A lovely little town situated on the quinessentially Tuscan drive between Montalcino and Montepulciano. What the town lacks in notoriety in comparison to its famous neighbours, it makes up for in beauty and grace. Almost completely redesigned between 1459 and 1462 and renamed on the orders of hometown son Pope Pius II, the main square is the picture of Renaissance architecture, while the surrounding houses retain old village charm. A highly recommended lunch stop for those doing a tour of the vineyards of Southern Tuscany.