Trying to pick the best places to visit in Italy is like being forced to choose your favorite nonna.

It can’t be done, because they can both whip up a mean risotto.

There’s no such thing as “the number one best place to visit in Italy.”

Every spot is steeped in its own special ragu sauce, and calls a different traveler to each place.

Those top 10 lists that rank the best places in Italy are doing it wrong.

What we can do instead: show you our faves (no rankings), and give you the insider intel on exactly when to go, (and when to skip).

If you want a handy-dandy guide for picking a spot that fits your vibe and vacay schedule, we have it all and more, below.

The 10 Best Places to Visit in Italy (And When to Go).

1. Rome

best places to visit in italy Rome

We’ll give Rome this: it’s one of the most beautiful cities on the planet. It’s home to a crazy cool city center that was made for history buffs and art lovers – you want to try and see The Spanish Steps, Trevi Fountain, Pantheon, Villa Borghese and the Colosseum at least once in your lifetime. Each neighborhood in Rome bursts with something distinctly delightful – from tasty trattorias in Testaccio to hipster hotspots in Monti and small-neighborhood feels in the Jewish Ghetto. Something for everyone.

When to visit Rome: Good times to go are May to June and September to October – the off-peak seasons, but still close to summer. July and August light a fiery furnace under Rome’s hot streets, so avoid planning your trip then.

Rock Rome, Venice, Florence and Cinque Terre like a local when you get your hands on our city guides – you’ll save money and have more fun, too.

2. Milan

best places to visit in italy Milan

When most people think about Milan, they picture fabulous fashion weeks, and va-va-voom vintage finds. Yes, most people here look like they stepped straight off the cover of Vogue Italia (it’s the best excuse to get your glam on) and it’s just so darn cool. Strolling past snow-flecked canals, the Duomo or an opera house with a fresh pair of leather boots makes you feel hella sexy and sophisticated.

When to visit Milan: Milan is a wonderfully wintry city and it has an airport (mega-bonus in Italy) – so it’s perfect for taking time off during the holiday season, from November-January. But really, you could visit Milan anytime except August. The Milanese leave the city in droves to take their summer vacations then, so you’ll likely find yourself sweltering in the heat, begging for a gelateria to open their doors if you visit in August.

3. Bologna

best places to visit in Italy Bologna

If you’re a foodie, add Bologna to your itinerary. If all you ever do in Bologna is pass your time with piles of pasta – you’re golden. Bologna is where you’ll find ridiculously rich ragu, perfectly hand-rolled pasta and magical mortadella. Bologna is also easy-peasy to access via other big European cities if you find yourself in Paris, Barcelona or Prague before hopping over because it has an airport. Big bonus!

When to visit Bologna: Another gorgeous spot for the winter, ‘cause what’s better than filling up on towers of tagliatelle when it’s snowing outside? There’s so much to do here, even when it’s cold. Spring and early summer (again, nix August – locals like to close up shop and hit the beach) will work, too.

4. Cinque Terre

best places to visit in Italy Cinque Terre

If we could shimmy anything close to a “number one spot” in Italy, surprise surprise – it would probably be Cinque Terre. We’re biased, since most of our team lives there and we take our clients to Cinque Terre over and over again.

Cinque Terre is made up of five main villages: Riomaggiore, Manarola, Corniglia, Vernazza and Monterosso. They’re all connected by a short train ride, and easy to explore over a couple of days (but please, stay at least a week if you can). Cinque Terre is where you go to spend all day on a dramatic hiking trail, in crystal turquoise water and finish it off with sunset aperitivo, overlooking all the pastels possible in Italy’s color palette.

When to visit Cinque Terre: Cinque Terre is your sunny seaside summer spot – June to September is gorgeous here. You gotta enjoy it when the weather is balmy and beachy. Avoid going between mid-November to Easter – it’s a seasonal place, and not everything operates year round. You need to book well in advance if you’re going to be there in the high season — accommodation is very hard to come by last minute.

Want us to show you Cinque Terre, Italian Fix style? Check out our private Cinque Terre tours! Wine tasting, hiking, walks through our fave secret spots — we’ve got it all. We’d love to show you our home ground with expert locals leading the way (and pouring the vino).

5. Florence

best places to stay in italy Florence

Our founder Bianca fell head-over-handmade-bootie-heels with Florence when she first studied here years ago … and if it’s possible, every time she returns, she loves it a lil’ more. Like Bologna, foodies will fall for Florence restaurants. Like everywhere else in Italy, art lovers will be inspired to whip out their acrylics in a second. We love strolling over bridges in Florence and doing all things vintage – whether that’s shopping the markets or hopping in a vintage Fiat 500 to cruise through Chianti, a short drive from the city.

When to visit Florence: Spring and winter are the best times to go. If you’re there in the summer, book one of the few hotels with a pool in the city, as it can get pretty baking in Florence — it sits at the bottom of a valley and begins to feel like you’re living inside a Tuscan bread oven come mid-July.

Want an up-to-date insider guide to Rome, Florence, Venice and the Cinque Terre that most people don’t have? Our city guides to Florence, Rome, Cinque Terre and Venice is your cheat sheet.

And if you’d rather just soak up our insider intel in person, our private Florence tours are just what you need!

6. Puglia

best places to visit in italy Puglia Matera

We dig two hotspots in Puglia the most: Matera and Lecce. Matera, Italy basically hasn’t changed since Christ was around (alright, maybe just a little) – so this clay-colored, rocky city is alluringly ancient. It was first occupied in the Paleolithic Era, and it feels like someone will pop out in a toga any second. Plus, it recently won the bid to become the European Capital of Culture in 2019, and only became a tourist destination in 2014… So it’s still an almost-well-kept secret.

Second – Lecce, aka the Florence of the South. If it was a brand, it would be Baroque Extravagance. We love Lecce for taking a moment to press pause and, the fact that it’s a classic Italian city — as a traveler you’ll feel like you have the place all to yourself.

When to visit Puglia: Italians come to holiday in Puglia – so if you dig peak heat but love to people-watch, this a fab place to come in August. Remember, this is the south of Italy, so shops close in the mid-afternoon because owners are escaping the heat and at the beach. You should follow their ideas and head to the beach in the afternoons too. You’ll love the carefree warm August nights in Lecce. May-June and September are still balmy enough to bask by any seaside spot. Or, come on our Southern Italy tour and we’ll take you to Lecce and Matera with our driver and our guides.

7. Venice

best places to visit in italy Venice

Ready to swap streets for canals and cars for gondolas? Park your tushie in Venice. It’s teeny-tiny but oh-so-magical – we love gettin’ cozy with cichetti in a tavern and market-hopping here. Don’t miss the best restaurants in Venice post. There’s always something happening in Venice. And when you wanna take it easy, its serene side streets are perfect for a glass of grappa.

When to visit Venice: Spring to early summer are perfect, from March to July. The weather is mild and easy-breezy, so you can rock your cute shorts but avoid sweating through your leather sandals. Bonus: Venice is the festival queen during this time – check the city’s calendar in advance so you catch some. High water season is October to January, so best to plan around those months. Carnevale is in February.

Want to save time, money and have more fun? Get the insider scoop on Rome, Venice, Florence and Cinque Terre using our city guides to Venice.

8. Amalfi Coast

best places to visit in italy Amalfi Positano

The Amalfi Coast is for classy, pastel-ly cliff sides. Our favorite village is Positano, which is the first stop on our Southern Italy tour – designed to help our clients grab their relaxation remote and press pause ASAP. Boating along the villa lined cliffs or basking on Fornello Beach. You choose – that’s all you have to decide here. Always try Positano-lemon gelato and trekking up hundreds of stairs, because hiking for a view here is always worth it.

When to visit the Amalfi Coast: We always take our people here in May-June and September-October – it’s warm and way more chill then. Most travelers and Italians fill it up in August, and it does get chilly in the winter – so late spring and early fall are perfect times to go. The official season starts at Easter.

9. Sicily

best places to visit in italy Sicily

This is where Italians love to vacay. Sicilian style is relaxed and welcoming — meals al fresco, cocktails under the lemon trees, Mediterranean views poolside, soaking in thermal waters at the spa, market shopping, swimming in the bay, wandering through Baroque cities. We love it so much, we even designed an entire Sicily tour, because it deserves to be shared.

Our secret sweet spots include the Aeolian Islands, Palermo (cruise through the catacombs), Syracuse (boat around this tidy limestone town to really take it in) and Taormina (views of the sea and an active volcano).

When to visit Sicily: We like to visit in May and October – it’s still warm, and we can enjoy having it all to ourselves. You’ll love dipping in the sea here anytime between May-June and September-October – Italians take over in August, but we love Sicily in August too if you’re keeping to the coast or mountains.

10. Lake Como

best places to visit in italy Lake Como

Lake Como loops around lush valleys and islands, and there’s no shortage of towns to cuddle up with your sweety in. We recommend Varenna over popular Bellagio, because it’s uber-romantic – with bougainvillea spilling everywhere and more blooms bursting through cracked cobblestone streets. Celebrities get hitched here for a reason: there’s no chance of being grumpy about anything. Lake Como is wonderful for warm swims in summer and roaming through gorgeous mountain ranges any time of the year.

When to visit Lake Como: Anytime between May-October is lovely for lakeside dips and evening aperitivo. Lake Como in winter is foggy and cold, but Christmastime is magical.


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