Pitigliano is located in the far south of Tuscany on the border with Lazio. It is about 75 km from Grosseto (the shortest way is the one that passes through Istia d'Ombrone, Scansano and Manciano) and about 110 km from Siena (along the via Cassia, you pass Monteroni d'Arbia, Buonconvento, San Quirico d 'Orcia, at Ponte a Rigo turn right for Sorano).

Pitigliano has been inhabited since the Bronze Age, subsequently, starting from the eighth century BC there was an Etruscan settlement, of this presence a short stretch of walls remains today, in large blocks of tuff, in the north-west part next to the Gate of Sovana. In the area around Pitigliano, the numerous necropolises further testify to the Etruscan presence. It was a Roman city and in the Middle Ages it became a fief of the Aldobrandeschi and from 1293 to the Orsini, under the Orsini family, Pitigliano became the capital of the county of the same name, became a bishopric, supplanting Sovana, and then was named a city. With the extinction of the Orsini family, it became a fiefdom of Pietro Strozzi and then of Cosimo I de 'Medici. At the beginning of the 17th century (1608) it became part of the Grand Duchy of Tuscany. The houses of the town are built on the edge of the cliff forming with it a single body and a rather picturesque whole. The Pitigliano cliff is surrounded on three sides by ravines which are full of caves carved into the tuff. After admiring the stupendous view of Pitigliano from the Church of the Madonna della Grazie, along the road that comes from Manciano, you enter the historic center from Piazza Petruccioli (from the terrace there is a beautiful view of the Medici aqueduct) crossing the door of the southern bastion of the Rocca. The Rocca, of Aldobrandesque origin, was renovated between 1543 and 1545 by Antonio da Sangallo the Younger, who had two polygonal bastions built (today transformed into private homes), replacing the existing circular towers. The historic center is spread over three main streets (via Vignoli, via Roma and via Zuccarelli), almost parallel, connected by a dense network of alleys. After crossing Piazza Garibaldi where you can see the two stairs that led to the ramparts of the citadel, you flank the arches of the Medici aqueduct (built between 1636 and 1639 on a sixteenth-century project (1545) by Antonio da Sangallo the Younger, the ancient aqueduct of Pitigliano is formed by two large arches supported by an enormous pillar in blocks of tuff, dating back to the Medici period, and by thirteen small arches made in the Lorraine period. The scenographic building rises above the tuff cliffs. Three fountains in the 'adjacent piazza della Repubblica constitute the terminal of the aqueduct) and you enter the large piazza della Repubblica dominated by the Palazzo degli Orsini, also of Aldobrandesque origin, it was restored by the Orsini between the end of the 15th and the first half of the 16th century. It currently belongs to the Episcopal Curia and is the seat of the Diocese of Pitigliano, Sovana and Orbetello. Palazzo Orsini houses two museums: the Civic Archaeological Museum and the Museum of Palazzo Orsini, together with the Library and the Municipal Historical Archives and the Library and the Diocesan Historical Archives. Externally the Palace has a characteristic terraced tower, the entrance portal is located at the end of an uphill ramp, which leads to the internal courtyard with a portico part with six arches, a hexagonal columned well is located next to the portal access to the Palace, in carved travertine and today the entrance to the Museum. Continuing along via Roma you arrive at Piazza San Gregorio, where the Cathedral is, with an eighteenth-century facade, the interior has a single nave. Next to the Cathedral is the Loggiato del Palazzo della Comunità and in front of it the “Monument to the Orsina progenies”. Behind the Cathedral is the characteristic Jewish Ghetto. In fact, starting from the 14th century and then after the definitive expulsion of the Jews from the Papal State in 1569, numerous Jewish families found asylum in Pitigliano, where a substantial Jewish community was formed. The Jewish Ghetto occupies the area between the Duomo and the Church of Santa Maria and is characterized by small and narrow streets, from the 16th century synagogue, restored in 1995 after years of neglect, from the Archives, from the Jewish School and from the oven; outside the town on the road towards Manciano is the small Jewish cemetery. Continuing from the Cathedral along via Gen. Orsini you reach the beautiful Church of Santa Maria, perhaps the oldest in Pitigliano (12th century), it was renovated between the end of the 15th and the beginning of the 16th century and has a 16th century facade, the the interior has three naves with frescoes from the Sienese school on the walls. Beyond the church you reach the Porta di Sovana from where you have another beautiful view of the houses of Pitigliano and where you can recognize parts of the Etruscan walls. In the surroundings of Pitigliano there are numerous so-called "vie cave", deep paths obtained by cutting the tufaceous rock. Some "routes" are over a kilometer in length, with walls up to 20 meters high. The main ones are that of the Gradone (where there is an interesting didactic-informative open-air museum), of S.Giuseppe, of Fratenuti, of S.Rocco and of the Madonna delle Grazie. Also worth a visit is the archaeological area of Poggio Buco, which houses Etruscan tombs from the 8th - 7th century. B.C