Brisighella, Emilia-Romagna

Nestled in the Apennine Mountains, Brisighella is a medieval town known for its dramatic landscape and well-preserved architecture. Its most iconic features are the three landmarks on its hills: the Clock Tower, the Rocca Manfrediana fortress, and the Monticino Sanctuary. Brisighella’s cobblestone streets, pastel-colored houses, and ancient olive groves make it a picture-perfect destination.

Local Delights: Brisighella is famous for its olive oil, one of Italy’s finest. Try the local olive oil and savor regional dishes like piadina flatbreads and homemade pastas.

Civita di Bagnoregio, Lazio

Civita di Bagnoregio, often called “the dying town,” is an ancient hilltop village perched on a cliff overlooking the Tiber Valley. Accessible only by a pedestrian bridge, the town has a haunting, otherworldly beauty. With crumbling stone buildings, narrow alleys, and panoramic views, Civita feels frozen in time.

Why It’s Special: Civita di Bagnoregio is a hidden gem due to its unique isolation and history. Spend an afternoon exploring the medieval architecture and enjoying breathtaking views.

Castelluccio di Norcia, Umbria

High in the Sibillini Mountains, Castelluccio di Norcia is renowned for its stunning, high-altitude plains that bloom in vibrant colors each spring and early summer. The “Fioritura” or “Flowering” sees fields of poppies, violets, and daisies painting the landscape with color, creating a breathtaking scene.

Best Time to Visit: Visit between late May and early July for the flower bloom. Castelluccio is also a great spot for hiking, with trails offering beautiful views of the Apennines.

Orta San Giulio, Piedmont

Located on the tranquil shores of Lake Orta, Orta San Giulio is a peaceful alternative to the busier Lake Como and Lake Garda. This lakeside town is home to charming medieval architecture, narrow cobbled streets, and an enchanting view of the nearby Isola San Giulio. Take a boat ride to the island, where you’ll find a serene abbey and stunning views.

What to Do: Stroll along the waterfront, take a boat to Isola San Giulio, and visit the Sacro Monte di Orta, a UNESCO World Heritage site featuring beautiful chapels and artwork.

Monteriggioni, Tuscany

Monteriggioni is a small, walled village in Tuscany that looks like it was lifted straight from a fairytale. Built in the 13th century, Monteriggioni was designed as a fortress town to protect against invaders. The town’s medieval walls and towers remain largely intact, creating a picturesque backdrop against the rolling Tuscan hills.

Local Experience: Walk along the ancient walls, explore the town’s charming streets, and enjoy some traditional Tuscan food and wine at a local osteria. Monteriggioni also hosts a medieval festival in July, bringing its history to life with costumes, music, and reenactments.

Tropea, Calabria

Perched on a cliff along the Tyrrhenian Sea, Tropea is a secret beach town in southern Italy with stunning white-sand beaches and crystal-clear waters. The town’s historic center is filled with beautiful old churches, cobblestone streets, and vibrant piazzas, making it a lovely spot for a relaxing seaside escape.

Why Locals Love It: Tropea is known for its laid-back vibe and its famous red onions, which are sweet enough to eat raw. Don’t miss trying local dishes that feature this unique ingredient, like ‘nduja (spicy sausage) and red onion jam.

Tellaro, Liguria

Located on the Ligurian coast, Tellaro is a small fishing village often overshadowed by the more famous Cinque Terre. However, Tellaro has its own charm, with pastel-colored houses, a quiet harbor, and dramatic views of the Gulf of La Spezia. The town is a haven for artists and poets, thanks to its peaceful atmosphere and scenic beauty.

Activities and Local Charm: Wander through the narrow lanes, relax by the sea, or take a short hike for panoramic views of the Mediterranean. Tellaro’s sunsets are especially enchanting, as the town’s colorful buildings reflect in the water.

Sperlonga, Lazio

Sperlonga is a charming coastal town with whitewashed buildings, narrow alleyways, and beautiful beaches. Located south of Rome, this town offers a Mediterranean atmosphere that feels worlds away from the city. Sperlonga’s history dates back to ancient Rome, and the ruins of Emperor Tiberius’s villa are a fascinating historical site in the area.

Best for Couples: Stroll along the town’s winding alleys, spend a day at the pristine beaches, and explore the archaeological museum, which houses artifacts from Tiberius’s villa.