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Castellina is bang in the middle of one of the world's top wine areas, Chianti Classico, so it's hardly surprising that there is the occasional wine-fest. One of the best is the Pentecostal Wine Fair, held (not surprisingly) over the Pentecost weekend. Now as Pentecost is one of those Easter-related feast-days that moves with the moon, you'll have to look up the dates, but they are easy enough to find. The important thing is that on the Friday, Saturday and Sunday evenings you can go along, buy a glass (usually around €10) and move from stand to stand in the vaulted gallery under the old town walls. There are usually around 50-100 exhibitors, each with between 3 and 10 wines, so there isn't a cat's chance in hell you can try them all. But you can have a great deal of fun trying, and then ask the growers of the wines you really like you like to ship you a case. Some of these vineyards only produce a few 1000 bottles a year, so you can find some spectacular wines you would never have a chance of discovering otherwise.
Here's a list of some of excellent local wineries in the area around Castellina, useful for anyone planning their own wine tour.
The late summer and early fall is the time of numerous food festivals in the area around Castellina in Chianti and a bit further afield. But within an hour of the town you can find activities that truly signal the end of summer. As the harvests arrive it is time to sample the local grown foods.
This includes the end of August Watermelon Festival, which is when the sweet melons reach their peek in this part of Italy. The town comes alive as local farmers sell their produce, and you can enjoy all types of fresh grown fruits and vegetables, but of course watermelon rules the day.
If you’re looking for a bit more “meat” then head down to the town of San Giovanni d’Assco, for the end of August Frog Leg Festival. After a day of sampling the grilled legs, you can enjoy local music under the stars. San Givoanni d’Assco is also known for its summer long Sniffing Out Summer Truffles Festival, which takes place on weekends all summer long!
September is the time for the Cheese Fair in Pienza, which is held in the old town center and includes evening entertainment including dancing in the town square. And what would cheese be without some wine? The Grape and Wine Festival takes part in neighboring Sinalunga in the Piazza Garibaldi.