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Castelluccio di Pienza and Cypress Road - Pienza (SI) - Val d'Orcia - UNESCO World Heritage- Tuscany

Along the way to reach Villa La Foce, you will admire the winding road with cypresses, which has become an icon of Tuscany... The Val d’Orcia, a #UNESCO World Heritage Site, includes the historic centers and much of the territory of the municipalities of Castiglione d’Orcia, Montalcino, Pienza, Radicofani, San Quirico d’Orcia... #tuttitaly

Castelluccio di Pienza and Cypress Road - Pienza (SI) - Val d'Orcia - UNESCO World Heritage- Tuscany

Il Castelluccio is located on a hill about 10 km from Pienza. Since 1320 it has been part of the Republic of Siena and, in particular, of the territory of Montichiello.


From 1390 until 1787, a part of the fort was donated to the powerful hospital of Santa Maria Della Scala (the coat of arms still stands on the facade). You can admire the chapel of San Bernardino da Siena, who stayed there.


In recent times, the Castelluccio was the residence of Antonio and Iris Origo (a well-known writer).

Like any self-respecting castle, this one has a legend created around Countess Giulia Maria di Montefiore, who did not have a satisfying life there.


The woman married Vannetto Tolomei, who died tragically soon after. She then chose to marry Ermelindo Grossi from San Casciano, from whom she had to separate.

At this point, the countess invited Duke Ranieri dei Pannocchieschi to Castelluccio and, later, also his friend Cesare di Sanseverino. At a certain point, the two men moved away, and the noblewoman thought of taking revenge. She later hosted a group of armed men and fell in love with Captain Don Jacopo del Taja. The latter, moved by the lady's story, agreed to eliminate the two: the poison for Ranieri and the dagger for Cesare. After a short time, however, the Taja fled for fear of being discovered as the perpetrator of the double murder. The countess, however, was arrested and beheaded in the courtyard of her residence.

Continuing our journey, we searched for the famous serpentine: a road that looks like a snake, with cypresses on one side and cypresses on the other, between which there are just some windows overlooking the beauty of the surrounding hills.


We stopped at the bottom of the road to take some photos, but not before waiting for the sunset to do as much justice as possible to the beautiful landscape. You can see the pictures by clicking the link below.

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