Casole d'Elsa lies on top of a hill, in the country between Siena and Pisa.
It’s a small town characterised mainly by its buildings of ancient brick, placed on the ridge of a hill which has a beautiful, panoramic view.

Originally an etruscan settlement and then a domain of the bishop of Volterra, Casole passed in the first half of the 13th Century under the control of Siena, in spite of the various rebellions provoked by the Porrina family for all of the first half of the next century. The sienese repeatedly reinforced and brought up to date the fortifications bacause of its defensive position. Casole's "terra" ( as a centre of habitation enclosed by walls used to be called in medieval times) had an almost pear-like shape, extending south to north for 420 metres and of a maximum width of about 130 meters. All around the confines ran the enclosing walls, a great part of which is still visible today particularly along the western side, through sometimes incorporated in the walls of the houses.

The main street runs south to north through the center, connecting the two gateways of the village: Porta Rivellino to the south , Porta ai Frati to the north. These two gateways no longer exist today; Rivellino was blown up by the nazis in the second word war.

La Rocca is the most important civil building in Casole, today the seat of the Town Hall.
An imposing quadrangular edifice with a massive stone tower in the northern corner and another smaller one at slight angle at the opposite corner. To the sides of the main entrance are still visible some well preserved arrow slits. Over the course of time there have been numerous alterations, giving the building a much changed aspect, although conserving the sense of the volume.