Located at one of the most important crossroads since the very ancient times, the village is reported for the first time in a document dating back to 1038 AD. The castle overlooking the village was once part of the properties of the Abbey of Agnano, and as of today keeps intact its charm of a mediaeval fortified borough.

Capannole is located at the junction of the road coming from Siena and continuing towards the Valdarno.
The importance of the place as a crossroads is highlighted by many archaeological findings: the most important of which is a late Roman bridge that has been restored throughout the Middle Ages.

Even the construction of the church (more recent than the bridge) confirms the importance of the place.
Mentioned in documents since 1038, the community of Capannole seemingly owns a ancient seal - portraying a castle and a shack.
Historians believe that the name of the village be just a nickname that was given to the settlement by the soldiers patrolling the road.
The castle of the borough (located on a hill beneath which placidly flows the river Trove) was formerly a fief of the Ubertini and then fell under the control of the Abbey of Agnano. In the end, it became property of the Vannucchi family.