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Castiglioncello del Trinoro was defended by fortifications, with five churches within the town walls and a town hall. Very little remains today of this glorious past, which may have Etruscan origins: the Romanesque church of Sant'Andrea, a door from the 14th century and the Town Hall. Its dominant position (at an altitude of 774 metres) on the Val d'Orcia turned it into a control centre on the roads that ran along the valley floor. And it would seem that, by taking advantage of this strategic position, Castiglioncello became the base for highwaymen who robbed travellers on that stretch of road, a reputation shared with Pienza. It has been suggested that the name derives from Castrum trium latronum, i.e. the Castle of the three thieves. In the spring of 2009, after meticulous excavation work by the University of Siena, the remains of an ancient fortress was unearthed, dating back to at least the eleventh century. It belonged to the Manenti counts, who, in 1117 and 1126, relinquished it to the Camaldolese abbey of San Piero in Campo in Val d'Orcia, which in turn, around 1250, turned it over to the Republic of Siena. The latter, in 1259, to meet the costs of the war against Florence, ceded it with other castles to the Salimbeni family. The noble family from Siena, which apparently often welcomed Catherine of Siena there, retained the property with varying fortune until 1418, the year in which it was requisitioned by Siena. In the meantime, the citizens of Trinoro rose up, with the intention of becoming a free municipality.