Pitigliano

Pitigliano is home to a series of artificial cuts into the tufa rock to varying depths ranging from less than 1 metre (3.3 ft) to over 10 metres (33 ft). At the bottom of these cuts (Italian: tagliate) are carved channels, apparently for water, although some take the form of steps. The purpose of the cuts is not known: the three main theories are that they were roads, quarries, or water conveyance schemes; they radiate outward from the base of the butte of Pitigliano, down to the rivers then back to the top of the plateau that surrounds the town. A few very brief Etruscan inscriptions are said to have been found on the walls of the cuts, but are ill documented.

• The former Cathedral of Santi Pietro e Paolo.
• The church of Santa  Maria.
• The Orsini Fortress, which achieved its present state in 1545 but represents a reworking of the earlier medieval fortress
• the town's walls and gates, the best preserved of which is the Porta Sovana.
• remains of a tall and very visible aqueduct at the very top of the butte.

For several hundred years Pitigliano was a frontier town between the Grand Duchy of Tuscany and, to the south, the Papal States. For this reason, the town was home to a flourishing and long-lived Jewish community, mostly made up by people fleeing from Rome during the Counterreformation persecutions. Jews of the town used one of the caves for their ritual Passover matzoh bakery, the "forno delle azzime" described in detail in Edda Servi Machlin's "Classic Cuisine of the Italian Jews." After the promulgation of racial laws under Nazi influence, all the Jews of the town reportedly escaped capture with the help of their Christian neighbors. Although there are almost no Jews left in town, not enough to provide a minyan, the synagogue (1598, with furnishings of the 17th and 18th centuries) is still officiated from time to time. It was restored in 1995.

The Tempietto ("Small temple") is a small cave, probably of natural origin but considerably reworked by human hands, lying a few hundred meters outside the central district, yet far above the Lente valley. Its purpose and builders remain unknown. Locally it is referred to as a "paleochristian tempietto", but this has never been confirmed; it must date to Late Antiquity or the early Middle Ages, although it may replace an Etruscan or Roman arcosolium.[4]