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Castiglione d'Orcia cited as far back as the year 714, it belonged to both the Aldobrandeschi family and the Abbey of the SS. Salvatore; it subsequently passed into the hands of the Republic of Siena. Castiglione d'Orcia is a picturesque one, evocative with little paved streets which converge upon the Piazza del Vecchietta, (dedicated to Lorenzo Di Pietro, known, in fact, as il Vecchietta). The paving of this town square was realised with river pebbles enclosed by lines of bricks forming a sunburst pattern, its spokes leading towards a well made from travertine stone dating back to 1618.
The most important religious building of Castiglione d' Orcia is the church la Chiesa dei Santi Stefano e Degna with its façade from the 1500's. At the highest point in town, one can still see remains of the original city wall which opens upon a view of the mountain Monte Amiata and upon the fortress Rocca a Tentennano. The fortresses' imposing tower, recently restored, may also be visited when the fortress is open to the public.
While there on its summit, enjoy the breathtaking 360 degree panorama from Siena to Radicofani, from Montalcino to Pienza and Montepulciano, and from Monte Amiata to Monte Cetona. Moving along past the Rocca a Tentennano, one enters into the village below called Rocca d'Orcia. Here worth a visit are the churches, the Pieve di San Simone, the Chiesa della Madonna delle Grazie di Manno, and the little main town square holding a cistern said to date back to 1262.
In the large area covered by the municipality, many other towns also deserve a mention: first there is Bagni San Filippo, a place known for its spa waters which gush out water at a temperature of 52 degrees centigrade (125° Fahrenheit) and which have deposited immense calcium deposits in the nearby Fosso Bianco (White Ditch). Then there is Campiglia d'Orcia, featuring an unusual historical centre spreading out like a fan beneath a rocky ridge and from which rises a fortress built in the year 973. Ripa d'Orcia, on the right side of the river, has one of the most evocative castles in the valley. At Vivo d'Orcia there is the Hermitage (Eremo, also called Contea), a palace built in the late Renaissance Age by the Camaldolensians and, upriver from town, hidden among chestnut trees, an attractive little Romanesque church (dell'Ermicciolo) with both the façade and the apse decorated with small columns.

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