South of Siena is a region of beautiful rolling hills also referred to as Val d'Orcia. Nestled in this area are some surprisingly well preserved medieval towns each with their own character and specialty products (wine, olive oil, cheese, etc.). Three of these towns are definitely worth mention:
Montalcino served as a last refuge of the Sienese ruling elite after Siena itself had been conquered by Florence in 1555. Montalcino is also the home of the world famous Brunello di Montalcino wine. A visit to a local winery can be arranged.
Pienza (originally Corsignano), was renamed after Pope Pius II who remodeled the town according to the Renaissance ideal. Pienza offers breathtaking views of the Orcia Valley and is known for its pecorino cheese (Pecorino di Pienza).
Montepulciano -just outside its Medieval town center- boasts the beautiful San Biagio church, considered one of the masterpieces of Renaissance architecture (it shares elements with Saint Peter's Cathedral in Rome). Montepulciano's Nobile wine is one of the classic wines of Southern Tuscany.