San Casciano in Val di Pesa is located along an ancient Roman road which connected Florence and Sena Julia and was originally probably a post station. During the Middle Ages, the city lived under Florentine rule, while keeping a good degree of independence thanks to its strategic location. The lack of walls however exposed the city to frequent raids in the 14th century and the walls were only completed in 1355. With the rise of the Grand Duchy of Tuscany, the city lost its military purpose and became a thriving agricultural town, specialized in the production of wines and oil.