My Favorite Cities in Italy to Visit (And the Surprises I Didn’t See Coming)

You know how everyone has that one dream trip they keep tucked in the back pocket of their wanderlust list? 

For me, that was Italy. But when I finally booked that one-way ticket to pasta paradise, I didn’t just hop between the big-name spots. I road-tripped, I train-hopped, I people-watched in more piazzas than I can count—and I fell madly in love with the unexpected.

So, if you’re wondering which cities in Italy to visit, friend, buckle up. I’m serving you my full, unfiltered guide—from postcard classics like Florence and Venice to the jaw-dropping charm of places like Matera and Genoa. 

I skipped the tour buses and went the Ava way—slow, curious, and maybe a little carb-heavy. You ready?

Which iconic cities in Italy are worth every cliché?

Let’s start with the big hitters. Yes, they’re crowded. Yes, they’re hyped. But you know what? They deserve it.

Rome 

Rome was my very first stop, and I swear I could smell the centuries. One moment I was grabbing a cornetto, the next I was face-to-face with the Colosseum, then strolling into the Vatican like I belonged there. This city is layers upon layers of history, with a side of spritz.

Florence

Then came Florence—cue the Renaissance daydreams. I spent hours at the Uffizi swooning over Botticelli and people-watched on the Ponte Vecchio until sunset. 

If art is your love language, Florence will whisper sweet nothings in your ear all day.

Venice

And Venice? I expected to love it, but I didn’t expect to cry a little on a quiet gondola ride at dusk. 

Between the crumbling canalside palazzos and the echo of church bells bouncing off the water, it felt like living inside a fairytale that hadn’t been rewritten for tourists.

What cities in Italy offer modern vibes with classic flavor?

Milan

Enter Milan—a city that struts. You don’t just walk here, you arrive. Between the high fashion and the majestic Duomo, there’s a sense of sophistication that’s still surprisingly welcoming. 

I visited The Last Supper, did some budget window shopping at the Galleria, and sipped espresso like I belonged on the runway.

Naples

Then there’s Naples—chaotic, gritty, and wildly authentic. The birthplace of pizza (trust me, the hype is real) feels like a city that doesn’t care what you think, and I love that about it. 

I danced around traffic in the historic center, ducked into underground Roman ruins, and caught a ferry to Capri before breakfast. Naples is the kind of wild I live for.

Which coastal cities in Italy will completely steal your heart?

Amalfi Coast

Two words: Amalfi Coast. It’s all cliffs, citrus groves, and color-drenched towns tumbling toward the sea. Sorrento was my base—a town that smells like lemons and sings like summer. 

I took winding buses to Positano, hiked the Path of the Gods, and lingered over Aperol spritzes with views that honestly made me gasp.

Cinque Terre

And if you want charm by the teaspoon, go north to Cinque Terre. These five pastel fishing villages are postcard perfection. I hiked between them with sea air in my lungs and pesto in my belly, and slept like a baby every night.

Lake Como

Don’t sleep on Lake Como either—it’s not just for celebrities. I stayed in Varenna, rode ferries to other lakeside towns, and watched clouds curl around snowcapped peaks while sipping pinot grigio on a boat deck. Luxury doesn’t have to be expensive if you know where to look.

Looking for cities in Italy to visit off the beaten path? Start here.

Matera

Let’s talk Matera. Ever slept in a cave? This ancient southern city carved into stone is like nothing I’ve seen. Wandering through the Sassi district feels like time travel, and the sunsets here turn limestone gold. Pure magic.

Bologna

Bologna, nicknamed “La Grassa” (The Fat One), is foodie heaven. I took a pasta-making class here that changed my life, and the medieval towers? Bonus points. It’s got grit, charm, and some of the best damn tagliatelle al ragù on Earth.

Genoa

I fell hard for Genoa, too. This underdog port city gave me labyrinthine alleys (Carruggi), unexpected views, and mind-blowing focaccia. I almost skipped it and I’m so glad I didn’t.

Palermo

Palermo in Sicily hit me with its energy—noisy markets, bold street food, and a cocktail of cultural layers. Plus, it’s way more affordable than most big cities up north.

So how do you choose which cities in Italy to visit?

It really comes down to vibe. Here’s a quick cheat sheet to help:

Pick 3–4 cities if you’ve got 10 days. Any more and you’ll be unpacking more than you’re exploring.

FAQ: You Asked, I’ve Got the Good Stuff

1. What’s the best time to visit Italy for city travel?

Spring (April–June) and early fall (September–October) are chef’s kiss. Fewer crowds, comfy temps, and outdoor café weather.

2. Should I rent a car or take the train between cities?

Trains are your besties. They’re fast, scenic, and drop you right in the center. Driving’s great in the countryside (Tuscany, Sicily), but cities? Parking = headache.

3. Is it worth visiting lesser-known cities over the famous ones?

Absolutely. Famous cities dazzle, but the hidden ones linger in your memory. I still dream about espresso in Siena and sunsets in Matera.

4. How many cities should I visit in one trip?

Three to five is the sweet spot. Give each one 2–3 days to really soak it in. Don’t rush—Italy is all about la dolce vita.

Final Scoop Before You Jump In

Italy doesn’t just hand you beauty—it smacks you in the face with it. 

From the eternal pull of Rome to the seductive calm of Lake Como, choosing which cities in Italy to visit is less about checking boxes and more about listening to what kind of adventure you’re craving.

For me, it was about slow mornings with espresso, impromptu detours into cobblestone alleys, and finding a slice of magic in every piazza.

Whatever your Italy looks like, trust your gut, bring stretchy pants, and always say yes to gelato—twice a day if needed. Happy travels, amico.