Vintage Festival

The Vintage Festival in Castiglion Fiorentino

Every year, in the heart of the Tuscan summer, the village of Castiglion Fiorentino, in the province of Arezzo, dresses up for the Vintage Festival: four days during which the historic center turns into a true time machine. Within the town's medieval walls, the atmosphere of the 50s and 60s—reminiscent of films like Grease and Roman Holiday—comes back to life, filled with rock'n'roll, retro outfits, gleaming cars, and live music at every corner.

Classic cars, motorcycles, markets, and music

The festival revolves around three main pillars. The first is the display of classic cars and motorcycles, showcased along the streets and squares of the village, delighting motor enthusiasts of all ages. The second is the grand Vintage Market: over a hundred exhibitors featuring retro clothing, rare vinyls, original accessories, books, collectibles, handicrafts, design pieces, illustrations, home decor, plants, flowers, and games for children. The third, and perhaps most captivating, is the live music: more than a hundred artists bring the city to life with the sounds of rock'n'roll, swing, jazz, and rhythm & blues, accompanied by vinyl sets and dance shows that get the crowd moving.

A widespread and free celebration

The beating heart of the event is Piazza del Municipio, but the entire historic center of Castiglion Fiorentino becomes part of the scene: streets fill with music, squares host concerts, and every alleyway features a themed detail. Admission is free, making the Vintage Festival one of the most beloved events in the summer calendar of the Valdichiana area, attracting visitors from all over Tuscany and Central Italy.

A festive village in the Valdichiana

Castiglion Fiorentino, with its skyline marked by the Cassero Tower, is one of the most charming villages in the Tuscan Valdichiana. During the Vintage Festival, its historical identity blends with the joyful and nostalgic spirit of vintage culture, offering visitors an experience that combines the pleasure of discovery, vintage shopping, and the energy of live concerts. It is the perfect opportunity to explore the historic center, its picturesque views, and the food and wine of the Arezzo region.