Castellina in Chianti is situated in a dominant position on a hill among the hills of Arbia, Elsa and Pesa. Castellina had an important role because it was built for will of Florence in the centre of a fortified line from Valle of Elsa to Valle of Arno. It was a fortified village which defended the countrymen from the raids of the wars between Florence and Siena . From 1203 it became more important because it was along the frontier, in a defensible place by the Florentine and along the main road between Siena and Florence . The defeat of Montesperti compels Florence to revise its defensive system. It creates defensive centres with more equipments and led by its officials. These new centres formed the Leagues. Probably before 1384 Castellina led the Leagues, later the centre of the commune's chief was Radda. Castellina was strengthened, however it was conquered by Castruccio in 1325 and then by Alberico da Barberino in 1397. After this event Florence decided that Castellina should be fortified again with walls. The works were made by the Opera of Santa Maria del Fiore and they lasted al lot of time. Maybe in 1430 the works ended, in fact in 1452 the aragonesi troops of the Calabria 's Duke, after a siege of forty days, weren't able to conquer Castellina.
In 1478 the Aragonesi and the Sienese attacked Castellina and this time it had to surrender.
Inhabitants and defenders were saved, but they had to leave the village to the Sienesi, who sacked all and then they settled there for five years, building the walls again.
In 1555 the Sienese Republic fell and Castellina lost its strategical role. The walls were used like support for the new houses, which were a reconstruction of the old houses except some Renaissance palaces. However, Castellina preserves part of its defensive system, such as a covered passage called Via delle Volte. In the centre of the village there is the Rocca, which is constituted by a very high defensive building, it was restored and become inhabitable in '30, today it is centre of the communal management. The ancient church of S.Salvatore is not there any more ; the present church was recently built and it houses a taken off fresco made by Lorenzo di Bicci which represents “The Virgin with Child”.
Not far from the walls there is an ancient mill, whose structures are in contrast with the rest of the landscape, that has maintained the original features. Near the centre of Castellina there is a big Etruscan grave dating back to the VI century b.C. and discovered in 1507. This is a witness of an ancient human presence in the area of Chianti. After a long period of indifference to it, the grave was restored and nowadays it can be visited. Because of its position could seem that there was an Etruscan village, whose witness are in Caselvento, where you can see parts of the old walls and a deep well. Saturdays and Sundays in August there are gastronomic stalls in the communal park and a dance in the square.