The landscape merges with the sight of two ancient castles: Radi di Montagna (year 1130) and Palazzo al Piano (year 1270), overlooking the village, and the nearby medieval settlements that take us to a prestigious past. Borgo il Poggiaccio dates back to 1330 and its history can be considered remarkable for the construction of major rich ancient architectural interventions. In facts, from historical research we find that in the year 1380 the oldest part of the castle was the outpost of Palazzo al Piano, owned since the beginning of 1300 by Giacomo Andrea Tolomei, the ancient exponent of Sienese noble family, whose origins date back to the Italian expedition of Charlemagne. Later, at the end of 1770, the entire property passed to the Chigi Conti D’Ardenghesca, the great lords of the Sienese Maremma castles, which in Rome (year 1659).

In the beginning, the castle of Palazzo al Piano served as a fortress to defend the town of Pieve a Molli. Il Poggiaccio was later used as customs and there goods and people in transit were controlled, by charging the famous gabelle – that is why this place has a pejorative suffix. Il Poggiaccio was then a small self-sufficient village and, as such, it had its own school, a blacksmith shop, a carpenter’s workshop, a baker’s shop, and so on.