The freshly-made pasta, the talking with their hands, the thousands of years of culture, the breathtaking art, the rolling countrysides and endless coastlines, it all makes people go crazy for Italy! I feel there is nothing not to love about Italy, and I would be rather satisfied spending a lifetime exploring it all. Imagine just spending a lifetime eating your way across Italy! Well I suppose after awhile I might have to hire someone to roll me across the country since I would have no self-control in a situation like that. But really, I imagine my hypothetical life in Italy to be something like the effortlessly chic adventures of Frances Mayes in Under the Tuscan Sun, or maybe something dramatic in a small boating town like in Beautiful Ruins. Oh it would be grand! These are what I consider to be the best cities to visit in Italy, those that I would visit in my lifelong tour of Italy and those that you should schedule into your travel itinerary too!
The Best Cities to Visit in Italy
1 | Rome
The capital of Italy, Rome was once also the center of the Roman Empire, so you can expect to find historic relics and important sights at every turn. Here you’ll see the Colosseum, the Pantheon, the Forum, the Vatican City, and more. Read more about falling in love with Rome here.
2 | Lake Como
Famed as the Italian getaway locale for the rich and famous, Lake Como boasts gorgeous villas and resorts on the banks of the lake that abuts the Alps. It’s a setting that’s easy to fall in love with, and it’s worth a visit to see it in person.
3 | Florence
It’s no surprise that as the capital of Tuscany, Florence has proved the perfect setting for Italy’s art capital. I would be inspired to create art if I lived here too! You’ll find the works of Michelangelo and Brunelleschi and others on display in Florence.
4 | Naples
Naples has a little more grit and character than other Italian cities. But it’s the birthplace of pizza, for which I adore it. And it is also a great base from which to visit Capri and the ruins at Pompeii. Don’t let the graffiti scare you off, Naples is worth a visit. Here are some tips of what to do there.
5 | Capri
I just could not get enough of Capri! This giant rock formation jutting up from the cerulean blue sea would seem an inhospitable vacation spot. And yet against all odds it is one of the loveliest places to visit! The port is small and charming, the town up on the hill is well worth the climb, and the views as you hike around the island just seem to get better with each passing stride. Don’t forget to try some limoncello while you’re there, bottled fresh on the island!
6 | Taormina
They say Sicily is like a country all it’s own. Or at least the Sicilians like to remind you that they’re different from other Italians! Besides Capri, the other Italian island you need to visit is Sicily, and while you’re there you can check out Mt. Etna, an active volcano, and Taormina, a hilltop town with ancient ruins.
7 | Venice
Venice is sinking, so it’s probably best to put this higher on your travel to-do list. A gondola ride through the canals seems too charming to pass up and despite the crowds, Venice is still a city you absolutely must visit in Italy!
8 | Milan
For high fashion in Italy, Milan is the place to go! You’ll also love to see the Duomo, whose intricate architectural detail is nothing short of mesmerizing. Since it’s a major financial hub, it leaves some travelers unimpressed but it’s worth a stop on the itinerary if only just for the Duomo!
9 | Bergamo
Nearby to Milan is the charming little town of Bergamo, complete with cobblestone streets, venetian walls, historic chapels, and a funicular to satisfy your need for a quintessential Italian experience. It’s charming and unassuming and you will totally love it!
10 | Siena
Home to just one of Italy’s numerous UNESCO World Heritage sites, Siena is a small hilltop town in Tuscany. Surrounded by all the beauty of Tuscany’s verdant hills, Siena is the perfect base to explore the Tuscan region. Laden with brick, Siena is the archetypal Italian medieval city, and it has the best wines and olive oils in all of Italy!
11 | Perugia
While crowds flock to Tuscany, you’ll find some peace and quiet in the nearby Umbria region, which shares many of the same qualities as Tuscany. Perugia is a medieval walled city and the capital of Umbria, making it a great base to explore the region and all of the olive farms and vineyards it has to offer!
12 | Portofino
For those looking to soak up some sun on the coast, Portofino is the picture-perfect spot to go! With homes of every pastel color nearly spilling over into the sea, this town is a photographer’s dream. And the fresh seafood and slow small-town pace make for an utterly addictive experience.
13 | Positano
Similarly, Positano is a cliffside town on the sea boasting great views from the land and the water. As part of the Amalfi Coast, Positano is one of many great places to explore in one of Italy’s most revered regions.
14 | Pisa
Come to Pisa to take a photo with the leaning tower of Pisa, but stay because of the incredible history that radiates from the walls of this town. As an education capital, Pisa is a city after my own heart, reminding me of my hometown Boston. And so you’ll find an enduring sense of intellectual curiosity and excitement that characterizes this town.
15 | Bologna
With potentially the best food in all of Italy, Bologna is the kind of city you will want to include on your itinerary twice, once at the beginning of the trip and once at the end. If you love Italian food, trust me you’ll love Bologna. Not to mention the sun-splattered red clay roofs and classic Italian architecture seen all around town that make this one of the prettiest towns in Italy.
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