer a total of 21 Italy 2-Week tours and itineraries with 78 customer reviews.

• Italy Travel Guide
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21 Italy 2-week itineraries and tours

• Starts Rome, Italy
• Ends Venice, Italy

Ultimate Italy

• Best price guaranteed
• No booking fees
• Tour Type Small Group Tour
• Activities Cultural, religious and historic sites & Countryside and village visits Cultural, religious and historic sites , Countryside and village visits , Sailing, yachting and motor boating , Walking tours & Art and architecture 'data-more-tripid='4952'>+3 more
• Accommodation Hotel & Villa
• Transport Train, Boat, Bus & Taxi
• Age Range 12-95 yrs
• Operated in English

Best of Italy

• Activities City sightseeing & Art and architecture City sightseeing , Art and architecture , Cultural, religious and historic sites , Museum and gallery visits , Cruise , Countryside and village visits & Natural landmarks sightseeing 'data-more-tripid='3788'>+5 more
• Transport Boat, Train, Bus, Private Vehicle & Ferry
• Age Range 15-99 yrs
• Brochure Price: US$ 4,580
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• Jun 24 Only 6 seats left
• Jul 01 Only 7 seats left
• View More Jan 1, 2019 Jan 2, 2019 Jan 3, 2019

• Starts London, England
• Ends London, England

Classic Europe

• Tour Type Group Tour
• Activities Active and outdoor & Cultural, religious and historic sites Active and outdoor , Cultural, religious and historic sites & Art and architecture 'data-more-tripid='37694'>+1 more
• Accommodation Hotel
• Transport Coach & Taxi
• Age Range 10-99 yrs
• Brochure Price: US$ 3,535
• Special Deal (30%): - US$ 1,058
• Total Price from: US$ 2,477
• Jul 02 Only 1 seat left
• Jul 07 Only 2 seats left

• Starts Venice, Italy
• Ends Rome, Italy

Journeys: Iconic Italy

• Activities Cultural, religious and historic sites & City sightseeing Cultural, religious and historic sites , City sightseeing , Countryside and village visits , Museum and gallery visits & Farm and plantation visits 'data-more-tripid='4957'>+3 more
• Transport Boat, Train, Bus, Minibus, Ferry & Private Vehicle

• Starts Naples, Italy
• Ends Monopoli, Italy

Italy: Amalfi Coast to Puglia

• Activities Beach
• Accommodation Resort, Villa & Hotel
• Transport Boat, Ferry & Private Vehicle
• Age Range 1-95 yrs
• Brochure Price: US$ 4,599
• Special Deal (10%): - US$ 450
• Total Price from: US$ 4,149
• Jun 27 10+ seats left
• Aug 15 Only 4 seats left

• Ends Amsterdam, Holland

The Great Adventure

• Activities City sightseeing & Walking tours City sightseeing , Walking tours & Art and architecture 'data-more-tripid='42674'>+1 more
• Transport Private Vehicle, Boat, Bus, Ferry, Flight & Train
• Jun 23 10+ seats left
• Jun 30 10+ seats left

• Starts Lazio, Italy
• Ends Lazio, Italy

A Taste of Italy: 14 Days

• Trip customizable
• Activities City sightseeing & Cultural, religious and historic sites City sightseeing , Cultural, religious and historic sites & Museum and gallery visits 'data-more-tripid='41491'>+1 more
• Transport Train, Boat, Bus, Coach & Taxi
• Age Range 7-99 yrs
• Jun 21 Only 10 seats left
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Trending Destinations in Italy

Italian Odyssey

• Activities Explorer
• Transport Coach & Boat
• Age Range 8-95 yrs
• Jul 01 10+ seats left
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Italia Amore Mio

• Activities Cultural, religious and historic sites
• Accommodation Villa & Hotel
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• Age Range 6-80 yrs
• Brochure Price: US$ 4,015
• Special Deal (6%): - US$ 241
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• Starts Palermo, Italy
• Ends Sliema, Italy

Sicily and Its Isles

• Activities Country side and village visits & Local culture
• Accommodation Resort & Hotel
• Transport Ferry & Boat
• Brochure Price: US$ 3,669
• Special Deal (4%): - US$ 150
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• Jul 09 10+ seats left
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Splendid Europe

• Activities City sightseeing & Cultural, religious and historic sites City sightseeing , Cultural, religious and historic sites , Art and architecture & Museum and gallery visits 'data-more-tripid='21137'>+2 more
• Transport Coach, Private Vehicle, Taxi & Train
• Age Range 5-99 yrs
• Sep 19 Only 7 seats left
• Oct 10 10+ seats left

• Ends Corfu, Greece

The Dalmatian Coast: Croatia, Corfu & Medieval Cities

• Activities Adriatic Cruise
• Accommodation Hostel, Resort, Villa & Hotel
• Transport Boat, Ferry, Private Vehicle, Train & Taxi
• Age Range 18-35 yrs
• Brochure Price: US$ 2,199
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Golden Italy and Beautiful Campania

• Activities City sightseeing & Cultural, religious and historic sites
• Transport Boat, Bus, Ferry, Train & Private Vehicle
• Jun 26 10+ seats left
• Jul 03 10+ seats left

• Ends Palermo, Italy

Highlights of Sicily

• Activities City sightseeing
• Brochure Price: US$ 3,799
• Special Deal (30%): - US$ 1,140
• Total Price from: US$ 2,659

Traveling to Italy for 2 weeks? Chat with a local travel specialist in Italy who can help organize your trip.

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ITALY ROAD TRIP: Two Weeks Itinerary By a Local!

In BLOG , EMILIA ROMAGNA , ITALY , ROME , TRIPS IDEAS AND TIPS , TUSCANY , USEFUL GUIDES by Clelia Mattana 1 July, 2022 104 Comments

Contents - Open To Read

Are you planning on visiting Italy? Then you can’t miss this excellent two-week itinerary for your Italy Road trip, created by a local Italian! You’ll love it, I promise!

Ah, Italy… my country, my pride, my love! Being Italian is truly a privilege, so let me transfer some of my knowledge to you with some fantastic tips to have the best Italian road trip experience of your life!

Starting from  Rome , my favorite city in the world, through the famous green hills surrounding all the Tuscany and Umbria regions, not to mention the jaw-dropping view provided by the  Cinque Terre  – What more can you ask from a country? Italy is simply magnificent!

If you want a truly unique Italian experience:  Road trip is the main word! Nothing beats a road trip in Italy, trust me . I took my driving license in Rome (crazy, I know!), and from there, I discovered every region by car. Slowly, savoring the panoramic scenery that only my beautiful country can offer. Using the train is also a great option, but nothing beats driving around Italy! 

Video of this two weeks Italian Road trip itinerary!

The main cities are well connected, but I suggest you take as many detours from the highway as possible because it’s driving across the countryside that you will find the real hidden gems of Italy!

Pro Tip:  You might want to see as much as possible of Italy during your epic road trip, but in my opinion is better to pick 3-max 4 cities or villages. You don’t want to miss any reason and leave the rest as a last-minute choice. 

TWO WEEKS IN ITALY ROAD TRIP: CONTENT

Click to check the relevant chapter

• Day 1 – 2 |Rome Itinerary and Vatican City
• Day 3 | Lazio  -Roman Castles
• Day 4 | Tuscany – Montepulciano
• Day 5 | Tuscany – San Gimignano
• Day 6 |Tuscany – Pisa
• Day 7 |Tuscany – San Miniato

SECOND WEEK + BONUS TIP TO SAVE MONEY!

• Day 8 – 9 | Tuscany trip – Florence
• Day 10 | Emilia Romagna – Bologna
• Day 11 – 12| Liguria-Tour Cinque Terre
• Day 13 | Piemonte – Turin
• Day 14 – 15 |  Milan and Lake Como
• How to save money when booking your hotels!

What is The best Italian road trip itinerary for 2 weeks?

-I will give you some great recommendations on where to stay and how to save A LOT on accommodation fees later-

I’m Italian, and before leaving my beautiful country to travel indefinitely, I explored it by car, discovering every Italian region, so we can safely say that you are in good hands here!  From Rome to Milan, ending in the enchanting setting of Lake Como for a 15-day epic journey that you’ll never forget. I promise!  

In This 2 weeks Italy Road Trip Article You Will Discover:

—  the best places you should include in your trip to italy  —, —  the most interesting things to do and see in italy —, — cool tours or experiences you can book directly online —, — my recommended hotels/b&b that are perfect for your tour of italy  —, — how to use a genius (free) tool to save money on your hotel bookings — .

Without further ado, here are the breathless places you must include on your Italian road trip.

The Italian Road Trip Itinerary Map

Click to enlarge the image

An article about a road trip in Italy wouldn’t be complete without showing you the map of the itinerary with the starting point, stops on the way, and ending point of this incredible trip around Italy.

Depending on what kind of flights you find, you can obviously do it in reverse, starting from Milan, with a little detour up north to Lake Como and back.

It’s just 1 hour and 30 minutes to get to Varenna, on a lovely route as well) and then go back to Milan and start your Italian Tour heading south and departing from Rome Fiumicino airport.

Either way, you’ll see spectacular landscapes along the road, don’t forget that on a trip like this, moving from one place to another is a massive part of it, so enjoy it , drive safely and slowly and let the beauty of Italy sink in! -Map data ©2022 Google-

2 WEEKS ITALY ITINERARY DAY 1 – 2 | ROME &  VATICAN 

Ah, Rome – It always makes me wonder: Is there a way to describe this city without using clichè words? I lived in the eternal city for more than 3 years, and I love it (and hate it) to pieces 🙂 Even if Rome is the most predictable stop on this itinerary, a trip to Italy wouldn’t be complete without a stop in its Capital, right? It would be like spending 15 days in the UK and not visiting London. Well, for as much as I love London too,  Rome is … Rome! Yes, being Italian, I’m biased, but not without reason.

Is it possible to have a glimpse of the beauty of  Rome in one day ? Definitely yes! I could even see the main attractions in the center, rushing a bit of course, in just 5 hours one time! I always find the time for a quick pit stop to Rome, and every time I discover something new!

WHAT TO SEE IN ROME IN ONE DAY:

Stroll around the historic center of Rome : It is a must! Driving can be challenging or better put: you must be fearless to drive in Rome, so park up and walk or take the buses or metro. Use public transport while you’re there. Remember to stamp your bus tickets once you get on the bus or subway, especially if you take the train! (more valuable tips for your first time in Italy in a post coming soon!) 😉

Most Famous Things To Do In Rome:

• Saint Peter’s Church and Dome
• Piazza Di Spagna /Pincio Terrace
• Piazza Navona
• Fontana di Trevi
• Colosseum and Via Dei Fori Imperiali (at night is a must!)
• Lungotevere Castel Sant’Angelo (At sunrise, I did it: Best experience in Rome ever)
• Pincio Terrace (At sunset, for the best view of Rome)
• Trastevere (For dinner, obviously!)

WHAT TO SEE IN VATICAN CITY IN ONE DAY:

I took two days to explore the inner part of the city – which gave me ample time to include a day in the Vatican City. Enclaved in the town of Rome, Vatican City is officially the smallest recognized state in the whole world . Home to the Pope, the Vatican is the beautifully preserved state of the Catholic Church. It is definitely worth a visit!

Most Famous Things to do and see in Vatican City:

• Visit the Musei Vaticani.
• Take a tour of The Sistine Chapel.
• Visit the Vatican’s beautiful gardens.
• Admire the view from the top of St Peter’s Dome!

Helpful Info : As with most famous sights, just remember to buy your tickets early or online. Otherwise, be prepared for a few hours waiting around peak times (still worth it if you ask me!)

RECOMMENDED BEST HOTELS IN ROME:

RESIDENZA MONFY

I could say it’s one of the best places to stay on a road trip to Rome. Gianluca, the owner, is helpful and will give you all the info you’ll need to have the best time in Rome.

Everything is clean and well arranged, and the location (Via Veneto, in the center) is  perfect for public transport or walking around the main attractions. Most importantly, it has a parking option.  Trust me: in Rome, you WANT to have that option. Finding a parking spot is a nightmare for everyone living or visiting Rome. Click to  Check the Hotel out!

RECOMMENDED BEST TOURS IN ROME:

Beautiful Castel Sant’Angelo, another spot (among the endless landmarks in the eternal city) you can’t miss! Tips: Go there at sunrise… trust me, I did it, and it was SURREAL, to say the least!

Do you think you don’t have enough time to see it all and/or are not keen on walking all day with the risk of missing something important?  Then an organized tour is what you need to set your mind at peace . Below are the ones I recommend the most:

Hop On-Hop Off Ticket:  

Super Touristy, I know, but when you don’t have much time is so worth it! I remember hating that red bus, and I ended up loving it when I had only one day in Warsaw, and I managed to see it all (at my own pace, but they don’t miss the important spots).  Check it out!

Three Hours evening Walking tour:  

As Suggested, Rome is even more magical at sunset, so this Tour will take you to the main attractions and to the Pincio Terrace right at sunset (I love that spot, you’ll see!). Highly recommended as the guides are usually locals.  Check it out!

Other Tours in Rome:

There are a million tours I could recommend, but you can  check them out   here   or below (click for more tours on the list) and see if something strikes your attention. I  love this website, and it’s the one I use the most when I have to book my tours online . Super convenient and hassle-free. I don’t like to spend my precious time waiting to buy my tickets, especially in touristy cities like Rome!

The “Skip the lines” tickets are exceptional, and you won’t regret buying them as they will save you SO MUCH TIME!

ITALY ITINERARY DAY 3 | ROMAN CASTLES

Rome itself has many sites to see even just outside the city itself! Roman Castles (or as we call it “Castelli Romani”) are an opportunity to leave the metropolis and  immerse yourself in the natural and artistic beauty of the small medieval villages outside Rome.

WHAT TO SEE AT THE ROMAN CASTLES:

Leaving Rome, you can drive by the  ruins of the Baths of Caracalla  and onto the  Ancient Via Appia by the Church of Domine Quo Vadis . This Tour of the Roman Castles will take you along the  ‘Road of the Lakes’  through one of the hilly areas of volcanic origin that characterize the outskirts of Rome, the Colli Albani, with its many growing villages.  

Most Famous Things to do and see in The Roman Castles:

Castel Gandolfo:   On the shores of a volcanic lake, this is the village where the Pope has his summer residence. You’ll enjoy a stunning view over the Lake and a great but tranquil atmosphere.

Rocca di Papa and Grottaferrata:   They are fascinating villages to visit in the Roman Castles area. Both are known for their culture, sights, and gastronomic delicacies, including the traditional “porchetta.”

Frascati :   Towards the northern part of the  Colli Albani , you can reach Frascati, popular with visitors for its beauty and wine production. Here you can stop for a taste of local wine and products in a local tavern and absorb the flavor of the authentic village life in the Lazio region.

RECOMMENDED BEST HOTELS IN CASTELLI ROMANI:

ATLANTIS INN 

A lovely central hotel with fantastic views over the Lake, the owner Francesco is friendly, like most people from Rome and surroundings!  Breakfast is included, and a parking space is available too , mandatory for a stress-free Italy road trip, right? 🙂 Click to  Check the Hotel out!

ITALY 2 WEEKS ITINERARY DAY 4 | MONTEPULCIANO

I’d like to take credit for “finding’” this town, but I accidentally stumbled across  Montepulciano, the medieval town in lovely Tuscany hills  by complete accident. It was a ridiculously beautiful town to stumble upon, providing a welcome opportunity to fill up on some fresh Bresaola and a little wine (for the non-drivers of course).   

WHAT TO SEE AND DO IN MONTEPULCIANO:

This lovely town is all about strolling around slowly admiring its beautiful historical buildings and the old medieval atmosphere, so take your time to enjoy it, find an excellent trattoria to eat, drink espresso and  take it “the Italian way” = EASY & SLOW 🙂  

Things To Do in Montepulciano:

The Main Square:   The lovely fountain on the side, the Duomo and Palazzo Tarugi, and Palazzo Contucci.

Palazzo del Comune Tower:  Do you want to admire the incredible views of the Tuscany Hills surrounding this lovely village? Climb the Tower, and you won’t be disappointed!

Gate Porta del Prato and Corso street:   Almost every medieval village in Italy has a main gate to the town. Cross “La Porta del Prato” and stroll around the “Corso street,” with its lovely shops, elegant palaces and renaissance buildings, the church of Sant’Agostino, and the Palazzo Cervini.

RECOMMENDED BEST HOTELS IN MONTEPULCIANO:

ALBERGO IL MARZOCCO

Located within the medieval walls of Montepulciano, this hotel is quite remarkable! Built in the 16th century, it is the oldest hotel in town. It has a bar, free Wi-Fi, rooms with views of Lake Trasimeno or the town, and free parking 🙂 Click to  Check the Hotel out!

RECOMMENDED TOURS IN MONTEPULCIANO:

Being a tiny town, after you have admired its historical center, there are many activities you can book for an even more memorable experience!

Montepulciano Terme: Wellness & Wine Experience:   Honestly? In my view, this is an absolute must (I’m a SPA and wine lover). After driving and walking for hours, you deserve a bit of relaxation! Check out this fantastic experience  here .

Montalcino/Pienza/Montepulciano Full day wine tour: This is one of the best-selling tours in the area and within reason! If you want to relax 100% and see 3 lovely villages instead of one (while tasting the best wines in the region), this is it! Check out all the details here .

TWO WEEKS ITALY ITINERARY DAY 5 | SAN GIMIGNANO

While many visit San Gimignano, the  town declared by UNESCO to be part of the World’s Architectural Heritage , for a very short time, there is plenty to do to keep you busy an entire day if not more!

How do you pronounce/spell “San Gimignano”?! Maybe the most challenging part is genuinely pronouncing its name correctly. Well then, I’m Italian, and I will help you out once and for all: San Gimignano pronunciation sounds like:  San jee mee NYAH noh . Try to repeat it a few times faster, and that’s it! 😉

THINGS TO SEE AND DO IN SAN GIMIGNANO:

I had the luck to discover the town I have declared the loveliest of the entire Tuscany Region during a Road trip from Rome to Florence. It was a super dark and rainy day, but my first reaction when I left the car in the spacious parking lot just before the town walls was:  WOW, WHAT IS THIS PLACE? 

As soon as you enter San Gimignano, you will feel like time has stopped, and you are either back to the medieval era or in a lovely fairy tale!

Things to do in San Gimignano:

A stroll down the entire town is required, as well as a visit to the Duomo di San Gimignano and the Palazzo Comunale to view the Pinacoteca of Medieval art.

Torre Grossa views:  C limb to the very top of the Torre Grossa, the tallest tower in town to enjoy the best view of San Gimignano ever. The green hills and spectacular Tuscany landscape will make it worth the effort!

Enjoy the food in Piazza della Cisterna:   From gelato to die for to a delicious lunch or dinner at the many restaurants specializing in Tuscan cuisine. I still remember the cute little restaurant in one of the small alleys, where I tasted the best spaghetti with clams (10 years ago!)

Montestaffoli Fortress:  Climbing up to the remains of the Montestaffoli fortress and lots of tastings of the local white wine, Vernaccia di San Gimignano, will round up your unforgettable visit to San Gimignano. You will fall in love with the town, I promise!

WHERE TO STAY IN SAN GIMIGNANO:

HOTEL BEL SOGGIORNO

One of the best hotels in San Gimignano! You’ll have everything at your doorstep: public parking just 50mt away, breathtaking views from the windows, and a superb location, right in the city center. This hotel will be the cherry on top of your fantastic experience in San Gimignano! Click to  Check the Hotel out!

RECOMMENDED TOURS IN SAN GIMIGNANO:

There are many tours, but they depart from other cities like Siena to visit San Gimignano, but since you are on your epic road trip, you don’t need those! The only one I feel I can recommend is actually a “detour” or a secondary option to your itinerary.

Visit Pisa and Lucca (and climb the lining Tower):   Your next stop on the map should be Pisa, but what if you want to slow down and stay a day more in San Giminiano? after all the beauty of these road trips is that you can change your itinerary on a whim. 

With this Tour, you’ll see both Pisa and Lucca; climb the famous leaning tower, and return to San Giminiano for another fabulous night before resuming driving the next day, heading to Florence via San Miniato.  If you like this alternative itinerary, check out the detail of the Tour  here .

14 DAYS ITALY TINERARY DAY 6 | PISA

An obvious choice for any visitor to Italy! Pisa and its famous leaning tower has become a symbolic representation of Italy across the globe.

WHAT TO SEE IN PISA IN ONE DAY:

Pisa’s historic town is relatively small and can be explored in as little as one day.  It’s the perfect place to stop en route between Cinque Terre and Florence. You can stop here for food and explore the Pisa Baptistry, The Leaning Tower in Piazza Dei Miracoli, and San Sisto. Don’t forget to strike “that cheesy pose” when you’re there! 🙂

Yes, I did it too… so why I didn’t put it in here? Because when I went there, digital cameras didn’t exist yet, so  we used the whole film to try and be in the right position for the photo. Only one had the right angle, but it was super blurry!  

RECOMMENDED HOTELS IN PISA:

HOTEL DI STEFANO

If you want to rest up and spend the night in Pisa, this is the perfect hotel for you; right in the city center, a mere 5-minute walk from the leaning Tower, it provides a parking space on-site, buffet breakfast, and has excellent reviews 🙂 Click to  Check the Hotel out!

ITALY ITINERARY FOR 2 WEEKS DAY 7 | SAN MINIATO

San Miniato is a gracious small town which is perfect as a quick (or long, it’s up to you!) pit stop on your way to Florence.

WHY YOU SHOULD SEE/STOP IN SAN MINIATO:

San Miniato has always given a warm welcome to (friendly) travelers! Hence why you should go! 🙂 As the main town was a major thoroughfare for medieval traders between Rome and the rest of Europe, San Miniato became shaped by its constantly changing population and exchange of exotic and sought-after goods.

Nowadays, the town still welcomes travelers from all over the world with  stunning sites like The Duomo, The Tower of Frederick, and the medieval precinct of the town . You can spend the whole afternoon here filling up on local olives! Isn’t that a good enough reason for you to stop in there? I know it would be for me 🙂

RECOMMENDED HOTELS IN SAN MINIATO:

HOTEL SAN MINIATO

Since this is YOUR road trip, you might decide to spend the night in San Miniato. In this case, I highly recommend this hotel, located in a former convent; it offers  free parking space and even a SPA and wellness center  to recharge your batteries 🙂 Pisa and Florence are only 45 min away by car! Click to  Check the Hotel out!

14 DAYS ITALY TINERARY DAY 8 | FLORENCE

I love visiting certain cities more than once, and Florence is one of my favorites for this purpose. I was 20 when one lazy afternoon my friends and I decided to hop on the first train available from Turin (I was studying at University then) to visit this glorious city!

It was a rather cold October weekend, and we slept without a tent at Piazzale Michelangelo, an amazing spot with amazing city views from the hill.  Florence may be an obvious choice to include on a road trip to Italy, but don’t let its popularity stop you from visiting . In fact, it’s never stopped me. Each time is completely different and unique.

WHAT TO SEE AND DO IN FLORENCE IN ONE/TWO DAYS:

This beautiful Tuscan city with its super friendly people has SO MUCH to offer that two days should be the minimum to fully enjoy it.

Best Things to do and see in Florence:

Oh my…where do I even start? Just like Rome, Florence is packed with unforgettable experiences and sights. I will try to give you a glimpse of what it can offer.

The Uffizi:   If you love Renaissance art, a stop at the Uffizi is mandatory. Obviously, the lines to get in are insane, but once inside, your jaw will drop from all the beautiful paintings by Botticelli, the statues, and the whole atmosphere.

Piazzale Michelangelo:   It will give you the most incredible view of Florence from above, especially at sunset. Perfect for photography lovers. If you go there, think about me sleeping with only a blanket on the ground. What an epic trip!

Giardini di Boboli:  We spent a whole afternoon there, and you can’t miss these gardens for anything in the world; the main word here is GREEN. So many green fountains, groomed trees, statues, and hidden caves. Go there and … RELAX!

OTHER THINGS TO DO IN FLORENCE:

Visit the “Duomo:   Famous for its red-tiled dome, colored marble facade & the Giotto tower. A beauty for the eye and impossible to miss when strolling around the beautiful historic center.

Santa Croce Church: Its gothic facade and the vast plaza are well-known landmarks in Florence, famous for being the final resting place of Galileo and Michelangelo. You can visit their tombs in Santa Croce.

Ponte Vecchio:   The oldest and more peculiar bridge in Florence, it still houses many jewelry shops and buildings, a typical practice back in the day. It is very suggestive to walk by the bridge or over the Arno river banks, especially at sunset, to admire it from the “outside.”

Ponte Vecchio at sunset. Such a peculiar and beautiful bridge. You won’t see anything like this anymore in Italy.

WHERE TO STAY IN FLORENCE:

HOTEL PITTI PALACE AL PONTE VECCHIO

This hotel has the most perfect location. It is easy to find at the very end of the famous Ponte Vecchio bridge. The hotel is spotless; it has a parking space available, and rooms have a super  view of the entrance to the bridge . Breakfast is served on the terrace on the 6th floor offers a lovely view of the Duomo and Florence skyline. What more can you ask for? Click to  Check the Hotel!

RECOMMENDED BEST TOURS IN FLORENCE:

If you stay for two days in this magnificent city, you will have some spare time to choose from some of the most incredible tours. Since there are so many to choose from, I put some of my favorites below, and  you can check out more tours by clicking on the whole list .

One I strongly recommend? The  “Fast line” ticket to enter the Uffizi Gallery ! You don’t want to waste your precious time waiting in an endless line, which will make you skip it, allowing you to discover much more of Florence.

14 DAYS ITALIAN ITINERARY DAY 10 | BOLOGNA

Often neglected on travel itineraries in favor of Italy’s more famous hotspots,  Bologna has plenty to offer tourists , from food (ah, the food guys!!) to art and hidden secrets.

Bologna is known in the Italian language as “la Dotta, la Rossa e la Grassa”: “ the educated one” in a nod to its University, Europe’s oldest; “the red one,” about the terracotta hues of its buildings and the city’s historic communist leanings; and most importantly, “the fat one,” about the delicious food.

THINGS TO DO IN BOLOGNA IN ONE/TWO DAYS:

I will give you one day in Bologna /Emilia Romagna only because I have to stay within the 2 weeks Italy Road trip Itinerary.  If you are free to change your plans a little (or are lucky to have more time), I would strongly recommend discovering Bologna and Emilia Romagna for at least 3-4 days .

Check out my article “What to do in Bologna and Emilia Romagna.”  I’m sure you’ll love it, I tried so many things, and the pictures speak for themselves!

Best Things to do in Bologna:

The Markets:   The markets in the center are great for fresh fruit and pastries. Via del Pratello is an excellent spot for lunch, and the student area near Via Zamboni has plenty of options for a filling “aperitivo” – but you can’t go far wrong wherever you choose to eat.

The Two Towers:   Believe it or not, Bologna’s leaning tower would put Pisa’s one to shame! The Two Towers are an iconic symbol of the city, and the shorter one, the Garisenda Tower, leans much more dramatically than Pisa’s leaning tower. It is well known (in Italy) that Dante Alighieri invoked this tower in his “Divina Commedia”, so look out for the plaque with the quote.

Giardini Margherita:   One of my favorites spot in Bologna to chill and relax to end the day after walking its gorgeous streets! You will find mostly local people, and there are so many hidden spots for a nice picnic while seeing the turtles in one of the ponds inside. Highly recommended (and easy to get there by bus too.

OTHER THINGS TO DO IN BOLOGNA AND EMILIA ROMAGNA:

Visit Ravenna: Lovely city easily reachable by train for a one-day trip and famous for Dante’s remainings and the many stunning churches.

Explore the Apennines:   Definitely, a must if you have some more time; it was the highlight of my trip to Emilia Romagna. Lake Baccio and Lake Santo are amongst the most beautiful places I’ve ever seen in Italy (and not a tourist in sight either!)

The beauty of the Apennines in Emilia Romagna. The tranquil landscape you can admire at Lake Baccio!

WHERE TO STAY IN BOLOGNA:

HOTEL CORONA D’ORO 

An excellent centrally located hotel with a private garage in a restricted traffic area, a great feature to have (since you’re in the middle of your Italian Road trip!). Friendly staff and great reviews. Abundant breakfast with lots of choices. The rooms are nice and clean, with comfortable beds, crisp linens, and many amenities.  Check this Hotel!

RECOMMENDED TOURS IN BOLOGNA:

As usual, in the most beautiful Italian cities (and Bologna is definitely one of them!), you will have plenty of choices if you want to book a tour online. What I recommend is going for the food tours . Bologna and Emilia Romagna are the top in terms of delicious dishes, so you can’t go wrong! Below are a few tour options, but click the button to see more and enjoy the experience 🙂

2 WEEKS ITALY TINERARY DAY 11 – 12 | CINQUE TERRE

One of my favorite coastlines in Italy and a must-see on any road trip around Italy,  Cinque Terre national park  is an area around 1.5 – 2 hours’ drive north of Pisa. The region is characterized by its dramatic, rugged landscape and of course, its 5 picturesque terraced towns that only beg to be explored (from North to South):

MONTEROSSO AL MARE  | VERNAZZA | CORNIGLIA | MANAROLA | RIOMAGGIORE

Even if not all the 5 villages show on this map, the train stops in each one of them. The road in white you see behind the red line is the road you should use my car, and it takes around 2 hours drive. Image credit: Map data ©2022 Google

One of the best tips I’ve learned is to leave the car at La Spezia city and take the train between these 5 towns . It’s usually the easiest way to discover them without the issue of finding a parking spot (unless you decide to choose one of the villages to stay in for the night).

THE 5 VILLAGES TO SEE IN CINQUE TERRE IN 2 DAYS:

Obviously the main attractions of the Cinque Terre National Park are the famous villages, so let’s check them out in detail to see what distinguishes one from the other, they are all marvelous and unique!

From the top: Riomaggiore, Manarola, Corniglia

1) RIOMAGGIORE:   The most southern village of Cinque Terre, Riomaggiore is a beautiful town to sit back and enjoy your afternoon. Grab some local food (especially fried calamari) from the street vendors and head for the rocky harbor front. Helpful tip: spend a good few hours dipping your feet and legs into the sea! This town is a fabulous place to watch the sunset, and why not take a swim and cool down after a day under the scorching Italian sun.

2) MANAROLA:   Arguably one of the most photographed towns in Cinque Terre, Manarola is a beautiful place to explore and, of course, grab a bite to eat! Every time I visit Manarola, I put on 4kg in weight! The gelato, the calamari, the wine … it’s all just too good!

3) CORNIGLIA:   Unlike the other four villages of the Cinque Terre, Corniglia is not perched on the seafront but at about 100 meters high on the top of a cliff. Warning: Trying to walk in the scorching midday heat is not the greatest idea – you could end up sweaty, hot, dehydrated, and no doubt looking a bit messy 🙂 you can use the connecting shuttle bus from the train station instead. It takes about 5 minutes to reach Corniglia. A perfect place to enjoy the views of this magnificent area!

Top: Vernazza – Bottom: Monterosso al Mare

4) VERNAZZA:   Dating back nearly 1000 years, the iconic Vernazza is still standing to show you a beautiful piece of historic Italian charm – that I fall in love with every time. This city really stole my heart! Don’t forget to see the Church of Santa Margherita and the hidden Vernazza beach just off Piazza Marconi.

5) MONTEROSSO AL MARE:   The westernmost of all the Cinque Terre villages is Monterosso al Mare, famous for its wider beach and for the many open spaces compared to other countries. What I love most about Cinque Terre is that it feels like a “personality test.” Everyone has their favorite village for very specific reasons. Monterosso al Mare is my least favorite town in the Cinque Terre, but that’s because my heart has already been stolen from Vernazza’s colorful houses (I love colorful houses) 🙂

BEST HOTELS IN CINQUETERRE AND LA SPEZIA:

LEVANTE RESIDENCE 

Just minutes from La Spezia center. Clean, spacious rooms with kitchen. A good option is to have a base there for your La Spezia Gulf or Cinque Terre trips. Safe, private parking and simple breakfast. The train station is within walking distance, and free parking is a plus. Highly recommended. Check out this Hotel!  

BEST TOURS IN CINQUE TERRE:

When you visit the Cinque Terre villages, you can take your time and explore them on your own or book a guided tour to discover the secret places, best restaurants, and panoramic views.

One of the best ones is definitely from Florence to Cinque Terre and it’s most suitable if you are flexible with your dates and are on an Italy road trip, coming from the south and ending in the northern part of the country, like in this case.

Depending on your budget, some of these tours, especially the boat ones, are worth the money . They will provide you with a completely different experience. As usual … it’s up to you to decide! Sometimes I like to opt for a tour, other times I prefer to discover an area on my own.

ITALIAN 2 WEEKS ITINERARY DAY 13 | TURIN

I lived in Turin for 8 years while studying at the University, and not only do I know the city well, but I love it pieces! Unfortunately, the city is one of the least known and appreciated by tourists. While most of those visiting Italy head for the Rome-Florence-Venice triptych, Turin remains off the tourist radar. What a shame.

Maybe is because the city has always been associated with Agnelli and his automotive empire (Fiat). However, people forget that another dynasty, not industrial but royal, chose Turin as its capital eight decades earlier.

Nineteenth-century Turin was also a favorite of intellectuals and artists such as Nietzsche, who loved the city for its austere elegance, atmosphere, literary cafes, and food. So, this seething city should definitely be on your wish list for your Italian road trip.

THINGS TO DO IN TURIN IN ONE DAY:

The beauty of Turin, compared to other Italian cities, is that it is easy to get around on foot and public transport is excellent . I have never used a car in 8 years, and I know every street as it is easy to walk to the city center and some of the most beautiful palaces and squares.

The beautiful Mole Antonellliana by night

Best Things to do in Turin:

Il Quadrilatero Romano: One of my favorite places in Turin for its many restaurants, aperitif bars, and lovely streets filled with history from the Roman empire. Great for an exciting night out in Turin!

La Gran Madre Church:   The “Gran Madre” is a Neoclassic-style church located in front of Piazza Vittorio. Straightforward to reach by foot from Piazza Castello through via Po (famous for its many shops, bars, and restaurants), it’s stunning at night.

Piazza Castello/Via Garibaldi:   Turin’s central square is lined with museums, theatres, and cafes. Dominating it is the part-medieval, part-baroque Palazzo Madama, the original seat of the Italian parliament. To the north is the beautiful facade of the Palazzo Reale, “The Royal Palace” built for Carlo Emanuele II in the mid-1600s. If you are up for some shopping, on the left of Palazzo Reale, you will reach Via Garibaldi, packed with high-end and budget shops (I used to live in the student house in that area!) 😉

OTHER THINGS TO DO AND SEE IN TURIN

Il Castello /Parco Del Valentino:   My favorite spot in town, a massive park with botanical gardens, statues, and, of course, the iconic castle. Perfect for a romantic walk or just to chill during the hot summer days. You can admire the spectacular views of the Valentino Castel by night just by crossing one of the bridges over the river PO. Highly recommended!

La Reggia di Venaria: Declared UNESCO Heritage Site, the Reggia di Venaria is a spot you can’t miss. The palace is marvelous, and during summertime, you can enjoy a wide array of events, from artists performing accompanied by relaxing music to video-mapping shows.

Basilica di Superga:   Another fantastic place to visit in Turin! The church is on a hill where you can admire the city from above. Perfect at sunset to see the city lights and chill after visiting the inside of the beautiful Basilica.

The beautiful Castello del Valentino in the “Parco Del Valentino (Valentine’s Park). One of my most precious places in Turin. Day or night it is truly marvelous!

Museo Egizio:   An excellent place for people passionate about Egyptian History, this museum is the most important one in Italy as it preserves some rare mummified human remains and several Egyptian statues.  

Palazzo Reale (Royal Palace):   Located in Piazza Castello; if you visit it, I promise that the inside will leave you totally speechless. I still remember the first time I saw it, admiring the beautiful dancing room, statues, paintings, and seemingly never-ending luxurious rooms in awe. No wonder it was included in the list of World Heritage sites in 1997. Totally worth it!

The beauty of Turin at sunset: Ponte Isabella over the River Po that divides the city in two.

WHERE TO STAY IN TURIN – BEST HOTELS :

HOTEL URBANI

Excellent location to head off in any direction and explore. The hotel itself is lovely. Accommodating and friendly reception staff. Delicious breakfast, charming rooms, and parking space. The perfect mix to set you up for the day and relax once back from your strolling in Turin.  Check out this Hotel!

14 DAYS TALY ITINERARY DAY 14-15 | MILAN & LAKE COMO

DISCOVER MILAN:

Milan is one of the trendiest cities in Italy . It is the city of fashion and the economic capital of Italy. Both traits are clearly visible when you’re walking around the city. Modern and trendy skyscrapers scattered here and there, surrounded by beautiful historical buildings throughout the city center.

Many of Milan’s most exciting sights and attractions are not readily apparent, so you’ll need to dig deeper to discover the gems that make the city unique.

Luckily, Milan is surprisingly walkable and, at times, feels more like a compact town than a major European metropolis. And once you start chipping away at its foreboding exterior, you’ll find untold treasures below the surface: priceless works of art, beautiful eccentric buildings, world-class restaurants, and oases of calm. Explore the best things to do in Milan and remember: appearances aren’t everything.

DISCOVER LAKE COMO:

Como is filled with luxury Villas you can visit, like Villa Balbianello here, a perfect setting even for weddings!

The itinerary for your Italy Road trip started in the glorious city of Rome, and it couldn’t end less gloriously in the fantastic Lake Como setting. Relax in the shade of a tree in front of the lake, admire its beautiful views … and, who knows? You might even spot George Clooney (owner of one of the most beautiful villas in Lake Como), his buddy Brad Pitt, Tom Cruise, or any other A-list celebrity, but there’s so much more to this destination than its famed visitors.

The glacial Lake Como is a mere 1.5-hour drive north of Milan and only 30 minutes or so from the border of Switzerland. The biggest draw to Lake Como is its natural beauty – especially the scenic mountainous region that always leaves me in awe.

Hop on the ferries that cross the lake; it’s a perfect way to explore the beautiful little towns surrounding it like Menaggio, Bellagio, and Varenna, to mention but a few of my favorites.

THINGS TO DO IN MILAN IN ONE DAY:

In Milan, as previously stated, it is super easy to get around by walking a bit or via their efficient public services (the underground system is excellent). This way you can do quite a lot in one day.

The most famous things to do in Milan are:

• The famous Duomo di Milano: The symbol of the city.
• Galleria Vittorio Emanuele II (on the left of the Duomo)
• Sforza Castle for a bit of history
• Parco Sempione to end your day in total relaxation!

THINGS TO DO IN LAKE COMO IN ONE DAY:

Honestly? If it was for me (personal taste!) I would spend just half a day in Milan and aim straight to Lake Como, but the itinerary is yours, so maybe you are a fashion addict and want to spend a whole afternoon shopping in Milan 🙂 Either way, Lake Como would deserve at least 2 days of exploring.

So, what to do and see in Lake Como?

• Visit Varenna, a lovely village with great views of the lake.
• Take the ferry! You’ll discover the hidden spots as well as the more popular sights.
• Visit Villa del Balbianello
• Discover Castello di Vezio for awesome views

Villa Del Balbianello, Lake Como

Best Things to do and see in Milan:

Il Duomo Di Milano:   Do I really need to tell you why you should visit it? There is so much information online, and the pictures speak for themselves. It goes without saying that this should be your first stop in Milan, no question about it. And it’s as beautiful as in the pictures. My only tip: go there early in the morning; you will make the most of the experience!

Castello Sforzesco: Nearby the Parco Sempione, the Castello Sforzesco (Sforza Castel) is a mandatory stop on your visit to Milan; apart from its famous towers, it hosts several museums from the Ancient Arts to the Pinacoteca and the Egyptian museum, just to name a few. If you love history, this is a great place to visit.

Galleria Vittorio Emanuele II: Just on the left side of the Duomo di Milano, its architecture (especially the roof) will leave you in awe. You’ll find many shops, from luxury ones to nice cafes where to sip an espresso and relax, bookstores, restaurants, and more. Since it’s in Piazza Duomo, you can easily make it your second stop in Milan.

Best Things to do and see in Lake Como:

Villa Del Balbianello: Located on the left wing of the Lake, near the village of Lenno, it is a must-see. Beautiful views of the Lake and the Villa with its terrace garden are genuinely out of this world! One of the best spots to admire Lake Como’s mighty beauty. It’s undoubtedly one of the most touristy and popular Villas to visit.

Villa Carlotta: Just a few kilometers away from Villa Del Balbianello (heading north of Lenno), it’s a true gem with its botanical gardens, museums, the staircase, and the stunning entrance to the Lake. Not to be missed! (I will write an article just for the villas to visit around Lake Como as they are jaw-dropping!)

Take the ferry:   One of the best ways to enjoy Lake Como is by Ferry. There are both public and private ferries. The public one is relatively cheap, but obviously, it doesn’t let you hop off to explore what you want. You can either find the private companies online looking for “private ferry lake Como” or, as I suggest below, I’d recommend the Tour from Milan without the hassle of driving there and back.

MORE THINGS TO DO AND SEE IN MILAN

I Navigli Di Milano: A system of canals running in the heart of Milan, surrounded by lovely cocktail bars, are the perfect location to spend your dinner and after-dinner time, not to be missed for an excellent aperitif. Great for a romantic walk at sunset as well. It’s easy to reach by public transport, which is always a bonus!

Parco Sempione:   Located in the heart of Milan, Parco Sempione is a lovely park where you can relax, chill and visit the Sforza Castel and the Arch of peace, two of the most famous landmark in Milan. 

Via Montenapoleone:   If you are in Milan and love fashion, via Montenapoleone is the place you want to be! Filled with luxury shops, whatever brand you are looking for, you will find it there! Splurge as much as you want and enjoy!

The famous Navigli Di Milano, great for the nightlife and the peculiar atmosphere

MORE THINGS TO DO AND SEE IN LAKE COMO

Trekking/hiking Lake Como:   If you have some time or, during your Italy Road trip planning, you decide to skip a place or two, this is one of the best and more rewarding activities to do, with breathtaking views over the lake. The most famous walks/hikes are the Greenway Del Lago and Spina Verde (suitable for everyone, they will take you to the top spots like Villa del Balbianello). For more advanced trekking and hiking, organizing with private companies is better.

Castello di Vezio:   Located in the middle of Lake Como, with an overview of Varenna village, it is a lovely spot for jaw-dropping sights of the lake and its history. It was built over a thousand years ago. Don’t forget to climb its famous tower to enjoy even more incredible panoramic views!

The stunning views you can admire at Lake Como are endless!

WHERE TO STAY IN MILAN AND LAKE COMO :

HOTEL BELLAGIO (LAKE COMO)

In the city center, accessed directly from Bellagio’s main square by 38 cobblestone steps, Hotel Bellagio is within walking distance of the town’s shops, cafés, and restaurants. Parking is available, free cancellation, and incredible views of the Lake.  Check out this Hotel!    If you prefer to take a day tour to Lake Como and base yourself in Milan, check out the  NH PORTA NUOVA hotel, which is convenient and well-located.

Considering the allure of Milan, not only as a tourist destination but also as a potential long-term residence, the prospect of renting an apartment in this trendy city opens up a world of possibilities. Imagine having the iconic Duomo di Milano as a backdrop to your daily life or strolling through the historic Galleria Vittorio Emanuele II for your daily dose of luxury and culture.

Beyond the famous landmarks, Milan offers a lifestyle that seamlessly blends modernity with history. Long-term rentals in Milan provide the opportunity to delve into the city’s hidden gems, from charming neighborhoods to authentic local experiences, creating a genuine connection with this cosmopolitan hub. As you embark on your exploration of the city, consider how  renting an apartment in Milan  not only grants you a comfortable abode but also an immersive journey into the vibrant tapestry of Italian life.

BEST TOURS IN LAKE COMO :

Given the proximity of Lake Como to Milan, you can opt for booking one of the grand tours from the Lombardy Capital instead of spending money (and time) using your car. Many people choose this option, and they can enjoy a full day in Lake Como without stress and see all the top sights stated above.

Usually, when talking about the tours, my advice is to decide which option is more suitable for you (car or tour) but in this case, the day trips from Milan are genuinely the best option, also money-wise. Highly recommended!

THE TAKEAWAY OF THIS ITALY ROAD TRIP ITINERARY

As you might have noticed, I tried to fit in as many “pit stops” as possible for your 15 days on the road in Italy. I know many people would rather rush a bit to see as many beautiful spots as possible.

That said, If you want to travel slower and stay more in one place, you can easily rearrange this itinerary by skipping a few places, no problem!

I hope you enjoyed my article and that you will be inspired to visit my beautiful Italy, loving my country as much as I do!

If you have any questions or locations you have visited that you particularly liked, shoot me a message in the comments below, I’d love to hear about your experience!

Images credits/attributions: Shutterstock.com (except for Emilia Romagna)

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This blog post has truly uplifted me and provided me with the guidance I was seeking. Thank you for sharing your experiences and insights in such an inspiring way. Your generosity and willingness to help others is greatly appreciated.

I like your blog! It is awesome! You give many information about travel! It’s really great! Also, Italy trip is great! I think We should travel to Italy.

I’m a foreigner living in Rome, and I must say that it is the greatest city in the world. The pros of living there are just too many, but one has to look for them. If you’re the kind of person that just wants a smooth, predictable life – let’s say 9 to 5 job, reaching home at 6 by train and finding your parcel delivered at the doorstep – then it’s not your kind of place. Rome is instead for the kind of people who like adventure, going out and having fun. You do your morning walk among the ancient ruins. You spend a lot of time in the bar with friends. You go to swim in the sea during summers, and to ski in the mountains during winters. You face day-to-day inconveniences, but in that situation you help each other, knowing that they’d help you too.

My personal take is that the things which distinguishes Rome and Italy from other parts of the developed world is that for better and for worse, there’s no “consumer” culture over there. The mentality is centered doing the bare minimum needed for survival, and not on getting the maximum output as is the norm elsewhere nowadays. Overall I wouldn’t say that Italians are (stereotypical) lazy, but just not hardworking and with generally modest expectations from life.

Hi Nicole, thanks for your insights! I agree with a lot of what you said and Rome no matter what will always be my favorite city in the world, with all its imperfections too. What I had to think about more is the work ethic and expectations. I would put it differently but I understand what you are expressing. The idea of us being stereotypically lazy is like everyone else thinking that in the US people are only driven by work and goals and can’t appreciate life. We don’t know if people don’t appreciate life there for real, this is our idea. Same with Italians (and you also need to do a big distinction between northern Italy and southern Italy) people might be thinking they have high expectations for their lives, also money wise but maybe compared to your personal experience we are not, and so on. So what I’m trying to say s that things are VERY relative and I try not no generalize a country (altough I know first hand how difficutl it can be) . Enjoy my beautiful Rome!!

VERY INFORMATIVE!! KEEP POSTING THESE ARTICLES!!!

Hey, thanks for sharing this fantastic information with us. Can’t wait to book our holiday to Italy! Thank you and please continue to share blog posts about Italy, they are very useful, especially coming from a local!

quite impressive

Thank you for a very interesting article. I greatly appreciate the time you take to do all the research to put together your posts. I especially enjoyed this one!!

What a great article! I have to say I did a bicycle trip in northern Sardinia, from Olbia to Santa Teresa passing by Maddallena. I have been to many many beaches in my life but I have never seen so beautiful beaches like in Maddalena. The colors of the sea was absolutely stunning! And the scenery in North Sardinia is unique, almost lunar.

This being said, we did a road trip in France from Nice to to Bordeaux avoiding the highways and going through the little villages. Back country road trip. In our mind, the road is as important as the destination. We prefer B&Bs (I think you call them agroturismo in Italy) where we can talk with the hosts and guests and get their ideas about the nicest places in their corner of the country..

So……we are planning a 3 weeks road trip in Italy, September 9 to 30, 2022 more or less. Probably from Venice to Rome and maybe going down to Sorento. We were planning to go to most of the places you mentioned in your article except for Milan and Torino which I’ve already been and not so keen to visit twice. So, adding a week to your 2 weeks itinerary, I was wondering if you have any suggestions for those additional days.

Thank you so much and keep on your good work!

Hey Stephan, wow I’m envious just reading all you will see on your road trip in my beautiful Italy! If you have 2 more weeks I would definitely go : 1) Val D’orcia in Tuscany, it’s BREATHTAKING, I want to make a photo post with the photo I shoot. Just that will convince you. I stayed in a lovely home rented in Castiglione D’orcia and it has been one of the best road trips ever. 2) South of Rome I’d go to Sorrento, Capri, and all the Costiera Amalfitana. It’s mainstream clearly but you can’t miss it! This would deserve a full week to fully explore all the little corners of this beautiful place.

There will be so many places I can add but I don’t want to overwhelm you. If I had these 2 additional weeks I would explore more of Tuscany in general, and the Val D’Orcia area in particular, and all the Costiera Amalfitana. It will make for a fabulous Italy Road trip!! Plus the time of the year is perfect, still warm but with fewer tourists. What can I add if not… Enjoy Italy!! 🙂

Cheers Clelia

Thanks for reaching out! We will definitely put Val D’orcia on our itinerary. Can you let us know what was the lovely home you stayed there? Always nice to go somewhere recommended by some one who stayed there. So 2 weeks from Venice to Rome and one week in the costiera Amalfitana, Right?

Hi Stephan, yes I’d say 1 week in the Costiera Amalfitana, not less… and the remaining 2 weeks you go from Venice to Rome. Oh, I envy you right now 🙂 Let me check the name of the place! I booked it with booking.com I remember so it still should be in my records 🙂 Ok, after a while I found it! It’s the lovely home called “ La Cantina di P ” I hope you didn’t book anything yet because this was a truly lovely place, especially the location was so amazing! Let me know if you need any more help and enjoy your road trip to Italy!

Fantastic! Thanks for the valuable information and we will definitaly book there, Covid permitting. Keep on the great work! Grazie

Thanks Stephan! I’m so glad you liked my Italy road trip itinerary, I’m supposed to create the second part, from Rome to … Sardinia because I had to leave out so much. Two weeks are not nearly enough to enjoy the beauty of Italy and everything it has to offer 🙂 Fingers crossed about the Covid yeah. We had some small trips in Italy so it’s not super bad but in winter it’s always a bit worse. With the proper precautions, I believe we will be able to have a sort of “normal” life again soon.

Wow what a wonderful article, spectacular pics. Italy’s a beautiful country and everyone should know this. I have been twice and looking forward to visiting it after the pandemic. Thanks for sharing with us this fab post.

Italy is Indeed a good place to visit in the world. Being a travel enthusiast I learn that Italy is a place where every city is beautiful as well as historical. You will find the different kind of travellers in Italy and its the place where you can meet new peoples and interact with them. Thanks for sharing this post with us.

Great pics and information. This is my dream destination, I would like to visit here someday. Hope to hear more from you. Thank you.

Very nice information thank you for sharing! We can’t travel to Italy right now but this will be a huge help for when we will be able to visit!

You should work for the Italian tourism department, they are in dire need of people like you. Unlike France and Spain who have done a great job in marketing themselves, in Italy international tourism is unfortunately restricted only to some areas of the country (city of Rome, Veneto, Lombardia, Liguria, Tuscany and maybe Sardinia). Nice to see that you mentioned Piedmont and Emilia-Romagna here. Then there is central Italy outside of Rome, and especially “Mezzogiorno” that I think is super underrated (I’m from Puglia and in my own biased eyes, it’s the closest thing to Paradise on Earth). Also, as much as I love Rome, my favorite city in the world will always be Napoli, which I would recommend to every visitor in Italy.

Ciao Gianmarco, thanks for your kind words, I sadly must agree with you about how we promote certain parts of Italy and completely disregards other parts, and actually this article is just part 1 of another than covers all the regions in Southern Italy. I have been to Puglia and LOVED IT!! (and it’s obviously included in the second article that Iìm going to publish). I’m from Sardinia so we can both say we are very lucky! Interesting about you loving Napoli so much! Why ? Mine is Rome (I have lived there for years) but also Napoli is beautiful for sure!

Napoli is just another city that has no equivalent in the world. First of all, it has the most beautiful landscape in all of Italy, if not the world (try searching “panorama più bello del mondo”). The city has the largest historic center in whole Europe, and just like Rome, it is full of castles, churches and ancient ruins (have you been to the underground areas). Despite everyone in the world consuming pizza these days, all others are fake except Neapolitan one. While the city center still retains it’s ancient vibe with narrow, chaotic streets full of people, some of the most beautiful metro stations of the world are located just below it, highlighting that Neapolitans and Italians in general continue to be great innovators of contemporary times, even if we are obsessed with with our past and aren’t obsessed with becoming “successful” by contemporary definition. Than of course the surrounding areas (Pompei, Amalifi, Capri, Amalfi, Sorrento) are also among some of the most breathtaking places. Overall, I find Rome and Napoli are very similar both in their good and bad aspects, except that Rome is less dense and more spread out. While I won’t trade Rome for any other city in the world, I give Naples the edge over it because of metro, surrounding areas and the overall vibe and sheer passion of the city.

I might say that Italy the most beautiful country in Europe and the world, considering that I’ve traveled to at least ten different locations in Italy, and that you have managed to mention so many amazing places despite touching only a quarter of whole Italy. But as a Frenchman, some things in Italy are really frustrating. Relying on public transport is a real pain, especially if you want to travel to smaller towns. Even if it is available, trains are poorly maintained and always late. Many places are dirty and not taken care of. And it gets crazier as you go southwards with Sicily being the worst, despite still being stunning and soon I’ll be there again. My Neapolitan friend jokes “To drive on roads of Naples, you must have the special ability to pray for San Gennaro”. And he’s so right. Sometimes, it really feels like the vehicles are there to hit you and traffic rules are meek requests. I think this can be said of almost all Italian cities. I do love Italy but I don’t see why Italians don’t acknowledge the clear superiority of the French.

I’m Spaniard and I’m a big fan of Italy. In Spain, Italy is seen as a dream girlfriend that drives you crazy yet you can’t stop loving her. Personally, my favourite Italian regions are the Alps, Veneto, Tuscany and Campania – but the country is very beautiful almost everywhere and there is no city or region in Italy that isn’t worth visiting.

Thanks Lucas, it means a lot especially now. I hope people will start to visit Italy again very soon. Be well!

I wish the same for Spain too. Just like Italy, we choose to ignore the warnings and go on with the fests and parties, and now we are in an even worse situation. Us Mediterraneans are too similar I think.

Indeed we are… I have no idea when this nightmare will be over. I hope people won’t fear traveling to our beautiful countries when all this will be over.

Great post. However, I would like to add my two cents. First of all, I think Milan and Turin, while fantastic, are probably the least breathtaking cities in Italy. Southern Italy and the two islands certainly feel less developed, yet they have an older and more exotic vibe, with better beaches. Finally, I think that something like a planned Italian road trip doesn’t exist. In Italy, you are always close to a centuries old streets and buildings. gorgeous landscape or beach. Apart from some must visit cities that are well known, one can simply drive anywhere between Bolzano and Reggio Calabria and easily discover a lot of magnificent yet unspoiled places all around the country.

Hi Clelia Thank you for your excellent road trip guide . We are travelling from Rome to Lake Como . We have booked most of the hotels you have suggested . We are doing a slight detour. Only concern i have is driving from Rome airport to Hotel Monfy in Rome. I know from visiting Rome previously the roads can be extremely dangerous if you are not a local. Thank you for your help.

Hi Paul! Glad you found my guide useful… As someone who actually took her driving license in Rome, I can relate with your concerns 🙂 I’m not going to lie, driving in Rome is an adventure! Dangerous, I wouldn’t say that maybe you will have to be super careful and prepared before you drive. Meaning knowing exactly your route, but these days using google maps as a navigator will do the trick. You have to be careful with the scooters driving around you but other than that, if someone like me with no driving license could take it and drive safely for 3 years in Rome, I think you won’t have a problem (and I didn’t even have any google maps navigator, at the time!)

Let me know if you need some more help! Cheers Clelia

I love Italy. It is, in many ways, a unique country where you can always find something amazing nearby regardless of the region where you are. From my experience with Italians in UK and Italy, I must say that they are group of humble, outgoing and loving people who are masters of enjoying life. What I don’t like about them is that most of them don’t value rules, work ethic and public property. But my general perception about Italians is quite positive.

I love Italy. It is, in many ways, a unique country where you can always find something amazing nearby regards of the region where you are. From my experience with Italians in UK and Italy, I must say that they are group of humble, outgoing and loving people who are masters of enjoying life. What I don’t like about them is that most of them don’t value rules, work ethic and public property. But my general perception about them is quite positive.

Hey Andre, thanks for your comment and point of view about Italy and Italian people. Just one thing (being Italian I might understand the dynamics a bit) 🙂 Many people think our work ethic is not good but it’s actually not entirely true. Sure there are “lazy” people everywhere and in Italy, we might seem lazy but we are not. We have simply a different approach when it comes to this part of our life, and when we are working we give 110% most of the time. Otherwise, we wouldn’t be able to be masters of “enjoying life” as you mentioned! Regarding the rules, yes you are right we don’t like them especially when they are stupid but also when they are ok. We tend to disregard them more but not in bad faith, we just give the rules less importance I guess. Right, wrong? It really depends on the situation I think. I remember when I first arrived in London people wanted to kill me because I didn’t know I had to stay on the right side of the escalator, while in Italy we just stay wherever we want, and funny enough, after a few years living in the UK, once back in Italy I was like “why people don’t stay on the right!!” so we are just laid back for a few things I guess. I’m sure you’ll find my next article coming soon about Italian culture quite entertaining then.

One of my favourite itineraries and absolutely right about staying at least 3-4 days in each location. Drives me mad to see people racing from photo op to photo op without taking the time to at least get a flavour of the locale…

Exactly my philosophy Gary, I understand that people want to squeeze as much as possible from their Italian Itinerary but going slowly is much more rewarding…

Hi Clelia, My husband and I have just decided to take a trip to Italy in May this year. We were not sure how we were going to travel thru the country but I found your blog and am convinced a road trip is the answer. I have read thru the itinerary and only wanted to know if in addition to the sites you highlight, are there any places that have recently become a no miss which you have not mentioned. We are travelling for 15 days. Thanks

Hi Lori! I’m so glad to hear that you’re taking a road trip to Italy because you read my article! (it took me forever to put it together so at least I know it’s useful) 🙂 As for your question…

oh my! I left out so much from this itinerary already because of the limited time but recently I visited a place where I left a piece of my heart: The “Val D’Orcia” and in particular the village of Castiglione D’Orcia where I stayed in a lovely house in the center behind the small piazza for one week. It’s out of this world. Not only the village but also the surrounding areas.

There are so many of the typical “Casali” with the famous Tuscan landscape and trees, I even spotted the gates of the house where the movie “The Gladiator” was shot and saw one of the best sunsets of my life. I usually never do this, but to give you an idea you can check this picture I took and put on Instagram and this other one which has a truly lovely story behind it. I even made a few Instagram stories of that place. I think I’m going to add this to the itinerary because I’m obsessed 😀

So yes, please Go to Castiglione D’Orcia ! If you want some advice about the accommodation, the place I obviously recommend is where I stayed LA CANTINA DI PI , cheap and lovely, everything was at walking distance and you can park the car for free in the parking lot at 5 min walk.

I hope you can make it and if you have time also visit Montalcino and, nearby Castiglione, also go to the (completely free) Terme called “Bagni di San Filippo” at just 10 min by car and super easy to reach. You’ll love it! If you need more info about it, given that I still have to write an article about my stay, feel free to ask in here!

Cheers! Clelia

Hi Clelia – thank you for the excellent information! I’m returning to Italy in May with friends and family for a 10 year anniversary trip and was hoping you might be able to help me. We are renting cars in Rome FCO and will be driving directly to a villa near San Miniato in the late afternoon 5/6pm. What would you suggest is the easiest route to take? We will not be making many stops or are concerned about scenery at this point – mainly just about getting there quickly and easily. Any suggestions?

Hi Aimee, glad that you liked my Italian guide! And what a lovely choice going nearby San Miniato, you’ll going to love it! As for your question, the easiest route is without a doubt to go towards Viterbo (the signs pointing to the E35/a1 towards Florence). before finding that road you’ll need to get into the Grande Raccordo anulare first and find the right exit. But If you have even google maps, you can put your point of departure and destination and let it guide you. But if it gives you more than one choice, you go with the E35.

It might be a bit tricky on the Raccordo Anulare, there are so many lanes and exits but if you drive carefully and study the indications on Google maps, you should be fine. Once you’re on the E35 you will go straight for at least 1+ hour, then you’ll have to stay alert again for the right exit (which depends on where you are heading exactly). The total time spent to get to San Miniato city is about 2:30 min with no stops, I’d say 3 hours with one stop and counting the traffic in the Raccordo Anulare.

Recently I took that road to get to a village in Tuscany but from Civitavecchia ferries port and it was a very pleasant ride even if you’re not looking for particular scenery. You still will find it quite nice!

I hope it helps and if you never drove in the Raccordo anulare, be careful because there are some crazy drivers in there so go at your own pace and everything will be fine! (I lived in Rome for years so I know the raccordo and the nearby roads quite well)

Italy is a fantastic country – I don’t think any other country can offer so much variety (natural, historical and cultural) in such a small area. But I must say that my favorite area in Italy is the south. I personally think that it is the most beautiful part of Italy, and as of now it is quite undiscovered, unspoiled and authentic. I also love people of that region – who have a “I don’t really care” attitude for most aspects of life, and seem to enjoy their lives in their secret paradise without having any ambition for the future. Apart from having been to the mainstream cities (such as Florence and Venice), I’ve enjoyed road trips from Naples to Reggio Calabria and Salento and it was fantastic to travel across the hilly countryside, beaches and old, magnificent towns.

Hey Oliver thanks for stopping by and saying so many beautiful things about my country! I agree the south is more relaxed (but hey we have ambitions, we are just not obsessed by them) 😉 You’ve been to awesome paces but you’re missing one…. my fabulous island Sardinia! I know I know, it might seem biased but trust me, not only we are also Italians but our culture and beaches are incredible! Cheers from Paradise!

Apart from so many great things, it needs to be said that Italy can surely improve infrastructures, customer service and cleanliness of public places (it isn’t bad, but not “top notch”). That prevents many potential northern European visitors who prefer Spain and France instead. But despite its flaws, I love Italy. It isn’t a place with a giant hotel in front of beaches, gentrified or renovated historic centers, fake friendliness just to please the visitor. In other words, it seems like a place which hasn’t sold it’s soul just to become richer. I’ll consider Sardinia in near future, for sure.

Oh you’re totally right. We are not that great when it comes to Infrastructures in Italy, in a way it’s bad, I reckon, but you know what? If it’s just a bit messy sometimes it’s because we are simply … ITALIANS 😀 We are chaotic, messy, chill out and we should clean up a bit more yes! Italy doesn’t even need to sell its sowl, there are so many beautiful places that we don’t need to overdo it! And if you complain about infrastructures in Italy, wait till you come to Sardinia… being an Island we are a bit behind and the public transports also are less than ideal, but when you see the beauty you tend to forget everything about it!

I totally get your point. And I won’t say it is as bad as some people say (Italians complain all the time). The worst, however are the large cities (Rome and Naples). I remember my first experience in Rome and it was a shock for me coming from Geneva. I learnt a few lessons : expect at least half an hour delay of any mode of transport, you DON’T really need to buy a ticket for getting into a bus, the concept of personal space doesn’t exist, don’t expect vehicles to stop for crossing the road, no one will mind you if you throw trash on roadside and that you may take three hours to reach your destination (but you’ll still be there before your Italian friends). I do get that the culture of Italy is different and organisation isn’t something to expect there. And as far beauty is concerned, no one can deny it.

How couldn’t agree with you? We are like this, some places like you mentioned more than others are affected by this. And you forgot to mention that for us there are no rules in the escalators. I discovered that in Europe is different the very first day I moved to London, innocently stayed on my left only to be hit by the rage of the English people saying that I was an animal basically 😀 I was in shock and didn’t understand why they were so mad at me. Then I realized that it’s just in Italy that we stay wherever we want 😀 The beauty and the irony of it is that after 6 years living in the UK, when I went back to Italy and used an elevator I felt our behavior was outrageous ahahahah, I’ve been civilized I think 🙂 Thanks for all these inputs, I should write a post about it!

Many good reviews here, we thoroughly enjoyed ourselves. Meeting up at the coach ‘station’ was a little disorganised but it worked and we had a great day out. Siena was beautiful, although we didnt read the small print – Cathedral guide not included. San Gimignano very pretty, the wine tasting was fun too, although with wine at 30 or 60 euros a bottle we didnt buy any. A good day out.

Glad that despite little not so perfect details, you had a good time in Italy! Cheers

Hi Clelia, your blog on road trip to Italy is just vividly marvelous. Further, I appreciate the pride you take in your country and I feel like visiting your fascinating nation very soon. Thanks a ton for your itinerary.

Thanks Albert! Indeed I am very proud of being Italian! Our country has so much beauty to be discovered, from north to South. A southern Italian Itinerary is coming soon (I couldn’t include that because of lack of time to visit everything of course). Italy is pretty big and even if people would love to have a taste of the north and the south on the same trip, if they use a car and don’t have at least one month or more, it is impossible.

Loved your blog, but what you have touched is barely the tip of an iceberg, and if Venice is added to the list, they are the places that are frequented the most by foreigners. Italy is SO MUCH more. Must visit places in the north include Alto Adige, Valle d’aosta and Trieste, all of which have a unique culture, even for a country as diverse as Italy. As you have not covered any part of Southern Italy (which, by any means, is NOT a region that can be left out), I must add that it is a region that is as worthy of visiting as the the places mentioned in this blog. As a Calabrese, I’ll say that it is arguably more beautiful, because the weather is better, cuisine is better and more diversified, beaches are much better than the north, the number of historical sites is higher (because of rich historical background) and people in general are very hospitable. Must visit places in South include Naples (a city that has probably no equivalent in Europe or World) and its surroundings (Sorrento, Costiera Amalfitana, Pompei, Caserta), Palermo, Catania, Siracusa, Reggio Calabria, Tropea, Pizzo Calabro, Matera, Ostuni, Alberobello, Brindisi and Lecce.

Hey Antonio, Thanks for your comment and of course I only touched the tip of the Iceberg! This was a specific Itinerary (and even a very crammed one to be honest) to include most of the popular sights, but I have another post or two coming for the rest of Italy, including the south (with all the places you have mentioned) and also another one for the mountain lovers. There is so much to see and do in Italy! By the way, I’m Sardinian and I visited Calabria more than once and loved it! We are very lucky indeed 🙂

Hi. I found your Blog by chance cause I’m searching for help with a road trip I’m taking with my husband and 10year old twins from Calabria to Puglia (excluding the heel) up to the whole east coast of Italy. Then cross quickly to Genoa to get the ferry down back to sicily. We have in total 28 days to discover and enjoy the East Coast. Whenever I search for tips, this area of Italy is hardly ever mentioned by travellers. Our trip starts soon, on the 1st August 2019, this is a short notice, but such an opportunity came up and we’re grabbing it. Do you have some recommendations of the NOT To MISS places and fun activities with kids?

THANK YOU Lorraine

Hi Lorraine, Thanks for stopping by! There are not much info about the east coast because the sea is not exactly nice for our Italian standards. I personally prefer the west coast with the exception of some places in Calabria and Puglia (not sure what u mean by not covering the hill as Puglia is definitely on it ). If you can, don’t miss Rossano Calabro, and in Puglia, the Gargano (and the national park of course), the “Trulli” and I also suggest to also take a day or two were you don’t plan and take the car exploring the little coastal villages along the way. I remember in Rossano Calabro there is a massive aqua park your kid would love, it’s called Odissea 2000, that could be a great place for you to relax and the kids have some fun! Unfortunately, it’s been a while since I last visited Calabria and if it weren’t last minute, most of my friends are from Calabria and Puglia so they could give you the real local insights, if you reply to this, tell me so I might try to contact them and ask for more precise info! Cheers Clelia

Your article was really helpful, 16 Day Itinerary Italy looks different and so amazing in this article. It was such a good read. Thank you.

Very nice, thanks for sharing! A very good overview of how to explore the north/northwestern part of Italy!

Thanks David!

HOW COME U DINT TOUCH UP ON VENICE?? AND AMALFI COAST

Good question! Italy has so much to offer that if I had made an Itinerary covering from north to south I would have needed to write a book 🙂 A second article with an Itinerary from Rome to Campania Puglia and Basilicata (including the Amalfi coast) is coming up soon! As for Venice, believe it or not, I’ve never been there and I am not planning on going because I see it as a trap for tourists. My friends who used to live close to the city can confirm that. Venice is like Disneyland to me, nothing truly authentic has remained. It’s certainly beautiful judging from the pictures but as an Italian giving advice to tourists, first I wouldn’t recommend a place I’ve never visited myself in Italy and second, I’d rather say what I think and then leave the last decision to you guys! Which means that if you don’t mind Venice being not the real Italy, by any means, go on and visit it! 🙂

Great info, Clelia, Gracie! Your country is my favourite country in the World (and I have been to a lot of places).. I am of Indian origin but have lived in the UK for 25 years. I agree. I have been to most places in Italy including Sardinia and Sicily. My favourite so far is Puglia- we cycled for 8 days around Puglia last year, ! Sardinia (again cycling !) is my next favourite!. We are planning to drive to Tuscany in our new camper van from the UK (with our bikes), in August 2019. This information will really help us.

We don’t want to rush it.. We want to spend two weeks in the region covering Florence, Pisa, Siena, Cinque Terre and maybe Genoa or Turin on the way in or back from the UK..

The villages of Italy,the country side, the food, the beaches would take up most of our time. We’ll spend hardly any time in tourist traps – though there are unfortunately must -do’s on most itineraries – Pisa, Siena, Florence ! Most Italian cities like Venice are now groaning under the pressure of mass-tourism.which is sad. Head away from the crowds, experience the lovely people of Italy and cover once region at a time -come back often, . – for a life time… that’s our plan !

Hello Clelia, these itineraries are just amazing for a traveler. Is it budget friendly for a solo traveler or its better to be with a group tour?

Hi Lydia, Thanks for your comment! To be honest with you, it really depends! As a general rule (and solo traveler myself) it is always slightly convenient to travel with friends or as a couple, if only just to share the hotel room bill, car rental etc. But this doesn’t mean that you can’t go on the cheap by yourself. I have done both and the freedom of just deciding where and when to go is so amazing!

Italy can be super expensive but also very cheap, you just need to research a bit beforehand for the best hotels or hostels if you are flexible, train or buses instead of cars and you are in business! I was able to have a great holiday in Sardinia (which is well known for being quite expensive) when I was a penniless student!

As for the tours, I recently came back from an amazing trip to Australia and generally I prefer to go by myself because I like the freedom of decision but due to Australia being soooo expensive and other practical reasons, in the end, I decided to go by tour for a few things I wanted to see and it was AMAZING. If you travel solo you also have the opportunity to meet new fun friends and exchange life experiences along the way. So if you think a tour around Italy is better for you, by all means, book that if it’s your cheapest option!

If you need some advice about tours, let me know! Being Italian I can guide you to the ones I think are the best value for money! Cheers Clelia

Lovely Post. Italy such a wonderful place to visit. All the photos are very good. This is an informative post. Thank you so much for sharing the list. I would like to share with my friends.

Thanks Gary, feel free to share the beauty of Italy and try it for yourself of course! 🙂

I have been reading your posts regularly.I need to say that you are doing a fantastic job by posting information regarding Italian beautiful and tour places.I will bookmark your site Please keep up the great work.

Please note that as per my comments guidelines I had to remove the name of your business and the link. Thanks for your understanding. Kind Regards Clelia

Amazing photos and information. thanks for sharing this! Love Italy!

Thanks Gabbar!

Oh man what a post! Lake Como, the italian tastes, the eye-candy accommodation… Have mercy!

Ahahaha I know, right! I was drooling over MY OWN COUNTRY while writing this post! Italy is just so beautiful 🙂

Never thought about a road trip round Europe but this looks amazing. I would want to take in San Marino for sure.

Hey Craig! Thanks for stopping by! Just for the records… San Marino is truly beautiful and it’s not on this list just because even being in Italian territory it is a state of his own, not politically part of Italy, just like the Vatican is. I mentioned the Vatican just because it’s basically inglobated in the city of Rome, but I should point out that it’s also a state of its own 🙂

Great list of things to do, really loved Florence and can’t wait to get to Venice

I also loved Florence, a marvelous city full of art!

Went to Italy in 2016, was one of our favorite countries to visit, need to get back ASAP!

Sounds a great way of giving a treat to myself and my wife for our anniversary! thanks for sharing this post, Italy is really very amazing and awesome, I can’t wait to visit one day!!

Italy is always a treat for every occasion I guess 🙂

Love this article! Going to Europe for a 2 month road trip this summer. This Italy road trip will fit in perfectly with my plan. Thank you!

Thank you! Glad you enjoyed it and I hope you’ll have a fantastic trip to Italy! 😉

Thank you for the article. We are going to visit this country with my wife. Hotels and cars have already booked. It remains only to have a good time

Hey Dylan, if you have everything sorted out, I’m pretty sure you’ll have a wonderful time! I have a friend now on a trip to Italy and he is having the time of his life apparently 🙂

I’ve mostly been a UK and France traveler, but the more I see and read about Italy, especially the ancient cities … ! Thanks for a great post. Your photos are amazing! I’m off to see what airfare looks like for next season!

Hey Phill, being Italian myself I might be biased but a friend of mine is currently traveling around Italy and he is sending me pictures of everything he sees in absolute wonder, you have to put it on your bucket list!! 🙂

Thanks for an informative post, Clelia! It is very well-written, as well. I love how you included a video to teach your readers on how they can make use of Pruvo. Italy has always been a place to visit and explore for me but have not gotten the chance to fulfill at this time. It’s also nice that lots of airlines these days are getting better with air travel services and amenities. Kudos!

Thanks Elizabeth! I hope you will be able to take an epic road trip to italy very soon, you will not be disappointed! 🙂

This was a really interesting post, thanks for sharing your travel experience.

Italy is the perfect place to visit and I would love to explore it more. You captured awesome pictures on your travel trip. Thank you so much for sharing this post.. Loved this!!

Thanks Samy! Italy is indeed a beautiful country and I’m a very lucky girl!

Wow! This post sounds amazing.. Italy looks awesome to explore. There are so many things to do. Love your post. I will be definitely adding to my bucket list. Keep posting!

Thanks Sammy! Italy should be in everyone’s bucket list and a road trip to Italy even more! 🙂

I think everyone would like Venice in Italy. Venice was my favorite place where I would like to hang out with friends.

I can’t talk about Venice as it is one of the few places in Italy I haven’t visited. Mostly on purpose as I see it as a place that has no real locals but just tourists. The pictures are surely nice and the atmosphere and views too, but somehow it never was on top of my list of places to see in Italy! Maybe one day I will. Just to see if I was right or wrong about my feelings towards Venice.

Extremely informative and well written. 🙂

Thanks! A lot of work went into it! Now on with the second part… the beautiful southern Italy, soon to be published (soon can mean 1 week to a month!) lol

It’s obvious by the quality that much effort was exerted to produce the article. I look forward to what part two offers..

The second part will also be a hell of a job but so worth it as it will cover some of the best parts of southern Italy like the Amalfi coast, Puglia, and other lovely places!

Italy sounds different and so appealing in this post. Loved the detailing! It was such a good read. Thank you.

Thanks Reshmaty!

I appreciate your blog post, Thanks for sharing. Air travel gets easier with airline sophistication. Its invention has revolutionized the entire travel arena.

Not sure how talking about airlines is relevant on a road trip article… but thanks for stopping by anyway!

Italy is a perfect place to travel as every city is to beatiful and historical. My favorite was Florence from the very well known ones but as I prefer less touristic destinations I enjoyed Bologna too for the students vibe.

Yes, Italy is beautiful no matter where you go you will always find something special! I also loved Florence and Bologna, they are less overwhelming than Rome and Milan for sure (even if my heart will forever stay with the eternal city!). Not sure if you have visited San Gimignano and Lake Como but they are seriously jaw-dropping locations! Now I’m preparing the southern road trip from Rome to the Amalfi coast, super excited as I love that part too 🙂

You did a lot of work to make this post. Italy is very beautiful, especially if you travell alone, without any excursion groups.

Thanks Jenny, Italy is beautiful no matter how you decide to visit it. Some people like you love to discover it without any guide but in certain circumstances, I recommend the tours (or at least using the services to skip the lines) as if you don’t have much time they can truly save a lot of time and some guided tours are also worth it because being the guide Italian you will have a fun experience and you will not miss the best parts or waste time to find them 🙂 to each its own! The most important thing is to just pack up and come to Italy no matter how you decide to discover it, it’s just too beautiful 🙂

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The Best 2 week Italy Itinerary with Amalfi Coast (+ Map)

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Italy is an absolute must-visit for any world traveler. From the Colosseum in Rome and the sprawling Duomo di Milano in Milan to the ruins of Pompeii, there are endless sights and activities to take in. Whether you choose to spend your days exploring cities or basking on beach fronts, visiting iconic destinations such as the Uffizi in Florence, or scoping out Milan’s fashion scene, here is the perfect 2 week Italy itinerary with Amalfi Coast to see it all!

2 week Italy Itinerary with Amalfi Coast

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Italy has a little bit of everything—from its rich history and art to off-the-beaten-path markets, festivals, and small towns. 

You can explore pristine landscapes in Northern Italy like the Dolomites or Lake Garda, admire masterpieces by Michelangelo or Leonardo da Vinci, and revel in vibrant street performances in Florence. 

Here is a snapshot of 2 weeks in Italy itinerary,

• Day 1 in Rome: Explore Rome’s iconic landmarks (Colosseum, Roman Forum, wander through the neighborhood of Monti  in the afternoon/evening) 
• Day 2 in Rome and Vatican City: Head to the Vatican City. In the afternoon visit Sant Angelo, Trevi Fountain, Spanish Steps 
• Day 3 in Rome : Visit the Pantheon, Piazza Navona (or Villa Borghese). Start for Venice in the evening 
• Day 4 in Venice: Wander the San Marco plaza and visit its main attractions, go on a gondola ride
• Day 5 in Venice: Head to the Venetian Islands – Burano, Murano, and Torcello. Start for Milan in the evening 
• Day 6 in Milan : Explore the finest in Milan – Cathedral, Galleria Vittorio Emanuele II, The Last Supper, etc.
• Day 7 in Florence: Start for Florence, visit Accademia, Ponte Vecchio & Arno river banks
• Day 8 in Florence :  Another day in Florence. Visit Florence Cathedral, Uffizzi Gallery, Piazza Della Signoria , and later the Piazza Michelangelo for sunset
• Day 9 in Pisa : Day trip to Pisa from Florence
• Day 10 in Chianti : Day trip to Chianti from Florence
• Day 11 in Siena : Explore Siena for a day
• Day 12 in Pompeii & Sorrento : Start for Amalfi. You can keep Naples or Sorrento as a base (this will allow you to visit Pompeii on a half-day tour) 
• Day 13 in Amalfi & Positano : Explore Amalfi Town and Positano
• Day 14 in Capri Island : Hang out on Capri Island, enjoy the Blue Grotto tour

Planning a trip to Italy for first-time visitors

Visiting Italy for the first time can be a daunting task. It is easy to become overwhelmed with all of the things to see and do. Let us help with these essential planning tips, 

Getting to Italy 

It’s important to understand the geography of Italy – it is located on the continent of Europe in the southern part, with Rome as its capital city and Milan being its largest city. 

If traveling from overseas, particularly from North America or Asia, it might be wise to start in either Rome or Milan because each has an international airport with multiple flight companies that offer direct connections. 

Visitors with US and Canadian passports do not require a visa to enter the country and stay for 90 days; however, from 2025, an online authorization – ETIAS – is required prior to travel. 

Those who need entry visas may already have them, as the same visa used for visiting European or Schengen countries will typically get you into Italy as well. 

That said, there are numerous ways to explore this gorgeous land once you are here. 

We recommend train travel, whilst enjoying the convenience of its high-speed service when traveling across large distances or opting for cheaper regional trains when hopping between cities at a slower pace. 

You can also choose day tours that show off some of the very best of Italy’s many destinations in a short period of time. 

Starting this 2 week itinerary with Rome

Rome is the perfect city to kickstart this 2-week itinerary. Rome is served by the Roma Fiumicino Airport (which is the largest in the country), and the Ciampino Airport. 

From either airport, you can take a train to get to the city center – Roma Termini (the largest train station) and then take trains to other Italian cities. 

Getting to Rome city centre from the airport,

• From Roma Fiumicino Airport, get to the city center via direct train service –  Leonardo Express (30 minutes), or shuttle buses (40+ minutes)
• If arriving at the Ciampino Airport, then you can book this shuttle bus ride

Commuting in Italy

We used a mix of day tours and trains (high-speed and regional) for our sightseeing plans in Italy, and it worked out very well. 

• Eurail Pass for Italy is great for train travel in the country
• We also used a city pass wherever we stayed for 2 days or more like the Vatican and Rome pass which offers free admission to certain sites, and free unlimited public transportation along with a hop-on and hop-off tour. This pass is valid for 3 days.

Where to stay in Rome

Staying at a centrally located hotel in Rome is the perfect way to make the most of your visit. 

From Termini Station to Piazza Navona and Pantheon, there’s an amazing selection of places to explore on foot – no matter how short or long your trip may be. 

We stayed at Prassede Palace Hotel and walked to the Colosseum early morning for pictures. 

The hotel also had cafes and restaurants nearby which made breakfast easy! The rooms were spacious for two, and the staff was very helpful! Book your stay here

Other hotel recommendations: Leonardo Boutique Hotel Rome Termini | Condotti Boutique Hotel

Now, let’s go over the day-by-day Italy itinerary,

Day 1 of the 2 week Italy Itinerary: Explore Rome

For the first 3 days of your Italy itinerary, you will explore the prime landmarks of ancient Rome. 

In the afternoon and evening, wander the lanes of the Monti neighborhood, and check out numerous piazzas, trattorias, and cute shops! 

Because we stayed at the Prassede Palace Hotel in Rome we walked to the Colosseum and arrived there in 15 minutes at sunrise. We had enough time to take photos and enjoy the grounds before the crowds started. 

It is free to visit the Colosseum complex, but there is an entry fee to visit the interiors. There are different ticket access levels where you can visit various floors, the arena, and the underground. 

A ticket to the Colosseum also includes entrance fees for the Roman Forum and the Palatine Hill, with or without a guide. Here is a detailed guide to visiting the Colosseum

Colosseum Complex: Roman Forum & Palatine Hill

The Colosseum is an incredible work of ancient architecture, symbolizing the advanced engineering and historical greatness of the Roman Empire. 

With its impressive four-story structure, it could accommodate up to 50,000 spectators at a time – which is quite something considering when it was constructed (and completed in only a decade)!

The Colosseum was built by Emperor Vespasian in 70 AD and opened in 80 AD by his successor Titus. 

Today, this impressive monument remains an iconic sight for tourists visiting Italy. It’s an enduring reminder of Rome’s glorious past and its achievements in art, architecture, and engineering.

This guided tour offered us an amazing fast-track entry inside bypassing lines and crowds. However, what really made it special was that we had a knowledgeable guide on hand to explain each site’s history with background stories, trivia, and interesting anecdotes. 

This made our exploration even more interesting as it enriched our understanding of the sites; we highly recommend this tour!

We explored the ruins site, along with the Roman Forum and Palatine Hill. The Roman Forum is undoubtedly one of the iconic photo spots in Rome!  

While this site was once a bustling public square during the ancient Roman Empire, it was left to decay as the empire fell. 

Now, what remains is a beautiful ruin site, with some of its most impressive monuments standing tall despite their age. 

The columns of the Temple of Julius which stand testifying to its former grandeur, and the Arch of Constantine which make it an awe-inspiring sight even in its deteriorated state, are some fine examples. 

A walk around the Forum will transport you back in time and leave you mesmerized at how history has survived time’s test!  It is truly a must-visit spot for anyone visiting Rome!

Once you have had your fill of the Colosseum and the Forum, head over to the Palatine Hill located on one of the Seven Hills of Rome. 

This hill is not only the most popular but also it is steeped in Roman history and legend. Some notable facts include that it was the area where several Roman emperors as well as nobility resided. 

You can explore what is left of this district during guided tours .

Highlights of Monti neighborhood

Monti is a wonderful neighborhood in Rome that deserves to be explored for at least 3-4 hours in the afternoon. 

From sights to sounds and smells, there are so many attractions to discover along these narrow lanes. 

In particular, Monti is home to several local boutiques filled with fashionable clothes and accessories, making it the perfect place for a shopping spree of one’s own. 

Not to mention, you will also find unique places tucked away behind piazzas that serve up some delectable Italian cuisine. 

So pick a trattoria or a cafe and sit down for lunch. 

Then cool off with a gelato at the Piazza dell Madonna dei Monti, one of the popular squares in the city.

Next, make your way to Trajan’s Market . 

With nearly two thousand years of history, it’s no surprise that the prominent site has attracted tourists since ancient times. Halfway down Trajan’s Market lies the renowned Church of Santa Maria di Loreto. 

Commissioned by Pope Pius IV in the 16th century, this Baroque structure features a wonderful facade and numerous frescoes, which are only a few of the spectacular features here. 

The Colosseum stands at one end, while at the other end you can experience a whole different kind of grandeur; just head to Piazza Venezia and marvel at the sights from this great pedestal!

Finish sightseeing at the Quirinal Palace . Being one of the three current official residences of the Italian President, the palace has years of history attached to it. 

Located high upon the Quirinal Hill – the highest of Rome’s seven hills – this is a perfect spot for catching magnificent sunsets from the large piazza surrounding it. 

Day 2 of the 2 week Italy Itinerary: Explore Rome & Vatican City

On day 2 of the Italy itinerary, visit Vatican City and its prime attractions such as St. Peter’s Basilica, Sistine Chapel, and the Vatican museums with a guide. 

After exploring the Vatican, stop by the Castel Sant’Angelo for an hour, before making your way to the heart of Rome. 

Created in 1929 after the Lateran Treaty, the Vatican City as it is known today, is a worldly example of a European microstate situated within the boundaries of Rome. 

Famous for being the centre of Catholic church control and its Holy See, the small country has much to offer, and you can easily spend one day in Vatican City .

For the purposes of this Italy itinerary, we will spend half-day only. 

Now, you can get to the Vatican quite easily. 

Depending on where you are staying you can even walk to Ponte Umberto (bridge), over the River Tiber, and then arrive at Saint Peter’s Square. 

We took the sightseeing bus tour and were dropped off right in front of the Castel Sant’Angelo, and then we walked to the Vatican. 

We had a hop-on and hop-off tour included with our Rome Pass . 

Vatican City Highlights

Once at the Vatican, take the time to wander St Peter’s Square and take in the ambiance of this unique microstate. 

At the square, you will find the 3 main attractions of Vatican City that we will cover in this itinerary. 

Start at the St Peter’s Basilica, which is recognized as one of the premier structures in all of Europe. It is open to the public and free of charge. 

Drawing world-renowned architects like Donato Bramante, Michelangelo Buonarroti, Carlo Maderno, and Gian Lorenzo Bernini during its period of construction in the late 15th century, it is often celebrated as a masterpiece of Renaissance architecture. 

For centuries St. Peter’s Basilica has been seen as one of the holiest places in all Catholicism due to it being home to the burial place of Saint Peter. 

In addition to that, some of Christianity’s most beautiful art pieces can be found within this Basilica such as Michelangelo’s Pietà, his frescoes on the ceiling, and Raphael’s tapestries. 

Next are the Vatican Museums . With 26 distinct museums, beautiful ancient Roman and Egyptian artifacts, religious objects, brilliant artwork, and more – this complex is one of the largest public museums in the world! 

Of course, the standout highlight is the Sistine Chapel, hosting masterpieces by some of the biggest names in the Renaissance era; Michelangelo, Sandro Botticelli, Pietro Perugino, Pinturicchio, and Domenico Ghirlandaio. 

Due to its immense popularity with locals and tourists alike, we suggest booking a guided tour in advance – tickets can otherwise be hard to come by! Here is a 2 hour tour that you can book

After sightseeing, you can grab a bite to eat in one of the restaurants in the Vatican before making your way to Rome! 

Castel Sant’Angelo

The first stop after the Vatican is Castel Sant’Angelo.

Castel Sant’Angelo was originally constructed by Emperor Hadrian to serve as his mausoleum. It served this purpose until the 5th century, and later on, it was adapted into a fortress and a castle by the Pope. 

Today, you can visit Castel Sant’Angelo to explore its ancient history as well as discover some interesting pieces of art housed in its museum. Here is an entry ticket to the castle (visit for 1 hour). 

As you wander through its halls, you’ll find a permanent photographic exhibition featuring several works of Italian photographers over the 18th and 19th centuries. 

Be sure to admire the River Tiber and various bridges from the museum. 

Up next is the Trevi Fountain. Built in the 18th century and located in the center of Rome, Trevi Fountain is an iconic monument renowned for its beauty. 

This stunning Baroque masterpiece is the largest fountain of its kind in the city, featuring sculptures of gods and deities alongside a stunning waterfall effect, it’s no wonder that Trevi Fountain continues to be one of the most popular attractions in Rome. 

Although it will be crowded in the afternoon, you can still capture a crowd-free photo here from the sides of the fountain!

End the day’s itinerary at the Square of Spain or Piazza di Spagna . Climb the steps to get to the Trinità dei Monti church, atop one of the city’s hills. 

Take ample photos and then enjoy the lovely square. 

The Steps are a crowd puller, but here is another reason why you should visit the Piazza Di Spagna – and it is for its shops and restaurants, and the vibe that the square oozes – it is always bustling with activities! 

Here you will find high-end designer stores such as Prada and Gucci which line up this area’s beautiful pavements. 

And if you’re hungry, there are plenty of cafes, bars, and restaurants to enjoy an exquisite Italian meal whilst cradled by Piazza Di Spagna’s romantic atmosphere.

Day 3 of the 2 week Italy Itinerary: Explore more of Rome. Start for Venice

On day 3 of this 14-day Italy itinerary, visit the Pantheon, followed by the Piazza Navona (you can swap this for Villa Borghese and museums). 

In the evening, start for Venice. 

Start your day bright and early at the Pantheon. 

Originally built in 27 BC and then rebuilt by Hadrian in 126 AD, the iconic architecture of the Pantheon has withstood two millennia of history and still stands as a stunning example of classical design. 

Once a temple dedicated to many Roman gods, it is now a Catholic Church and it is completely free to explore. 

Set aside 30 minutes to an hour to visit the interiors and then sit down for coffee and croissant at one of the cafes located at the square. 

Being free, and a touristy site, visitors line up at the entrance 30-40 minutes prior to the gates opening – so we highly recommend heading there before 08:00 am to beat the rush. 

Piazza Navona

After the Pantheon, it is time to visit another popular spot in Rome – Piazza Navona . This piazza is another free attraction, and it is home to many beautiful Baroque architectures such as Bernini sculptures, and fountains. 

Wander the square, enjoy some souvenir shopping or take photos! If you like, you can chill out at the square with gelato! 

Alternate attraction: Instead of Piazza Navona, you can visit the Borghese Gardens (for free), along with the Villa Borghese (art museum) before bidding adieu to Rome!

Read : Our detailed 3 day itinerary for Rome

In the evening, start for Venice . We recommend opting for a high-speed train. It takes about 3 hours to get there. Regular trains take 3 hours 45 minutes. 

• Trains depart from Rome Termini Station and arrive at the Venezia Santa Lucia . 
• Driving takes 6+ hours, one way. 

Where to stay in Venice? 

For a short trip to Venice, we recommend staying by the Grand Canal or the Saint Lucia Station. If you are looking for budget options, the neighborhood of Mestre is a good option.

On our very first trip, we stayed at the Campanile Venice Mestre and loved it. The room was spacious and the Grand Canal was a short bus ride away. It was a mid-budget property, which was very well-maintained and clean.

Lots of nice places to eat around, but nothing fancy though. 

Here are some hotel options in the heart of Venice : Palazzo Veneziano – Venice Collection | Hotel Campiello  

Day 4 of the 2 week Italy Itinerary: Sightseeing in Venice

Enjoy your first day in Venice with a nice breakfast by a canalside cafe. We were up bright and early, and enjoyed the quiet canal lanes in the morning. 

After breakfast, we head to the landmark San Marco Piazza to check out the St Mark’s Basilica, Campanile tower, and the Doge Palace. 

We highly recommend joining a 3-hour guided tour like this one – Piazza San Marco, and the Doge Palace tour to cover all the important sights. 

Piazza San Marco and highlights

San Marco Piazza inspiringly combines stunning architecture, incredible views, and a one-of-a-kind atmosphere, making it an absolute must for any traveler to Venice. 

The centerpiece of the square is none other than St. Mark’s Basilica – an iconic structure of incomparably beautiful Byzantine design and gold mosaics; climbing up the Campanile bell tower that stands right beside it, will reward you with spectacular views of the city. 

St. Mark’s Basilica is one of the most beautiful churches in the world. Although it is not the oldest or the largest church in Venice, its Byzantine architecture and stunning interiors pull any traveler to it. 

With its intricate designs and beautiful setting on the waterfront, St. Mark’s Basilica is a must-see for anyone visiting Venice.

Doge Palace is another iconic building in Venice. The palace was originally built as a residence for the Doge or the administrator, and over the years the palace complex has been extended and modified. 

With a guided tour, you can visit the museum and its art galleries, as well as check out the opulent rooms. 

We recommend booking a 3 hour tour of the complex which includes a combined guided tour of the Doge’s Palace & St. Mark’s Basilica.  

The tour also walks you to the Bridge of Sighs. The Bridge of Sighs is one of the popular Venice Instagram spots.

As part of this tour, you can also climb to the San Marco bell tower and take in the views of Venice and the waterfront area. With a ticket, you can go up and down the bell tower exclusively via lift (no steps). 

Note that in some months, due to extreme weather conditions, access to the tower may be suspended.

Next, wander the waterfront of San Marco Square. 

But don’t leave without stopping by one of the two popular cafes at St Mark’s Square – Caffè Lavena or Caffè Florian – the latter being particularly worthwhile since it dates back all the way to the 18th century. 

After a quick stop at the cafe, walk along the Riva degli Schiavoni , which is the waterfront area of Venice. This location is perfect to capture everything that Venice is known for – waters, gondolas, and beautiful architecture! 

You will see the San Giorgio Maggiore Church from across the canal, which is breathtaking. 

Read : How to spend one day in Venice

Lunch and Rialto Bridge

Plan to get to the Rialto Bridge next. The Rialto Bridge is one of the most famous and beautiful bridges in Italy. 

It spans the Grand Canal and connects the San Marco and San Polo districts in Venice. 

The bridge dates back to 1524 when it was built to replace an older wooden bridge that collapsed. The current version of the Rialto Bridge was completed in 1990 after being destroyed by fire during World War II. 

We recommend sitting by the Rialto Bridge for lunch, choosing a restaurant or cafe – opposite Riva del Ferro, or by the promenade. 

It is touristy, and maybe a little pricey but it was so amazing to sit by the canal, and enjoy a pizza and wine whilst taking in the bustle and hustle of the surroundings!

Go on a gondola ride

Late afternoon (after lunch) instead of walking, go on a gondola ride in Venice ! This still remains to be one of our favorite memories from our first Italy trip. 

You can choose a private ride (35-45 minutes) , or a shared gondola ride (shared by 5 other guests with or without a commentary). 

We opted for a private gondola ride with a photoshoot, and it was a beautiful experience. 

With a gondola ride, you can see all landmarks and quiet alleyways from the comfort of your seat. This will really allow you to appreciate the beauty of Venice – a city built on canals!

A gondola experience can be expensive when booking a private tour, but you can save money by booking a group ride. GetYourGuide runs specials on rides, so do check it out.

T Fondaco Rooftop Terrace 

After the ride, head over to the rooftop of T Fondaco – a shopping complex where you can enjoy an amazing view of the city from above. This is perfect during sunset!

T Fondaco is located near the Rialto bridge, and it is completely free to visit the terrace (but it does require you to reserve a time slot online). 

Alternate sightseeing: San Polo District and Castello district

If you are not keen on the gondola ride, feel free to swap that for a walking tour of the San Polo district.  

This district is located on the west end of San Marco and across the Grand Canal (via the famous Rialto Bridge).

You can visit the Basilica of Santa Maria Gloriosa Dei Frari and the Church of San Giacomo di Rialto. There are lots of places to hang out and eat dinner in the district. 

From San Polo, you can also explore the Castello district. The neighborhood of Castello is the largest of all the districts, and it borders St. Mark’s Square and is home to luxury hotels, as well as some casual bars. 

Here you will find the Instagrammable Libreria Acqua Alta (bookstore). The shop means, “Book Store of High Water” and it is one of the popular places in Venice for its unique ambiance. 

Day 5 of the 2 week Italy Itinerary: Visit the Venetian Islands, then start for Milan

On day 5, go on a half-day tour to the Venetian Islands. We took a guided tour, but you can plan this yourself. In order to get to the islands, water buses or Vaporetto is the main mode of transport. 

Here is the 5.5 to 6 hour day tour that we booked, and we left on a motorboat from the St Mark’s area. 

We recommend starting early (right after breakfast) to make the most of your day.  

Just off the coast of Venice, are the three islands of Burano, Murano, and Torcello .

Burano is renowned for its brightly painted houses, often in pink and rainbow hues, while Murano is famous for its glassworks. 

On a visit to Torcello, you can observe many ancient sites such as a 7th-century cathedral and bell tower which were built using local limestone. 

Each island is located a 15 to 20-minute ferry ride away from one other. You will find sightseeing attractions as well as restaurants where you can grab a bite to eat. 

We particularly loved Burano’s colorful quarters, and also visited the glass-making factory in Murano and picked up a few souvenirs. 

Each island offers its own unique attractions, and you can spend a couple of hours in each, before returning to Venice by evening (to get to Milan by train). 

Start for Milan in the evening: Milan is served by the Milan Malpensa Airport, which is one of the busiest airports in the country. 

But because you are in Venice you can take the high-speed train and get to Milan in about 2.50 hours.

• Trains depart from Saint Lucia Station in Venice and arrive at the Milan Centrale  
• Driving takes 3 hours, one way

Where to stay in Milan?  

For a short trip, we recommend staying at the center (Zone 1 of Milan or near the Duomo), or Milan Centrale Station. 

We stayed near the Central Station at the c-Hotel Atlantic Milano and it was perfect. Rooms were spacious for two, and there were lots of affordable restaurants nearby. 

Other hotel recommendations : Starhotels Anderson | Park Hyatt Milan  

Day 6 of the 2 week Italy Itinerary: Explore Milan

We enjoyed exploring Milan, and we think it is a perfect base to explore the Lombardy region and other places in the northern part of Italy including Lake Como and Cinque Terre villages, or travel all the way to the Principality of Monaco .  

For this 14-day Italy itinerary, you only have one full day to explore, and we will cover the primary city landmarks!

Milan Cathedral

The most important attraction in Milan is its Duomo. We highly recommend starting at the cathedral in the morning, and if you want the best photos then be there at sunrise or at least before 08:00 am. 

It is a 7-minute ride from c-Hotel Atlantic Milano , where we stayed.

Duomo di Milano is the largest church in Italy, the second largest in Europe, and the third largest in the world! 

Along with being the most iconic landmark of the city, it has quite a remarkable history; it took almost six centuries to build but now stands as one of the prettiest cathedrals in Europe! 

Visiting the Duomo is not free, you can book the tickets here . 

Although from the outside you can only witness part of its grandeur, visiting the rooftop offers expansive views and gorgeous terraces to wander, and we highly recommend adding this to your one day in Milan itinerary .

Set aside 1-3 hours here including exploration time at the archaeological site located underneath the Duomo.  

We booked our cathedral tickets with rooftop access by lift and the archeological and museum site. You can book the tickets here

Up next is the Galleria Vittorio Emanuele, one of the oldest shopping arcades in the world. And it is located just in the Piazza Duomo, and there are cafes and restaurants nearby where you can stop for brunch or lunch!

Spend time inside the Galleria and admire all the beautiful ceilings and if interested pop by designer shops – you will find all the major designer brands here including Prada Milano!

The Last Supper, hop on and hop off tour, shopping

After lunch, make your way to see Leonardo da Vinci’s The Last Supper. It is located in Santa Maria Delle Grazie and is a popular attraction in the city. 

Do book tickets to the Last Supper early to avoid disappointment.  

We recommend using the Hop-on and Hop-off tour to get to Santa Maria Delle Grazie, and along the way see the Sforzesco Castle and in the evening get down at the Sempione Park . 

If you wish to go shopping, then you can skip the park and instead head to Via Montenapoleone and the famous Quadrilatero Della Moda. 

Read : How to explore Rome Florence Venice in one week in Italy itinerary

Day 7 of the 2 week Italy itinerary: Arrive and explore Florence

On the morning of day 7 of your Italy itinerary start for Florence in Tuscany. 

There are 20 direct trains from Milan to Florence each day, and when you stay by the Milan Centrale catching an early morning train will be a breeze (plus there are lots of coffee shops inside to warm up).

Getting to Florence,

• Milan to Florence by high-speed train is less than 2 hours
• Driving time is 3.50 hours+

Where to stay in Florence?

We recommend staying at the center of Florence for this itinerary. Firenze Santa Maria Novella or Stazione di Santa Maria Novella (train station) is located within walking distance of the centre. 

We stayed at the La Terrazza sul Duomo B&B and which had amazing views of the Florence Cathedral from its terrace. 

You can access the rooftop at any time of day for sunset views, coffee, or pizza time! The boutique B&B was clean with a private bathroom and their breakfast was very generous too. 

Other hotel options: Grand Hotel Cavour Florence | Hotel Vasari

Florence is one of Italy’s hidden gems, a beauty that cannot be matched. An amazing range of art and culture awaits visitors in this ancient city, making it unlike any other. 

It is the birthplace of the Renaissance period and its streets are filled with inspiring markets from that time; iconic sights such as Piazza Della Signoria boast awe-inspiring creations like Michelangelo’s David, while other world-renowned museums hold unforgettable masterpieces by Da Vinci, Botticelli, and Raphael. 

Galleria dell’Accademia

With half day for sightseeing in Florence (on day 7), check off one of the museums – Galleria dell’Accademia. This is where you will find the statue of David and other art exhibits. 

You must book a timed entrance ticket ahead of time to avoid disappointment. Set aside 1.50 hours to visit and see everything inside the Galleria dell’Accademia. 

In the evening, wander down cobblestone streets lined with large open-air markets and vibrant cafes and then take a leisurely stroll along the Arno riverbank taking in its many famous bridges. 

Ponte Vecchio , a medieval arch bridge, built over the Arno River is an important city landmark, so don’t miss it. 

For dinner, head back to the Duomo area. There are small trattorias where you can grab a drink, pizza, and tiramisu. 

If you like to shop, you will find a lot of high-end designer brands as well as affordable labels in the city centre. 

Day 8 of Italy Itinerary 2 weeks: Explore more of Florence  

Spend the next day in Florence exploring another Renaissance museum and this one is quite popular as well. 

The Uffizi Gallery in Florence is every art lover’s paradise! This amazing Renaissance-era gallery houses some of the most beautiful and esteemed pieces of artwork in the world, from centuries past to ones still being produced today. 

From Giotto and Raphael to Boticelli and Michelangelo, many historically significant Italian painters are represented here. 

You can view ancient sculptures, cultural masterpieces, precious religious artifacts, and stunning medieval frescoes in the gallery.

You will need at least 3+ hours at the Uffizi Gallery. We highly recommend booking tickets ahead of time as it gets sold out for weeks. Here is where you can book your tickets.

From the Uffizi, make your way to the Piazza Della Signoria, which is a large public square. This piazza is surrounded by iconic Florentian landmarks such as the Palazzo Vecchio (which is a town hall today), a copy of Michelangelo’s David statue, fountains, and other stunning statues.  

You can sit down at a trattoria by the square – there are sit-down cafes to casual bars where you can grab a bite to eat. 

In the afternoon, you can visit Museo Galileo – perfect for science lovers. This museum is housed in an 11th-century building known as Palazzo Castellani. 

The collection dates back to the Medici and Lorraine Grand Dukes’ era and includes some originals belonging to the great astronomer himself. Book your entry ticket here

Another option is to go shopping or wander in and around the pretty Piazza Della Repubblica. This is the Roman heart of Florence and the main square in the city, and it is surrounded by shops and cafes (you can also stop here for lunch if you like).

The Column of Abundance is located here and it marks the area where the Roman Forum once stood. This column dates back to 1431.  

Piazza Michelangelo

From the heart of the city, make your way to Piazza Michelangelo. It is a short walk or a hike to get there, but it is all worth it for the views! 

You can also get to the entrance of the viewpoint by bus or taxi, and there are small cafes and a parking area. 

Piazza Michelangelo is a free attraction and we highly recommend visiting for sunset. The entire city of Florence with its iconic landmarks will greet you from this viewing platform!

Read : 2 days in Florence itinerary | 3 day Florence itinerary

Day 9 of Italy Itinerary 2 weeks: Day trip to Pisa from Florence

Keeping Florence as a base, embark on a few day trips to explore more of the beautiful Tuscany region ( we will share tips to customize this 2 week Italy itinerary below if you do not wish to spend a lot of time in Tuscan y). 

Now, Pisa is located approximately 90 kilometers (56 miles) from Florence, and the best way to get to Pisa is by train. 

It is home to centuries of history, culture, and heritage and is a must-add to your 2 week Italy itinerary.

Getting to Pisa from Florence

• Trains take about an hour and 20 minutes
• Day tours are a great option for getting guided sightseeing, and round-trip transportation

Once you’re in the city, getting around is easy; everything is within walking distance of the Leaning Tower. Pisa is quite a compact city so the best way to explore it is on foot.

Things to Do in Pisa

From the iconic Leaning Tower of Pisa to a variety of museums and historical sites, there is no shortage of things to do in Pisa. 

The Leaning Tower of Pisa : 

Of course, no trip to Pisa is complete without seeing the famous Leaning Tower. This bell tower was built between 1173 and 1372 and is one of the most recognizable landmarks in all of Italy. 

You can climb the 294 stairs to get a spectacular view from the top or simply admire it from the ground. 

Being a popular attraction, lines start forming as early as 9:00 am and don’t get any shorter all through the day. 

We highly recommend buying skip-the-line tickets, especially since you are going to be in Pisa for just a day.

Here are the tickets – Combined ticket to Leaning tower of Pisa and Cathedral

You can also book a guided tour of the Tower (tickets extra), the Cathedral, and the Baptistery

Piazza dei Miracoli: 

The cobblestone streets surrounding this large plaza are home to several iconic monuments and structures including the Leaning Tower, Pisa Cathedral, and Baptistery. 

This square has been declared a UNESCO World Heritage Site due to its unique architectural beauty. 

Pisa Cathedral:  

This Romanesque-style church dates back to 1092 and features beautiful marble sculptures throughout its interior. 

It also houses many important works of art such as mosaics, frescoes, and stained glass windows that are worth checking out during your visit.

Cemetery Campo Santo:  

This cemetery is one of the seven UNESCO World Heritage Sites in Tuscany. The interiors of Camposanto are an example of early Renaissance art which adorn the walls of the impressive buildings of the Camposanto. 

There is an entry fee to get inside, and here you can also see the ancient Roman sarcophaguses and frescoes of the Master of the Triumph of Death.

Santa Maria della Spina:  

The Santa Maria della Spina is a small Gothic church located on Lungarno Gambacorti on the banks of the river Arno.

Here is a detailed one day in Pisa itinerary to help you plan your trip! With so much natural beauty combined with rich cultural heritage, it’s no wonder why people love visiting Pisa every year. 

Day 10 of Italy Itinerary 2 weeks: Day trip to Chianti from Florence

Day 10 of the Italy 2-week itinerary is all about taking it slow and enjoying rolling hills, picturesque vineyards, and delicious wines in Tuscany, the birthplace of Chianti. 

Tuscany has long been known for producing some of the world’s best wines, and Chianti is no exception. This full-bodied red is made with a blend of Sangiovese grapes grown in the villages surrounding Siena and Florence. 

You can book a guided wine tour that includes pick up and drop off from your Florence hotel. 

Depending on the chosen tour, you’ll explore several different types of Chianti, from traditional Tuscan blends to super-Tuscan versions made with other grape varieties like Cabernet Sauvignon or Merlot. 

Some tours such as this one also include a light lunch.  

Other than sampling you can also visit vineyards and talk to experts – learn about the history and culture behind them. 

You’ll get an inside look at how local winemakers craft their wines using traditional techniques passed down over generations. 

We enjoyed our wine-tasting tour, and it was a fun way to explore Tuscany, take it slow and also taste some great Chianti wines.

Day 11 of Italy Itinerary 2 weeks: Explore Siena for a day

The Tuscan city of Siena is an old-world city teeming with rich culture and history. This beautiful Italian city is full of winding streets, stunning architecture, and delicious food. 

It’s the perfect place to explore for a day or make your home base while traveling through Tuscany. 

Siena can be easily visited from Florence,

• Florence to Siena is 1.25 hours by train
• You can also get to Siena by bus . Buses leave right outside the Santa Maria Novella station in Florence and cost around the same as a train ride
• Day tours combine multiple stops in Tuscany from Pisa, Siena, Chianti, and San Gimignano

Here’s all that you can discover in one day in Siena, 

The Piazza del Campo: 

This world-famous square in the heart of the city is the main attraction in Siena. 

It dates back to medieval times and hosts many festivals throughout the year, like the Palio di Siena horse race which has been running since 1659 (when it was formally organized). 

The race is held twice a year in the summer months of July and August. 

In addition to its tourist attractions at the piazza, it also offers plenty of cafes and restaurants where you can enjoy a traditional Italian meal or just watch the locals go about their daily lives. 

Visit Siena Duomo (Cathedral):  

The Duomo dates back to 1196 and features intricate marble floors and frescoes as well as breathtaking stained glass windows. 

To enter the cathedral, you can book a Cathedral guided tour that covers the Cathedral, Piccolomini Library , Museum, Panorama and “Duomo Nuovo”, Crypt, Baptistry, Beneath the Cathedral, and Gate of Heaven (which is at the very top of the cathedral). 

Explore museums : 

Siena has a number of fascinating museums which are perfect for art lovers or those looking to learn more about Italian culture and history. 

Head to the Museo Civico , located on the first floor of the city hall – Palazzo Pubblico to learn about Siena.

Then there is the Museo della Tortura aka Torture Museum, just a few steps from Piazza del Campo – all showcasing the unique history and culture of Siena!

Right across the Duomo is Santa Maria Della Scala , a museum. It was a medieval hospital before and is considered to be one of the oldest in Europe. 

You can discover fresco-laden hallways, archives of archaeological finds, and exhibits in the hall of relics. 

Here is a detailed guide to spending one day in Siena

Traveling to Rome and then the Amalfi Coast:

In the evening of day 11, start for Rome and stay there overnight. This will allow you to connect to Amalfi/Sorrento for the last leg of your 14 day Italy itinerary.

We are traveling from Florence to southern Italy via Rome to break the journey and make use of time for sightseeing on day 12. 

You can also travel by train overnight to get to Sorrento (a 7 to 8-hour ride). 

Another option is to stay back in Tuscany and explore more of the region (and even travel to San Marino – we will discuss this in an alternate trip sample below). 

Read : Rome and Amalfi Coast itinerary 7 days

Day 12 of Italy Itinerary 2 weeks: Start for Amalfi from Rome. You can keep Naples or Sorrento as a base (this will allow you to visit Pompeii on a half-day tour) 

After arriving in Rome make your way to the south. We recommend keeping Sorrento as a base and then exploring the Amalfi Coast. 

If interested, this is the perfect opportunity to stop by Pompeii and Naples before checking into your Sorrento hotel. 

• Rome to Sorrento: Trains from Rome to Sorrento via Napoli Centrale and Napoli P. Garibaldi take around 3.50 hours. Flixbus offers routes that take around 4.50+ hours, one way. 
• Rome to Pompeii is 240 km (149 miles) away. The easiest way is to take a train from Roma Termini station directly to Pompeii Scavi-Villa dei Misteri station, which is located right outside the archaeological site. The journey takes about 2 hours via high-speed trains, and tickets can be purchased at the train station
• Pompeii to Sorrento train station is 30 km (18 miles) away. It will take about 30 minutes to arrive in Sorrento

Once you arrive in Pompeii, set aside 3 hours to explore the archealogical site and grab lunch/food before starting for Sorrento. 

Although the city of Pompeii was destroyed by a volcanic eruption in 79 AD, it has been remarkably well-preserved due to the thick layers of volcanic ash that blanketed the city. 

Today, Pompeii is one of the most popular tourist destinations in Italy, and it’s easy to see why. A visit to Pompeii is like stepping back in time – there are numerous homes, temples, public baths, and more to explore, all well-maintained and full of treasures.

Be sure to visit the Roman Forum, which was the main square in Pompeii where people would gather to socialize and do business. 

When you are short on time, a guided tour will be super handy!

Plan to arrive in Sorrento by evening, and check in to your centrally located hotel like the Elys Suites . 

After that, head outside for a walk in the city centre and enjoy your dinner in Sorrento. 

Tip: You can also skip Pompeii, directly arrive in Sorrento and explore the city, and make arrangements for sightseeing on the Amalfi Coast.

Tours: You can visit Pompeii from Sorrento and back as well, on a day tour

Where to stay on the Amalfi Coast?

There are countless hotels and Airbnbs on the Amalfi Coast. However, we recommend keeping Sorrento as a base. 

We will share our favorites below,  

• Elys Suites (Sorrento) : Elys Suite is centrally located and each room has its own balcony and is spacious inside. The hotel is located in the central part of the city, and from here you can easily get to sightseeing in Sorrento and beyond. Book your stay here
• Other places to stay in Sorrento:  Hotel Regina Sorrento (with a view) | Sorrento Pool&Suites (affordable) 
• Terrazza Duomo (Amalfi town) : Amalfi Town is a good spot to call home and this one, in particular, is located by the Cathedral, and you can also book rooms with views of the piazza and the Duomo. Click to check availability here
• Rosa e Valentino (Ravello) : Another village where you can stay overnight is Ravello. Rosa e Valentino is a simple accommodation for a comfy stay. They offer a buffet breakfast, and you can even rent bicycles from the property. Check prices and book your stay here

Day 13 of Italy Itinerary 2 weeks: Explore Amalfi Town and Positano

Soak in the beautiful cliffside views of the Amalfi on days 13 and 14 of your Italy itinerary. Start for Amalfi town and Positano from Sorrento. 

You can use public transportation (bus, ferry) or you can book a day tour that covers both towns from Sorrento. 

Getting to Amalfi and Positano:

• From Sorrento to Positano , ferries depart approximately every two hours and take about 40 minutes to get there
• After exploring Positano, you can take the bus to get to Amalfi town (one-hour bus ride) Or a taxi will take you there in 30 minutes
• Day tours: There are lots of day tours available from Sorrento to Amalfi and Positano, such as this one
• You can also add a third village such as Ravello on a day tour

Day tours are great if you want a guide to take you around, without having to figure out all the parking and public transportation routes. However, if your plan is to relax at the beach, then this will not work for you – as tours are slightly fast-paced. 

Things to do in Positano and Amalfi town

Rent a sunbed and enjoy the sun at the Spiaggia Grande or Laurito Beach in Positano. 

Spiaggia Grande is the main beach of Positano (also known as Positano Beach or Marina Grande), and it is located super close to the city center. 

You can rent sunbeds and umbrellas for around 20 euros. You will also find a restaurant here along with shower stalls and washrooms. 

You can also opt to eat at any of the cafes with water views such as Il Tridente or La Terra to enjoy a nice Italian meal!

Beyond the beaches, there are landmarks such as the Santa Maria Assunta which you can visit. 

You must set aside the second half of the day for Amalfi town. Positano to Amalfi town is 40 to 55 minutes by road. 

If Positano was super crowded, you can also rent an umbrella or sunbed at the Spiaggia Grande Amalfi beach here. This beach is located by the SITA bus stop, and it also has a small free area.

You can also walk the waterfront area and later go sightseeing. 

Amalfi Duomo is one of the primary cultural highlights on the coast. This cathedral dates back to the 9th century and boasts a stunning exterior with large arched windows and intricate mosaics adorning the facade. 

The entry fee is 3 euros, and it is worth spending time to see the inside. 

There are tons of cute trattorias and decades-old baked shops where you can savor local delicacies such as the Pasticceria Pansa. 

Read : One day in Amalfi itinerary

Day 14 of Italy Itinerary 2 weeks: Hang out on Capri Island, enjoy the Blue Grotto tour

On your very last day in Italy, enjoy a small group tour of Capri Island , and the Blue Grotto from Sorrento. 

Gorgeous Capri Island is known for its glamor and glitz on the coast with its blue waters dotted with yachts. 

People from all over the world including celebrities flock to the area to unwind on the beaches and the villas. 

With this day tour, you will get to explore this unique place and also enjoy an excursion to the Blue Grotto. 

The tour includes a ferry ride to Capri where you will explore the island along with the Natural Arch and the Faraglioni Rocks, and then visit the Blue Grotto on a boat.  

Being a full-day tour, you will also have time for a swim and go snorkeling. Snacks are also provided onboard. 

This excursion includes pick up and drop off from your Sorrento hotel and when back, you can return to Rome to fly out. 

Read : 4 day Amalfi Coast itinerary

2 weeks Italy Itinerary Sightseeing Map

14 day Italy Itinerary with Cinque Terre and main cities

The above Italy itinerary for 2 weeks covered the best of cities, and beaches with the wine region. There are some days when overnight or evening travel will be needed to make the most of your visit. 

If you wish to take it slow, we recommend keeping 3-4 cities as a base and then taking day trips to explore more of the region. 

In the itinerary below, you will be able to keep Milan as a base city to visit the Lombardy region and also take a day trip to Monaco . 

It also gives you 3 full days in Cinque Terre so you can hike and explore all 5 villages with ease. 

It, however, doesn’t include any time in Tuscany or the Amalfi Italian coast. 

Visiting Cinque Terre: Quick tips

The beautiful coastline of Cinque Terre is known for its picturesque views, colorful cliffside houses, Mediterranean climate, and delicious food. 

It is a region located on the Italian Riviera in Liguria. 

The name translates to “five lands,” which refers to the five villages that make up the area— Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. 

The villages are connected by a network of trails that offer breathtaking views of the Mediterranean Sea and nearby vineyards. 

How to get to Cinque Terre:

The best way to get to Cinque Terre is by train from cities such as Milan or Florence. The villages are on the Genoa – La Spezia line, with Monterosso being the only one served by long-distance Intercity trains.

• Milan to Cinque Terre is 3+ hours by train
• Driving takes about 2.50 hours

There is no shortage of things to do in Cinque Terre! From hiking on one of the many trails that connect the villages together to sunbathing on one of its many beaches, you can make your trip as active or as relaxed one as you like. 

Cinque Terre is also compact as compared to the Amalfi Coast, and here you can also explore some of the local wineries or take part in some water sports like kayaking or snorkeling around Manarola’s harbor. 

14-day Italy Itinerary with Tuscany and main cities

This 14-day Italy itinerary excludes any beach time and focuses on city sightseeing and cultural experiences. 

It is not super fast-paced as you can keep Florence as a base to visit Tuscan villages in one week of your 2-week trip. 

About San Marino:

San Marino is a European microstate and you can explore it from Florence (via Rimini) using trains. Here is a detailed guide to transportation from Florence to San Marino . 

Alternatively, if you would like to swap any of the day trips from Florence above, you can visit Cinque Terre on a day tour. More details here

Read: Most beautiful cities to add to your Italy bucket list

Italy Travel Guide

Planning a trip to this amazing country should be an exciting experience, but it can also be overwhelming if you don’t know where to start. 

Fortunately, we’ve got some tips to make planning your Italian holiday a breeze. Let’s take a look at what you need to do before booking that flight! 

Step 1: Pick your Destination(s) and Accommodations 

The first step when planning any trip is deciding where you want to go and where you want to stay. Are you looking for a romantic getaway in Venice? Or would you rather explore ancient ruins like those in Pompeii? 

Based on your personal style you can customize any of the 3 itinerary samples above. 

Once you’ve selected a destination, we recommend making hotel or Airbnb reservations early to avoid disappointment.  

Step 2: Consider Your Transportation Options 

Once you know where you want to go, it’s time to think about how you plan on getting there. 

Rome and Milan are perfect entry points to the country. 

But…Italy also has several major airports and high-speed trains that make traveling between cities relatively easy. 

You could also rent a car and navigate around the country on your own schedule if that appeals more than relying on public transportation. But keep in mind in most cities and even on the Amalfi driving, and parking are a hassle. 

Instead consider small group tours to make the most of your visit. 

Whatever method of transportation works best for your needs, be sure to book it as soon as possible so that everything is set for when you arrive. 

Step 3: Make Plans for Sightseeing and Activities 

Italy is full of historical sites, beautiful scenery, delicious food, and other attractions worth exploring while visiting the country. Research which places are must-sees during your stay—and then make sure they are part of your itinerary! 

Book tickets ahead of time if necessary (or make reservations) so that nothing gets missed during your travels. 

And don’t forget about booking tours with local guides who can provide insider knowledge into the areas being visited. 

Step 4: Budget  

You can make your trip to Italy as affordable as you want, or splurge! 

Italy is not one of the most expensive countries in Europe, and by visiting in the off-season and choosing smaller towns to explore you can keep your travel expenses low. 

• Plan ahead: By planning ahead for your trip to Italy, you can save hundreds (if not thousands) of dollars. Booking flights and accommodations in advance is one way to save money, as is researching restaurants and attractions before you leave home. 

• City transport passes: You can also take advantage of discounts offered by certain hotels and attractions if you book far enough in advance. Additionally, many cities throughout Italy offer discounted passes for multiple attractions—be sure to look into these before booking individual tickets for each attraction separately. 
• Be flexible: We do recommend staying at a centrally located hotel, but this will require a moderate budget. If you want to keep expenses lower, you can look at hostels or Airbnbs outside major tourist centers. Note that cities charge a tourist tax, which is levied per person, per day in hotels. It is to be paid in cash when you check out. Tax amount varies by the city administration.
• Eat Like a Local: Eating is one of the best ways to immerse yourself in the culture when traveling abroad—and it doesn’t have to break the bank either! One way to save money on food without sacrificing quality is by eating like a local whenever possible. Instead of dining at touristy restaurants with inflated prices, hit up local cafes (trattorias) for cheap yet delicious meals that will give you an authentic taste of Italian cuisine (and maybe even some insider tips from locals). A coperto (charge of 1-3 euros) is real, and it is usually added to any sit-down restaurant or where servings of bread and, oil is made available at the beginning of the meal.  

Step 5: Packing for your trip to Italy 

Here is the Italy packing list to ensure your trip is stress-free and enjoyable. 

• Clothing: Since each region of Italy has its own climate, it’s important to pack accordingly. For summer trips, light layers are best, such as cotton shorts and t-shirts during the day, and a lightweight jacket for cooler evenings. 
• For winter visits, pack warmer options like jeans, sweaters, and a coat or jacket with a hood that can protect from rain. You may also want to bring an umbrella if visiting during the rainy season (November –February). 
• When it comes to shoes, comfortable sneakers are essential for sightseeing all day long – but don’t forget dressy shoes if you plan on going out at night! 
• And sun protection essentials – hats, sunglasses, and sunscreen are must-haves! 

Other travel essentials 

In addition to clothing necessities, here are some travel essentials that will come in handy while traveling around Italy: 

• a good camera
• reusable water bottle
• Universal adaptor
• phone charger
• passport/visa documentation (if required)
• credit cards/cash; medications/first aid supplies

Italy is a beautiful country teeming with vibrant culture, exquisite cuisine, and spectacular sights. 

From the bustling streets of Rome to the peaceful canals of Venice, there’s so much to explore! 

And don’t forget to sample as much of the local cuisine as possible—olive oil-based kinds of pasta and fresh seafood are must-tries! 

No matter what type of traveler you are, an Italian vacation will provide an unforgettable exploration into one of Europe’s most treasured countries.

Pin: 2 weeks in Italy itinerary with Amalfi Coast: Italy Travel Guide

Mayuri is the founder & editor of ToSomePlaceNew. An Indian-Canadian globetrotter, she has traveled to over 100 cities and 40+ countries.

Mayuri has a graduate degree in History and is an MBA. She loves traveling the world particularly Europe, capturing historical nuances, and discussing that over a cup of coffee with her husband, Salil. 

She has lived in Portugal, Canada and India.

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2 Weeks in Italy: The Perfect Guide From Napoli to Sicily

Please note that some of the links may be affiliate links , and at no additional cost to you, I earn a small commission if you make a purchase. I recommend only products & companies I love and use, and the income goes back into making this little blog successful!

I have spent many months in Italy over the past 2 years , and I have the cutest little road trip guide for you – perfect for two weeks in Italy – especially southern Italy from Napoli all the way down to Sicily.

Between the Sicilian pasta, Neapolitan pizza, gelato, and good old Italian wine, I gained about 5 pounds – and regret absolutely nothing!

Now to the itinerary, complete with hidden gems and the best places to eat, what to do, and where to stay for an adventure that can only be described as La Dolce Vita.

Table of Contents

2 Weeks in Italy “At-A-Glance”

Here is the whole trip at a high level, including where I recommend you lodge for a few nights and the logistics of public transportation if you choose not to rent a car for any part of the trip.

A few notes about logistics:

• Uber is not something you can count on in Italy .
• I’ve linked where to get your ferry tickets in the detailed itinerary below, but no travel day took more than 2-3 hours.
• Having a car will make it easier, especially for the second half of the trip when you have to get to Maratea and Sicily. In fact, there are a few Hidden Gem Italian Towns in South Italy that are worth exploring if you end up renting a car.

Here’s what I use to check car rental options and prices:

▶️ DISCOVER CARS: Check Prices for Italy! ◀️

Before you hit the road, make sure you review  Renting a Car in Italy: Common Mistakes & Tips , where I go into a few unique road rules, documentation requirements, and experience driving through the land of La Dolce Vita.

2 Weeks in Italy Itinerary

Let’s dive into the 2 week itinerary for Italy, including tips on where to stay and how to spend your time.

Day 1: Arrive in Napoli

Welcome to Napoli! When I first set out on this 14-day trip in Italy, I almost skipped Naples because of how many people warned me about the dangers – “hide everything”, “gangs of gypsy thieves!”. This is a bunch of bullsh*t.

You should absolutely practice caution any time you travel , but I found the city to be bustling, alive, friendly, chaotic, and all the good things I imagined a slice of local Italian life to be.

Where to Stay

📍 Le Sciantose Relais (Spanish Quarter)

You’ll be making Naples home base for three nights. I booked myself a lovely spot in the Spanish Quarter (Quartiero Spagnolo), which is within walking distance of the main attractions and the historic center.

What to Eat

Do not leave the city without eating a Neapolitan Pizza or the Traditional Ragu. Neapolitan cuisine, in general, is renowned for its use of fresh ingredients and simple yet flavorful recipes. Here are my top recommendations for each!

• L’Antica Pizzerie da Michele – Neapolitan pizza, great any time of the day and wonderful jetlag recovery food.
• Tandem Ragu – Traditional ragu over handmade pasta in a low-key nook of town. Make sure to get a reservation for dinner.

Day 2: Explore Napoli

The city of Naples is often overlooked by travelers to Italy, who go for better-known destinations like Rome and Florence.

But those who take the time to explore Napoli for at least a full day will be rewarded with a wealth of history, culture, well-renowned museums, art galleries, churches, parks, and overall natural beauty. That said, the city is huge, busy, and you’ll want a guide .

➡️ For a historical guided tour that makes Napoli come alive, book Naples Private Walking & Food Tour .

My Favorite Spot on the Tour: Museo Cappella Sansevero , a chapel that is adorned with a number of intricate sculptures, including two life-size figures of chained sinners. The most impressive sculpture is “The Veiled Christ,” a marble statue of Christ shrouded in a thin layer of transparent marble, which is in one word “heavenly”.

Day 3: A Trip to Pompeii

So don’t repeat my mistake and go to Pompeii without a guided tour , paying only for the entrance ticket and boring audio guide; you’ll end up tuning out anyway. It will be like walking through history blind – beautiful and intriguing, but you’ll be lacking the depth, story, and impact.

👉 If I was to do this day again , this is how I would think about it: Rome to Pompeii Day Trip: The Smart Way vs. The Hard Way .

Day 4: Arrive on the Amalfi Coast

Grab the ferry from Napoli to Amalfi ( 2 hours for about $30 ) and head out in the morning. The town of Amalfi is absolutely picturesque and small, easy to explore in one day.

A little secret from locals and travelers alike is that the best way to see the Amalfi Coast is from the sea. So once you arrive and settle in, grab some lunch, head to the harbor again, and get a boat for the afternoon.

➡️ This is the Amalfi Coast Boat Rental I got so I didn’t have to spend extra money on a skipper – zero regrets!

📍 Albergo L’Antico in the Town of Amalfi

This will be your home base for the next four days. I got a little room close to the main square and Cathedral, more expensive than Naples but within walking distance of everything. Because the AirBnBs are expensive and a little run down in the town of Amalfi, my favorite part about this hotel is that it was central, and felt super Italian in its decor.

Day 5: Explore Ravello

Ravello is a town in Italy that sits high above the Amalfi Coast. Though it’s small, there’s plenty to see and do – the main attraction being Villa Rufolo . It sits atop a cliff with incredible views of the coastline and has a beautiful garden. And some nights, live shows!

Day 6: Explore Positano

Positano is one of the most beautiful places in Italy, and it’s easy to see why. The colors are absolutely breathtaking, and the views are simply WOW!

Although it is a popular tourist destination, there are still plenty of hidden gems to be found.

➡️ This was one of my favorite days on the trip because I took the road less traveled and hiked from Amalfi to Nocelle in Positano via the Path of the Gods Hike .

Day 7: A Day on the Island of Capri

A day trip to the island of Capri is a must for this itinerary. The island is known for celebrity vacations, crystal-clear water, and picturesque towns.

You can take a boat around Capri from Amalfi, and then spend the rest of the day on the island soaking in the Mediterranean vibe.

➡️ This is the Private Boat Tour of Capri I took to capture the picture below – I liked it so much that I actually did it again on a separate trip back to the little island!

Here are a few highlights you can’t miss:

• Giardini di Augusto – Get ready for the most stunning views of the sea and Via Krupp.
• Arco Naturale – My favorite lookout point, an easy walk/hike from Giardini di Augusto.
• Marina Piccola – Swim in the azure waters of Marina Piccola, overlooking the famous Faraglioni rocks.
• Explore the many quaint shops and restaurants in the town of Capri.

❌ Do NOT take the fancy-looking taxis on Capri , as they are expensive.

The best way to get around Capri is the little funicular from Marina Grande to the town of Capri, from which you can walk to all of the recommendations I outlined above.

There is also a bus if time allows you to go further to Marina Piccola or Anacapri.

Day 8: Relax in Maratea

After all the boogie-ness of the Amalfi coast, I headed south by train to Maratea in the region of Basilicata. This is a sleepy little town along the coast of Italy (in the Basilicata region) known for its dramatic coastline.

The Church of San Biagio is a beautiful example of Baroque architecture, and the views from the bell tower are not to be missed.

Not only that, there are a number of excellent restaurants serving fresh seafood, and the town is surrounded by olive groves and vineyards. Go for dinner at HOST di Viceconte Antonio and try the ravioli!

📍 Villa Venezuela (1 night)

A night of relaxation and a stunning sunset in Villa Venezuela . Book ahead of time! As a peek, this is the view from the room!

Day 9: Onward to Sicily

From Maratea to Taormina, today is a travel day, by train to ferry to train again. This was enough to have me questioning my itinerary – the silver lining was the beautiful views the train gives as it makes its way down the beautiful coastline.

I did have this thought …. should I just go back up the coast or keep going south – Which is Better: The Amalfi Coast or Sicily? Bottom line, Sicily is the place to be if you’re looking for an authentic south Italian experience .

📍 Terra Rosa Residences near Isola Bella

I stayed a little outside of Taormina near the beach of Isola Bella for 2 days at the most beautiful residence: Terra Rosa . The town was a lovely 15-minute walk up the stairs. The sunrises, sunsets, and views of Isola Bella along the path took my breath away.

Day 10: Explore Taormina

This picturesque town is located on a cliff overlooking the Mediterranean Sea. From here, you can enjoy stunning views of Isola Bella, explore the ancient Greek theatre, and sample some of Sicily’s best gelato and cannoli.

It is worth mentioning that I quite seriously ate my way through Taormina. That being said, here are some quick hitters for a self-guided walking tour:

• Teatro Antico di Taormina – Great for sunset with views of Mt. Etna.
• Villa Comunale di Taormina – For quiet walks and naps in the park.
• Piazza IX Aprile – cafe central!

Day 11: A Beach Day on Isola Bella

From my little residence at Terra Rosa , I walked down the stairs to Isola Bella and spent the day relaxing on the beach, drinking granitas , and snacking on fruit.

I met fellow travelers in the sun, and we ended up chatting and going out in Taormina the whole night. I went to bed at sunrise – perfection!

Day 12: Explore Isola Ortigia

Grab the train further south to Ortigia ( thankfully, trains are a great place to nap ). This little island is located in the city of Syracuse on the southeastern coast of Sicily. Although it is only about a kilometer in size, Ortigia is packed with history and culture.

Once the center of Greek civilization, its ancient ruins are now a UNESCO World Heritage Site. Today, the island’s streets are lined with shops and cafes, making it the perfect place to spend an afternoon exploring.

Day 13: A Day in Noto

A quick train ride from Ortigia, Noto is the best place to spend a day in Sicily. The entire town is a UNESCO world heritage site , and it’s easy to see why.

The town was rebuilt in the 18th century after a devastating earthquake, and the resulting baroque architecture is simply stunning.

Start your morning with a stroll down Corso Vittorio Emanuele, the main drag, which is lined with cafes and shops. Then visit the Noto Cathedral , followed by all the other churches and palaces that line the streets, each more beautiful than the last.

Finish up with a stroll through the picturesque gardens of Villa Comunale , and head home to Ortigia for dinner!

Day 14: Time to Fly Home!

And that wraps up what I hope will be many more itineraries to explore La Dolce Vita of the Italian coast. Take the train to Catania Airport, and connect to wherever you call home. Don’t forget to send postcards before you go!

2 Weeks in Italy Map

This is the route I took for the trip. I flew into Naples and flew home from Catania, Sicily.

If you have MORE than 2 Weeks in Italy

If you have a couple more days, here are a few more spots and adjustments to the itinerary I would make:

✅ Spend a few more days in Capri .

On another trip, I ended up spending a long weekend on the island of Capri itself (lodging in Anacapri) and treated myself to a solo relaxation holiday!

✅ Spend more time in Sicily .

On yet another Italy trip, I spent a whole two weeks exploring Sicily. Here are the best of the best recs:

• Palermo – The capital of Sicily, this is a full-on immersion into Sicilian everything – from the churches to the food, to the impossibly winding tiny streets of the old town. Just amazing!
• Isola di Favignana – Take the ferry from Trapani and rent a bike to wander this beautiful little island for a day or two!
• Erice – A gorgeous historic town on top of a mountain, this is a great day trip from Palermo on the way to Scopello!
• Scopello – Find your way to this little retreat beach – Cala Mazzo di Sciacca .
• Cefalu – Also found on many postcards from Sicily, this little town rounds up some of my favorite northern spots in Sicily!

If you have LESS time in Italy

If you have less than 14 days in Italy, try not to be sad. Just promise you’ll be back! Jokes aside, here are a few adjustments you can make to this itinerary:

✅ Skip Maratea and focus on the Amalfi Coast & Sicily. I would start the trip with a roundtrip flight from Naples to Sicily (flying into Catania Airport near Taormina). And of course, there is the ferry from Naples to the Amalfi for the second portion of your trip.

✅ Spend only two days on the Amalfi Coast , prioritizing a day trip to Capri and seeing Positano from the sea ( check out the recommendations I made in the itinerary to save money on boat rentals ).

However you customize your trip, something about Italy just makes you feel alive. The food, the wine, the history, and the culture all come together to create a magical place that I couldn’t help but fall in love with.

Travel Tips Before You “Andiamo!”

There are a few frequently asked questions I’d like to get out of the way.

Can I tour Italy in 2 weeks?

While 14 days in Italy may seem short for some ( or their entire vacation time for Americans ), it’s actually the perfect amount of time to explore the major cities and 1 to 2 regions without feeling rushed.

As an aside, I loosely split Italy into three regions:

• The North – Think mountains, skiing, Lake Como, Milan, Venice.
• The South – Naples on down to Sicily, including Pompeii and the Amalfi Coast
• The Chunky Middle – The capital of Rome, the Vatican, the rolling hills of Tuscany

Hiking in the Italian Dolomites & Swiss Alps

If the mountains are more your calling, consider heading to North Italy for some of the most epic hiking of your life. This is my favorite region of Italy, and I say this very seriously because I know how pretty the Amalfi Coast and Sicily are!

How long do I need on the Amalfi Coast?

The Amalfi coastline is one of the most popular tourist destinations in Italy, because, yes, it really does look like the pictures – dramatic cliffs and turquoise waters galore.

I think a long weekend will give you plenty of time to relax on the beach, take day trips to nearby islands, and explore the charming villages, like Positano and Ravello, that dot the coast.

Do I need travel insurance for this trip?

Yes, if you’re planning to stay in Italy for an extended time OR you’re going to be hiking and driving long distances, you should consider reviewing the 5 Best Medical Insurance Policies for traveling in Europe , because shit happens.

This is what I use ▶️ Check Prices for SAFETYWING Insurance ! ◀️

The idea is that if something does go wrong, you’ll have peace of mind knowing that you’re covered.

How much does it cost to stay in Italy for 2 weeks?

I was worried 14 days in Italy would break the bank – especially with the Amalfi Coast and Taormina on my itinerary – but it didn’t!

There are a number of ways to save money while traveling , such as staying in hostels or AirBnB rather than hotels, eating at local restaurants rather than tourist traps, and taking advantage of free activities such as walking tours – all of which I did.

Here is the price breakdown for my 14-day stay in Italy, which totaled around $1,500 ( sans flights because I use credit card points for this ).

• Transportation : $100/week ( ferries, trains, Uber – still cheaper than renting a car )
• Housing : $40-100/night ( places like Maratea will be less expensive, Amalfi on the more expensive end )
• Meals : $15-30 for some of the best pasta, seafood, and desserts of your life
• Wine : $3 a glass for amazing Italian wines ( and the Italians always pour a little extra every time . .. bless them! )

When should I visit Italy?

While that depends on what you want to see and do, I went on this trip in June!

That said, spring or fall is ideal if you’re interested in exploring the country’s major cities . The weather is pleasant, and there are fewer crowds compared to the summer months.

If you’re more interested in spending time outdoors , then summer is the best time to visit . Italy is also a great destination for winter sports, as the Dolomites offer some of the best skiing in Europe.

What should I pack?

First and foremost, the Italian sun can be incredibly strong, especially during summer.

You’ll want to pack light, comfortable clothing that can be easily layered – firstly because the temperatures can vary widely, and secondly because you’re traveling by public transport most of the time. Minimalism is key !

I’ve put together a quick checklist of Comfy Road Trip Outfits for this itinerary- pay special attention to the summer capsule wardrobe for Italy.

Conclusion: 2 Weeks in Italy from Napoli to Sicily

Planning a trip to Italy can be a big task, as this country has so much to see and do.

I went for a whole month, journeying from Rome all the way down to Bari and Sicily, one gelato cup at a time, living the “dolce far niete “, meaning “the sweetness of doing nothing” before writing this little guide.

To be fair, I think even if I went a thousand times, there is still more to see. All that said, with a little careful planning, it is possible to get a good sampling of Italy in just 14 days.

Mariana Barbuceanu is the owner and author of the Road Trip EuroGuide, a blog that inspires fellow travelers to explore Europe more authentically through slower travel and digging deeper into the culture of a place. When she isn't writing about her adventures, she is planning trips for her community and coaching people on how to take that next step towards a much-needed sabbatical.

The World As I See It

One Ontario lady with a passion for travel and inspiring others to get outdoors and explore more

• Europe / Italy / Travel

2 Weeks in Northern Italy: A Dreamy Italy Itinerary

by Stephanie · Published January 14, 2019 · Updated December 18, 2023

Italy is one the top dream destinations for traveler across the globe. It’s home to a wealth of history, mouth-watering cuisine, and enchanting cities. However, you can easily spend months traveling from one end of the boot to the other, and from coast to coast, and never see it all. So, I’ve done part of the planning for you with this outstanding 2 weeks in Northern Italy itinerary.

You’ll find all the best travel tips for an epic Northern Italy vacation in this guide! Discover the top places to add to your road trip itinerary, what to do in each location, where to stay, and more! If ever there was a great time to travel to Italy, it’s now!

This post contains affiliate links. By booking through these links I make a small commission at no extra cost to you.

Getting in & Around Northern Italy

An essential part of travel is knowing how to get around the places you’re travelling in. It is quite easy tor get around Northern Italy, whether you’re travelling by train, plane, or planning to road trip by car. Below you’ll find information about airports, train trail, and tours in Italy.

There are 17 airports across Northern Italy. The largest airport is Milan Malpensa. In turn, the Milan airport has the most international flights flying into it. If you are flying from within Europe your options are wider. Depending on where you are beginning your two weeks in Northern Italy you can fly into Venice or Genoa. However, if you’re flying from North America you’ll probably find more flight options into Milan.

Try CheapOAir for great flight deals!

Train travel in Europe is convenient, fast, and a beautiful way to get around. If you are not flying into Italy there are numerous train routes you could take from neighbouring countries. Train travel in Italy is the perfect way to get between all of the locations in this Northern Italy travel itinerary. All of the stops are 2 to 3 hours apart by train.

You do not need a Eurail pass for your 2 weeks in Northern Italy. It will be cheaper to buy the tickets as you go. The ticket machines are in English and easy to navigate. However, if you’re visiting more than Italy, consider purchasing a Eurail pass . There are a variety of options available.

There are endless tour operators you can chose from if you’re looking to take a guided tour of Italy. Some range from a day to weeks. Here are a few great tours of Italy!

If you’re looking for a great tour company then check out Walks of Italy . They offer an assortment of tours across Italy. And if you’re short on time Walks of Italy has tours that will help you skip the line.

Places to Visit in Northern Italy

I have Italy in my blood in more ways then just my Italian heritage! It’s one of the places I also highly recommend and return to again and again! So, if you’re looking to plan the ultimate Northern Italy trip itinerary, I have everything you’ll need!

In this Northern Italy travel guide you’ll find all the best places to visit from the Alps to Venice and the Ligurian coast ! You’ll discover the best things to do in each location, day trips, tours, and hotels! So, get ready to start planning an epic tour of Italy filled with history, amazing food, and so much more!

So many forget about adding Genoa to their Italian bucket list. Located on the northeast coast, Genoa is the capital of Italy’s Liguria region, and has so much to offer, from history to crave-worthy food. Plus, it makes the perfect starting out point for your 2 weeks in Northern Italy itinerary. If you’re coming in from France, Genoa is only a few hours train ride.

You can easily spend a couple of days exploring Genoa. It is a city of stark contrasts, from gritty neighbourhoods to polished palaces. Genoa’s hidden gems will surprise you. One gem I found was a beautiful waterfall in a magical park in the middle of the city.

There are so many things to do in Genoa! Wander through its narrow streets and you’ll find Italy’s best pesto dishes. Visit the spectacular palaces along Via Garibaldi. A few other notable attractions in Genoa include the Aquarium, Castelletto, and the harbour.

If you’re looking for a day trip from Genoa then consider visiting Santa Margherita. This charming and colourful harbour town is located 35 kilometres southeast of Genoa on the Italian Riviera.

Tours in Genoa

Do Eat Better Experience Food Tour – Foodies will want to try this walking tour of some tasty cafes and restaurants in Genoa.

Where to Stay in Genoa

Hotel Nologo – The budget hotel has a music theme and is a 15 minute walk from Palazzo Ducale and Genoa Aquarium. I stayed here and enjoyed the area and felt safe as a solo female traveller.

Hotel Britannia – This mid-range hotel is in the historic center of Genoa. It’s close to the train station and has a terrace with hammock, a bar, and even a telescope!

Hotel Bristol Palace – For a lovely stay in a historic building, this four star hotel is located centrally and close to the Piazza De Ferrari. It has stylish rooms as well as a restaurant and coffee shop.

Start planning your Italy vacation by booking your stay in Genoa now

Cinque Terre

To me, Cinque Terre is the gem of the Mediterranean. This stretch of coastline is home to five picturesque fishing villages that rise up from the sea, vibrant buildings hanging precariously on cliffs, and a winding historic trail that connects it all. The five villages of Cinque Terre, Italian meaning five lands, is one of the most beautiful places to visit in Europe.

The five villages of Cinque Terre are Monterosso Al Mare, Vernazza, Manarola, Corniglua, and Riomaggiore . They all lie within the Cinque Terre National Park, which is a UNESCO World Heritage Site. Many spend the day hopping from village to village, as it’s only a five minute train ride between each. But I encourage you to at least spend two days in Cinque Terre.

There is so much to do, from wandering around old castles, exploring the charming alleyways in search of stunning views as well as indulging in refreshing gelato. Each village has its own incredible things to do and see.

And of course, hiking the famous Sentiero Azzurro is a must for any hiker! The Sentiero Azzurro, also known as the Blue Trail, links each of the villages and offers outstanding views of the region including the vineyards and sea.

Tours in Cinque Terre

Sunset Boat Tour Experience – Enjoy a wonderful boat tour from Monterosso. You can sip Aperitifs and prosecco, jump in the water to snorkel, or just sit back and take in the views.

Walking Tour with Local Wine Tasting – This guided tour takes you around Manarola. Wander the vineyards and learn about their history and techniques, then end of with a tasting.

Where to Stay in Cinque Terre

Hotel 5 Terre – Located near the beach in Monterosso al Mare, this mid-range relaxed hotel has a restaurant as well as free breakfast and parking.

Arbasia De Ma – In the village of Corniglia, this charming guesthouse offers rooms with sea views and is a three minute walk to the beach.

Affittacamere Le Giare – This mid-range guesthouse is steps away from the train station in Riomaggiore. Some rooms even have balconies that are perfect for sunsets!

Milan is northern Italy’s magnanimous metropolis. The city is home to legendary artwork, like Leonardo da Vinci’s The Last Supper fresco, the impressive Duomo, and everything else from castles to canals.

Milan is Italy’s second most populous city after Rome. And even though there is a wealth of things to do, you can easily see the best of Milan in one day .

I highly recommend spending a few days in Milan! That way you can indulge in its great cafes, wander its historic neighbourhoods, spend an afternoon in Park Sempione, stroll through the Galleria Vittorio Emanuele, and check out a bunch of museums.

If you are looking for one of Milan’s hidden gems don’t forget to visit the canals of Milan. The Navigli neighbourhood of Milan is home to canals that will transport you a world away from the bustling city.

Day Trips from Milan

For those choosing to use Milan as a base during part of your 2 weeks in Northern Italy then you’ll find plenty of places nearby to visit on day trips.

Lake Como – The train takes less than an hour to get from Milan to Lake Como. It’s easy to visit as a day trip and you can take the ferry to get to the main towns.

Lake Maggiore – Home to gardens and stunning scenery, this lake on the border of Italy and Switzerland is only 1.5 hours by train from Milan. Alternatively, you can visit on this half day trip tour that includes transportation and a guide.

Bergamo – Surrounded by Venetian walls, filled with cobblestone streets, and home to delicious risottos, a day trip to Bergamo is a must! It’s only an hour northeast of Milan by train.

Tours in Milan

Walking Tour with Skip-the-Line to Duomo & Last Supper – This walking tour takes you to all the top attractions, including the Milan Cathedral, plus gives you skip the line access to the Last Supper!

Where to Stay in Milan

Ostello Bello – In the city center and close to the Cathedral, this accommodation offers budget-friendly dorm rooms as well as privates. It has terraces with hammocks and will greet you with a free drink!

B&B Hotel Milano Sant’Ambrogio – This charming mid-range bed & breakfast is close to the Sforzesco Castle, offers bike rentals, and is pet-friendly!

Grand Hotel et de Milan – Located steps from La Scala opera house and the metro, this luxury hotel has everything you need including two restaurants, a bar, fitness center, and is set within a historic building.

Book your stay in Milan today!

A trip to Northern Italy is not complete without a visit to Venice. It’s the perfect place to end your 2 weeks in Northern Italy. There are countless things that make Venice special.

The magic of Venice is different for all! For some, it’s in getting lost in its endless alleyways. For others, it’s sipping a coffee in San Marco Square and watching the birds take flight when the church bells ring. And one of the big magic moments is watching the sunset over the Grand Canal.

While it is doable to simply spend the day in Venice. I feel like it doesn’t do it justice. There is more to Venice than can be seen in a day. If you spend a couple days in Venice you can do a day trip to colourful islands Burano and Murano.

Other things to add to your Northern Italy trip itinerary include visiting St. Mark’s Campanile. Located in San Marco Square, this bell tower is best visited early. Head to the top and take in one of the best views of Venice.

Seek out Libreria Acqua Alta, one of the most enchanting book stores in the World. Plus, discover what lies on the other side of each and every bridge.

One thing that I highly recommend is to take a gondola ride to a ride along the canals! It will not disappoint!

Tours in Venice

Walking Tour and Gondola Ride – I LOVED this walking tour with a local guide! Learn about the top attractions as well as hidden gems, plus a gondola ride is included and tours start at only $63 CAD!

Murano & Burano Islands Tour by Private Boat – Take advantage of the fully guided tour of islands that starts at $54 CAD. Learn about the islands, watch glassblowers, and more!

Where to Stay in Venice

Hotel San Salvador – I LOVED this charming hotel in the heart of Venice, close to St. Mark’s! It’s a budget-friendly option with a great location and even has Murano glass throughout!

Hotel Carlton on The Grand Canal – This mid-range hotel overlooks the Grand Canal, has a rooftop bar as well as special rooms. The Santa Lucia Train Station is only a five minute walk away.

Venezia Palazzo Barocci – An elegant hotel with Grand Canal views, a café, garden, and private dock. Plus, it’s close to a ferry stop!

Start planning your time in Venice by booking your accommodation today

For those looking for sustainable travel tips, check out my guide to Responsible Travel in Venice

Other Notable Locations to Visit in Northern Italy

There are endless hidden gems in Northern Italy. While the above four main stops can comfortably be explored in two weeks. If you are a fast paced traveller and enjoy packing in as much as you can, or if you have a few extra days, the following locations can easily be seen in one day or added to your Northern Italy itinerary for an extended stay.

If you’re looking for dreamy or romantic places to visit in Italy than Verona is the place you’re after. Considered the Florence of the north. The medieval old town of Verona is famous for being the setting of Shakespeare’s ‘Romeo and Juliet’. It’s here you’ll find ‘ Juliet’s House ’, with a 14-century tiny balcony that overlooks a courtyard.

While Juliet’s balcony may be Verona main attraction, it is also home to the Verona Arena. This large Roman amphitheater, from the first century, is one of the best preserved ancient structures in the world. It is still used today and hosts an array of performances, from concerts to operas.

Travel Tip: You can enjoy a nice day trip out to Lake Garda if you’re staying in Verona for a few days. There are trains and buses available that take 20 minutes to one hour respectively.

Tours in Verona

Verona Walking Tour of Must-See Sites – Explore the city and its top sites, like the Juliet Balcony, and learn about its neighbourhoods and interesting little-known facts.

Fascinating Verona: in the Footprints of Romeo and Juliet – This in-depth tour offers a guide to Verona through the words of Shakespeare while learning about the city’s Roman and romantic past.

Where to Stay in Verona

Relais La Torre – With a central location, close to the Arena in Verona, this mid-range guesthouse is partially set within a medieval building and offers stylish rooms.

Due Torri Hotel – This posh five star hotel is across from the Sant’Anastasia church and a short walk from the Verona Cathedral and bus station. It has an acclaimed restaurant, courtyard café, and terrace with views of the city!

Another incredible place to stop in Northern Italy is Bologna. This historic capital of the Emilia Romagna region is home to beautiful piazzas, great cafes, and stunning medieval and Renaissance architecture. Bologna is known for its medieval city centre, striking beauty and incredible food scene!

Some of the top things to do in Bologna include; climbing Italy’s tallest leaning tower – Asinelli Tower , visit Basilica of San Petronio, and wander its porticoes and markets. One of the best porticoes that should be added to your Northern Italy itinerary is the Portico of San Luca . It’s the world’s longest portico and home to stunning frescoes.

Day Trips from Bologna

Bologna makes for a great place to use as a base to the Emilia Romagna region. Many top destinations, as well as hidden gems, are within a couple of hours from Bologna.

San Marino – This microstate in the mountains is only two hours away by train. San Marino one of the smallest countries in the world! Spend a day or half day wandering the cobblestone streets in this magical medieval place with castle-like citadels.

Florence and Pisa – As the capital of the region of Tuscany, Florence is home to plenty of things to do, including museums and churches. Plus, you can easily do both Florence and Pisa on a day trip as Florence is only a 35-minute train ride away.

Tours in Bologna

Taste of Bologna Walking Tour – This walking tour combines a visit of some top places in the city with local tastings of Bolognese food like Parmigiano Reggiano as well as tales of ancient recipes.

Bologna City Walking Tour – For under $30 CAD you can enjoy a wander through the historic centre of the city, find hidden gems and learn about the interesting stories behind Bologna.

Where to Stay in Bologna

Starhotels Excelsior – Across from the Bologna Train Station, this mid-range four-star hotel is within walking distance to many attractions. It offers modern rooms, a restaurant, and gym.

Royal Hotel Carlton – For a little more luxury without breaking the bank, this hotel features Turkish baths, wellness treatments and has a great buffet breakfast. It also has parking on site.

Located just over the border, Turin is a great start to your 2 weeks in Northern Italy itinerary if you’re coming from France. Turin is the capital city of Piedmont and has the Alps rising over the city to the northwest.

Turin is home to striking architecture and delicious food! Here you can wander its grand squares, charming cafes, and stand in awe of its baroque buildings. One of the best landmarks in Turin to visit is the Royal Palace, which is also a UNESCO World Heritage Site.

Some other top things to do in Turin include; the Mole Antonelliana – a towering museum, the Egyptian Museum, Valentina Park, and Cathedral of Saint John the Baptist to see the world famous Turin Shroud.

Did you know that Turin is known as the capital of chocolate in Italy?

Tours in Turin

Turin Patisserie Tour – This sweet food tour takes you to many of the best cafes and shops in the city. Learn about the history and taste dessert and pastries, like gianduiotti.

Underground Turin Walking Tour – This budget-friendly tour takes you off the beaten path and below the city. Discover tunnels, palaces, mysteries, and more under the streets of Turin.

Where to Stay in Turin

Arcadian Suites & Rooms – Located in downtown Turin, this mid-range bed and breakfast offers rooms and suites.

J Hotel – This mid-range 4-star hotel is located on the outskirts of downtown. It offers polished rooms as well as a bar and restaurant.

For those looking for luxury and relaxation consider visiting Lake Como. Set in Italy’s Lombardy region, at the base of the Alps, Lake Como is home to breathtaking scenery. It’s known as the Italian Lake District and a luxury resort area for the rich and famous, but there’s something for everyone here.

The city of Como is home to a waterfront promenade, a grand cathedral, as well as gardens and museums. Plus, don’t forget to take the funicular that takes you up to a beautiful mountain town, Brunate. From the top you can enjoy sweeping views. Another must-do is to take the 30 minute ferry ride across Lake Como to Bellagio.

Pro Tip: If you’re looking for an alternative to Lake Como then visit Lake Maggiore.

Tours in Lake Como

Lake Como Food Tour – Sample the local cuisine of Northern Italy in Como’s old town. Learn about the area’s wine and food and visit some of the local favourite cafes and restaurants.

Como Sightseeing Tour and Lake Cruise – This full day tour takes you around Como and out on a cruise of the lake. Depending on the time of year you’ll stop at a few stunning places like Bellagio or Brunate.

Where to Stay in Lake Como

B&B dei Laghi – This cozy budget-friendly bed and breakfast is located in the small town of Magreglio. Rooms have a country chic vibe with renovated bathrooms.

Hotel Baia di Paré – Set on the shores of Lake Como, this mid-range hotel is close to the beach and has a pizzeria restaurant. Rooms have views of the lake or mountains!

One of the dreamiest places to add to your 2 weeks in Northern Italy itinerary is the Dolomites! This mountain range is approximately three and a half hours north of Venice, making it a great day trip from Venice.

The Dolomite Mountains are popular with outdoor adventurers. With towering peaks and stunning green valleys, it’s home to epic hiking trails, mountain climbing, and skiing. An awesome hike to do in the area is the nearly 10 km Tre Cime di Lavaredo that takes you across three different mountain peaks.

Nevertheless, there’s still plenty of things to do in the Dolomites for those looking for a relaxing visit. The region is full of charming mountain villages, incredible cuisine, and museums. Plus, the culture here is distinct as the region was part of Austria until just after WWI.

Tours in The Dolomites

Dolomites Full-day Tour from Lake Garda – If you’re staying in the Lake Garda area, this awesome full-day tour shows you the best of the Dolomites. It includes stops in towns, at viewpoints, and more!

Where to Stay in the Dolomites

Hotel Castel Pietra – With a spa, wellness centre, restaurant and free garage parking this 4-star hotel is unbelievably budget-friendly! Plus, it’s a short walk from Fiera di Primiero.

Hotel Garni La Roccia – Located in Andalo, this family mid-range hotel is close to the Paganella ski resort. Rooms are elegant and large. Plus, the hotel has a free wellness centre!

Molaris Lodge – This luxury hotel is in the centre of Rio Di Pusteria and has a garden, pool, playground and is close to the ski elevators. Rooms are cozy and most have balconies with mountain views.

Frequently Asked Questions for Visiting Northern Italy

When planning your two week northern Italy trip itinerary many questions will arise. So, below you’ll find travel tips to help with your frequently asked questions about planning a northern Italy trip! You’ll learn what is considered north Italy, the best time to go, where to spend time, and more!

Where is Northern Italy? – Northern Italy is flanked by the towering snow-capped Alps to the north and the green, rolling Apennine Mountains to the south. And the picturesque Ligurian Coast, home to Cinque Terre, to the west and the enchanting Venetian Plain to the east.

Best time to visit Northern Italy? – This all depends on what you want to do! If you’re planning to ski in the Dolomites then the best time is February and March. For those just looking to explore and not ski then the best time to plan your north Italy itinerary is between April to June or September and October. Temperatures are more comfortable and you will avoid peak season.

Things to do in Northern Italy – Take a gondola ride, Milan Cathedral, San Marco Square, hike the Dolomites, Juliet’s Balcony, hike in Cinque Terre, eat in Emilia-Romagna, take a food tour, the leaning towers of Bologna, and Garibaldi Palaces.

Top places to go in Northern Italy – Venice, Cinque Terre, Milan, Emilia Romagna, Verona, Lake Como, the Dolomites, Genoa, and Turin.

Italy Packing List – Packing for Northern Italy all depends on the time of year you’re visiting. But no matter the time of year, some Italy packing essentials include sun screen, a hat, comfortable shoes, portable power pack, and a scarf (which is great in the summer to cover your shoulders when visiting churches.)

Train vs. Car – Train travel in Italy is easy to navigate and will get you to all the main cities and smaller towns. However, if you are planning an Italy road trip a car is very convenient at times. But make sure you book your rental car far in advance. Also, if you are unfamiliar with driving in Italy, and Europe in general, you may find it difficult. You’ll need to learn the rules of the road, where to find parking, and more.

2 Weeks in Northern Italy Itinerary

I’ve generated a few sample itineraries for the perfect Northern Italy trip! Whether you’re planning a Northern Italy road trip for 2 weeks or looking to extent it to three, you’ll find a few great options below!

14 Day Northern Italy Itinerary

4 Days in Milan

3 Days in Genoa

3 Days in Cinque Terre

4 Days in Venice

2 or 3 Weeks in Italy Itineraries

2 Days/3 Days in Milan

1 Day/2 Days in Lake Como

1 Day in Turin

2 Days/3 Days in Genoa

2 Days/3 Days in Cinque Terre

2 Days/3 Days in Bologna

1 Day in Verona

1 Days/2 Days in Dolomites

2 Days/3 Days in Venice

Other European Itineraries you may like:

4 Days in Paris – The Perfect Paris Itinerary

4 Days in Venice & Why You Need More than One Day

The Perfect England 2 Week Itinerary

Northern Italy is full of natural wonders and incredible cities that are bursting with history. This 2 weeks in Northern Italy itinerary is the perfect starting point to start planning your dream-worthy Italian vacation today.

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I'm a Canadian gal with a passion for travel, the great outdoors as well as coffee and books. I hope to inspire others to feel the same way! Traveling mostly solo, I love to explore my own backyard of Ontario as well as exotic cities around the world.

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Matt rife taking two weeks off tour after medical emergency, matt rife two-week hiatus on comedy tour ... nearly fainted pre-concert.

Matt Rife 's taking some much-needed time off from his comedy tour -- putting a pause on a string of shows after nearly passing out from exhaustion ... TMZ has learned.

According to a message received by upcoming date ticketholders -- viewed by TMZ -- Rife was on his way to his show at the University of Indiana to perform two shows Wednesday when he experienced symptoms of extreme exhaustion and nearly passed out.

Rife's medical team advised him to immediately take a break ... and, that's exactly what he's doing -- scheduled to pick up the tour again on June 12 in Memphis. So, 2 weeks off.

Matt's cancelled his upcoming shows at The Chicago Theatre and Ryman Auditorium in Nashville, TN. He's rescheduling the Chicago shows for the end of December. The Nashville show is currently cancelled with a new date TBD. If ticketholders are unable to attend future dates, they will be refunded.

The comedian was scheduled to perform 8 consecutive sold-out shows starting tonight at the Chicago Theatre... which would have broken the theatre record.

As we reported ... Rife canceled his shows yesterday at the eleventh hour -- citing a medical emergency and pissing off a ton of fans who looked forward to seeing the big-time star take the stage.

Matt apologized on his social media, writing this is the first time anything like this has happened to him, as he has been doing 40+ shows a month for a year and a half ... and, showing his love for the fans.

With this new message, it seems he's putting his health first ... which is all you can ask for from someone.

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Houston life, saluti invite the taste of italy into your home with these inexpensive wines.

Javana Vela , Houston Life Producer

Houston – It’s no secret that Italy’s diverse wine regions offer a rich tapestry of flavors and experiences. It’s also no secret that Italy is a great place to vacation. It’s one of the top travel destinations this summer.

But, if you can’t book a flight to Italy, why not have a flight...of wine! Wine and travel expert Daniela Garrido joined us again to give us a mini tour of Italy. And she started with something classic and bubbly

For the spritz lover

she recommends The Riunite Lambrusco Spritz. Garrido says an aperitivo is her favorite kind of drink. Something to enjoy after a long day of work. Using long-time staple Riunite Lambrusco you can pour this over ice and garnish with a rosemary or orange slice. You can also mix it up with Maschio prosecco and make the Lambrusco Spritz like how Derrick and Tessa enjoyed it on the show

For the prosecco lover

If you’re looking for something more elevated than a glass of wine, Garrido says the Lamberti prosecco offers a light and fresh sparkling option. There are notes of candied lemon, white peach, and yellow apple. With a price tag of less than $20, it’s a no-brainer for your summer gathering.

For the white wine lover

Legend says, Frank Sinatra wouldn’t dine at a restaurant unless this wine was on the menu. It’s the Bolla Soave Classico . Soave, which means “soft” in Italian, it has soft floral and pear flavors. This pairs perfectly with a flaky summer fish, it has medium acidity and a nice mineral backbone. Garrido recommends this as an alternative to pinot grigio or sauvignon blanc this summer.

For the red wine lover

Even though it’s summer, Garrido didn’t forget about the red wine lovers. She highly recommends this Poderi Melini Granaio Chianti Classico . She says it’s ideal for warmer temperatures and the acidity will cut through juicy meats if you’re having a backyard BBQ. She would put the bottle on ice and serve slightly chilled.

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Javana vela.

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Five Cinderellas who could factor at U.S. Open

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PINEHURST, N.C. – The Schefflers, Schauffeles and McIlroys will take center stage at this week’s U.S. Open, and rightly so. The game’s best will be expected to contend at Pinehurst No. 2, and many of them likely will.

But the U.S. Open’s beauty lies in its meritocracy; any player with a handicap index of 0.4 or lower can attempt to qualify for the United States’ national championship in men’s golf. It cultivates the opportunity for mini-tour pros, promising amateurs, and even the country’s 9-to-5ers to compete for one week against the game’s best – some first advancing through 18-hole Local Qualifying, and then qualifying for the U.S. Open via 36-hole Final Qualifying, known as Golf’s Longest Day. (Yes, this week’s field includes a high-school science teacher, whom we’ll get to shortly.)

Nineteen years ago, Jason Gore made magic at the U.S. Open at Pinehurst, playing in Sunday’s final group as a Korn Ferry Tour member. That day didn’t go as planned (he shot 84 and finished T49), but the energy and support from that week propelled Gore to three Korn Ferry Tour wins and his first TOUR title later that summer. It’s something about the U.S. Open that can’t be quantified but is very real – any highly skilled player can tee it up against the game’s best. As far as high-level sporting competitions go, it’s a melting pot that stands alone.

Which Cinderella-type stories could unfold this week amidst the Carolina pines? Read below for five qualifiers in this week’s field who could author them.

1. Colin Prater

The U.S. Open is known as golf’s ultimate meritocracy, where anyone can shoot the scores and tee it up – whether it be a firefighter (like Matt Parziale in 2018 and 2019) or a schoolteacher (like Colin Prater this year).

Prater, 29, qualified to compete at Pinehurst via Golf’s Longest Day in Oregon, earning one of two available spots. The Colorado native is a highly competitive amateur golfer – he qualified for match play at last year’s U.S. Amateur – but he holds a full-time day job as a high school science teacher at Cheyenne Mountain High in Colorado Springs, where he also coaches the boys’ and girls’ golf teams. He was a four-time Division II All-American; he began his career at Colorado Mesa before transferring to Colorado State-Colorado Springs.

Maybe Prater could have thrived as a professional golfer, but the week-to-week traveling circus isn’t for everyone – he’s a husband and father, with his wife expecting their second child in July. After graduating from college in 2019, he made plans to play professionally and acquired financial backing, he told NBC Sports’ Brentley Romine. But after completing student teaching at Doherty High in Colorado Springs, he realized he no longer wanted to play professionally, he told Romine. Now he teaches biology to roughly 120 ninth graders, loves it – and this week he will experience a summer vacation unlike any other.

2. Michael McGowan

If any U.S. Open qualifier’s tale read like a movie script, it would be that of Michael McGowan. The 33-year-old grew up in nearby Southern Pines, the son of two-time TOUR winner Pat McGowan and the late Bonnie Bell McGowan, the daughter of World Golf Hall of Famer Peggy Kirk Bell, a lifelong women’s golf advocate.

McGowan has spent time on the Korn Ferry Tour, PGA TOUR Latinoamérica and various mini-tours, but he had never competed in a PGA TOUR event. After advancing through Final Qualifying in Dallas, his first TOUR start will be a home game. Shortly after he earned his spot via a playoff on Golf’s Longest Day, a group chat was buzzing that included several of his peers from 2015 PGA TOUR Latinoamerica including TOUR pro Keith Mitchell. It’s evidence of McGowan’s enduring likability, Mitchell said, as several in the golf world celebrated this story along with the University of North Carolina alum and his inner circle.

Pat McGowan went 4-for-4 in made cuts at the U.S. Open, and his son looks to make that 5-for-5 in their national championship. No matter how McGowan’s week or career unfold from here, though, it’s an experience the family will cherish forever.

Mini-tour pro Michael McGowan qualifies for hometown U.S. Open at Pinehurst

3. Jackson Buchanan

It’s one of the U.S. Open’s great traditions, an amateur ascending onto the early leaderboard, prompting Google searches to learn more about the new name on the big stage. Think Omar Morales last year at Los Angeles Country Club, or Davis Thompson at Winged Foot in 2020.

This year it could be rising University of Illinois senior Jackson Buchanan, who finished stroke-play runner-up at the 2023 NCAA Championship as a sophomore and was named Big Ten Golfer of the Year as a college junior this past season.

Buchanan wasn’t the most highly sought-after junior player, as reported by Andy Johnson of Fried Egg Golf (a premier Illinois golf expert), but he has flourished with the Fighting Illini under well-respected head coach Mike Small – who has competed in three U.S. Opens and has a knack for developing under-the-radar talents into TOUR-quality players. The Georgia native earned his spot at Pinehurst via Final Qualifying in Georgia, and this week he’ll make his first start in a TOUR-sanctioned event.

Baseball was Buchanan’s first love (his dad played college baseball at Mercer), and nobody in his family played golf, he told the Illini Inquirer in 2023. But after suffering a torn ACL playing basketball, he decided to give golf another shot. It has led to a start in a major championship.

Jackson Buchanan qualifies for U.S. Open after college season at Illinois

4. Matteo Manassero

The sports world loves a good comeback story, and Italy’s Matteo Manassero has been writing one of late.

Manassero, 31, advanced through Final Qualifying in England to earn his first major start since The Open in 2019. Flash back some 15 years, and many would’ve pegged Manassero for consistent contention at majors. He finished 13th at the 2009 Open Championship at age 16. He held the No. 1 spot on the World Amateur Golf Ranking in 2010, and he made the cut at the 2010 Masters at age 16. Later that year, he became the youngest DP World Tour winner at age 17. He was a four-time DP World Tour winner by age 20. The sky appeared the limit.

He hit a dry spell in his 20s, though, falling back to the Alps Tour (two tiers below the DP World Tour), where his comeback began to crystallize with a 2020 victory to snap a seven-year winless drought. He won twice on the 2023 Challenge Tour to secure a DP World Tour return, and he earned a long-waited fifth DP World Tour title this year.

Now he returns to the game’s major stage, a few years older but perhaps all the wiser – and still with plenty of runway for success in professional golf.

Matteo Manassero drains a 17-foot birdie putt at ISPS HANDA

5. Harry Higgs

It might not be an expected name on this list, but there are several parallels between Higgs and one of golf’s most memorable Cinderella stories – Jason Gore at the 2005 U.S. Open at Pinehurst No. 2, who played in Sunday’s final pairing as a Korn Ferry Tour member.

Higgs is a three-time Korn Ferry Tour winner, including back-to-back victories in the last month, and he continued this magic carpet ride by advancing through Final Qualifying in Durham, North Carolina. It’s a dramatic turnaround after struggling in the past two PGA TOUR seasons – finishing outside the top 125 on the FedExCup in both 2022 and 2023. It was an unexpected slide after the affable Kansas City native became one of the game’s most popular characters in his first two TOUR seasons in 2020 and 2021 – including a T4 at the 2021 PGA Championship at Kiawah – but technical and mental struggles led to a downturn that put his TOUR career in doubt.

Perhaps Higgs will make similar memories amidst the Carolina pines.

Harry Higgs' incredible eagle hole-out to force playoff at AdventHealth Championship

Kevin Prise is an associate editor for PGATOUR.COM. He is on a lifelong quest to break 80 on a course that exceeds 6,000 yards and to see the Buffalo Bills win a Super Bowl. Follow Kevin Prise on Twitter .