Check your mirrors before screeching to a halt and indulging in an orgy of photography on the approach to this spectacularly sited hilltop stronghold. Organically sprouting from a volcanic rocky outcrop towering over the surrounding country, the town is surrounded by gorges on three sides, constituting a natural bastion completed to the east by a manmade fort. Within the town, twisting stairways disappear around corners, cobbled alleys bend tantalisingly out of sight beneath graceful arches and quaint stone houses are crammed next to each other in higgledy-piggledy fashion.
Originally built by the Etruscans, Pitigliano came under Roman rule and then in turn became a fiefdom of the wealthy Aldobrandeschi and Orsini families; the Orsinis, who were from Rome, enlarged the fortress, reinforced the defensive walls and built the imposing aqueduct. Their rule came to an end in 1608 when the town was absorbed into the grand duchy under Cosimo I de' Medici.
In 1944, 88 local residents were killed and many buildings were damaged during Allied bombings. A plaque near Piazza della Repubblica commemorates the victims.