Chitignano is the smallest town of the Casentino valley, it was erected on a spur of the west side of the Catenaia alp. It was first cited in 967 as a feud given to Goffredo d’Ildebrando, passed on to the Counts of Chiusi and then to the Counts Ubertini that remained its owners almost until the end of the 18th century, except for a small period of time in 14th century when the owners were the Tarlatis from Pietramala.

When Arezzo was permanently subdued by Florence in 1384, Chitignano was not annexed to the Florentine republic but was some sort of protectorate ruled by the Ubertinis that granted military support in war times in exchange of obedience, military and political protection. This rural Signoria made the Ubertini control the territory for four centuries but with the law of the 14th of April  1780, Leopold II, Grand Duke of Tuscany cancelled the autonomy granted by the protectorate and Chitignano became a town of the Grand Duchy of Tuscany.

The castle of Ubertini is located on the road that connects Rassina and Chiusi della Verna is one of the most ancient fortilices in Casentino. The mansion dates back to the 10th century and its name comes from the family that held it almost without interruption since 1261, when it was given to the powerful bishop of Arezzo Guglielmino of Ubertini, to 1830 the year in which the actual owners took it.

The castle was renovated in the 16th and 17th centuries but the Guard House, the justice room, the jails, the weapons’ room and the Fortification are still visible.

The coat of arms and the people of the Ubertini family are depicted in the room, some of them are frescoed onto the walls. It is worth remembering the private baroque chapel and the chamber that was used by the Aretinian bishops by whom the place was used as a holiday house for a long time.

Not far from the castle there is the Podesteria, created by Florentines at the beginning of the 15th century. Inside this building there is a fresco of the 1610 that depicts the “Annunciation”.

In the outskirts of the town there are two buildings from the 17th century, the rural church of st. Vincenzo and Pietro, following a desire of Pier Francesco Ubertini, was consecrated in 1614. Its bell tower with clock is from the middle of the 19th century. The church of st. Lorenzo has an interesting and elegant archway on its sides and its sinuous lines.

Near Chitignano are located the small towns of Taena and Rosina, whose toponyms are of Etruscan origin and are a sign that these places were populated in ancient times. Even the presence of sulphur-iron thermal water, that has healing properties, was one of the reason why people came to the area where Chitignano is. Chitignano was famous in the past for the contraband of tobacco and gunpowder.

The Museum of the gunpowder and the contraband, part of the circuit of the Ecomusei of the Casentino valley remember those illegal activities that nevertheless were a job the people of Chitignano.

Inside the forest outside the town lies the Path of the Armoury of Hell, an evocative itinerary alongside the stream Rio that goes near what was an authentic open air farm where the gunpowder was made. The inhabitants of this place obtained the sulphur and the saltpetre, for the fact that these were used in agriculture. Hidden in the forest they mixed these ingredients and the running water of the river preserved the products from an accidental explosion.

Travelling near the armoury there are many curious manufacts like the “pillo”, a pit dug inside the sandstone used as a mortar to beat by hand the ingredients of gunpowder, or the wooden “mazzapicchio”, a tool that served for the same purpose but used the hydraulic power instead.