My family and I recently rented a house in the hills above Gaiole in Chianti (above Barbischio to be more specific). It was a fantastic vacation spent pottering around the nearby villages and eating at amazing restaurants. Castellina in Chianti (and the Antica Gelateria Castellina), Badia a Coltibuono, and Brolio were highlights. Volpaia's restaurant La Bottega was fantastic (the involtini stuffed with pecorino were great.)
This is not the place to go if you're looking for rocking nightlife, but for a quiet vacation with beautiful surroundings, excellent food and wine, Chianti is a great bet.