A walk of approximately one hour through the woods, starting at the farmhouse on the left of the Paneretta road, leads to the ruins of Castle of Cepperello. The fortification is first found in the records in 1163, when Cepperello was mentioned as a border point between the dioceses of Siena and Florence. The Sienese Pope Alexander III wanted to define the territories of the two cities in an attempt to put an end to their continuous struggles. The strategic position of the castle, situated on the slopes between the Elsa Valley and the Chianti region, made it ideal for controlling the valley of the Drove stream and the border itself. The 13th century was a particularly prosperous period for the inhabitants of Cepperello judging by the huge amounts of grain given in tithe to the Florentine troops traveling towards Montaperti. After the Guelphs’ defeats the Ghibellines punished Cepperello. They dismantled its walls and demolished some houses, a mill and two noble mansions. The fortified structure was reduced to a rural village, completely impoverished by the 15th century. The ruins in the woods show architectural features datable to the 13th and 14th centuries: evenly aligned stone walls, wide-arched windows and elegantly carved stone window-sills.

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