A charming, under-the-radar town that offers a refreshing break from Tuscany's busier tourist destinations. Known for its Renaissance frescoes and beautiful churches, it also hosts one of Italy’s most famous antique markets. The medieval streets feel authentic and less crowded, perfect for wandering at a slower pace. Cozy cafés and local artisans add to the timeless atmosphere.

Distance: 1 hour by train or 1 hour by car

A foodie’s paradise, Bologna is often hailed as the culinary capital of Italy. Endless arcades and porticoed streets give the city a distinctive character, while the historic center is alive with culture and architecture. An energetic student population adds vibrancy to its cafés, piazzas, and nightlife. Handmade pasta and rich regional specialties make every meal memorable.

Distance: 1 hour by train or 1.5 hours by car

Five colorful seaside villages cling to the cliffs of the Ligurian coast. Hiking trails between them offer breathtaking views of turquoise waters and rugged landscapes. Visitors can swim, sunbathe, or savor fresh seafood along the harbors. Each village has its own unique charm, from pastel houses to lively piazzas.

Distance: 2.5 hours by train or 2.5 hours by car

A hilltop gem that rose to fame through the book and film Under the Tuscan Sun. Sweeping views over the countryside create an atmosphere of romance and timeless beauty. Cobblestone streets are filled with artisan shops, historic churches, and trattorias serving local flavors. Its rich artistic legacy makes Cortona a favorite for culture lovers. 

Distance: 1.5 hours by train or 1.5 hours by car

Italy’s style and fashion capital, Milan is a place where luxury shopping and design thrive alongside history. The magnificent Gothic Duomo, dominates the skyline, while world-class museums showcase art and innovation. Beyond fashion and architecture, the city buzzes with modern energy, blending old and new in endlessly fascinating ways.

Distance: 2 hours by train or 3.5 hours by car

A captivating mix of history, scenery, and unforgettable food. Naples brims with energy and flavor, from wood-fired pizza to lively piazzas. Between Naples and the coast lies Pompeii, where ancient ruins bring the past to life. Farther south, winding coastal roads reveal dramatic cliffs, lemon groves, and glittering seaside towns. Sorrento and Positano stand out as highlights, each with breathtaking views and coastal charm.

Distance: 3 hours by train or 4.5 hours by car

The Eternal City is a living museum of ruins, monumental architecture, and artistic treasures. Iconic landmarks such as the Colosseum, Vatican, and Trevi Fountain make it a bucket-list destination. Each neighborhood reveals its own character, from lively piazzas to quiet cobbled lanes. Best enjoyed over several days, Rome captures the essence of Italian history and culture.

Distance: 1.5 hours by train or 3 hours by car

A picturesque medieval town known for its striking skyline of towers. Narrow streets and stone buildings transport visitors back in time, while Vernaccia wine offers a taste of local tradition. Artisanal shops and sunlit piazzas add to the charm, with every corner feeling like a postcard come to life.

Distance: 1 hour by train or 1 hour by car

A city unlike any other, Venice is built on canals and steeped in romance. Gondolas glide past palaces and under stone bridges, creating an atmosphere seemingly frozen in time. Iconic landmarks such as St. Mark’s Basilica and the Doge’s Palace draw visitors from around the world. Staying overnight reveals a quieter, more magical side after the day-trippers depart. 

Distance: 2.5 hours by train or 3 hours by car