Castellina in Chianti is a tranquil and prosperous hilltop community on what was once the front line in the interminable wars between Florence and Siena. Via delle Volte, a vaulted gallery that was once a part of the town’s fortifications, is a remarkable survival of that period. Municipal offices now occupy the old fort in the town’s main square.
The communal territory of Castellina in Chianti amounts to a total of 99.45 kilometers (38.4 square miles) and is situated on the hills that separate the Elsa, Pesa and Arbia valleys. It is entirely located in the Chianti Classico zone. Due to the presence of two mountains, Macia Morta and Monte Cavallaio, the maximum altitude exceeds 600 meters (1,968 feet). About 2,500 persons, 30.4% of whom are engaged in agricultural activities, inhabit the area. About half of the land is cultivated in cereals, while vines and olives occupy the remainder. Other occupations involve production of terra-cotta and wrought-iron objects and woodworking.
The most substantial archaeological discoveries in the Chianti region have occurred in the vicinity of Castellina. The entire zone is rich in artifacts and places whose names refer directly to settlements established during the Etruscan and Roman periods. Castellina was mentioned for the first time in the 11th century as a possession of the nobles of the castle of Trebbio and of the faction of the Counts Guidi. Afterward, the town played a leading role in the contest between Florence and Siena, which dragged on for many years. Castellina’s position on the shortest route linking Florence and Siena favored the town’s growth, which resulted in its designation for a period as the administrative center of the League of Chianti when it was formed. At the end of the 14th century, the town became embroiled in the war in which Florence opposed the Duke of Milan, an ally of Siena. Sacked and burned, Castellina was so badly damaged that the Florentines built new fortifications, much of which survive. The structures within the walls have generally preserved their original aspect with the sole exception of the parochial church, which was constructed later in a neo-classical style. Numerous castles dot the countryside around Castellina, some of which, like Monternano, were owned by feudal dynasties. Its ruins still bear witness to the power of the Squarcialupis. Other ruins are scantier, like those of Rencine, which provide only a faint reminder of the small fort erected outside the walls of Monteriggioni. Among the other castles are those of Pietrafitta and Grignano, mentioned in the donation made by Marchese Ugo to the Abbey of Marturi in 998, and that of Leccia, which was later transformed into a villa-estate. The area also features churches and related buildings that have retained traces of their original Romanesque structures: the parish churches of Sant’Agnese, Lilliano and San Leonino in Conio, the rectory at Rencine and the churches of Piazza, Ricavo, Monternano, Cispiano, Montanino, Protine and Leccia