Chianti and other Tuscan wines are famous all over the world. Visiting Tuscany in late August–early October you can see how it's made and even participate in the harvest. Go to Montepulciano or Chianti and try a stay at a farmhouse and enjoy the simple life of local farmers. You can also take a guided tour, or simply volunteer to help.
Working side by side with farmers to hand pick grapes may be one of your most memorable experiences in Tuscany. Along with the work, the harvest is a time for celebration, so lots of food, wine tastings, and music are guaranteed as well. Some farmers are looking for volunteers during vendemmia offering bed and food, but make sure you apply in advance as many Italians living in cities take time off to help with grape picking, so competition is pretty high.