Along the Umbro-Casentinese way, between Castiglion Fiorentino and Cortona, the shape of the castle of Montecchio Vesponi appears almost like a dream.
The manor is cited in a document redacted in 1014 with the name Castrum Montis Guistoni, when the emperor Henry II conceded to the Benedictine abbey in Farneta a guarantee on the ownership of the area. In those times, the castle, built in the 10th century, was under the jurisdiction of the Marchiones.
In 1234, the fortified complex was purchased by the municipality of Arezzo that, during the following years, enlarged and fortified the place. Its placement on a hill from which it could watch over the Chiana and Chio valleys, made it a strategic outpost used to control a wide area and important towns such as Cortona and Castiglion Fiorentino.
In 1281, Montecchio became a free town, though depending on Arezzo for the approval of its laws. During those times, the walls enclosing the castle were enlarged following the line of the hill with 9 towers, of which, nowadays, only 8 are still standing. In 1289, after the defeat of Aretinian Ghibellines in Campaldino, the castle passed under the rule of the Florentine Guelphs.
Returned under the rule of Arezzo at the beginning of the 14th century, for many years the castle was a point of contention. The Tarlati from Pietramala, lords of Arezzo, kept the castle and Castiglion Fiorentino, with the name Castiglion Aretino, since the beginning of the 1300s until 1340, then it was under the rule of Perugia until 1369. After that year, the castle returned under the sphere of influence of Arezzo until the beginning of the 1380s, when it was conquered by the soldier of fortune John Hawkwood, who was known also as Giovanni Acuto. The soldier was recognised by Florence as the legitimate owner of the castle in 1384, the year in which Arezzo entered under the Florentine Republic.
After the death of Giovanni Acuto, in 1394, his widow Donnina Visconti gave the fortress to the Florentine Republic that gave it to the condottiero Ludovico Racaniello, who kept the fief until his death in 1441. Then, the castle fell into a long phase of ruin until 1641, when Tommaso Capponi established another fief for 6 years. Montecchio then stopped being a municipality in 1774, when it was included under the municipality of Castiglion Fiorentino.
In the 1870s, the bank owner Giacomo Servadio bought the grand ducal farm and the castle, starting its restoration, the neo-Guelph crenellation was his idea. In 1890, his successors sold both buildings to the Budini and Gattai families who, in 1979 sold again the entirety of the complex to its current owners, the Floridi Viterbini family, who started another restoration.
In addition to the city walls and the towers included in them, inside the castle there are still well kept parts such as the keep (Cassero), built in the 13th century, and the Judge’s House, called Courthouse, built in the 12th century. This last building, together with the adjacent tower, represented the power of the municipality of Arezzo at the moment of their construction. The church, dedicated to st. Biagio, and the houses of the farmers are lost.
Courtesy of the willingness of the owners and their love for the place, Montecchio Vesponi is a place where events, commemoration, school projects and archaeological excavations are all done to better understand its history. The association InCastro, to this day, organises some guided tours to the fortified complex to give some news about the discoveries and to give to everybody the opportunity of travelling back in time and living the mediaeval atmosphere of one of the most well-kept castles in Italy.