In the late 12th century there was already a small fortified city walls in Piancastagnaio enclosing the uppermost part of the current town, In the following century, with economic development and the birth of the municipality, the town expanded much beyond these walls.
The main attractions include the Pieve of Santa Maria Assunta, in Baroque style but existing from before 1188, the Palazzo Bourbon Del Monte, and the Rocca Aldobrandesca (“Aldobrandeschi Castle”).
The palio of Piancastagnaio is the crowning event of the life of the four districts (contrade) in which the municipality is divided; the four districts are:
Hamlet (yellow-blue colours, armorial “salient–horse prancing turned left“)
Chorus (red-black colors, Crest “Eagle with open wings and head turned to the right“)
Castle (red–green, emblem “two castle towers, of which the keep right”)
Voltaia (white-black, coat of arms “oak in an arched doorway“)
The event traditionally takes place every August 18 and after the palio follows a night of celebration for the winning contrada with choruses of joy and light banter.