Calendar · 3 min read

Three dates that will decide your autumn

Everything else in Chianti between now and November is optional. These are not.

Autumn is the only season here with a fixed spine. Three dates, six weeks, and if you book around them you get the best of the year — if you book into them by accident, you get a car park and a queue.

Expo del Chianti Classico, Greve, 10–13 September. The 54th edition, and the one fair where producers from every commune in the Classico pour in the same square. A glass and a tasting carnet cost €20, and Riserva, Gran Selezione and Vinsanto burn two tickets each, so the carnet goes faster than you plan for. Go on Thursday or Friday. By Saturday afternoon the big names have queues three deep and the growers you actually came for are pouring to nobody.

Festa dell'Uva, Impruneta, 27 September. The hundredth edition. Four rioni spend a year building allegorical floats and one afternoon trying to humiliate each other with them, and 2026 is the centenary of the oldest grape festival in Italy. Standing in the piazza is free; the grandstand is ticketed through TicketOne and will go. It is 25 minutes from Greve and worth every one of them.

L'Eroica, Gaiole, 3–4 October. Eight thousand riders on pre-1987 steel, 51 countries, and a 209km route that leaves Piazza Ricasoli at 4:30 in the morning. If you are riding, you already know. If you are not, understand that the strade bianche around Gaiole are effectively closed all Saturday. Ride it, watch it, or be somewhere else — the one thing that does not work is trying to drive through it.

We have had all three wrong at some point. The year we booked a Gaiole agriturismo for the first weekend of October without checking anything is still brought up at dinner.

Every place we mention is on the map, with what's open today.

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