In the enchanted woods surrounding Casole d’Elsa

Keeper of ancient stories, a place of worship and a meditative retreat: the Montagnola Senese is a mysterious and fascinating mountain relief with forests that touch on the territories of Casole d’Elsa and Monteriggioni. While the surface is covered with dense forests and dotted with tiny hamlets, the subsoil is rich in Broccatello, a prized variety of yellow marble.

This particular route winds through the forests of the Montagnola Senese, where everything is a mystery and surprises are veiled by the trees of the forest. 

Our journey leads from Casole d’Elsa to the heart of the Montagnola Senese, along asphalted and dirt back roads, all with little traffic. A gravel bike and lots of interesting sights stimulated by isolated and tranquil locations are the perfect companions to delve into this realm of animals such as wild boar, deer and all kinds of birds. 

There are so many hidden wonders to be discovered that a trip organized over two days would not only relieve fatigue but be very pleasing to the eyes and body.

The road where our itinerary begins winds placidly for 6.2 miles (10 kilometers) until Pievescola, famed for its mushrooms (including a dedicated food fair!) and a haven of tranquility. From here, set off along one of the most popular roads for cyclists that, after 11 miles (18 kilometers), leads to the 1657 feet (505 meters) of the Incrociata pass. In the surrounds, it is common to see large herds of pigs raised in the wild and bearing an unmistakable trait—their dark coat and typical white ‘belt’ can only mean the presence of the prized Cinta Senese.

We then move toward Ancaiano, which we encounter as a steep descent that hints at becoming smoother. We are now at the 13-mile (21-kilometer) mark of the journey. In view, set upland, stands the Romitorio di Cetinale, an ancient place of meditation and pilgrim accommodation. We ascend once more to take the dirt road of Cerbaia, amidst chestnut trees and centuries-old holm oaks, with a route to Borgo Tolomei, where Pia de’ Tolomei—the noblewoman from Siena mentioned by Dante in his Purgatorio—is said to have lived.

We begin the descent that connects to the SP541 provincial road, set to embark on the most challenging climb of the route, immersed in the dense trees that extend until reaching the enchanted forest of Selva di Sogno—‘Dream Woods’—where artist Deva Manfredo has created original sculptures that blend into nature, made of stones and discarded materials. Not far away stands the meditation center of the Osho Miasto Institute.

Yet, we must leave these places of art and spirituality to resume our climb. Reach 2336 feet (712 meters) and enter the woods of Radicondoli. Here, you come to the Castello di Falsini, foretold by a beautiful cypress avenue at the edge of the Cornocchia State Reserve.

After exploring the unspoiled alleys of Mensano, a terrace charged with guarding the undulating Colline Metallifere, we return to the paved road leading back to Casole d’Elsa. Here you have the fun option of visiting the Civic Museum of Archeology and the Collegiate Church to partake in a search for contemporary works scattered throughout the village.