Formed as a county during the Middle Ages under the Ubertini, a noble Arezzo family, it retained jurisdiction over its territory until 1779 when the grand duke Leopold of Lorraine put an end to its old feudal privileges for good. This long-standing political and administrative independence, together with its particular geographic position as a border crossing, created the conditions for the manufacture and smuggling of controlled goods like tobacco and gunpowder.

The centuries-long practice of smuggling, which ensured the survival of many a Chitignano family, continued up to and beyond the Second World War, and ended up influencing the behaviours and mentalities of the whole village, becoming its very culture. Romanticised tales abound of smugglers up against revenue officers, of alarms sounded and tip-offs passed, of adventurous journeys as far afield as Livorno and Genova. And the figure of the smuggler with a sack over his shoulder, roaming alone in the night over secret trails, cannot fail to stoke our imaginations too, especially if the person telling the tale is one of the village's old men or an elderly sigaraia, one of the women whose job it was to roll the cigars.

Gunpowder, initially produced clandestinely along streams using earth-tampers or water-driven pestles, later in veritable factories, represented another important economic resource for the village. Such activity, which conjures up images of bursting bombs and cannon-fire, seems an invitation to visit the Ubertini castle. The heart of this mini-state of a few hundred souls that survived nearly to modern times, the castle is the result of several rebuilding efforts between the 14th and 17th centuries. It still displays features that speak of the ancient functions it used to perform, the most significant being the guard posts and the rooms for the administration of justice and capital punishment, with a niche that was probably an altar for condemned prisoners.

Almost in a spirit of expiation, the figure of the smuggler, the brigand, is flanked in this zone by another suggestive image, that of the pilgrim on his way to the Eternal City.

An old mediaeval road, the Via Romea dell'Alpe di Serra, seems to have passed not only through Chitignano but also Rosina and Taena, interesting rural villages located nearby. Therapeutic hot springs, another feature of the village, must have made it an attractive stopping place for wayfarers and pilgrims.

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