Castiglione d’Orcia, which existence is recorded since 714, was held by the Aldobrandeschi. It became a free city in 1252, and afterwards a possession of Siena in the Fourteenth century.
The historic center, with its old cobblestone alleys, is especially picturesque, reaching the height of romanticism in the Vecchietta Square, dedicated to Lorenzo di Pietro also known as “Il Vecchietta”, a Fifteenth century painter, sculptor and architect. At the center of the sloped square is a beautiful fountain of travertine built in 1618. Opposite is the Palazzo Comunale, inside which is a fresco of the Sienese school, Madonna with Child and two Saints, from Rocca d’Orcia. The walk inside Castiglione must also include the beautiful Romanesque church dedicated to S. Mary Magdalene, recently restored. The Thirteen century facade and the Fourteenth century apse support the splendid bell tower. The church of Saints Stephen and Degna has less impressive interiors; however, it was the most important religious building of Castiglione for the wealth of works of art it held. Its facade is from the Sixteenth century, and its interiors included a Madonna and Child from 1320 by Simone Martini and another Madonna and Child by Pietro Lorenzetti.
The San Giovanni art room is located in the fraternity by the same name and preserves the paintings executed for Castiglione and Rocca d’Orcia by some of the greatest exponents of the Fourteenth and Fifteenth century Sienese school : Simone Martini, Lorenzo di Pietro “Il Vecchietta”, and Giovanni di Paolo. A series of liturgical furnishings from churches and fraternities in the area accompany the paintings.
A short climb leads to the Rocca Aldobrandesca, which dominates the town. The walls are still intact on the north side, while the top plateau was arranged as a park. The view is extraordinary towards Castiglione, the Mount Amiata, and the Fortress of Tentennano.
The latter stands on an outcrop of limestone in the heart of Val d’Orcia. Built in the Thirteenth century by the Tignosi Counts of Tintinnano as a garrison on the underlying Via Francigena, in the Fourteenth and Fifteenth century it belonged to the Sienese Salimbeni family. The imposing fortress, which also hosted St. Catherine of Siena, has always held an important strategic role for the control of the territory south of the ancient state of Siena. At the time of the War of Siena, it became a cornerstone of the Sienese defense system that protected the Republic of Siena, retreated in Montalcino, against Imperial Army attacks. From its summit you can enjoy splendid views.
Castiglion d’Orcia is part of the Natural Cultural and Artistic Park of the Val d’Orcia. The other milestones of this important park are Montalcino, Pienza, San Quirico d’Orcia, and Radicofani.

Like a Medieval Troy, through the centuries the Rock of Tentennano has seen a number of wars, invaders and owners, and it was once destroyed and rebuilt as we see it today.
Owned since 1100 by the Tignosi family Count of Tentennano, as of 1170 the castle was part of the family’s possessions with Bagno Vignoni, a third of San Quirico d’Orcia and other castles of the valley. In 1188 a family member, Rolando, became the abbot of the powerful monastery of San Salvatore, and in 1247 Aldobrandino of Tentennano commanded the troops of the Republic of Siena against the army of Perugia.
In 1207 the Tignosi enacted a freedom act, which gave the inhabitants of the Rock rights towards the Tignosi rulers, which hitherto had been absolute rulers. In 1251, the fortress, and the castle passed into the hands of the Sienese, who destroyed it and rebuild it anew in 1262. That is the version that today still stands in Val d’Orcia. The Sienese gave the fortress and the castle to Salimbene Salimbeni as warranty against the loan he had made to Siena to pay off the victorious army of the Monteaperti battle.
In 1274 the Rock was ceded permanently to Salimbeni. This was the beginning of a long period of struggles, battles and skirmishes between the family and Siena, to the point that in 1380 Catherine of Siena stayed at the rock with the purpose to reconcile the Salimbeni with Siena. Nonetheless, the war ended only in 1419, when a certain Giovanni Zolla opened the doors of the rock at night bringing the Sienese army in. Cocco Salimbeni, the ruler at the time, took refuge on the tower with a small loyal group, his the wife and the rest of the family. Cocco pushed back all the assaults, but a council of citizens decided that they want to be governed by Siena and swore allegiance to the Republic, so that Salimbeni was forced to surrender.
The fortress then became one of the strongholds of Siena that from here pushed back the raids of Cesare Borgia, Machiavelli Valentino, and Fabrizio Maramaus, aka Maramaldo. In 1553, the inhabitants surrendered without fighting against the troops of Charles V, but conquered again the fortress and Castiglione d’Orcia a few months later. This did not prevent the Imperial troops to recover the territory, loathing and destroying dozens of houses, event that determined the decline of the Rock of Tentennano.