Castellina in Chianti is a comune (municipality) of c. 2,800 inhabitants in the province of Siena, in the Italian region Tuscany, located about 35 kilometres (22 mi) south of Florence and about 15 kilometres (9 mi) northwest of Siena. It is part of the Chianti Hills, between the valleys of the Arbia, Pesa and Elsa rivers. The territory of Castellina in Chianti borders the following municipalities: Barberino Val d'Elsa, Castelnuovo Berardenga, Greve in Chianti, Monteriggioni, Poggibonsi, Radda in Chianti, Tavarnelle Val di Pesa. The first settlements in the area dates from the Etruscan age, and they were probably devastated by Gaulish invasions at the time of the latter's invasions against Rome. In the early Middle Ages the town was known as Salingolpe; in the 11th century Matilda of Tuscany gave it as fief to the counts Guidi and, subsequently, to the Trebbio. In the early 15th century it became a stronghold, of which today the Rocca remain.

Vagliagli is a village in Tuscany, central Italy, administratively a frazione of the comune of Castelnuovo Berardenga, province of Siena. At the time of the 2001 census its population was 386. Vagliagli is about 16 km from Siena and 27 km from Castelnuovo Berardenga.

Fonterutoli is a village in Tuscany, central Italy, administratively a frazione of the comune of Castellina in Chianti, province of Siena. At the time of the 2001 census its population was 80. Fonterutoli is about 20 km from Siena and 5 km from Castellina in Chianti.