9 Most Charming Towns in Italy

Bellaggio may be Lake Como’s most famous town, but Jetsetters will find plenty to recommend in Tremezzo, just a 20-minute ferry ride across the lake. A chance to sleep at the Grand Hotel Tremezzo is reason enough to make a detour from Milan—the glamorous grand dame built in 1910 is famed for its Art Nouveau architecture, lakefront suites named after famous guests like Greta Garbo, and extremely 'grammable floating pool. While you’re here, visit the nearby Villa Carlotta, an aristocratic palazzo now open to the public where you can admire Neoclassical sculptures by Antonio Canova and relax in the serene gardens filled with roses and citrus trees overlooking the lake.

One of the five coastal towns that form the Cinque Terre, Manarola is hands-down one of Italy’s most photogenic places. Buildings in cheerful Mediterranean colors spring out of the cliffs, turquoise waters lap at the shore, children run down winding narrow streets, and hiking paths connecting the regions various villages offer up panoramic views. You could spend days exploring the fairytale landscape, stopping to admire the terraced vineyards, sandy beaches, and artisanal shops. It’s also a great place to go snorkeling, scuba diving, and kayaking.

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Surrounded by Tuscany's rolling hills, vineyards, olive groves, and cypress trees, this walled village’s claim to fame is its fifteen medieval towers that jut up into the sky. As you wander the narrow streets around the enchanting Piazza della Cisterna and its ancient well, you’ll feel like you’ve stepped back in time. Shop for antiques and artisanal goods in town and don't miss the wine tastings from nearby Chianti region.

Imagine Tuscany without the tourists and you have Umbria, a landlocked region in the center of Italy. There are plenty of charming towns, but Gubbio is the best—large enough to keep you busy but small enough to explore on foot. Stay at the Park Hotel ai Cappucini, a converted monastery, and stroll the cobblestone streets lined with medieval buildings. Spend you time shopping for ceramics and truffles, and feasting on mouthwatering pasta. Just brush up on your Italian—you won’t find restaurants with English menus here.

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About an hour outside of Rome, Tivoli is an inviting village with cobblestone streets and cafes lining the piazzas. The main attractions here are the ancient ruins of Hadrian’s Villa and the majestic 16th-century Villa d’Este, both UNESCO World Heritage sites. As you tour the gorgeous Renaissance palace and gardens filled with manicured hedges, flowers, and fountains, you might be overcome by daydreams of moving to Lazio and buying an old villa—or maybe that’s just us.

Of all the enticing towns on the impossibly stunning Amalfi Coast, Ravello might just be the best (IOHO). Because of its out-of-the-way location perched high on a cliff overlooking the Mediterranean, it’s blissfully free from the selfie-stick-wielding crowds that descend on nearby Positano and Amalfi, but offers plenty of small-town charm. Head up to Villa Cimbrone’s gardens and infinity terrace for jaw-dropping views and stop by the luxurious Palazzo Avino or Belmond Hotel Caruso for an Aperol Spritz at sunset. Every summer, the town hosts the Ravello Festival, which brings classical music and dance to picturesque Villa Rufolo.

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There’s no other town in the world quite like Alberobello, famed for its ancient trulli with their distinctive round shapes and conical limestone-tiled roofs. These whitewashed structures built for migrant workers—some with astronomical symbols painted on their walls—are quite a sight to behold. Though many are privately owned, some have been converted into luxurious vacation homes you can rent through villa companies like The Thinking Traveller. The town is a great base to explore this under-the-radar region where city-dwelling Italians escape for a seaside summer vacation.

In the past few years, the mysterious village of Matera in off-the-beaten-path Basilicata has undergone a bit of a renaissance. Decades of economic struggles meant that the Sassi di Matera—the prehistoric caves that make up the town’s center—remained neglected, many without proper plumbing or electricity. But these fascinating structures are now being renovated and transformed into boutique hotels like Sextantio Le Grotte della Civiltà, where the original stone walls are accentuated by rustic furniture and candlelight and you can dine in a 13th-century church carved into the hillside.

Legend has it this village on Sicily’s eastern shore was born out of the tragic love story of a shepherd named Aci and the beautiful nymph Galatea. Whether or not you believe the myth, there’s something romantic about this coastal village with its handful of baroque churches and a rocky shoreline formed by volcanic lava from Mount Etna. On summer mornings, locals start the day with an affogato made by pouring espresso over granita (the origin of Italian ices you find in the U.S. except much better) and dunking a buttery brioche into it. When the heat gets too intense, do as the Sicilians do and dive off the rocks into the water to cool off. Dinner is the day’s catch pulled out of the sea by weathered fishermen---you’ll find the freshest seafood at Il Sole e Il Sale, a rustic agriturismo with gorgeous sea views.