When in the Val d’Orcia, stop at Montalcino, and buy a bottle of the fantastic Brunello wine, one of the most prestigious in the world. Returning to Siena, make sure you go through the Val d’Elsa, where natural beauty and artistic heritage meet.
San Gimignano, a hilltop town inside fortified walls, is an outstanding example of medieval town. 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.
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 market of the Valdelsa area, offering 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.