There’s An Italian City For Everyone

When everything in life fails you, there’s always Italy.

Bologna Italy
Checking out Bologna. Photo: Kaitlyn Rosati

Narrowing down which cities to visit in Italy can feel overwhelming. It’s a fairly small country with an abundance of options.

After traveling extensively throughout Italy, I’ve created a guide to help you decide which cities to spend time in.


Highlights: Fashion, Luxury, Veal, Navigli, A Gateway to Lake Como.

Milan is the fashion capital of Italy, maybe even of Europe, maybe even of the world! Yes, I truly believe Milan gives Paris a run for its money when it comes to high-fashion. As soon as you land, you will see chic women and men in outfits that probably cost more than your flight.

Of course, the biggest sight to see in Milan is the Duomo. The architecture is incredibly intricate and it only costs 3 euro to go into the cathedral. You also have the option to climb to the top which ranges from ten euro to twenty euro depending on if you take the stairs or a lift.

Right aside the Duomo is Galleria Vittorio Emanuele II, a large shopping center with glass ceilings. Inside, you will find plenty of restaurants, gelato shops, and high-end luxury stores.

Milan is also home to the Sforzesco Castle (one of the largest citadels in Europe). Inside, you can find art by da Vinci and Michelangelo.

The food of Milan is notoriously rich (and that’s no coincidence: Milan is much more expensive than most of Italy). Most dishes contain a fair amount of both meat and butter, and risotto alla Milanese is distinct because it contains saffron. And you’d be a fool to go to Milan and not try some cotoletta alla Milanese (veal cutlet)!

If you’ve had enough of being fancy in Milan, head to Navigli; a fun neighborhood filled with bars serving up appertivo.

Geographically, Milan is close to Lake Como as its located in the north. It also is just a quick bullet train ride away from Bologna.


Highlights: Bolognese, Fountain of Neptune, Piazza Maggiore, A Gateway to Modena.

Bologna is often overlooked by its more popular neighbors of Milan and Florence, but after finally visiting, I can assure you, it’s 100% worth seeing.

Bologna does indeed have its own international airport, but if you arrive by train, the station is situated pretty close to the city center.

Bologna’s most major attraction would probably be Piazza Maggiore. Here, you can find basilica di San Petronio, a church that dates back to 1388. Be sure to get a picture next to Fontana del Nuttuno, or the fountain of Neptune. And check out those mermaids!

Aside from the orange / yellow shaded streets and major attractions of Bologna lies the biggest star of all…the food. Bologna’s food, in my opinion, is the best in all of Italy. Bologna is, naturally, known for Bolognese, the classic tomato / meat sauce. I had some lasagna at a quiet café right outside of Piazza Maggiore, and it may have been the best meal I’ve ever had in Italy. Be aware, though, since this area is touristy, the prices are jacked up. I paid 12 euro for this lasagna and while it was completely worth it, you could probably find something similar for 9 euro elsewhere. Bologna is also home to tortellini, so later in the evening, I went to Sfoglia Rina, a little shop where you write down your order, hand it to a waiter / waitress, and before you know it, you will be given the best tortellini you’ve ever had in your life. Be prepared for a wait, though- this place is popular for a reason.

Bologna is also close to the quaint town of Modena, home of the world famous “best restaurant in the world” Osteria Francescana. So, if you decide to stay a few nights in Bologna, why not take a day trip out to the country side and try to snag a reservation?


Highlights: Gondola rides, Seafood, Burano.

Venice was my first stop in Italy, and what a perfect cliché way to begin my Italian travels! I believe Venice is by far the most touristic out of anywhere else in the country. A day or two should be sufficient time to get a good feel for this canal-based city. There are no roads in Venice, meaning, no cars! It is a fun city to walk around, but it’s indeed pricey and because of the tourism, I feel it overall lacks in quality. I still think it’s worth seeing just to ride a gondola (did you really go to Italy if you didn’t ride a gondola?) and checking out Saint Mark’s Basillica. Also, give yourself enough time to check out the colorful island of Burano!

Finding good food in Venice can be a challenge, but if you want to stick to regional cuisine, try something with seafood. A popular item is risotto al nero, a squid-inked based risotto giving it a jetblack color.


Highlights: Duomo, Michelangelo, Ponte Vecchio, Wild Boar Ragu, Steak, Truffles, Gateway to Tuscany and Pisa.

Ahh, Florence. Now, I’m just going to admit I’m biased: Florence is my favorite Italian city, but I’ll try to keep this more factual than straight-up gushing about how much I love it here.

Florence’s main attractions are the Duomo, Palazza Vecchio, Ponte Vecchio, Piazza della Signoria, Piazzale Michelangelo, …to name a few. Florence is jam-packed with sights to see and after spending over two weeks there, I feel like I have hardly scraped the surface.

A wonderful thing about Florence, aside from the beauty in the city itself, is it’s centrally located making it a great hub for day trips. It’s a short-distance from Pisa, Tuscany (Chianti region, particularly), Cinque Terre, and Siena. With that being said, if you plan to visit Cinque Terre, I would recommend doing more than one day as there’s a lot to see.

Florence Italy
Beach at Cinque Terre. Photo: Kaitlyn Rosati

And, of course, we can’t forget about the food! Mercate Centrale Firenze is a great way to try a few different things without running all over the city, and while the quality doesn’t suffer at all, the prices are a little steeper. Il Vinaino is a great option for eating a quality meal for under 10 euro. I ordered the tartufo tagliattele and paid 9 euro for a giant plate of pasta covered in truffles.

Speaking of eating in Florence, bring a buddy with you to try some famous fiorentina bistecca, a giant steak meant for a minimum of two. Also, get your hands on some wild boar ragu, and definitely don’t skip out on the wine.


Highlights: The Colosseum, Pasta, Vatican City, Gateway to Pompeii.

What Italian holiday is complete without a visit to the capital? Narrowing down what to see in Rome can feel like a grueling task in itself; but have no fear. You can truly get all of it done in just a few short days as all of the major sights are within close walking distance of another. You won’t want to miss the Trevi Fountain, and from there you can skip on over to the Colosseum. If you are on a time crunch, make sure to buy a “skip the line” pass, or be prepared to wait an average of two hours. You’ll want a day to explore Vatican City (which is its own country!), and you can hit the Panthenon on the way. Rome also has the infamous Spanish steps, a great way to work off some of the carb-loading you’re bound to consume from traditional Roman food (bucatini alla’amatriciana is my personal favorite, but make sure you go for some carbonara and cacio e pepe too!). And if you need a vegetable, don’t miss Roman artichokes.

Rome Italy
Vatican City. Photo: Kaitlyn Rosati

If you’re unsure as to where to stay in Rome, just keep in mind anything near Termini station is going to be overpriced. A great neighborhood to consider is Trastevere, a young hip area filled with bars and restaurants, in a much quieter more authentic setting.

Rome is a great hub to Pompeii and the Abbruzzo region.

The Amalfi Coast

Highlights: Capri, Positano, Limoncello, Beach.

The Amalfi Coast is probably the most instagrammed place in Italy due to its picturesque coastal flair. You have the option to stay in either Positano, Sorrento, Amalfi, or Ravello. I opted to stay in Sorrento because it was easier to travel to (a ferry takes you directly from Naples) and I saved some coin by doing so. While this may not be for everyone, I stayed with a family and it was a life-altering experience. Try finding a proper bed and breakfast on Airbnb if you’re looking for something different. They lived on a lemon farm and I ate fresh mozzarella and tomatoes with them every night, chased with some homemade limoncello.

Positano is the more popular option, but be prepared to pay. While Positano is definitely worth visiting, there isn’t tons to do other than take glamorous photos, drink limoncello / eat lemon sorbet (the lemons here grow to be the size of your head!), and sit on the beach. The beach is rocky and small, but beautiful nonetheless. I found Positano to be the most expensive place I visited in Italy, and I thought one day was enough time to truly explore it.

Aside from the Amalfi Coast itself, it’s a necessity to head over to Capri and visit the Blue Grotto. Don’t feel bad if you don’t make it into the Blue Grotto: I have yet to see it because the day I was there, the weather was too windy and therefore it was deemed unsafe. Capri is glamorous and also fairly overpriced, but you can grab some seafood and torta caprese, walk around the island, and check out all of the blooming flowers.

Hopefully that helps you narrow down how you’d like to plan your Italian vacation! These are just the major cities (minus Naples, which I have unfortunately not spent enough time in to be a fair judge), but don’t be afraid to venture out and see some of the small villages.

As I always say, when everything in life fails you, there’s always Italy.

Kaitlyn spent one month in Italy.

Kaitlyn Rosati


Originally from New York, Kaitlyn was a musician/bartender before she left it all behind to embark on a solo round-the-world backpacking trip. She is passionate about preserving the environment, learning about gender equality throughout the world, eating anything that’s placed in front of her, saying hi to every animal she meets, and jumping off of cliffs into pretty blue waters.

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