Bolgheriannual, first week of September2 to 3 days
The Consorzio Bolgheri walk-around tasting at the Castello della Gherardesca and the Frantoio of Casa Carducci in Castagneto Carducci, followed by the kilometre-long Cena dei Mille on the cypress-lined Viale dei Cipressi.
Tip: The Cena dei Mille on the Viale dei Cipressi seats one thousand and books out months in advance; the walk-around tasting is easier to secure.
Panzano in Chiantiannual, third weekend of September3 days
Twenty-three producers of the Unione Viticoltori di Panzano pour Chianti Classico Panzano UGA bottlings, Conca d'Oro single-village reds and IGT Toscana from stalls around Piazza Bucciarelli. Over 80 wines are typically open across the weekend.
Tip: The Conca d'Oro sub-zone within Panzano produces some of Chianti Classico's longest-lived bottlings; ask producers to compare a Riserva to a Gran Selezione side by side.
Greve in Chiantiannual, second weekend of September, Thursday to Sunday (11 to 14 September in 2025; 10 to 13 September in 2026)4 days, Thursday to Sunday
Greve in Chianti hosts producers from across the Chianti Classico area for four days in Piazza Matteotti. The 54th edition in 2026 listed 64 producers, with tastings at the consortium pavilion or at individual producers' stands, a programme of art and cultural events and meetings with winegrowers in their vineyards and cellars. Tastings need an official glass at 20 euros that includes seven tasting tickets.
Montespertoliannual, nine days from the last Saturday of May to the first Sunday of June (30 May to 7 June in 2026)9 days
Montespertoli turns its town centre into a route of producer stands for nine days, with the main venues in Piazza del Popolo and Piazza Machiavelli. The 68th edition in 2026 had 21 wineries with stands plus two guest producers, tastings with the official festival glass at 5 euros, food stands run by 13 local associations, a Torneo delle Contrade and a historical parade on the final day. The festival grew from the town's traditional livestock fair, to which organisers proposed adding wine in 1957, with the first wine fair following in 1958. It was known for many years as Mostra del Chianti until a new organising committee restored the name Festa del Vino.
Radda in Chiantiannual, a weekend in late May, Saturday and Sunday (23 and 24 May in 2026)2 days, Saturday and Sunday
Radda in Chianti presents its own wines once a year: more than thirty Radda producers pour their labels at counters along Viale Matteotti, tasted with a personalised glass with a carrying strap at 25 euros and no advance booking. The 2026 edition, on 23 and 24 May, marked the event's 28th year. A booklet lists the producers and wines poured, restaurants and wine bars in the village offer special menus, and the organisers also run a seminar and a Radda Vintage tasting that need advance booking.
Rufinaannual, a Thursday to Sunday core around the last weekend of September (29 September to 2 October in 2022; 26 to 29 September in 2024; 25 to 28 September in 2025, the 50th edition, when the Carro Matto reached Florence on Saturday 27 September)4 days, Thursday to Sunday
Rufina, the Chianti Rufina wine town east of Florence, holds a long weekend of wine and food events, exhibitions, workshops and concerts, centred on Villa Poggio Reale, which houses the Museo della Vite e del Vino. In the 2024 programme the Consorzio Chianti Rufina ran tastings in the villa's main hall on Saturday and Sunday and a Friday dinner, and wine bars opened in Piazza Umberto I and at the villa. The Carro Matto, an ox-drawn cart carrying a pyramid of wine flasks, travels to Florence in a costumed procession through the historic centre.