NeighbourhoodRegion-wide
Whenannual, last weekend of May
Duration2 days

Tip: Most cellars accept walk-ins but star Brunello and Bolgheri estates require advance booking through the Movimento Turismo del Vino regional site.

Also in Region-wide

Calici di Stelle ★ 4.5

Region-wideannual, late July to mid August (centred on 10 August)approximately 4 weeks of events around the 10 August night

Vineyard tastings paired with stargazing under the Perseid meteor shower on the Night of San Lorenzo. Member estates host open-air dinners, telescopes and music; the 2025 program spanned 25 July to 24 August across more than fifty Tuscan venues.

Tip: Vinci, Montalcino and Castelfalfi run the most production-heavy programs; check the Movimento Turismo del Vino events calendar in early July.

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More wine festivals in Tuscany

Calici di Stelle ★ 4.5

Region-wideannual, late July to mid August (centred on 10 August)approximately 4 weeks of events around the 10 August night

Vineyard tastings paired with stargazing under the Perseid meteor shower on the Night of San Lorenzo. Member estates host open-air dinners, telescopes and music; the 2025 program spanned 25 July to 24 August across more than fifty Tuscan venues.

Tip: Vinci, Montalcino and Castelfalfi run the most production-heavy programs; check the Movimento Turismo del Vino events calendar in early July.

Bolgheri DiVino ★ 4.7

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.

Vino al Vino, Panzano in Chianti ★ 4.5

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.

Expo Chianti Classico

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.

Festa del Vino di Montespertoli

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 nel Bicchiere

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.

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Taste your way around Tuscany while you are in town

Cantine Aperte runs 29 to 30 May. These are the wine tours and tastings in Tuscany to book for the days around it; most cancel free up to 24 hours ahead.

Wine tastings and winery visits in Tuscany (124) · Wine tours and day trips in Tuscany (250) · Wine and cheese tastings in Tuscany (18) · Cheese tastings and dairy visits in Tuscany (6) · Wine tours by bike in Tuscany (30)

See all 2334 bookable experiences in Tuscany

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