The distinctive feature of the castle is the cylindrical tower on its corner. The Castle di Montauto, together with villa La Barbolana and Castello di Galbino, was one of the residences of the old Galbino family. Here Francis of Assisi, not yet a saint, is said to have rested for a few days, after he had received the stigmata at La Verna in 1224. While here, Count Alberto gave Francis a new priest's habit in exchange for the old, stained one. This was soon considered a precious relic and was kept in the castle’s chapel until 1502 when the Florentines brought it to Florence. The habit of Montauto is now displayed in the Santuario della Verna.
According to some 14th century chronicles, this settlement was once “a little castle with a house”, while in the 15th century it became the residence of the famous mercenary Baldaccio d’Anghiari (who was mentioned by Machiavelli in his Florentine Histories). After Baldaccio was murdered in Florence on the 6th September 1441, the castle was taken over by the Pichi family, who transformed it into its current form. The presence of this settlement is linked to the existence of an important road network which crossed the valley.
Despite some architectural modifications in the 19th century, this building has maintained the appearance of a Renaissance residence. The towers on the corners and a loggia of two orders remind the observer of other, famous 16th century architecture. This is one of the houses built by the Galbino family, the land-owners of the area, together with the “fortress-house” of villa La Barbolana and the Castello di Montauto. Historical chronicles tell that in 1178 the Aretinians destroyed the castle of the Galbino family, who, however, re-built the Castello di Montauto in a more defendable place.
This settlement was a Commune from the 12th century to 1385. The original layout is no longer clearly visible, even though it is possible to spot several early structures. At the settlement’s core there is the church of San Clemente, which has undergone a number of modifications over time; on the other hand, the apse that can be seen today dates back to the 13th century. This area, which is so peaceful today, has witnessed tragic events in the past. On the 17th July 1944, in the area called Tortigliano, Don Domenico Mencaroni, the priest of Toppole and Verrazzano, was shot dead by the retreating German forces for complying with his own spiritual mission: to help his neighbour.
Built by Federigo Barbolani, a descendant of the Galbino family, in the late 16th century, the “fortress-house” was built thanks to the concession granted by Giulio de’ Medici, the future Pope Clement VII, who was welcomed in the castle of Montauto when he was exiled from Florence in 1494. Apart from the 18th century clock tower in the middle, the villa’s corner bastions and its bulk clearly come from the military needs of fortified structures. It is interesting to note the relationship between this villa and the Covento dei Cappuccini in Montauto, connected as they are by a straight tree-lined road.
This is an important example of a medieval “castrum”. The defensive walls are mostly well-preserved, as well as the tower at the main entrance. Owned alternatively by the Camaldolese order, the Tarlati family and the lords of Galbino, this castle, along with Anghiari, came under the control of the Florentines in 1385. The medieval settlements in the Sovara valley, such as Valialle, Pianettole and Toppole, appear to be very diverse due to many strong local power struggles. Records confirm that the Parish dedicated to St Peter and St Paul in Pianettole had 102 inhabitants in 1833.