Three days dedicated to Valdichiana wines in the Cloister of San Francesco in Castiglion Fiorentino
The Valdichiana Wine Festival is the premier wine event in the municipality of Castiglion Fiorentino, located in the province of Arezzo in the heart of eastern Tuscany. Every year, at the beginning of May, the lush Renaissance cloister of Piazza San Francesco becomes a wine lounge: a path of tasting desks where producers personally present their labels, ranging from historic denominations to small artisanal estates.
The festival brings together over fifty wineries and offers around three hundred wines for tasting. The focus is on the Valdichiana territory, covering both the Aretine and Sienese sides, complemented by producers from Umbria and guests from other Italian regions. Alongside local wines, visitors can sample great Tuscan denominations such as Vino Nobile di Montepulciano and Brunello di Montalcino, in a comparison that spans different styles and territories.
A key part of the festival is dedicated to limited-seating masterclasses, led by sommeliers, oenologists, and producers. These sessions provide an opportunity to delve into the characteristics of grape varieties and denominations, often featuring guest wineries from outside the region. The program also includes book presentations and thematic meetings on wine culture.
One of the most appreciated features is the Wine Shop, which allows you to purchase bottles from participating wineries at prices more advantageous than standard retail. To complete the experience, there are pairings with local products from the Valdichiana, creating a dialogue between wine and local gastronomic traditions.
Visiting the festival is also a way to explore Castiglion Fiorentino, an Etruscan-origin village that overlooks the Valdichiana from its hillside perch. The event is organized by the Municipality in collaboration with the Barolo vs Brunello association, the Strada del Vino Terre di Arezzo, and the Pro Loco, and is a staple in the town's spring calendar.
The 2026 edition of the Valdichiana Wine Festival confirmed the format that made the event popular: tasting desks with producers, thematic masterclasses, and pairings with local products, all within the setting of the Cloister of San Francesco in Castiglion Fiorentino.
Among the novelties, the Wine Shop allowed for the purchase of bottles at advantageous prices, alongside a program of cultural insights into the world of wine.
Over 50 wineries present with about 300 labels for tasting, including producers from the Aretine and Sienese Valdichiana, Umbria, and guests from other regions.
Chiostro di San Francesco, Piazza San Francesco, 52043 Castiglion Fiorentino (AR), Tuscany.
By car: take the Monte San Savino exit on the A1 motorway, then follow signs for Castiglion Fiorentino; alternatively, use the E78 expressway (Siena-Bettolle-Perugia) or the SS71. By train: the Castiglion Fiorentino station is on the Florence-Arezzo-Rome line, a short distance from the historic center.
Entrance tickets with access to the tasting desks can be purchased directly on-site. Masterclasses have limited seating and require mandatory booking by calling +39 338 862 4562 or emailing [email protected].
No photos yet. Share yours!
5 photos max, 5 MB per photo (JPG, PNG, WebP)
Help us keep this listing up to date. Every proposal is verified by our team before publication.
No rating yet — be the first!
No comments yet. Be the first!
Share your experience with the community.
Chiostro di San Francesco
Piazza San Francesco, 52043 Castiglion Fiorentino