This stage is easy until you reach the 10th km where Pievescola, the town of mushroom, displays all of its peacefulness. From Pievescola, one of the most beloved roads to cyclists will take you, after 18 km, to the Incrociati passage with its 505 meters. Cycling through the woods and fields of Simignano it is possible to encounter groups of pigs raised in the wild and notice their unmistakable trait: a dark coat with a white stripe typical of the valuable “cinta senese”.
Ancaiano, an ancient Senese municipality and a lively meeting spot for peace and quiet lovers, is met when the steep downhill starts slowly decreasing. At the 21st km of the journey you will find a great opportunity to take a detour towards the Romitorio of Cetinale, only accessible from Villa Cetinale through a long staircase of six hundred meters and 300 stone steps. It is a place of meditation where hermits used to live and offer shelter and care to the sick and hospitality to the pilgrims following the Via Francigena. If Villa Cetinale was built to celebrate the election of Fabio Chigi to Pope Alessandro VII, the Romitorio is, on the other hand, the object of strange stories since it appears it was built by a powerful cardinal in order to make good on the guilt after killing a love rival. Stories from another time, but in the Montagnola everything is a mystery and surprises are always hiding behind the corner.
After rapidly passing through Sovicille, you climb up the beautiful road leading to Tegoia and then take the Cerbaia dirt road towards Tonni, cycling through chestnut trees and holm oaks to Borgo Tolomei, said to be the home of Pia de’ Tolomei, a Senese woman mentioned by Dante Alighieri in his Purgatory.

From Tonni, you descend until meeting the SP541, a highly navigated road you will leave after just a few hundreds metres later to pursue the most challenging uphill of this route, immersed in the deep woods of Cotorniano, to reach finally arrive at the “Selva di Sogno”. This enchanted forest was an idea of the creative Manfred Flucke, who has realized a series of original sculptures able to camouflage in the green of the wood using rocks and waste materials. The Osho Miasto Institute of meditation is situated not far from here.
After leaving this place of art and spirituality, you keep climbing up to 712 metres, right after passing the Tafano farmhouse. The Castle of Falsini, announced by a stunning avenue of cypresses, is met at the margins of the Cornocchia Natural Reserve. Then, you are quick to reach another paved road leading to Casole d’Elsa without missing a detour through Mensano’s intact streets, a terrace guarding the Colline Metallifere. In Casole, you will find some time to relax while thinking of returning to discover secrets of the journey still left to unravel.