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Overcoming the plan for the Koran, the town suddenly appears at the sight of the visitor that comes from the SS-74 perched on a striking bedrock outcrop surrounded on three sides by deep ravines. By the curve in the Madonna delle Grazie area, where stands a church built as a votive offering to the plague of 1527, you can admire the beautiful scenary with the latest turns of access to the Pitigliano, the arches of the Orsini acqueduct and the road that leads to Sovana. Scenic memorable impression, a place that seems unreally coming straight from the earth.

The name Pitigliano derives, presumably, from the gens Petilia, which owned a ground of Rome, and gathered the locals on the tufa rock. Nearby were found evidence of ancient times, including groups of Etruscan tombs, both room and bin styled.

Similarly to other countries of Etruscan origin, Pitigliano stretches on a flat tuff rock where houses rise, narrow and high, from the edge of ravines that surround it on three sides and at whose feet flows gurgling the streams Lente, the Prochio and Meleta. An air of mystery surrounds the town which is surrounded on the north-western side by a short stretch of wall at the Porta di Sotto, round-arched, and still visible not far away from the ancient road to Sovana.

The village entrance is very picturesque: the road is carved into the tufa until the reach of the square on which a double door, surrounded by ramparts, is the only way to get in the citadel. Passing through the door you enter the Piazza Garibaldi, which overlooks the Town Hall and the Theatre Salvini. To the left stand the arches of the Orsini dated 1545, then the Republic Square, overlooking a wide view, a side to the sea and the city of Manciano and the other to the road to Sorano.

The building that borders one side of the square is leaning against the castle keep with three arches built on the ancient moat that separated at one time the castle from the citadel. Inside the building, after an inclined ramp adorned by a bear with leonine head, opens a courtyard with a porch partially enclosed by an external staircase leading to the premises formerly connected to Keep. On the left side of the courtyard is located a beautiful hexagonal shaft, flanked by two columns with capitals and travertine architrave. Along the access ramp to the building, built around the structure of an old mill, was recently obtained the chapel of Gethsemane.

From Piazza della Repubblica, there are three ways, almost parallel, the main one of which, via Roma goes through the medieval town square dedicated to Gregory VIIth on which stands the Cathedral entitled to Sts. Peter and Paul (being restored back in the fifteenth century, underwent renovations until 1970). On the left side of the church stands the bell tower (35 meters tall), of particular architectural conformation. Opposite the cathedral is the cornerstone dated 1490, surmounted by a bear, which tells in Latin couplets, the legend of the roses placed in the Orsini coat of arms. Down the Via Generale Orsini, in the western part of town, is the trapezoidal planted Church of St. Mary (St. Rocco) symbol of the district "Capisotto".

After visiting the medieval part of the town you should return to Gregory VIIth square and go down to the staircase that brings you to the synagogue which stands in the center of the "ghetto". The Jewish temple was built in the sixteenth century as a place of worship for the local Jewish community and was repeatedly subjected to restoration. Nearby is the typical bakery from which the Jews baked unleavened bread. At the conclusion of the tour of the ghetto, is worth visiting the Jewish cemetery site on one of the curves of SS 74, just outside the town towards Manciano.