Perhaps not everyone knows that Castiglione d'Orcia is the town that is competing with Siena for the birth of Vecchietta, a painter, sculptor and goldsmith well known in the 15th century. However, from Piazza del Vecchietta, we can move on to visit the Romanesque stone church of Santa Maria Maddalena and that of Santi Stefano e Degna. Two churches and two prayers are enough to secure your blessing along a fascinating yet challenging journey.
The road to Poggio alle Rose allows us to admire the most mountainous part of the journey with a view of the Amiata.
Seggiano is reached through thick woods and a sea of olive trees. The Sedriano olive is highly sought after and, together with the local cheese, constitutes a strong point for a good diet. What is surprising is the Sanctuary of the Madonna della Carità, the only example of late sixteenth-century architecture in the Siena and Grosseto areas.
From Seggiano to the village of Pescina to Vivo d'Orcia, we start breathing mountain air, since the prohibitive inclines in this area reach up to 917 meters above sea level. Still, these slopes did not instill any fear in Primo Volpi, a famous cyclist from Castiglioni from the time of Coppi and Bartali.
Vivo d'Orcia, a village immersed in chestnut woods, is the highest point in the Amiatino and the Val d'Orcia areas. It features a tiny hermitage located above the town, at 1100 meters above sea level, dedicated to San Benedetto. But the greatest attraction and value is given by the springs of pure water that flow from the Ermicciolo, which provide nourishment for the Siena and Grosseto areas.

From Vivo we head to Campiglia d'Orcia, a small and charming village overlooking the entire Orcia Valley. The town is an important center for the “adoration of the brown”, as in the prized chestnut of Amiata.
Descending towards Bagni San Filippo, one of the most beautiful thermal destinations in Tuscany, is very pleasant. We can soon feel that the landscape has started to change thanks to the view of the very white and spectacular limestone deposits of the “Balena Bianca” and the “Fosso Bianco” below.
From Bagni San Filippo, we take a dirt road known as a popular variant of the Francigena.
After reaching the farming village of Gallina, located at 43rd parallel, we take the Cassia road, where the hills to the right anticipate the arrival at another famous thermal town, Bagno Vignoni. Known since ancient Roman times, the thermal centre has been frequented by important figures and used as the setting for many films, including Andrei Tarkovsky's famous Nostalghia.
After leaving the spa, we return to the road that leads to Castiglione d'Orcia, not without making a stop near Rocca d'Orcia. Rocca d'Orcia offers its visitors an authentic spectacle of a medieval village, with the majestic Rocca di Tentennato that has served for many years as the strategic control center of the Via Francigena. It was right at the Rocca that Santa Caterina da Siena, illiterate until this very moment, received the gift of writing. And right at the foot of the Rocca every year, on the night of May 1st, the “Maggiaioli” sing their octosyllabic quatrains.
The GATE of Castiglione d'Orcia is just a stone's throw away. Rest is welcome, maybe even with a taste of the Maggiaioli's bread and anchovy.