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Many travelers head to Italy to experience la doce vita.  It has to be the country on more bucket lists than any other.  We have traveled to Italy more times than we can count both by car and by air and it is a wonderful place to get lost. We love the feel of the country and have met many great people during our travels.  The biggest mistake people make when traveling to Italy is trying to do too much.  I probably didn’t travel south of Rome until my 10th visit to the country.  There is just so much to see and do and we are always discovering more.

If you are planning a trip to Italy, you are probably wondering which cities are the most beautiful and interesting. In addition to an almost endless Mediterranean coast, the Italian peninsula is known for beautiful cities such as Rome, Milan, Venice and many more. Whether you are planning a weekend getaway or a longer trip, here is a list of the most beautiful cities in Italy.

The Ultimate Guide to Italy's Most Beautiful Cities

Rome, Italy

Rome – Unforgettable Journey Back in Time to Antiquity

Rome is not only the Italian capital but also the largest city in Italy. If you want to follow in the footsteps of the country’s millennia-old history, you should plan your short trip as soon as possible.

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Between the world-famous Rome sights such as the Colosseum, Pantheon, Trevi Fountain and Vatican City, you should definitely explore the city off the usual tourist paths. For example, during your visit, you must climb the highest viewpoint (Monte Mario) in the city, explore the authentic district of Testaccio or find a cute place to stay in the back streets.

A quick tip:  Stay near the Metro station.  The train is a wonderful way to get all around the city with stops near the Vatican, Colosseum, and more.  And the best part is it is inexpensive.

Milan – Italy’s Fashion Metropolis

We continue with one of the top Italian cities: welcome to the northern Italian fashion metropolis. Whether on a stopover or for a city trip, the lively city always welcomes you with open arms.

In addition, Milan is worth a visit at any time of the year. The Lombard financial centre naturally offers more besides the numerous luxury boutiques.

On the other hand, the scenes at the Milan Cathedral alone or a visit to the church Santa Maria delle Grazie with da Vinci’s world-famous Last Supper promise a varied stay. If you are looking for the hip and creative side of the city, the trendy districts of Tortona and Brera or the north of Loreto are among the must-see Milan tips.

Having stayed in Milan a number of times, I can tell you that Milan comes alive at night.  Well worth a visit.

Naples – Pure Italy

If you are looking for the most beautiful coastal cities in Italy, you should take a look in the south of the country. There you can get to know the picturesque metropolis of Naples.

Between transience and beauty, one of the top Italian cities offers you everything you could wish for on a Mediterranean holiday. With proximity to the active volcano Vesuvius, the archaeological site of Pompeii, the enchanting Amalfi Coast or numerous Italian islands, you absolutely have to plan enough time in the region.

In addition, you will find a very special charm in the old town of Naples and you have the chance to discover exciting underworlds. Finally, you absolutely have to enjoy traditional Neapolitan pizza.

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Incidentally, this is just a small selection of the numerous Naples tips, and the city is almost predestined for a city trip to Italy.

BTW, Naples can take some getting used to. It is a large, crowded, terrible to drive in city.  But just take that in stride, and soak in the beauty and charm of Naples.

Florence – Exciting cultural city of Tuscany

The cradle of the Renaissance is undoubtedly one of the most popular tourist destinations in Tuscany. If you are planning a road trip through Italy, a stopover in Florence is an absolute must.

You can combine a holiday in the Tuscan mountains with an exciting cultural program. On the banks of the Arno, you have to marvel at impressive historical works.

In addition, the world-famous art collection of the Uffizi is one of the top Florence tips. During mild summer nights, you should capture the atmosphere around the landmark of Florence Cathedral or walk across the historic Ponte Vecchio bridge.

After you have unwound your cultural program, it is worth walking to the Piazzale Michelangelo viewpoint. You will discover cute bars in the dreamy alleys. One of Tuscany’s highlights!

Bologna – Fascinating University City

If you are looking for one of the top cities in Italy, you should take a closer look at the university city of Bologna. One of the underrated travel destinations combines trendy vibes with historical sights.

As soon as you approach the oldest university city in Europe, you will be surprised by the numerous medieval treasures and unmissable arcades of Bologna. There the typical terracotta-coloured brick buildings will take you to a culinary paradise. Let yourself be convinced!

Bari – Capital of Puglia

While you are still enthralled by Bologna, another gem awaits you to the south of the ‘boot’. Just like the previous destinations, the port city of Bari is one of the most beautiful cities in Italy.

Believe it or not, the former trading town will have a fantastic surprise effect on you. The attractive old town of Bari Vecchia along with its ancient scenery is one of the incomparable highlights.

When the sea calls, you have some dream beaches right in front of the door, and you will be perfectly attuned to your holiday in Apulia.

The Ultimate Guide to Italy's Most Beautiful Cities

Venice by day tends to be over-crowded with day-trippers. Stay over night for a truly magical experience.

Venice – A Dream of Italy

The lagoon city of Venice is undoubtedly one of the most famous cities in Italy. Nobody says anything to the contrary, right?

For many of you, the city of Venice is still one of the longing destinations in Italy, despite its great popularity. By the way, rightly so, because the numerous canals, famous gondolas and romantic backdrops exude a wonderful and unique ambience.

I have said it many times and in many articles.  I hate, hate, hate Venice during the day.  It is too overcrowded and filled with souvenir shops.  But the night is amazing and one of my favorite places to be.  Filled with music in the air, and no longer any crowds, the real Venice comes alive.

Pisa – Around the Leaning Tower

One of the most famous Italian cities is, undoubtedly, the Tuscan city of Pisa. The city is world-famous for the landmark of the Leaning Tower of Pisa.

But so much more awaits you on site. On the banks of the Arno, one of the oldest university towns in the country welcomes you with a lively atmosphere and irrepressible joie de vivre.

In the shadow of one of the world’s most famous buildings, you have the chance to marvel at the impressive, magnificent and sacred buildings (Cathedral of Santa Maria Assunta) and experience a colourful cultural programme. But the proximity to the seaside resort of Marina di Pisa also promises exciting variety.

Just a tip:  If you are driving get to the leaning tower late afternoon.  The tour buses are gone and it is not over-crowded any longer.  When Kati and I went, we bought a ticket and went straight up the Leaning Tower with no wait.  It was sensational.

Bergamo – Journey through Lombardy

Back in northern Italy, it is worth checking out the city of Bergamo. Located between the Po Valley and the foothills of the Alps, the Italian city has long been considered an important strategic location.

Today, this industrial city is characterized by an upper and lower town. The former tells a moving story and is bordered by preserved, mighty city walls.

You can reach the medieval district of Città Alta traditionally with a cable car and immerse yourself in a picturesque UNESCO World Heritage Site. Framed by the Venetian walls, you should take the chance to pause for a moment and let the incredible ambience work its magic on you.

Turin – Holidays in the North-west

If you are considering a trip to the lesser-known region of Piedmont, one of Italy’s top cities will also find a place on your to-do list. Because at the foot of the Alps, you can explore the completely unjustly underestimated metropolis of Turin between tradition and modernity.

Surrounded by historic, baroque magnificent buildings, you absolutely have to enjoy the delicious Turin cuisine and taste the wines of the region. In addition, between the car industry, football, Olympic flair and traditional coffee houses, you will experience a city on the upswing that is just plain fun.

As soon as you start planning, you should add a few days to your stay in Turin and visit the beautiful wine regions of Langhe and Monferrato. You can also enjoy the white truffle in the city of Alba or you can buy the sparkling wine of the same name in the city of Asti. 

Our Final Word

Italy is an amazing country and if you are like us, will make you go back time and time again.  These 10 cities are great and a good starting point.  But do not skip the lakes in the north like Lake Como or Sicily in the south.  Also, the Amalfi Coast is beautiful as well as may other places in-between. In reality, we could not decide the most beautiful city and it is worthless to try.  Every area of Italy is different with a different history.  The people are different, and the sights, sounds and smells are different.  That is what makes Italy so special.  We hope to see you there.

Trip map created using Wanderlog, a road trip planner app on iOS and Android

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