There's a lovely route that winds along the northern slopes of Monte Altissimo, offering beautiful views of some peaks of the Apuan Alps and a rich marble quarry. It brings to Castiglione d’Orcia, first mentioned in historical documents in 714 and initially held by Aldobrandeschi before becoming a free commune in 1252. In the fourteenth century, however, it came under the control of Siena and was constantly contended between this town and the Salimbeni. The center, with its old paved road, is particularly picturesque.
The Piazza Vecchietta deserves a visit, it is dedicated to Lorenzo di Pietro (1412-1480), a painter, sculptor and architect. In the Palazzo Comunale, you’ll find a fresco by the Sienese school, Madonna con Bambino e due Santi, from Rocca d’Orcia.
A visit to Castiglione should include the splendid Church of Santa Maria Maddalena. this Romanesque church has recently been restored, it boasts a thirteenth century façade and the apse is more than a century old.
The Church of San Stefano is also noteworthy, thanks to the artwork it contains. Its façade was created during the sixteenth century. Inside, you’ll find several works including the Madonna and Child (circa 1320) by Simone Martini and another Madonna and Child by Pietro Lorenzetti.
A short climb will lead you to the Rocca Aldobrandesca, which dominates the countryside. Its ancient walls still exist on the northern side while the mount’s summit is park-like. Visitors will appreciate wonderful views of Castiglione and the Amiata area in addition to the panorama of Rocca Tentennano.
Not far from Castiglione d'Orcia, amid the beauty of the Val d’Orcia and the woods of Monte Amiata, take a visit to Bagni San Filippo, known as one of Tuscany’s most stunning spa towns, largely due to its trademark backdrop of white calcareous deposits, which make a lasting visual impact. It's the case of the Balena bianca, a thermal waterfall that has given rise to wondrous and crystal-white calcareous deposits over the years