Duration: Maximum 6 hours.

Radicofani

Located on basalt rock of volcanic origin, Radicofani is a picturesque medieval town dominated by a massive keep which was commissioned by Pope Adrian IV (XII century) to protect the Papal Statesfrom the threat of the Republic of Siena. In the framework of the political struggles to dominate this place, around 1295 Ghino di Tacco, a decadent nobleman from Torrita di Siena who became a bandit, took possession of the area and robbed travelers on the Via Francigena, an important route for pilgrims going to Rome. Ghino ambushed wayfarers, evaluated the real nature of the goods they were carrying, and then stripped them of almost everything,while leaving them enough to survive and offering them a banquet. For this reason, he is called the Robin Hood of the Orcia valley.

Castiglione d’Orcia, Rocca d’Orcia, Castello di Spedaletto

Situated on a high hill overlooking the underlying valley, Castiglione d’Orcia, had its heyday during the Middle Ages. Until 1174,the village wasowned by the noble Aldobrandeschi family, and later it was owned by the Republic of Siena; still later, it became the possession of the Salimbeni family before returning permanently to Siena until the Medici conquest. Among the principal landmarks, sponsored by UNESCO, is the main square dedicated to the great sculptor, painter, and architect Lorenzo di Pietro, who was known as Vecchietta; the Aldobrandeschi Fortress, and the Oratory of Saint John, with important medieval paintings by Simone Martini, Giovanni di Paolo and Lorenzo di Pietro.

The tour continues with a stop in Rocca d’Orcia, a pretty medieval village dominated by the Tentennano keep,from which you can see a beautiful view of the surrounding countryside.
The medieval castle of Spedaletto is a striking place located in the heart of the Orcia valley. Since 1236 the complex had been administered by the Hospital of Santa Maria della Scala in Siena as a fortified farmhouse (granary) and a shelter for pilgrims and travelers along the Via Francigena. The structure
was called the Hospital of the Orcia Bridge due to the presence of a span close to the castle that permitted crossing of the Orcia River, thereby improving the strategic position of Spedaletto. Among the famous people who stopped here were Charles II of Anjou and Pope Pius II. The complex is still in good condition and has long been used as a private farmhouse.

Monticchiello

With a medieval castle founded by the Sienese in the early thirteenth century as an outpost to defend the southern border of the Republic of Siena, the village of Monticchiello is a highly recommended stop for those who want to experience the thrill of a blast from the past. The small town, located in the municipality of Pienza, still manifests the medieval wall and fortress, an ancient garrison of the Sienese Republic. A visit to the parish of Saints Cristoforo and Leonardo, a Gothic church which houses ancient frescos of the Sienese school, is also recommended.