The Italian boot is studded with many shining gemstones to see and do as the Italian locals do when they escape to sip an Aperol spritz in a secluded beach setting away from the crowds. These 13 towns are ridiculously perfect and compact, with incredible history, culinary delights, and beautiful views on display at each turn. Enjoy your dolce vita on the cover of your favorite storybook, from seaside romance to sirens and hilltop medieval castles.
This enchanting town in eastern Tuscany, an hour south of Florence and two hours from Rome's glamour, will envelop you in so much charm that it gives cities a run for their money. Enjoy quick access for a day trip, or visit for the whole weekend to catch the Sunday weekly antique market on Piazza Grande for shopping and local culture. The town of inspiring beauty is the hometown of Italian filmmaker Roberto Benigni, and the backdrop for the Oscar-winning movie "Life is Beautiful."
If the Hollywood bona fides weren't enough, the stunner expresses its vintage vestiges like no other, a real accomplishment for a nation overflowing with rich heritage. Stroll along the impeccably preserved medieval architecture and the striking Piero della Francesca murals throughout the churches, and spend some time at Arezzo Cathedral admiring Donatello's sculpture.
Brisighella is not just your typical charming small village of around 7,100 residents, between the Renaissance cities of Ravenna and Florence, with a unique kitsch. It is "the village on three hills" in Italy, with a lot to explore and wonder about while getting in some exercise—just what you need after gorging on that pasta in Florence. Hike to the 14th-century castle, La Rocca, on the first hill and climb the second to pay respects at an 18th-century church sanctuary, the Monticino. Visit the third hill and set up an outdoor picnic under its clock tower from the 19th century.
You can also save room to recharge in town with some culinary delights in this town, in the province of Emilia-Romagna, which is renowned for its gastro-cultural traditions. Try a starter with the pera Volpina, a firm pear variety that adds a flavorful touch you won't find anywhere else, and wash it down with local specialty Sangiovese wines. Continue your gluttonous ventures with a pork dish from the local Mora Romagnola pig breed and stock up on some Conciato cheese that ripens in chalky caves. There's no better way to absorb the local culture in Brisighella than a visit to one of the local thermal baths.
With a population of under 150 living on top of a steep 5,000-foot hill above sea level, Castelluccio is a charming sight to behold. This highest village in the Apennine Mountain Range, with a backdrop of snow-capped mountains and a forefront of verdant plains with seasonal blooms, conveys an overwhelming emotion with the scenery and atmosphere.
Although since 2016 Castelluccio has been virtually unlivable after an earthquake, visit for the never-waning natural beauty on a stroll through red poppies, violets, and rapeseed in the spring and wintertime fun on the mountainside. There are also some very welcoming shops and restaurants at the hands of the remaining locals, and the heartbreaking charm will make you truly wish them a quick recovery.
Cefalù, a postcard-like medieval town, is a real eye-opening feast at every corner, with a retro atmosphere that grabs hold of you and induces nostalgia upon leaving. The town of under 15,000, just an hour's drive from Palermo, is also a movie star after making repetitive appearances in a number of films, including the much-loved Cinema Paradiso.
Explore Cefalù on foot, with various thematically beautiful sites to highlight each day, like a stroll along the aesthetic streets or a church tour in and around the numerous mosaic-adorned cathedrals. Take in the scenery along the picturesque seafront promenade, a favorite spot for locals to mingle, and finally catch the eye-catching sunset from the top of La Rocca, towering above the town.
Find this big-time charmer perched on its own little isle, on Puglia's Ionian coast, with easy access from the mainland via a causeway. From the air, Gallipoli is a real sight of mazed alleyways with flat-roofed whitewashed houses, interspaced by Baroque courtyards, glorious church peaks, and the eye-catching 13th-century Angevin fortezza.
Stroll through the sun-bleached town, named after the Greek word for "beautiful city," under the enchanting vibes, from its coastal sea views to a compact historic downtown. Meander your way around the narrow passageways to the bastion wall, with the shimmering, turquoise sea on the other side. You will find some of the most beautiful beaches in Italy when you veer to the right, along with excellent restaurants serving local fish and seafood cooked fresh any way you like.
Among the Cinque Terre, the three small, multicolored coastal villages, Manarola boasts one of the most beautiful seaside landscapes in Italy. The tiny village hanging on a cliff is a vision to behold and a real experience from an insider's perspective as if strolling the cover of a romantic novel. Access Manarola via the dell'amore path and wander around for sights at every turn, with many hotspots to catch the sea views.
Take a path north along the coast towards Corniglia in the evening for a spectacular sunset stroll, while the romance back in the village only intensifies to become most vivid at night. The unforgettable atmosphere when the lights of the village cut through the darkness to reflect in the sea makes for a real "La dolce vita" moment that envelops you together with the town in one soft glow.
Orta San Giulio, Piedmont
The little town along the smallest Italian lake is wrapped in bucolic charm on the little promontory of Lago d'Orta's south-eastern shore. It is a refreshing oasis with a speck of a town, often overlooked for the far more touristy Como and Maggiore, where you will feel part of the medieval atmosphere with unobscured views. Stroll around the retro lakeside along the cobbled streets with ancient stone buildings that rendezvous at Piazza Motta.
Find a cafe on this paved central square for people-watching over an espresso and traditional tiramisu to devour with a small spoon. The surrounding hills are great for outdoor strolls while catching sight of the town behind. You can also catch a fresh sea breeze ride to the mystical next-door island of San Giulio and learn how St. Julius floated on his cloak there to rid it of snakes and dragons. Sightsee the Basilica from AD 392, the church he founded after his feat.
Portofino is a must-see town in Italy, with postcard-like sights around every corner. Plan to visit during the winter alongside mostly local daytrippers and under the holiday glow. The seaside town is ridiculously perfect, with clay and sand-colored homes that appear fiery-stark against the deep slash of a natural harbor and the stage set of cafés and restaurants along the turquoise and cerulean waters.
The wooded hills around hide the neighboring Agnellis and the Dolce & Gabbana villa itself. Come during the hazy summer months to lounge on the famed Portofino beaches alongside simple locals, watch mega-yachts drop anchor, and feast luxuriously at the chic little Chuflay at least once for its grandstand view of the piazzetta. Eat simply deliciously at Taverna del Marinaio, and choose Belmond Splendido Mare for, ahem, a splendid rest.
This wonder villa on the Amalfi Coast is one of Italy's most spectacular sites, suspended from the rock wall like an architectural miracle or a natural cliffside growth. Take a cruise from Nerano or Sorrento and relish in the ridiculous scenery that locals get to see and experience every day between the sea and the mountains. Writer John Steinbeck wrote about it as a "dreamy place that doesn't seem real when you're there, and you feel a great nostalgia when you leave."
Meander along the street levels and down the village's ribbon of asphalt, narrowing on the descent into the waters, to the white and pastel houses along the shores. The sun-struck rocks and peaks reflect in the turquoise sea, creating a scenery that makes you doubt your perception and stop trusting your senses.
Calabria, the southern Italian region with Greek origins, is in the shadow of neighboring Sicily. Its shining gems, like Scilla, have beauty and tales left for the most curious to uncover without the crowds. Scilla is the small town that Homer wrote about "falling from Charybdis into Scylla," referring poetically to falling from one danger into another.
Although you may never get to see the much-feared monster of the Strait of Messina today, you will fall for the Scilla sight as soon as you see it from the water on the Tyrrhenian coast. This dangerous liaison is just as luring on the inside, like the district of Chianalea, with undeniably suggestive charms along its winding streets lined by fishermen's houses.
Sorrento is a must-visit coastal town in Italy, despite the year-round string of tourists. This real charmer, once home to the sirens, according to Greek mythology, will impart you with a gamut of impressions and emotions and leave you with a lifetime of memories. Just like the sirens lured the sailors with their beautiful songs to crash against the rocks offshore, Sorrento lures visitors from its southern Italian shore with seascape panoramas, sun-kissed beaches, and dining galore.
Sorrento, a holidaymaker's choice along the Neapolitan Riviera, charms at first sight with around 16,000 locals, a surprisingly humble atmosphere, and easy access to explore further into the Bay of Naples. Visit this old town straddling the dramatic, rocky cliffs overlooking the ocean off-season and venture to the Amalfi Coast to the east, Pompeii to the north, and the island of Capri offshore.
The charming village of Tropea is splendidly perched on the knobbly bit of toe in the boot of Italy, along the Capo Vaticano peninsula. Book a room at the five-star Villa Paola, a former 16th-century convent turned into an adults-only hotel, and plan your outings over some good ol' red onion gelato to keep with the unique theme. Tropea literally hangs onto a rock overlooking the seascape, with a cliff-face vertical plunge into the open waters and just a crescent of sand at the bottom.
Stroll along palazzo-filled alleyways to the dizzying edge of town, where even the volcano island of Stromboli smokes quietly offshore at such a sight. Tropea is a secret local "hangout" to enjoy all this scenically charged atmosphere without crowds in a real cultural experience on a quick getaway with a lifetime of impressions.
The steepest and loveliest of the Cinque Terre villages, with under 1,000 residents, will envelop you in charm and an atmosphere you will never want to leave again. Vernazza slopes down with picturesque streets lined by candy-colored one- and two-level fairy-tale-like houses, with sea views through the buildings and Instagram sights at each turn as you descend. The small, sandy beach at the bottom is the only natural harbor in between all the Cinque Terres.
Find these most impressive vistas that go well with the ditto cuisine at the iconic Belforte seafood restaurant inside the double-ditto 11th-century castle, and wait for it at the tip of the harbor. There are also so many gelaterias throughout this Cinque Terre village that you might as well come back for a separate tasting tour.
From hang-cliff villas to glam beach slices throughout the boot, these are Italy's 13 most charming towns. Enjoy easy access from a major city after an espresso in Rome or Milan to wander through the narrow medieval streets or enjoy gelato on a stroll to the beach by lunchtime.
Choose a sleepy Sicilian seaside villa or a Tuscan hamlet to escape on a drive or relax on a breezy cruise, with great regional train connections between the picturesque small towns. These quintessential Italian charmers, without the beelines for attractions and marred views, let you really immerse yourself in local culture.