A Guide to Cities in Italy

Every weekend, I find myself on a train traveling to a new city in Italy. From Milan to Naples, I’ve explored different regions, written down all the restaurants I’ve tried, and kept a running list of the places I must visit again (spoiler alert: it’s most of them).

Florence

Florence is my favorite big city in Italy, and not because of its proximity to Siena. I love the river Arno, the narrow streets, and the endless restaurants. There’s nothing like the view of Brunelleschi’s Duomo from Piazzale Michelangelo, and no other city houses museums like the Uffizi or Academia. There are an endless number of places to explore in Florence, so its conveniently an incredibly walkable city. Even though it seems like I pass more Americans than Italians, Florence is one of those cities where the reality constantly exceeds my expectations.

Restaurant Recommendations: Trattoria Sabatino & Pensavo Peggio

Pros: Great nightlife, walkable

Cons: Salt-less bread

Pisa

After looking at the Leaning Tower of Pisa for fifteen minutes, you end up looking at your travel companions thinking now what? Other than the Piazza del Duomo, Pisa lacks other significant tourist sites. We spent an afternoon in Pisa, which was the perfect amount of time to stroll down the Arno, eat gelato, and scroll Wikipedia to understand why the Tower hasn’t collapsed.

Must-Dos: Rent a scooter

Pros: Ryanair flies out of Pisa airport

Cons: Embarrassing poses at the Tower

Venice

Siena has been referred to as “Venice without water,” which is probably why I loved Venice so much. The windy streets, canals, and complete lack of cars made this city one of my favorites. While you can get away with looking at most Duomos from the outside, it is imperative to go inside St. Mark’s Cathedral in Venice. The ceilings are covered in gold mosaics, and the skip-the-line tickets were inexpensive. The gondola ride is exactly as cool as you’d think it’d be, and an aperetivo at a tourist trap restaurant is worth it for the view of the canals alone.

Restaurant Recommendation: Trattoria alla Rivetta

Pros: Venice invented the Aperol Spritz

Cons: They put olives in their Spritz

Verona

I couldn’t spend a semester in Italy and not visit the setting for Shakespeare’s Romeo and Juliet. One afternoon was enough time for me to romanticize every street I walked through, and I recommend fair Verona with every fiber of my being. The colosseum was stunning, in excellent condition, and far less touristy than Rome’s. Visiting Giulietta’s Balcony was equally as exciting, but it was the busiest tourist site I’ve been to.

Pros: The potential to find Romeo

Cons: No Romeo

Milano

My first view of Milan was emerging from the Metro and gazing up at the Duomo lit up in the night. I was blocking pedestrian traffic just gazing up at the Cathedral like a tourist I desperately try not to be. Once I got over this initial shock, Milan let me down. While this has more to do with personal taste than the place itself, Milan feels like a large metropolitan city and lacks the charm that places like Florence have. The highlight of my time there was watching a Serie A game between Empoli and Milano (if you support Inter, kindly find taste)!

Must Dos: Da Vinci’s The Last Supper

Pros: Metro, active nightlife

Cons: Slightly unsafe at night

Crema

At the train station, a girl asked me why a bunch of Americans were in Crema. She’d never seen tourists there before. My Italian wasn’t good enough to explain that we were there to see the filming locations of the movie, Call Me By Your Name, so I pretended like we were just exploring the Lombardy region. 10/10 recommend if you love Timothèe Chalamet enough to spend more time traveling to Crema than you spend in Crema.

Must Dos: Rent a bike!

Pros: Tiny city

Cons: Tiny city

Naples

The south of Italy is stunning and known for two of my favorite things: the coast and pizza. The pizza in Naples is a once-in-a-lifetime experience. You will question everything you’ve ever known. You’ll strongly consider living in Italy forever. Then, you remember you’re in Naples and resign yourself to a life of subpar pizza. While Naples is in a beautiful location, and close to the Amalfi Coast and Pompeii, the city itself is not a place I would willingly spend time in. Our Airbnb was just outside the train station, and there was a dramatic moment where I thought this is the end. The city can be unsafe, and if you go outside of the main tourist areas or walk around at night, it is a recipe for disaster.

Pros: Life-changing pizza

Cons: You’ll never be able to eat pizza anywhere else again

Positano

Pictures don’t do Positano justice, and the photos are jaw dropping. I am in love with this city on the cliffside and cannot say enough incredible things about my time there. Its remote location does make it difficult to access, and cities like Sorrento are closer to Naples and equally as beautiful. The best thing I did in Positano was taking a cooking class at La Tagliata. We got to pick vegetables from their garden, make the gnocchi by hand, and drink their entire cellar’s weight in white wine. Sincerely, I think they were trying to kill us. I lived though, and I am happier because of it.

Must Do: Buy something with the iconic hand painted lemons

Pros: Everything

Cons: Inconvenient location, expensive