Located on top of a hill, in a beautiful panoramic position, Castiglione d'Orcia, it is as its name indicates, an ancient castle, dominated by the imposing ruins of the Rocca degli Aldobrandeschi. Designated by medieval documents under the name of Petra, was ruled by the Counts Aldobrandeschi by the XI to XIII century. In 1252 it is free commune but during the XIV century falls under the power of Siena becoming the center of rivalry between the family of Salimbeni and the Sienese. Thanks to its position geographical became an important bulwark over a long stretch of the Via Francigena so much so that there are still some interesting ones preserved settlements related to the use of the pilgrimage route medieval.
Overlooking the village, there is the area of the castle characterized by a masonry structure of stones in filaretto and traces of walls in bricks, belonging to a seventeenth-century building built by the Marquis Riario of Bologna. The medieval village is typified by narrow streets that wind along a central road axis with medieval buildings overlapping with stately mansions. Of the fortified walls that encircled the town... medieval remains, two towers, one square-shaped,
one with circular plan and the Upstairs Gate, the only one of the four originally left...present.
The heart of the historical centre is represented by Piazza Vecchietta dedicated to Lorenzo by Pietro known as Vecchietta (1412-1480), a Sienese artist who for long thought he was born in Castiglione d'Orcia. The square in
bricks and river pebbles, which are composed according to a elaborate convergent radial pattern at the centre where it is placed the travertine well dated 1618, represents one of the more interesting and original medieval urbanistic realizations.
The medieval houses of medieval origin are the backdrop to the Town Hall of the XIII-XIV century characterized by the bell tower a beail and from the clock on the facade, inside is preserved a fresco by the Sienese School depicting the Madonna and Child with two Saints.
CHIESA DEI SANTI STEFANO E DEGNA
church of Santo Stefano, located inside the castle walls he inherited the plebeian function and the title of Saint Worthy from the old woman church that was located "out of the land..., about 200 miles away... footsteps. Destroyed to enlarge the cemetery in 1787 was therefore reunited with St. Stephen's. The church was consecrated on the 22nd September 1566. The facade, which appears as the most original and best preserved of the building, is in trachyte drafts and is punctuated by two corner pilasters and two thinner pilasters in the center that encloses a small eye remade in the era next. In the middle a sixteenth-century sandstone portal has sculpted in the space enclosed between the arch and the two pilasters decorated with candelabra, which support the eardrum, two coats of arms: on the right a castle (emblem of the town of Castiglione) and on the left an armament noble. The current appearance of the interior, with a cross shaped layout is the result of restoration work carried out over the years. 1891-1892.
CHIESA BY SANTA MARIA MADDALENA
Located outside the walls, the oldest nucleus dates back to the 12th century. It has a facade with an arched portal in square blocks of travertine, engraved with flowers and crosses. The bell tower is in Sail, with the archway divided by a small travertine column.
HALL ARTWORK BY SAN GIOVANNI
The Sala d'Arte San Giovanni, is located in the ancient seat of the confraternity of the same name and preserves the paintings executed for Castiglione and Rocca d'Orcia by some of the major exponents of the Sienese school of the XIV and XV centuries: Simone Martini, Lorenz of Peter called the Old One and John of Paul. To these yes flanked by a series of liturgical furnishings from churches and fraternities in the area.