The Rocca di Montauto is an imposing ruin of a castle and fortifications partially hidden by the lush vegetation of the Montauto nature reserve along the Fiora river a short drive east of Capalbio. Orginally an ancient Etruscan settlement, settled by the Romans, and disputed by Saracens, Popes, and Frankish kings in the middle ages, the castle was built by the Aldobrandeschi family in the 12th century.

The most interesting thing about it, though, was that at the end of the 15th century the last ruler of the Eastern Roman Empire in Constantinople, Anna Paleologa, was going to move her entire court and retinue of 100 families to the castle complex following their defeat by the Ottomans. The project was shelved only because the ruling Republic of Siena was beaten by the Grand Duchy of Tuscany, who nixed the idea, after which the castle fell into ruin.