Pitigliano and its area were inhabited in Etruscan times but the first extant written mention of it dates only to 1061. In the early 13th century it belonged to the Aldobrandeschi family and by the middle of the century it had become the capital of the surrounding county.
In 1293 the county passed to the Orsini family, signalling the start of 150 years of on-again/off-again wars with Siena, at the end of which, in 1455, a compromise of sorts was reached: Siena acknowledged the status of county to Pitigliano, which in exchange placed herself under the sovereignty of Siena.
From then onwards the history of Pitigliano resorbs into the gradually wider ambit first of the Grand Duchy of Tuscany (1562) then of the united Kingdom of Italy.
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.
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.
Sorano was probably inhabited by Villanovan culture, but the first historical mentions are relative to the 3rd century BC, when it was an Etruscan city under the influence of the more populous nearby Sovana.
Disappearing from history under the Roman domination, it is again known in 862 when a county was founded by Emperor Louis II, under the Aldobrandeschi suzerainty. The Aldobrandeschi were the most powerful feudataries of southern Tuscany for more than four centuries, disappearing in 1312 when Margherita, son of Ildibrandino, died without male heirs. His daughter Adelaide married to Romano di Gentile Orsini, who added the city to the family fiefs.
The county of Pitigliano-Sorano fought against the Republic of Siena, but was forced to accept its suzerainty from 1417. It regained a full independence in 1556, when the latter was annexed to the Duchy of Tuscany. The fortress, due to its strategic position, was frequently attacked; it was also the seat of fratricidal fights between the Orsini. In 1604, with the death of Alessandro di Bertoldo, it became part of the Grand Duchy of Tuscany.
Etruscan by origin, Sovana became a Roman municipium, and, from the 5th century, an episcopal see. Conquered by Lombards in 592-605, it was chosen as their administrative center in the area. Later, when Roselle was abandoned due to Saracen ravages, it became the centre of the county under the Aldobrandeschi family. In the Middle Ages it was known as Soana, where was born the pope Gregorio VII (Ildebrando from Soana).
Its importance declined when the county was acquired by the Orsini, who moved the capital to Pitigliano. In the mid-16th century Sovana was annexed to the Grand Duchy of Tuscany by Cosimo I de' Medici.