The drive into Pitigliano produces one of the most theatrical first views in Italy: a wall of tufa rising vertically out of the gorge, with the village built directly on top of it, its houses appearing to grow out of the cliff. Inside, the medieval streets are largely untouched and the views back across the ravine are constant.
The Jewish quarter on the west side of town is the most distinctive sight: the small synagogue dating from 1598, an underground complex of wine cellars and a ritual bakery cut into the tufa, and a careful museum that tells the story of the community. Up in the centre, the Orsini Palace contains an archaeological museum and a remarkably grand kitchen. Allow half a day; the wine made from the local Bianco di Pitigliano grape is worth tasting.