5 Italian Cities Worth Your Time (And 2 You Can Skip, According to a Traveler Who’s Visited All 20 Regions)

When someone tells you they’ve seen all of Italy, you should listen. Not the tourist traps, not the highlight reels—the real country, from the snow-capped Alps to the sun-baked shores of Sicily. I’m Kaitlyn Rosati, and I’ve spent more time in Italy than out of it. I’ve visited every single one of the 20 regions, most of them multiple times. And if there’s one question I get asked more than any other, it’s this: “Which cities are actually worth visiting, and which ones are overhyped?”

After dozens of trips and hundreds of conversations with locals and travelers alike, I’ve developed a clear—and sometimes controversial—list. Here are five cities I strongly recommend you add to your itinerary, and two that I’d confidently skip.

The 5 Cities I Recommend Visiting

1. Rome: The Eternal City Delivers Every Single Time

Let’s start with the obvious. Rome is iconic for a reason. I’ve visited dozens of times, and I still have to pinch myself when I walk through its streets. It feels like a movie set—one that doesn’t shift with trends or get remade every few years. That’s why it’s called the Eternal City.

What to do: Yes, hit the big landmarks—the Colosseum and the Pantheon are non-negotiable. But for the real Rome, skip the tourist-packed piazzas and head to neighborhoods like Monti, Pigneto, and Testaccio. These are where Romans actually live, eat, and drink. You’ll find authentic trattorias, hidden courtyards, and street art that tells the city’s modern story.

What to eat: Roman cuisine is a masterclass in simplicity. Try carciofi alla Romana (artichokes Roman-style), pasta alla gricia (a rich, peppery pasta with cured pork and pecorino), and scrocchiarella—a thin, crispy pizza that’s a Roman specialty.

Where to eat: Two of my favorites are Trattoria della Stampa, tucked just around the corner from the Trevi Fountain (and far less crowded than the square itself), and Trattoria da Zacca ar 20, near Vatican City. Both serve honest, traditional Roman food that won’t break the bank.

Why it’s unmissable: Rome is a living museum. You can’t replicate its energy, its history, or its food anywhere else. It’s not just a city—it’s a feeling.

2. Perugia: The Medieval Hilltop Oasis You’ve Overlooked

I’ll be honest: Umbria was my 18th region out of 20. I saved it for last, and I was wrong to wait so long. Perugia, the capital of Umbria, is perched high above the hills, surrounded by ancient walls that date back to Etruscan times. It’s a medieval fairytale come to life.

What to do: Walk the old town. The dramatic landscape alone is worth the climb. But Perugia isn’t just about views—it’s about chocolate. The city is home to Baci Perugina, Italy’s most famous chocolate brand. Chocolate is so central to Perugia’s identity that one of Europe’s largest chocolate festivals, EuroChocolate, is held here every year.

What to eat: Obviously, chocolate. But don’t miss torta al testo, a flatbread stuffed with greens, cheese, or cured meats. It’s Umbria’s answer to a sandwich, and it’s perfect for a casual lunch.

Why it’s unmissable: Perugia is intimate, romantic, and wildly overlooked. It gives you that “I found a hidden gem” feeling without any sketchy compromises. Plus, it’s a perfect base for exploring the rest of Umbria—like Assisi, Spello, and the hilltop town of Gubbio.

3. Palermo: The Dreamy Street-Food Capital of Italy

Sicily is a world unto itself, and picking just one city is tough. But if I had to choose, it’d be Palermo. This is a city that grabs you by the senses and doesn’t let go. It’s chaotic, vibrant, and deeply authentic.

What to do: Walk the markets—Ballarò, Capo, Vucciria. These aren’t tourist attractions; they’re living, breathing markets where locals buy their daily bread, fish, and vegetables. The architecture is a mash-up of Norman, Arab, Byzantine, and Baroque influences—a testament to the island’s complex history.

What to eat: Palermo is a street-food paradise. Try arancini (fried rice balls), panelle (chickpea fritters), sfincione (Sicilian pizza with a thick, fluffy crust), and cannoli (because, yes, you must). Don’t leave without tasting pasta con le sarde—pasta with sardines, fennel, pine nuts, and raisins. It’s a flavor bomb you’ll never forget.

Why it’s unmissable: Palermo is raw. It’s not polished or curated for Instagram. But if you love food, history, and real culture, this is where you want to be.

4. Bari: The Underrated Port City of Puglia

When people think of Puglia, they think of the trulli houses in Alberobello or the whitewashed beaches of Polignano a Mare. But Bari, the region’s capital, deserves way more love than it gets. It’s a gritty, lively port city with an old town that feels like a maze of secret courtyards.

What to do: Walk the Bari Vecchia (old town). It’s narrow, chaotic, and full of life. Watch the nonne making orecchiette pasta by hand in the streets—yes, really. Visit the Basilica of San Nicola, where the relics of Saint Nicholas are kept. And don’t skip the seafront promenade.

What to eat: Bari is the birthplace of orecchiette pasta, often served with broccoli rabe and anchovies. Also try sgagliozze (fried polenta squares) and focaccia barese, which is soft, oily, and addictive.

Why it’s unmissable: Bari is real. It’s not a museum or a resort. It’s a working city with soul, and it’s the perfect gateway to the rest of Puglia—the stunning coastline, the olive groves, and the historic villages.

5. Turin: The Elegant, Underrated Capital of the Alps

Turin gets overshadowed by Milan and Rome, but it’s a city of quiet grandeur. It was Italy’s first capital, and it shows in the broad, tree-lined boulevards, the regal piazzas, and the coffee culture.

What to do: Visit the Museo Egizio (the Egyptian Museum, second only to Cairo’s). Walk the Piazza Castello and Piazza San Carlo. Climb the Mole Antonelliana for panoramic views of the Alps. And if you’re a car person, the National Automobile Museum is fantastic.

What to eat: Turin is the home of gianduia (chocolate-hazelnut spread), so try it in every form—hot chocolate, gelato, and the famous gianduiotti chocolates. Also eat agnolotti (stuffed pasta) and drink bicerin, a layered coffee-chocolate drink.

Why it’s unmissable: Turin is sophisticated without being pretentious. It’s a city of chocolate, coffee, and elegance—and it’s far less crowded than its rivals.

The 2 Cities I’d Skip

1. Milan: All Hype, Little Substance

I know this is controversial. Milan is a global fashion capital, a financial hub, and home to the iconic Last Supper painting. But honestly, it’s the most overrated city in Italy.

What’s wrong: Milan is expensive, overcrowded, and lacks the warmth of most Italian cities. The historic center feels like a shopping mall. The Duomo is impressive, but once you’ve seen it, there’s not much else that grabs you. The city is designed for business and tourism, not for living.

What you’re missing: Genuine Italian character. Milan feels like it’s trying to be New York or Paris, and it doesn’t succeed. The food is good, but not great—and certainly not worth the inflated prices.

When you might still go: If you’re a serious fashion or design enthusiast, or if you need to see The Last Supper (book months in advance). Otherwise, give it a pass.

2. Positano: Beautiful but Overrun

Positano is one of the most photographed towns on the Amalfi Coast. And yes, it’s stunning. But that’s the problem—everyone knows it.

What’s wrong: Positano is a victim of its own success. In summer, it’s a nightmare: packed beaches, gridlocked roads, and restaurants with average food and sky-high prices. The famous “vertical” town layout means you’re walking up and down hundreds of steps to get anywhere. It’s exhausting, not relaxing.

What you’re missing: The same spectacular coastline can be found in neighboring towns like Ravello (quieter, more elegant), Atrani (smaller, more authentic), or Vietri sul Mare (ceramics and charm without the crowds).

When you might still go: If you have the budget for a luxury hotel with a pool and private access to the beach, and you’re visiting in the off-season (April, October). Otherwise, skip the chaos and choose a less-touristy alternative.

Final Take: How to Plan Your Italy Trip

Italy is not a “one-size-fits-all” destination. The beauty of visiting all 20 regions is realizing that each one has a distinct personality, cuisine, and rhythm. For a first-time traveler, I’d recommend a balanced itinerary: start in Rome for the history, head to Perugia for the charm, then down to Palermo for the food. Skip Milan and Positano unless you have a specific reason to go.

And when in doubt, eat local, walk slow, and let the country surprise you. It always does.