How a Small Tuscan Village Became the Capital of Vintage

How a Small Tuscan Village Became the Capital of Vintage

From a few hundred curious visitors to fifty thousand: how the Vintage Festival of Castiglion Fiorentino grew over the years.

Every Ferragosto, Castiglion Fiorentino turns back the clock: for four days, the historic center becomes an open-air stage set to the sound of swing and rock'n'roll, filled with vintage cars, retro markets, and dancing in the piazzas.

The Event

Period: four consecutive days, usually between August 13th and 16th

Vintage Market hours: every day from 5:00 PM to midnight

Location: historic center of Castiglion Fiorentino (AR)

Admission: free, including all scheduled concerts

The History of the Festival: Born in 2017

The Vintage Festival was born in 2017, an initiative of the Municipality of Castiglion Fiorentino, the first to believe in the bet of transforming the village into a genuine film set straight out of the 1950s and '60s. Its origins were recounted by Deputy Mayor Devis Milighetti: an event conceived for the entire historic center, bringing together music, live shows, and a market dedicated to the antiques and objects in vogue during those decades.

The idea also grew out of a clear need: to give Castiglion Fiorentino, a village in the Tuscan inland with no coastline, a strong tourist draw right during Ferragosto, when most visitors head elsewhere. Within a few years, the bet paid off: from a few hundred curious visitors in its earliest editions, the Festival grew to draw around fifty thousand people over four days, becoming one of the driving forces of summer tourism in the province of Arezzo.

The Festival's artistic direction, led by Marco Talladira, played a decisive role in its growth, building programs over the years capable of attracting some of the finest international performers of 1940s, '50s, and '60s music: in recent editions, over a hundred artists have taken part, with bands from Spain, France, the United Kingdom, Sweden, Norway, Germany, and the United States, alongside some of Italy's leading vinyl DJs and international dance schools able to draw thousands of dancers into classes, masterclasses, and open rehearsals. Local shopkeepers, organized into a natural shopping district supported by Confcommercio, also make a meaningful contribution to the event's success, keeping the streets of the center lively throughout the festival.

An Open-Air Stage

At the heart of the Festival is the Vintage Market: over 100 vendors from across Italy fill the streets of the center with retro clothing and accessories, vinyl records and books, design pieces, handmade crafts, home decor, and collectibles. Vintage cars and motorcycles parade through the streets, while dance floors set up between Piazza del Comune, Parco Presentini, and the Giardini di Porta Fiorentina host dance instructors and dancers throughout the event.

A Day at the Festival

Every day, from 5:00 PM until midnight, the historic center comes alive with dozens of musicians, DJs, and dancers: free dance classes open to everyone take place before the evening concerts, while the piazzas alternate between vinyl DJ sets and live performances of swing, rock'n'roll, and rhythm and blues. Only a few advanced workshops led by international instructors require payment and booking.

Why the Festival Matters to Castiglion Fiorentino

In under a decade, the Vintage Festival has turned Castiglion Fiorentino into one of Tuscany's most anticipated summer events, proving that even a small inland village can rival the region's more established destinations in drawing power. Today it stands as a rare example of a themed event able to involve the entire village "without borders," carrying the same genuine, original spirit that made it beloved from its very first edition.

Where to Stay for the Vintage Festival

Villa Santa Margherita is just a few minutes' drive from Castiglion Fiorentino, the ideal base for enjoying the Festival's days and returning comfortably to the hotel in the evening, perhaps after one last dance in the piazza. Discover our rooms and the offers available for the festival period.