Pitigliano
Pitigliano was a small county on a tufa cliff in southern Tuscany. It passed to the Orsini family in 1293, and Count Guido Orsini ruled it in 1337.
The Orsini fought intermittent wars with neighbouring Siena until a settlement in 1455 recognized Pitigliano as a county under Sienese sovereignty. It later followed Siena into the Grand Duchy of Tuscany. In 1604 Count Giovanni Antonio Orsini ceded the fief to Grand Duke Ferdinando I de' Medici.