Situated at the heart of the Val d'Orcia, not far from the Via Cassia, the town lies on a hill in the southern foothills of the Monte Amiata and also comprises the parishes of Rocca d'Orcia (with the medieval fortress of Rocca di Tentennano or Tintinnano), Campiglia d'Orcia, Vivo d'Orcia, Ripa d'Orcia (with the castle of the same name), and the thermal baths of Bagni San Filippo.
The Rocca Aldobrandesca viewed from Rocca d'Orcia
The town was first mentioned in the records as long ago as 714, when Castiglione d'Orcia, in those days still known as Petra, was in the possession of the Aldobrandeschi family. In 1252 the municipality won its independence, which it retained for almost a century. In 1274 the town came under the control of the Contea di Santa Fiora and the estates of the Aldobrandeschi family were split up. We know with certainty that in around 1300 Castiglione was already in the possession of the city of Siena, which transferred control of the town to powerful families from the region such as the Piccolomini and the Salimbeni in return for financial considerations. The latter subsequently started their revolt against the Republic of Siena from here. Over the course of the following centuries, Castiglione passed into the possession of the city of Florence, which placed the town under the control of the noble Riario family from Bologna in around 1605.
Monuments and Sights
The most famous monument in the municipal area of Castiglione d'Orcia is without doubt the Rocca di Tentennano. This imposing fortress sits on a limestone crag high above the Val d'Orcia and watches over the medieval gem of Rocca d'Orcia. Between the 9th and 14th centuries, the fortress served as a strategic guard post and was the site of bitter battles between the Salimbeni family and the Republic of Siena, into whose possession the fortress once again fell in 1408. After a further two centuries, during which it continued to be used as a sentry point, in the 16th century another dispute ignited over the fortress, this time between the cities of Siena and Florence. It should be pointed out that in both disputes, the fortress was only conquered due to betrayals. Even if today many inhabitants are convinced that the Rocca di Tentennano is a fixed part of the town of Castiglione d'Orcia, for the sake of accuracy it must be mentioned that both places, even though they were so close in geographical terms, continued to record their own historical events until 1777. This only changed when the municipalities of Rocca and Castiglione were merged in that year.
The Rocca di Tentennano in the parish of Rocca d'Orcia
Another, extremely impressive, fortress is the Rocca Aldobrandesca, which looks directly at the Rocca di Tentennano high above Castiglione d'Orcia. The Piazza il Vecchietta, is another important site in art history terms. It is named after the painter, Lorenzo di Pietro (1412-1480), better known as il Vecchietta, who was born here. The central square in the heart of the town is home to the local town hall, the Palazzo Comunale. The inner courtyard, which is paved with river pebbles, contains a fountain from the 15th century. Inside, the building houses a fresco from the Siena School, showing the Madonna with Child and two saints. The Chiesa di Santa Maria Maddalena and the Pieve dei Santi Stefano e Degna are also worth seeing. The Chiesa di Santa Maria Maddalena is of Romanesque origin and has only recently been restored. The Pieve dei Santi Stefano e Degna is considered to be the most important sacred building in Castiglione d’Orcia. Its interior is Romanesque, whilst the façade dates from the 15th century. The numerous works of art that the church houses include, among others, the Madonna with Child by Simone Martini and the Madonna with Child by Pietro Lorenzetti. Also worth mentioning are the church and grotto of San Filippo Benizi, the Chiesa di San Biagio, the Chiesa della Compagnia di San Giovanni Battista, the Chiesa della Madonna delle Querce, the Chiesa della Madonna delle Grazie di Manno, the Chiesa di San Sebastiano, the Chiesa di San Simeone, the Eremo del Vivo hermitage with the Pieve di San Marcello and the oratory of San Bartolomeo.