Burano, Venice, Italy

Italy Road Trip: How to Spend Two Weeks in Italy

January 9, 2024

If you are reading this article, it means that you probably like Mediterranean countries like Italy as much as we do. That’s right, we’ve never made it a secret that we’re big fans of Mediterranean countries, Italy being one of them.

Italy is one of the largest countries in Europe and also one of the most famous. Well deserved, because few countries can offer their visitors as much beautiful and varied scenery, as fascinating a cultural experience and as unique a sense of life as Italy. If you’ve never been to Italy, now is the time to experience on your next trip what Italy has to offer.

We visit Italy quite often, about 6-10 times a year. Sometimes we just go for a few days, sometimes we organize longer trips. Because we know the country well enough, we hope this article will help you plan your trip to Italy. In this post, we share the itinerary of a two-week road trip around Italy.

So on this two-week tour of Italy, you can get to know Italy’s most beautiful cities, its best photography spots, its top hiking destinations, and much more that’s worth knowing about Italy.

There are a few things about Italy you should pay attention to.

If you want to see nearly all of Italy in two weeks, the pace will be quite brisk. So if you have more time than two weeks, of course plan more.

If you’re also looking for a longer itinerary, we recommend this one-month Italy itinerary.


Add in the journey there and back (by car or plane in most cases), because it’s a completely different time for everyone.

You can, of course, start your trip anywhere you like, depending on where you can start based on your arrival. We planned to start in Milan, because the north of Italy is usually the first destination for most tourists arriving by car, and several flights land in Milan.

How to get around Italy

By car

We definitely planned it for a car road trip, unfortunately it is quite difficult to do this with anything else. But don’t worry, although the Italian driving style may seem chaotic at first, you can actually get used to it quickly.

Public transport in Italy

If you prefer to use public transport within Italy, we can give some ideas. First, there are plenty of domestic flights in Italy, so you can fly between major cities. Otherwise, the Milan-Bologna-Florence-Florence-Rome-Naples route is also connected by a high-speed train, which can get you from one city to another relatively quickly. The Milan-Naples journey takes around 4.5 hours by train and Milan-Rome just over 3 hours. If you prefer to travel by public transport, this is an option you may prefer. So train transport between the big cities in Italy is pretty well organized.

The only thing left to solve in this case is getting to the countryside, which can be problematic without a car. In Italy, there are also Flixbus and local bus services as options.

Alternatively, taxis can be a solution in Italy, but they can be too expensive for longer distances, and are only a good idea within cities.

Best time to visit Italy

Italy is a fantastic destination year-round, offering diverse experiences with each season.

In spring, you can enjoy blooming flowers and pleasant temperatures. Summer is ideal for beach lovers. Autumn treats you to colorful landscapes, especially in regions like Tuscany. Although winter is quieter and fewer places are open, the lights of the cities and in some places the snow-capped mountains give a festive atmosphere.

Overall, we personally recommend May, June, September and October for a two-week road trip to Italy.

However, if you’re planning a winter trip to Italy, use this suggested Italy winter guide to discover the best snowy destinations for a memorable Italian winter trip.

How to spend 2 weeks in Italy

So here’s a two-week itinerary for Italy with the most important Italian attractions:

Day 1: Milan

On day one, you either arrive in Milan, Italy or you’re already here. Spend as much of the day as possible getting to know Milan. The area around the Duomo or the Arco della Pace are fantastic tourist destinations. The Galleria Vittorio Emanuele II, next to the Duomo, is a well-known location on social media. If you have time, everything in the city centre is close together, such as the Castello Sforzesco or the Royal Palace of Milan. Only the Stadio Giuseppe Meazza (San Siro) is a little further away from the city centre for football fans.

Day 2: Lake Como or Lake Garda

Unfortunately, both rarely fit into a day, but nothing is impossible.

Lake Como is a picturesque lake in the Italian mountains, with a slightly longer detour from Milan. In ancient times it was one of the favorite resorts of emperors. It offers the best views, especially in spring or summer. The most seen place in social media on the shores of Lake Como is the garden of Villa Monastero in Varenna.

Lake Garda, located next to the A4 highway, is the largest lake in Italy. It is a very popular Italian destination, often very crowded. The two most famous towns on Lake Garda are Sirmione in the south and Riva del Garda in the north. Both are worth a visit, although we think Sirmione is more spectacular because of its castle.

Day 3: Dolomites

Continue north for a few days. Our two-week trip to Italy can’t miss our personal favorite Italian region, the Dolomites.

On the way, Lake Carezza is the closest, which takes a couple of hours. Then up to the Alpe di Siusi plateau, where it’s worth staying the night. The Alpe di Siusi is a breathtaking place for hiking in summer and skiing in winter. Truly, Italy’s little hidden wonderland. In fact, the whole Dolomites are like that.

If you still have time, Seceda is also worth a visit. You can get there by two different cable cars.

Day 4: Dolomites

On day 4, go to other parts of the Dolomites. It’s worth visiting Lago di Braies, where you can hire a boat. Then travel on to Misurina, where you can visit the Misurina Lake. Along the way you can see several other lakes such as Lake Dobbiaco and Lake Landro.

In the afternoon, head to Tre Cime if you have a few hours and energy left. There’s a toll road to Tre Cime, so consider carefully whether it’s worth the effort. The last time it was over €30. Above you can choose from three main hiking trails. The first two are long (minimum 3-4 hour hike), the third is a little shorter. The first takes you around the three peaks, offering stunning views, the second takes you past the three peaks to the small lakes called Laghi dei piani, and the third takes you in a completely different direction to the Cadini di Misurina mountain group. This may not mean anything to you at first, but if you search for the Dolomites, you’ll see lots of photos. We just call it: small man – big mountain. 😀

If the weather is worse, stay down around Misurina and Cortina. You might want to check out Passo Giau, a winding, very scenic pass.

Day 5: Venice

Continue your journey to Venice in Italy. In the afternoon, you can enjoy the fascinating charm of the monuments of Venetian history. The city of Venice looks as if it has been untouched for hundreds of years. Walk around San Marco Square, and if you want, visit the Basilica and the Doge’s Palace from the inside. It’s also worth checking out the Rialto Bridge and the Academy Bridge for some of the best views of Venice.

Day 6: Venice

Another place to visit around Venice is the island of Burano. This is the most colorful and beautiful little island in Italy, which you can easily walk around in a couple of hours. The easiest way to get there is by vaporetto.

For the rest of the day, don’t miss what’s left of Venice. It is worth trying the local Italian restaurants. If you have the chance, you can also enjoy a gondola ride.

Day 7: Florence

It’s worth traveling on to Florence and the surrounding area. On the way, Bologna is also an interesting tourist destination in Italy.

However, Florence has even more to offer. Florence is particularly famous for its art, so art lovers might want to spend more time in the city. You can find an itinerary for an art-themed visit to Florence here.

Among the attractions, our favorite is Piazzale Michelangelo, from where you can see almost the whole city from above.

The area around the Duomo in Florence is also famous. Close by you can see the world famous David of Michelangelo statue in the Galleria dell’Accademia museum.

Another great sight in Florence is the Ponte Vecchio (bridge).

Day 8: Cinque Terre

Travel to one of Italy’s most photographed and stunningly beautiful destinations, the Cinque Terre. While a day is tightly scheduled to visit all five towns, if you can’t make it, Vernazza, Manarola and Riomaggiore are not to be missed. If you’re traveling in the summer, stop by the Nessun Dorma restaurant in Manarola for fantastic views and delicious local food.

Day 9: Rome

In the morning continue your journey to Rome. On the way, stop in Pisa to see the world famous Pisa Tower.

You arrive in Rome in the afternoon or evening. You can still visit some sights, like the Vatican or the Castel Sant’Angelo. The Vatican has a very interesting museum and St Peter’s Basilica is a popular destination.

Day 10: Rome

Rome awaits with its many attractions. Just to list the most important ones: Colosseum, Roman Forum, Trevi Fountain, Pantheon, Spanish Steps. It’s a busy day to see it all, but well worth the effort.

All we can say is that it’s worth throwing money into the Trevi Fountain, we got our wish!

Day 11: Naples

In the morning, continue to the south of Italy, to Naples. Here you have to be most careful with the car. The driving style around Naples is incredible. Broken cars and rubbish everywhere. That’s why we didn’t like to spend much time here. So take a quick look at the city of Naples, the attractions such as Castle dell’Ovo, Castle Nuovo, or Castle Sant’Elmo, from the last one you can get a fantastic view of the city from above.

Day 12: Amalfi Coast

Another must-see in Italy: the Amalfi Coast. Despite the bad road network, the Amalfi Coast is an absolute must-see in Italy.

The two most visited destinations are Positano and Amalfi. Choose which you like better. Both are similar and magically beautiful. Traffic and parking is a bit chaotic there, so arrive early, plan ahead how you’ll get there and where you’ll park. Unfortunately, there are a lot of bad reviews about the parking lots around there. Be careful.

If you feel like it, you can take a boat trip and see the coastline even better.

Day 13: Naples area

Other must-sees around Naples are the city of Pompeii and the Vesuvius volcano. You can visit the ancient city of Pompei with a ticket, it’s a very fascinating attraction. The Vesuvius volcano can be reached either by bus or car, but the last one kilometre is on foot on a steep, gravel road. You will also need a ticket. You can walk relatively close to the volcano’s crater, and it sometimes smokes. An interesting tourist destination in Italy.

If you still have time, the Caserta Castle is also near Naples. It is one of the most beautiful castles in Italy, with a magical atmosphere and a huge garden.

Day 14: Milan

Unfortunately, on the last day you have to travel back to Milan. As it takes about 9 hours by car, you can either take the whole day to get there by car (maybe if you missed something, you can fit in a shorter programme).

To mention public transport, from Naples to Milan it takes about 4.5 hours by train and 1.5 hours by plane. If you are not traveling by car or have somewhere to leave the car, these can be time-saving options.

Here is what we think you can see in two weeks in Italy. These two weeks will be quite active and we can promise you will see the most popular places of Italy. We hope you enjoyed our two-week itinerary to Italy and are inspired to plan a similar trip to Italy.

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