Duration: Maximum 6 hours.

Morning: Montalcino and Sant’Antimo Abbey

Birthplace of the famous Brunello wine and entirely surrounded by vineyards, the urban complex of Montalcino, enjoys a splendid panoramic position overlooking the Orcia Valley. Still characterized by fourteenth-century Gothic buildings, Montalcino offers breathtaking scenery for anyone who is keen on the Middle Ages. Do not miss the visit to the impressive keep dominating the whole town. The fortified complex was built by the Republic of Siena in 1361 as a very important defensive garrison for the southern territories of the city. A great ally of Siena, Montalcino was the last Sienese possession to be conquered by the Florentines in the year 1559.

A few kilometers away from Montalcino is the Sant’Antimo Abbey, a wonderful place for nature, art, and history. Founded by the Benedictines in the VIII century as an important pilgrimage stop and destination along the Francigena Road, in the 10th century the abbey was awarded the imperial seal by Charlemagne, becoming one of the richest and most important places of the early Medieval period. Completely renovated in the first half of the XII century, the abbey church, the only building surviving in the entire monastic complex, is still a rare expression of a pilgrimage church in Italy, the result of Nordic workers linked to France and Lombardy. Splendid indeed are the thirteenth-century wooden sculptures inside the church and the sculpted three-dimensional decoration of the capitals, carved into travertine, onyx, and alabaster.

Afternoon: Spedaletto Castle and Radicofani

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.

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 States from 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.