San Casciano in Val di Pesa is the Chianti commune closest to Florence and it displays, in the pattern of its landscape and architecture, the positive influence of the Florentine late Renaissance. The headquarters of the Consorzio del Marchio Storico—Chianti Classico are located in a hamlet of the commune, Sant’Andrea in Percussina, and occupy a residence where Niccolò Machiavelli lived during his exile from Florence (1512-1520) and where he wrote his major works.
The communal territory amounts to 107.98 square kilometers (41.7 square miles). It is perched on low hills, with altitudes not exceeding 400 meters (1,312 feet), that divide the Pesa from the Greve valley. It is situated almost entirely in the Chianti Classico area. Only the section on the left bank of the Pesa is excluded from the zone. The population totals about 16,200 persons of whom only 9% are involved in agriculture.
Archaeological finds and place names prove the antiquity of settlements in the territory and the density of population in the past appears to be indicated by the existence in the area of four parish churches (Decimo, San Pancrazio, Sugana and Campoli) and a large number of dependent churches. The pattern of high-density settlement, which is still characteristic of the countryside around San Casciano, clearly originated in the Middle Ages. Initially, the process was favored by the many castles in the zone, which have since become villa-estates. Afterward, the spread of the practice of rotating crops and the rise of the sharecropper system were important factors in the development of agricultural production and the formation of scattered settlements and market centers. In documents of that period, San Casciano is mentioned for the first time as a feudal possession of the bishop of Florence but in the second half of the 12th century the signoria of the Tuscan capital secured direct control over the commune. Soon afterward, San Casciano became the administrative center of the League and, then, the seat of the jurisdiction of a podestà. The Statutes of the Podestà of the city of Florence, dated 1325, attributed the importance of San Casciano to its position on major trade routes. The commune has preserved some traces of its medieval past, including a few segments of its 14th-century walls, several towers and a gateway in the vicinity of the church of Santa Maria al Prato. In the countryside, the parish churches of San Pancrazio, Campoli a Decimo ande Sugana have preserved important structures of the Romanesque period. The small Romanesque church of Sant’Andrea a Luiano and the Gothic churches of Santa Maria a Bibbione and Sant’Angelo a Vico l’Abate are of interest from an architectural standpoint, especially the latter with its altarpiece by Ambrogio Lorenzetti. As to the innumerable villas dotting the countryside around San Casciano as well as the zone closer to Florence, those owned by the Guicciardini, Tattoli, Corti, Borromeo and Casarotta families deserve mention.