About a 25-mile drive southeast of Siena in the rolling hills of Tuscany’s Crete Senesi region, San Giovanni d'Asso is home to just a few hundred people. The highlight is the 12th-century castle, which now houses town offices. Directly opposite the castle is Villa San Giovanni, complete with a hanging garden, which is rentable by the week. The town is home to two lovely old churches, San Giovanni Battista and San Pietro in Villore. Every November, San Giovanni d'Asso holds a Truffle Festival.