When it comes to cities of love, Italy has so much more to offer than Florence, Venice, and Lake Como. In fact, some of its most dreamy holiday destinations are little-known towns and villages off the beaten tourist track. From low-key Sicilian seaside escapes to medieval hamlets in the Umbrian countryside, we’ve rounded up Italy’s 10 most romantic small towns.
Cefalù, Sicily
Wedged between mountains and coastline, the tiny Sicilian town of Cefalù is perfect for couples looking for a low-key seaside escape. Besides its windswept, rugged beaches, there’s a picturesque harbor, charming centro storico (historic center) with one of the island’s most beautiful duomos, and lots of cozy restaurants. Tempio di Diana, a fourth-century temple ruin overlooking the entire town and coastline, is the best place to watch the sun set.
Urbino, Le Marche
It’s not hard to see why Urbino was said to have inspired the work of Renaissance painters Piero della Francesca and Paolo Uccello: The town is a cluster of towers and domes centered around the beautiful Palazzo Ducale and perched dramatically atop a steep hill. (So magnificent, it was deemed a World Heritage Site by UNESCO in 1998). With its 200-year-old botanical gardens, neoclassical churches, and lovely, café-lined piazzas, it’s relaxed and romantic without being cheesy or cliché.
Trapani, Sicily
The town of Trapani itself is romantic in its own right—it’s home to beautiful medieval ruins, ancient cathedrals, pretty trattorias, and unspoiled beaches like Lido Paradiso. But what you’re really here for are the day trips: Trapani is the gateway to the magnificent Egadi Islands, located just a few miles off its coastline. Hop on a ferry and spend the day swimming in Favignana’s Lovers’ Grotto or sunbathing on the deserted, clothing-optional beaches of Marettimo. Not into beaches? Venture to nearby Marsala for a tasting of Italy’s best dessert wines.
Spoleto, Umbria
Backed by the snow-capped Apennine mountain range, the sleepy Umbrian hill town of Spoleto offers one of the most gorgeous backdrops in all of Italy. You can spend a whole day exploring the beautiful architecture—there’s a Romanesque cathedral, a second century amphitheater, and a spectacular medieval fortress—or simply eating pasta and drinking wine in one of its candlelit trattorias. Added bonus: Being just two hours from Rome by train, Spoleto makes for the perfect day trip.
Gaeta, Lazio
Set between Rome and Naples, Gaeta is set on a scenic promontory overlooking (not surprisingly) the Gulf of Gaeta. The small, walled town is postcard-pretty: narrow cobblestone streets lined with warmly-lit trattorias, pastel-colored villas and 13th-century castles carved into the cliffs. Spend the day swimming at one of its seven beaches, or pay a visit to Montagna Spaccata, a mountain supposedly split in half by an earthquake.
Gallipoli, Lecce province, Puglia
With its beautiful Baroque chapels and sweeping harbor, Gallipoli is the prettiest town on Puglia’s Salento peninsula. It’s perpetually filled with honeymooners, and no wonder: Gallipoli has all the ingredients for a romantic getaway, from the warm turquoise waters at Spiaggia della Purita to its dozens of aristocratic palazzi—many of which you can stay in. At Il Giardino Segreto (The Secret Garden), you can eat beneath leafy lemon trees laced with fairy lights.
Sperlonga, Lazio
Sperlonga, a quiet seaside town just south of Rome, was the former hideaway of many Roman emperors and today remains one of Lazio’s best-kept secrets. Here you’ll find luxuriously peaceful beaches, a nature reserve, and beautiful Roman ruins (including Emperor Tiberius’ old villa). Spend the day meandering through the lush reserve or sunning on the deserted beach south of the headland, then watch the sun set from the terrace of the oceanfront Bazzano restaurant, glass of rosé in hand.
Gubbio, Umbria
Thanks to its perfectly preserved Gothic architecture and old-world grandeur, the medieval town of Gubbio feels timeless and unchanged, as if time had stood still for centuries. It’s tucked away in the landlocked Umbrian countryside, so there’s not much to do besides get lost in its labyrinthine cobblestone streets or sip coffee in one of its many lovely piazzas—but that’s exactly why you should go. Castello di Petroia, a stunning 15th century castle in the leafy outskirts of town, is an ideal hideaway.
Iseo, Lombardy
Lake Como might get all the glory, but the picture book-pretty Lake Iseo is more tranquil, less crowded, and (dare we say) much more romantic. For starters, the town of Iseo itself, perched on the lake’s southern shore, boasts dramatic views over its crown jewel, Monte Isola—a mountain that soars from the center of the lake. And unlike nearby Como, Iseo is free of tourists, which means you'll have its charming piazzas, Romanesque churches, and medieval castles all to yourself.
Piombino, Tuscany
Piombino, once dubbed “Little Paris” by the Grand Duchess of Tuscany for its extravagant Renaissance architecture, is a perfect honeymoon destination or Valentine’s Day getaway. Grab a bottle of wine and a wheel of Tuscan pecorino and head up the sea cliff to Piazza Bovio, where you can take in views of the harbor and see all the way to Elba Island, home to some of Italy’s best hidden beaches.
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