Tastings, dinners, and music in Vicolo dei Galli, the chill heart of Porta Romana
Il Vicolo di… Vino is one of the most beloved food and wine events in Castiglion Fiorentino, a village in the Valdichiana area in the province of Arezzo, Tuscany. Every year, for two weekends in May, the narrow and evocative Vicolo dei Galli, in the heart of the historic center, dresses up for the occasion and becomes the open-air lounge of the Rione di Porta Romana: an intimate, illuminated, and meticulously curated space that many call the "chill soul" of the district.
The event was born in 2016 from the desire of the Rione's volunteers to showcase a hidden corner of the town, transforming it into a meeting point dedicated to fine wine and good food. From one edition to the next, the event has maintained its essence: authentic hospitality, far from the chaos of large festivals, where you can sit among the stone walls of the alley to savor a glass of wine and a charcuterie board in peace.
The common thread is the promotion of wines from small wineries, often lesser-known, and local zero-kilometer products. Throughout the evenings, starting at 6:30 PM, tasting and sales stands are active with over ten labels on the menu, to be paired with boards of bruschetta, cured meats, and cheeses. Over the years, the festival has also hosted masterclasses and guided tastings for enthusiasts, in collaboration with wine industry experts.
The heart of the event is the themed Saturday night dinners, which require reservations and have limited seating, each accompanied by musical entertainment. Among the recurring appointments, "Agreste" stands out, a dinner that revives Aretine peasant cuisine with dishes like pasta with meat sauce and roasted meats, alongside proposals that change from year to year, such as dinners dedicated to game and venison.
Il Vicolo di… Vino is part of the broader Maggio Castiglionese calendar, a month of events that brings Castiglion Fiorentino to life with culture, traditions, and district celebrations ahead of the Palio. For visitors, it is the perfect opportunity to discover an authentic Tuscan village, away from the beaten path, and to experience the conviviality of a community that opens the doors of its alley to anyone wishing to share a glass and an evening of music.
For the 2026 edition, Vicolo dei Galli lit up again for four evenings, on May 9, 10, 16, and 17, confirming the successful formula of the Rione di Porta Romana festival in Castiglion Fiorentino. Every evening, from 6:30 PM, tasting and sales stands were active with over ten labels on the menu and boards of bruschetta, cured meats, and cheeses. The two Saturdays hosted themed dinners by reservation with limited seating, each accompanied by musical entertainment.
Dinner dedicated to Aretine peasant cuisine, featuring traditional dishes like pasta with meat sauce and roasted meat. By reservation, limited seating. Musical entertainment with Disco Spaghetti.
A new themed dinner focusing on the flavors of game and venison, using various cooking techniques. By reservation, limited seating. Musical entertainment with Cranium.
Vicolo dei Galli, historic center of Castiglion Fiorentino (AR), Rione di Porta Romana.
By car: take the Monte San Savino exit on the A1 motorway, then follow the SS73 towards Castiglion Fiorentino; by train: Castiglion Fiorentino station on the Florence–Rome line, a few minutes' walk from the historic center.
Tasting activities begin at 6:30 PM. Saturday themed dinners require reservations and have limited seating.
To participate in the themed dinners, it is necessary to book in advance through the Rione di Porta Romana channels. Tasting stands are freely accessible during the festival evenings.
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Vicolo dei Galli
Vicolo dei Galli, 52043 Castiglion Fiorentino