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From a distance, the medieval stone houses of Pitigliano look as if they melt into the cliffs upon which they are perched. Etruscan tombs, which locals use to store wine, are connected by a network of caves and tunnels. At the beginning of the 14th century the Orsini family moved its base from Sovana to the better-fortified Pitigliano. They built up the town's defenses and fortified their home, Palazzo Orsini. Later, starting in 1543, Antonio da Sangallo the Younger added to the town's fortress, building bastions and towers throughout the town and adding the aqueduct as well.

Pitigliano has become a trendy locale for Italian vacation rentals, making the town center lively in summer. Restaurants serve up good meals that, as a result of the tourist boom, have inflated prices. Bianco di Pitigliano (Pitigliano white wine) is a fresh and light, dry wine produced from the vines that thrive in the tufa soil of the area.