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Football is like a national pastime in Italy and Tuscany is no exception. If you have a chance to see a game, by all means, go. La Fiorentina is Florence's team and now that they are in the Premier League, it may be a bit more difficult to get tickets. Siena and Livorno are also places to catch a football game. There's nothing quite like the experience of watching a football game amidst die-hard Italian fans. Have you seen the World Cup lately?
But football is not the only thing happening for sporting activity. Every November, the Florence Marathon takes place. There are also opportunities for swimming, skiing, rowing (if you want a completely different perspective of the Ponte Vecchio bridge, trying rowing underneath it) and biking. The latter is especially popular - there seem to be bike tours popping up all over the place to explore the countryside of Tuscany.
And for something truly bizarre and wonderful, there is the Bravio delle Botti - every year in late August, eight neighborhoods compete in a barrel-rolling contest (yes, that's right, barrel-rolling) in the town of Montepulciano. They roll empty wine barrels down the streets to the Piazza Grande and the winning neighborhood gets a cloth with the image of San Giovanni Decollato, and of course the bragging rights until the next year.
Actually they push barrels UP to Piazza Grande; these barrels weight less or more 80 kg., the race is 1800 meters long, and the spingitori (men that push barrel), 2 each barrel, do this in a bit more than 9 minutes. There are a lot of events connected to the race (it takes part every last Sunday of August) during the all week before and all along the Sunday such as: historical parades on Thursday night and Sunday afternoon, flags throwing, medieval shows and dinner in the contrade (the neighborhoods) almost every evening.