Castiglione D’Orcia is one of the many hill towns dotted about the Val d’Orcia area, but is distinguished by having not just one, but two castles crowning its highest points. The Rocca Aldobrandesca rises directly above the medieval town of Castiglione, whilst the even more impressive Rocca di Tentennano rises on a nearby adjacent hilltop. The first record of the town dates back to 714 AD.

Rocca Di Tentennano

The Rocca di Tentennano rises precipitously above the surrounding countryside, and is a significant landmark for many miles around. The earliest fortifications were built in the 11th Century, but renovated after 1250 when the castle passed into the possession of Sienna. It is the only castle in Val d’Orcia that was never stormed by force.

The castle is open to visit for a small entrance fee and there is a small garden area surrounding the castle tower.

It is possible to climb all the way to the top of the tower, the last bit out onto the top of the tower being a bit of a squeeze through a narrow roof openning. From the top, there are views across the Val d’Orcia, and also across to Castiglione d’Orcia and the neighbouring Rocca Aldobrandesca.

Castiglione d’Orcia

The old part of Castiglione d’Orcia has a very ancient feel to it, with a maze of narrow streets and medieval buildings and churches. The small central piazza is the Piazza il Vecchietta, named after the 15th Century artist and sculptor Lorenzo di Pietro who was nicknamed il Vecchietta – it was believed he was born in the town though it now appears he was from Sienna. With the weeds growing through the cobbles and its rather rustic buildings, the Piazza feels much older than many of the other town centres in Val d’Orcia.

The local Town Hall on one side of the piazza is again a simple, rustic looking building.

There are two significant old churches in the town. The oldest is the Santa Maria Maddalena, probably built in the 12th Century, a small simple church in Romanesque style.

The interior of the church was easily the most simple and basic of all the churches we visited in Val d’Orcia.

The other church is the Pieve dei Santi Stefano e Degna (Parish Curch of Saints Stefano and Degna), which can be seen at the end of the alleyway in the image below.

Dating from the late 15th Century, this is a slightly more ornate church, particularly the domed apse.

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