Already along the Via Volterrana, among ridges and slopes, when coming from Florence, the combination of nature and history can be perceived. After the Pesa, in the proximity of the stream Virginio, there is the Montegufoni castle, built in 1386 by the Acciauoli family. On the road called Via di Castiglioni, between the Virginio and the Pesa valleys, there is the church San Michele in Castiglioni. This road is an open-air eco-museum surrounded by churches, oratories, castles and villas dating back to the late Middle Ages and the Renaissance. A few kilometers away there is the village of Poppiano, dominated by the castle of the Guicciardini family. Facing south you can see Montespertoli, where the Sonnino Castle can be found right before entering the village. Piazza Machiavelli is the historical part of the town: there is an ancient well and a XVII century small palace, with two towers that house a clock and an anemometer. Continuing towards Lucardo it is possible to reach the Lucardo castle which, together with the Romanesque church, dates back to the 10th century. Together, they dominate the surrounding valleys.