Castiglioncello del Trinoro was defended by fortifications, with five churches inside the walls, a stronghold, and a town hall. Very little remains today of this glorious past, which may have Etruscan origins: the Romanesque Church of Sant’Andrea, a 14th-century gate, and the palace. Its dominant position (774 meters above sea level) over the Val d’Orcia made it a control center on the road that ran through the valley floor. It seems that, exploiting this strategic position, Castiglioncello became a hideout for thieves who robbed travelers on that stretch of road, and its name is believed to derive from Castrum trium Latronum, meaning Castle of the Three Thieves, later softened to Castrum Leoncelli Trinaurum, Castle of the Little Lion of the Three Golds. However, this remains in the realm of speculation laced with legendary elements. Recently, the remains of an ancient fortress, existing at least since the 11th century, have been recovered, along with the access to the Sienese castle and the continuation of the protective city walls. From the foundations, now visible in a sort of archaeological garden, two watchtowers can clearly be seen. Historical documents show that it belonged to the Manenti Counts, who in 1117 and 1126 ceded it to the Camaldolese Abbey of San Piero in Campo in the Val d’Orcia, which in turn, around 1250, passed it on to the Republic of Siena. In 1259, to cover the expenses of the war against the Florentines, Siena ceded it along with other castles to the Salimbeni family. This noble Sienese family – which is said to have often hosted Saint Catherine of Siena – maintained ownership with alternating fortunes until 1418, when it was requisitioned by the Republic of Siena. Meanwhile, the citizens of Trinoro had risen up to proclaim themselves as a Commune. Siena accepted the proposal, making them promise not to allow any members of the Salimbeni family into Castiglioncello. In 1497, the agreement was confirmed. Subsequent events were tied to the Republic of Siena. It is worth noting that the Medici also applied a process of neo-feudalization here, transforming Castiglioncello into a marquisate and assigning it to the Sarteanese family de’ Salamandri, later known as Cennini. Today, the village hosts a luxurious diffused resort.
