San Gimignano, a hilltop town inside fortified walls, is an outstanding example of medieval town planning. Enter at Porta San Giovanni and head the tower houses of Piazza della Cisterna to Piazza del Duomo and the Collegiata. While in the town, make sure you taste the Vernaccia di San Gimignano, a delicious white wine from the area.
Not far away stands the town of Monteriggioni. Founded in the early thirteenth century by the Republic of Siena as a defensive outpost against Florence, its historic walls with their fourteen towers are still intact, a rare example of medieval military architecture. Occasionally in Monteriggioni is organized an open-air market, called Mercatale, which is a project of the Valdelsa area, where one can buy farm-to-table products.
It is precisely this, the mix of nature, art and food which gives rise to these beautiful Tuscan destinations, renown throughout the world.