Greve in Chianti is a great place to visit at almost any time of the year, but especially during the spring and autumn. Below are the main festivals and fairs taking place in Greve and in nearby Montefioralle.
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Annual Flower Festival (Festa dei Fiori) :: usually the first weekend after 1 May. This a sale of shrubs and flowering plants that transforms the main piazza of Greve in Chianti. More about the Greve in Chianti "Festa dei Fiori".
Chianti Classico wine festival - every year on second weekend of September and the preceding Thursday and Friday, 11 - 14 Sept 2014. On Thursday, the festival starts at about 5 pm, and on Saturday and Sunday at about 11 am and the stands close at about 8 pm. The idea is that you buy a wine glass from the Segretaria and are then free to taste any and all wines offered at the stands. I have heard but not seen that they can run out of glasses.
Grape harvest - the date varies from year to year depending on the ripeness of the grapes, but the vintage usually takes place in late September or early October. An extremely interesting time to be around. More on theChianti Classico wine harvest.