Upcoming Chianti wine festivals

The Chianti Classico wine zone of Tuscany is the home to several really good wine festivals where you can taste a wide range of Chianti Classico wines and talk directly to the producers. On 23 and 24 May 2026, in the attractive village of Radda in Chianti there is a wine tasting event, Radda nel Bichiere, taking place that is well worth a visit if you are in the area. A bit later in the year, on the first weekend of June (6th and 7th) 2026, there is another wine festival taking place in Lamole in Chianti, I Profumi di Lamole. And the Chianti wine festival takes place in Montespertoli from 30 May to 7 June 2026. To take in some or all of these wine tasting occasions, you could find a place to stay on the Panzano in Chianti website.and for the Montespertoli Chianti wine festival on the Montespertoli website.

At Radda nel Bichiere

For September 2026, there are two upcoming Chianti wine festivals to note in your agenda.

Chronologically, the first is the Chianti Classico wine fair taking place in Greve in Chianti, 45-60 minutes south of Florence and reachable by bus from Florence. The official name is the Il Rassegna del Chianti Classico (54th Expo of Chianti Classico wines). In 2026, this wine festival takes place from the 10th to the 13th September 2026 in Piazza Matteotti, the main piazza of Greve in Chianti. Note that you might have to park some distance from the venue due to heavy traffic - this fair is very popular. If you also plan to drink some wine, that's just one more reason to take the bus.

The Terre di Melazzano booth at the Rassegna del Chianti Classico

 

The way it works is that you buy a wine glass from the Cassa and Informazioni booth and this allows you to try a certain number of the wines displayed. You can both buy and order wine and olive oil at the booths. In addition to the wine tasting, a variety of events is offered during the four days, but I wouldn't over-estimate their intrinsic interest. Click here for the 2026 programme. The Greve Chianti wine fair has a good number of Tuscan wineries represented, each offering all of the wines that they produce - mainly Chianti Classico, of course. My only objection to this fair is that when the weather is hot, few of the exhibitors take any steps to keep their wines cool. Some of them are left in direct sunlight and are distinctly warm when you taste them.

The second wine tasting event is Vino al Vino, taking place one week later in Panzano in Chianti, 10 minutes drive in the direction of Sienna from Greve and also accessible by bus from Florence. Vino al Vino takes place from 17 to the 20 of September 2026. To some extent, I prefer Vino al Vino over the Chianti Classico Expo if only because it is smaller, with about 21 wineries presenting their wines and olive oil, and has a more intimate atmosphere. I also find the food on sale better than in Greve. There's live Jazz on Saturday & Sunday from 6 until 8 pm.

Vino al Vino Panzano Chianti wine festival

For accommodation nearby the venues:

Greve in Chianti accommodation.

Panzano in Chianti accommodation.

Villa hotels.

Chianti wine festivals on Facebook.

Don't forget to visit my Tuscany Travel Guide! Up-to-date news on what to see and where to stay in Chianti and all of Tuscany. Tuscany Travel Guide

Author: Anna Maria Baldini

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