Val di Chiana

Castle of Montecchio Vesponi
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The Castle of Montecchio Vesponi in the province of Arezzo

The Castle of Montecchio Vesponi is located in the municipality of Castiglion Fiorentino, in the province of Arezzo. Located at the southern entrance to the Val di Chio, the castle stands on a hill of 364 meters which dominates the underlying village of Montecchio and the valley itself. Thanks to its excellent state of conservation, this is considered one of the most interesting medieval castles in the Arezzo area and among the most beautiful in all of Tuscany.


The first settlement on the hill of Montecchio dates back to Etruscan-Roman times, and may have been a pagan sanctuary. The castle was built around the 9th century, when it was a feud of the Marquises of Tuscia. At the beginning of the thirteenth century, the castle of Montecchio Vesponi allied with the city of Arezzo together with the other castles of Mammi and Monticello. Around 1234 it was acquired by the municipality of Arezzo, which made it a stronghold against Castiglion Fiorentino and Cortona. In 1281, the people of Arezzo took care of reinforcing the castle walls, but a few years later, following the battle of Campaldino in 1289, the fortress passed under the control of Florence.

It returned to Arezzo in 1303 and was used as a stronghold in the frequent wars with Perugia during the first half of the 14th century. The castle was besieged in 1352 by the inhabitants of Cortona led by Pier Saccone Tarlati and Bartolomeo Casali, but Montecchio managed to resist and the besiegers were forced to retreat. Around 1383, the famous English captain John Hawkwood (also known as Giovanni Acuto) took the castle taking advantage of the fact that Arezzo was now unable to defend its territory.

After Hawkwood’s death (1394), Montecchio passed first to the leader Ludovico Racaniello and then became the property of the Municipality of Florence which installed the officials who administered justice in its municipality. Following the autonomous reforms implemented by the Grand Duke Pietro Leopoldo towards the end of the 18th century, the municipality of Montecchio was suppressed and merged with Castiglion Fiorentino.

Between the 19th and 20th centuries, the castle changed ownership several times and the various owners carried out some restoration and restructuring interventions which allowed for a good conservation of the complex.

Castle of Montecchio Vesponi
Castle of Montecchio Vesponi

The castle

If you take the road that leads from Castiglion Fiorentino to Cortona, you cannot help but be attracted by this splendid complex. Even if the castle can hardly ever be visited inside but only from the outside, it is certainly worth making a detour to admire this fortress up close.

The castle still today has an imposing 263 meters long wall with Guelph merlons, interspersed with 8 towers. At the center of the complex stands a very slender tower that reaches 30 meters in height and is clearly visible even from a considerable distance. Next to the tower is the keep which is now used as a private residence by the current owners.

How to get to the castle of Montecchio Vesponi

Montecchio Vesponi is located about 4 km south of Castiglion Fiorentino, 7 from Cortona and 18 from Arezzo. It can be easily reached by car and possibly also by bus.

If you travel by public transport you have to get to Castiglion Fiorentino, even by train, and then take the bus.

By car from Castiglion Fiorentino and Cortona you must take the Regional Road SR142. From Arezzo you must first take the State Road 73 and then follow the SR142. Those arriving from the A1 motorway must take the Monte San Savino exit and then continue on the Provincial Road 25 up to Castiglion Fiorentino; from there SR142 to destination.
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