Best Wine festivals to attend in Tuscany in 2026
Darya Boronilo
Best Wine festivals to attend in Tuscany in 2026
The end of summer marks the beginning of the grape harvest and Wine festivals in Tuscany, one of the most famous and prolific wine regions in Italy. The region’s most beautiful villages hold countless Tuscany wine festivals, dedicated to wine and centuries-old winemaking traditions. These days wine experts and amateur wine lovers enjoy the unique atmosphere, stroll through these towns with a glass in hand, and discover the best of the region’s famous products.
August
Barrel race at Montepulciano
Bravìo delle Botti, 30 of August
One of the most interesting events among Tuscany wine festivals, he Bravìo delle Botti is the challenging barrel race between eight districts: Cagnano, Collazzi, Le Coste, Gracciano, Poggiolo, San Donato, Talosa and Voltaia, all located along the historic city center. They compete for a painted cloth by rolling barrels of about 80 kg each, along an uphill path of over a kilometer. The barrels are pushed by two athletic "pushers", while the route of the race winds through the picturesque streets of the historic center of the city of Poliziana until the arrival, located in the churchyard of the Duomo in Piazza Grande. It’s one of the most spectacular wine events in Tuscany.
Photocredit: Dream of Italy
September
Chianti Classico Expo in Greve in Chianti
12th to 14th September
Expo Chianti Classico presents a great opportunity of getting to know Chianti Classico wine in the beautiful region where it is produced. The event is organized by the Municipality of Greve in Chianti, and it brings together producers of all the Chianti Classico Municipalities.
It is undoubtedly one of the most important opportunities to get to know the world of Chianti wine. The program also consists of rich artistic and cultural events and allows visitors to meet local winemakers, as well as to visit their vineyards and cellars.
Grape Festival in Chiusi
26 to 28 September
During this grape festival, wine and local food producers gather together. Visitors are offered tastings in the traditional cellars, at the tasting points, and in the shops of the town. As a part of this great experience, guests can try the most typical, original, and appetizing dishes, attend itinerant shows and musical entertainments, and make connections with the local community.
Photocredit: Dooid
Castelnuovo Berardenga Wine Festival
the last week of September
Castelnuovo Berardenga is the Grape Festival taking place in the Village of Vagliagli during the last week of September. This traditional festival is among the most important and most interesting on Siennese territory due to the high quality of the activities offered. It consists of various interesting cultural and oenogastonomic events that are not to be missed!
Grape Festival in Impruneta (Festa dell'Uva)
The last Sunday of September
One of the region’s most famous feasts is definitely Festa dell'Uva in Impruneta, dating back to 1926 and maintaining its rural character. It has always attracted many Italian and foreign visitors during the autumn season of wine festivals in Tuscany.
The float parade is the most important part of the feast, in which the four quarters of the town take part: Fornaci, Pallò Sant'Antonio, and Sante Marie. In addition, many folkloristic dances, shows, tastings of the local products, and local craft exhibitions take place during the feast.
Bacco Artigiano and the “Crazy Wagon”
Late September
Rufina has always been the wine territory “par excellence” producing prestigious wines due to its ideal climate and positioning. Today it takes an important place among Tuscany wine festivals and pays the tribute to its old winemaking traditions with the “Bacco Artigiano” event when the entire town gets together for large-scale celebrations. Historically during the days of the Florentine republic farmers used to set immerse Carro Motto (“Crazy Wagon” ) filled with new wine to depart towards Florence. Today this ritual is revived, and a steady pyramid of 1500 well-organized wine bottles is set up on the float. Apart from the opportunity of following the wagon procession, the visitors can also enjoy music, workshops, concerts, and of course wine and food delicacies of the region.
October/November
Radicondoli Festa of roasted chestnuts and wine
late October or early November
Autumn takes over with the smell of wet soil, rain, and the smell of roasted chestnuts on the fire. This annual festival has deep and ancient roots and the tradition of people gathering to roast chestnuts goes back to very ancient times. This event stands at the top of the most authentic and spectacular wine festivals in Tuscany. From very early morning the town’s band begins to play, marching from farmhouse to farmhouse and waking people up. During the day everyone enjoys local snacks and a good glass of wine. The day is then spent with the town community gathered at the park located at the highest point of the town. There the whole population enjoys a picnic on the grass while the band goes on playing until nighttime.
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