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Piancastagnaio, registered as the location of a castle at the end of the XIIth century, was for a long time the object of contention between the Abbey of SS. Salvatore, the Aldobrandeschi family and the people of Orvieto and Siena; its historical events have often been connected to border conflicts between dioceses or states.
The decline of the Aldobrandesca Countship (end XIIth century) determined its passage to the Municipality of Orvieto. After a brief period of submission under the Counts Orsini of Pitigliano, in 1415, the town tertiaries decided to definitively submit to the Republic of Siena to become, subsequently, part of the Dukedom of Cosimo dei Medici (1559).
In 1601, Piancastagnaio was enfeoffed by the Grand Duke Ferdinando I to the Marchese Giovanni Battista Bourbon del Monte, the famous condottiere. The territory of the Municipality, exposed to the South, extends along the slopes of the mountain as far as the valley of the river Paglia. Piancastagnaio derives its name from the presence of a number of imposing chestnut trees on the upland plain above the town. Another naturalistic presence in the territory of Piancastagnaio is the biotype of the "Pigelleto" fir-tree, which provides evidence of what the natural habitat of the Amiata mountain must have been like in the Prehistoric Age.
To the West, along the road to Santa Fiora, you will come across the village of Saragiolo (956 m a.s.l.), also surrounded by centuries-old chestnut trees. One thing of note at the locality Tre Case, is the "il leccio di San Francesco" (St. Francis's holm oak), which is one of the largest in Italy.

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Siena and environs