Although larger, the village of Castiglione d’Orcia is somewhat less visited than Rocca d’Orcia, its sister village. The reason is that the once dominant fortress/castle of Castiglione d’Orcia lies in ruins, while the Rocca di Tentennano of Rocca d’Orcia has been well-preserved. This, however, does not mean that the town is not worth a visit. Their historical value is the same.
The charming if tiny central piazza of Castiglione d’Orcia, the Piazza il Vecchietta, is dedicated to the Senesi painter, sculptor and architect, Lorenzo di Pietro (1412-1480), known as Il Vecchietta. In the center of the cobbled and sloping piazza there is a beautiful travertine fountain. The cobblestone piazza and its lovely fountain were built in the 1600s, but the rest of the town consists mostly of beautifully preserved medieval structures and streets.
The Town Hall lies across from the Piazza il Vecchietta, where a fresco from Rocca d’Orcia is kept; this is a beautiful Madonna and Child with Two Saints, from the Sienese school. Several shops and artisans’ galleries add to the attractions of Castiglione d’Orcia.
Among these attractions is the recently restored Romanesque Church of Santa Maria Maddalena. Its beautiful facade was constructed in the 13th Century, while the apse is nearly one hundred years older. The other notable religious structure in Castiglione d’Orcia is the Chiesa di Santi Stefano e Degna, which formerly housed two of southern Tuscany’s most important art treasures. Two Madonna col Bambino portraits, one by Simone Martini and the other by Pietro Lorenzetti, both among Siena’s greatest early Trecento masters, were normally at rest in Santi Stefano e Degna. Both paintings are currently kept in Siena, where they are undergoing restoration. When complete, the plan is to house them in a new museum dedicated to the ancient art of the Val d’Orcia. These two paintings are the planned nucleus of the museum.
One of the highlights of any visit here is the wonderful view of the valley below, which can best be admired from atop the short slope leading to the ruins of the ancient Rocca, which dominates the town. A rustic park has been built at the summit of the fortress hill, and from there the visitor can see out over Castiglione, as far as the Monte Amiata, and as close as the Rocca di Tentennano in the next village (Rocca d’Orcia).