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1. San Gimignano (Tuscany) – The Town of Towers

San Gimignano is a perfectly preserved medieval hill town famous for its skyline of 14 ancient towers, which earned it the nickname "Medieval Manhattan." Once home to over 70 towers, the town thrived during the Middle Ages as a trading hub. Wander through Piazza della Cisterna, visit the Collegiata Cathedral, and try the world’s best gelato at Gelateria Dondoli.

2. Positano (Campania) – The Jewel of the Amalfi Coast

Positano is one of the most picturesque cliffside towns in the world, with colorful pastel houses cascading down to the Tyrrhenian Sea. The town’s steep staircases, boutique shops, and beachside restaurants serving fresh seafood make it an unforgettable experience. Relax on Spiaggia Grande, hike the Path of the Gods, or take a boat trip to nearby Capri.

3. Civita di Bagnoregio (Lazio) – The Dying Town

Perched atop a crumbling plateau and accessible only by a dramatic pedestrian bridge, Civita di Bagnoregio is a breathtaking, almost surreal medieval town. Often called "The Dying Town" because of erosion, it’s a must-visit for its stone houses, narrow alleyways, and stunning views over the Tiber Valley. Time seems frozen here.

4. Alberobello (Puglia) – The Trulli Town

A UNESCO World Heritage Site, Alberobello is famous for its whitewashed Trulli houses with conical roofs, which look like they belong in a fairytale. The Rione Monti district has over 1,000 Trulli, and many have been converted into shops, restaurants, and charming accommodations. The local orecchiette pasta and burrata cheese are must-tries.

5. Montepulciano (Tuscany) – The Wine Lover’s Paradise

A Renaissance hilltop town surrounded by vineyards, Montepulciano is renowned for producing Vino Nobile di Montepulciano, one of Italy’s finest red wines. The Piazza Grande is lined with stunning palaces, and the town’s winding streets offer incredible views of the Tuscan countryside. Wine tasting in one of the underground cellars is a must.

6. Manarola (Liguria) – The Most Beautiful of the Cinque Terre

Manarola, one of the five villages of the Cinque Terre, is a postcard-perfect coastal town with vividly colored houses clinging to the cliffs above the Ligurian Sea. The best way to enjoy it is by hiking the Via dell'Amore (Lover’s Path) or sitting by the harbor with a glass of Sciacchetrà, a local sweet wine.

7. Orvieto (Umbria) – The Cliffside Wonder

Built atop a volcanic tuff rock, Orvieto is a town of spectacular views, history, and architecture. The Orvieto Cathedral (Duomo) is one of Italy’s most stunning Gothic churches, while the underground labyrinth of tunnels and caves reveals a fascinating history. The town is also known for its crispy white wine, Orvieto Classico.

8. Matera (Basilicata) – The City of Caves

Matera is one of the world’s oldest continuously inhabited settlements, famous for its Sassi cave dwellings, which were once homes, churches, and monasteries carved directly into the rock. Today, many caves have been transformed into luxury hotels and restaurants, offering a truly unique stay. The town’s rugged beauty made it the setting for many films, including James Bond’s No Time to Die.

9. Castelluccio (Umbria) – The Town in the Clouds

Located at 1,452 meters above sea level in the Sibillini Mountains, Castelluccio is Italy’s highest town and famous for the breathtaking "Fiorita" (flowering) in late spring, when fields explode in a sea of red, blue, and yellow wildflowers. It’s a paradise for hikers and nature lovers.

10. Portofino (Liguria) – The Playground of the Rich & Famous

A glamorous fishing village, Portofino is known for its luxury yachts, high-end boutiques, and pastel-colored buildings surrounding a perfect harbor. Despite its exclusivity, visitors can still enjoy its charm by strolling along the waterfront, hiking to Castello Brown for panoramic views, or dining on fresh seafood at a harbor-side trattoria.