Trip Ideas sky water outdoor Sea Coast reflection promontory cliff City scene headland evening terrain morning tourism dusk rock cape cityscape dawn Village horizon coastal and oceanic landforms Sunset bay Ocean landscape tree cove klippe colorful
Trip Ideas

9 Most Charming Towns in Italy

Sure, cities like Rome, Florence, Venice, and Milan have timeless appeal, but you’d be remiss not to squeeze in detours to Italy’s smaller towns, where life still revolves around family, farm-to-table isn’t a buzzword but a way of life, and impeccably preserved buildings make you feel like you’ve walked into a time machine.

An avid Italophile, Laura is always on the hunt for the next great travel trends, luxury hotels, best places to eat and drink, and hidden gems. Her writing has appeared in dozens of publications. She also co-wrote "New York: Hidden Bars and Restaurants," an award-winning guide to the city's speakeasy scene.

See recent posts by Laura Itzkowitz

Trip Ideas outdoor grass sky water tree monument statue Lake cloud plant tourism Sea landscape memorial leisure recreation reservoir sculpture park
Trip Ideas building outdoor landmark night reflection palace plaza cityscape metropolis estate Downtown lit condominium
Trip Ideas indoor room window wall bed floor ceiling hotel property chair estate Bedroom home interior design Suite real estate living room cottage furniture mansion decorated
Trip Ideas outdoor sky Town landmark vacation Sea scene tourism cityscape Coast travel
Trip Ideas tree outdoor water mountain mountain village Coast waterway Harbor Town Lake scene sky City Village bay River mount scenery Sea tourism reflection promontory fjord hill station water transportation real estate landscape mountain range lake district long colorful traveling line

Tremezzo, Lombardy

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.

Book Hotels in Lake Como
Trip Ideas ground outdoor chair Town flower alley neighbourhood street house outdoor structure plant facade floristry Balcony window Courtyard road
Travel Tips Trip Ideas outdoor sky grass tree vegetation Nature mountain wilderness Coast hill plant promontory hillside water mount scenery landscape terrain hill station cliff tourism rock green escarpment Sea national park plantation overlooking lush
Hotels Trip Ideas sky outdoor water Coast Sea geographical feature reflection horizon evening Ocean Sunset rock cityscape dusk bay Beach terrain cliff

Manarola, Liguria

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.

RELATED: Italy Special: 5 Cities, 25 Incredible Hotels

Book Hotels in Liguria
Trip Ideas building way scene sidewalk alley Town outdoor brick wall street medieval architecture history neighbourhood arch City road tree window historic site stone
Trip Ideas grass outdoor mountain sky agriculture Vineyard Nature field leaf rural area hill landscape mount scenery plain plantation Farm grassland grassy lush pasture hillside highland
Trip Ideas building sky outdoor Town landmark City historic site town square brick history wall evening tower tourist attraction medieval architecture Downtown middle ages tourism arch facade basilica dusk ancient history bell tower Church window plaza night stone
Hotels Romance Trip Ideas sky outdoor grass building landmark historic site City castle ancient history Village old Ruins archaeological site tree tourism cloud middle ages stately home field landscape

San Gimignano, Tuscany

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.

Book Hotels in Tuscany
Trip Ideas mountain outdoor building sky landmark historic site City Town urban area ancient history medieval architecture history roof fortification Village middle ages arch archaeological site tourism
Trip Ideas ground outdoor chair property building swimming pool estate home real estate interior design Villa Resort outdoor structure furniture backyard Deck area
Trip Ideas indoor wall floor room property ceiling Suite Bedroom cottage estate interior design real estate furniture decorated
Trip Ideas building outdoor tree grass mountain village City Town Village sky mountain historic site ancient history Ruins tourism archaeological site landscape bird's eye view estate overlooking

Gubbio, Umbria

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.

RELATED: Three Under-the-radar Italian Regions to See Now

Book Hotels in Umbria
Trip Ideas sky outdoor water reflection mountain Nature Lake pond tree mount scenery daytime reservoir River leaf bank tourist attraction cloud landscape green mountain range plant water resources grass alps national trust for places of historic interest or natural beauty tourism surrounded computer wallpaper watercourse
Trip Ideas tree outdoor building structure estate Garden ancient history grass stately home Ruins mansion plant archaeological site park palace column hacienda outdoor structure landscape arch ruin
Trip Ideas tree outdoor water Nature landmark water feature tourist attraction estate watercourse sky fountain Lake Villa tourism mansion national trust for places of historic interest or natural beauty plant Garden reflection leisure pond City palace landscape mount scenery landscaping botanical garden hacienda château resort town tours plaza historic site surrounded

Tivoli, Lazio

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.

Book Hotels in Lazio
Pool and terraces at Palazzo Avino, Ravello
Hotels Romance Trip Ideas sky outdoor reflection water horizon Sea morning dusk cloud evening vacation cityscape River Ocean Coast sunlight landscape dawn Lake Sunset bay waterway clouds overlooking day
Hotel Palazzo Avino
Trip Ideas mountain outdoor sky Nature Coast mountainous landforms mount scenery Sea hill station mountain range promontory tree Lake City bird's eye view bay hill background Village cloud horizon tourism highland mountain village alps water reservoir River panorama landscape valley cape aerial photography overlooking hillside surrounded lush

Ravello, Campania

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.

RELATED: Your Ultimate Guide to the Amalfi Coast

Book Hotels in the Amalfi Coast
Trip Ideas building ground alley outdoor Town infrastructure road street neighbourhood way sidewalk sky window arch facade City house door apartment stone doorway dirty
Trip Ideas sky outdoor snow Town urban area City wall roof Village tourism tree outdoor structure cityscape building house panorama
Trip Ideas outdoor tree ground Town alley street sky wall Village road neighbourhood stone City facade window house history cottage
Trip Ideas sky outdoor Town house neighbourhood Village tourism vacation facade place of worship cottage residential

Alberobello, Puglia

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.

Book Hotels in Puglia
Trip Ideas building outdoor sky historic site wall history ancient history facade stone fortification medieval architecture Ruins tourism archaeological site Village old
B&B Boutique Country Drink Eat Historic Hotels Romance Romantic Trip Ideas Wine-Tasting building stone chair house Town Fireplace old brick Courtyard cottage home Village furniture hacienda ancient history alley area
B&B Bedroom Boutique Country Historic Romance Romantic Trip Ideas building stone brick arch wall Architecture ancient history estate crypt hacienda middle ages temple monastery vault basement
Trip Ideas sky building outdoor Town historic site geographical feature landmark human settlement cityscape ancient history Ruins tourism Village residential area landscape Coast panorama unesco world heritage site ancient rome ruin

Matera, Basilicata

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.

Book Hotels in Basilicata
Trip Ideas building outdoor sky classical architecture landmark metropolitan area Church basilica place of worship cathedral Town historic site medieval architecture town square byzantine architecture parish plaza metropolis City facade old tourism tourist attraction palace Downtown tours estate ancient rome ancient history abbey stone government building square
Trip Ideas outdoor sky rock rocky mountain Sea Coast Nature promontory cliff headland klippe cape terrain coastal and oceanic landforms stack tourism building formation fortification hillside
Trip Ideas mountain water outdoor sky Nature Sea Coast coastal and oceanic landforms headland rock promontory highland bay cape overlooking loch Ocean shore peninsula horizon Lake inlet hill cloud tourism mount scenery fjord tree fell cove hillside surrounded

Acireale, Sicily

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.

Book Hotels in Sicily

Women’s Ultimate Italian Vacation Outfit

For info on these editor-selected items, click to visit the seller’s site. Things you buy may earn us a commission.

Want More?



All products are independently selected by our writers and editors. If you buy something through our links, Jetsetter may earn an affiliate commission.