From Casole we first pass Mensano and then Monteguidi, from where we can reach Radicondoli, leaving behind the characteristic landscape of the Colline Metallifere. The beginning is the prelude to the great commitment and attention that you will have to put into the journey.

From Radicondoli to Chiusdino, this is painful for the body but joyful for the mind. The former can be mitigated by the attitude to be held, which must be prudent and curious. The advice, therefore, is to make many stops starting from Belforte, Anqua and Gerfalco, villages so out of time that they can be considered real «land islands». The Cornate pass is at 818 meters with stretches at 16%. The dirt road is a constant, as are the woods and the wild animals. Once past Ciciano, from where you can catch a glimpse of the beautiful Val di Merse, you'll find the panoramic GATE of Chiusdino.

This is the easiest stage, so to speak, with lots of dirt road. The extraordinary Abbey of San Galgano and the sword in the rock make the stop even more inviting. GATE in Monticiano.

From Monticiano you pedal towards the «sea of Brenna» and a bath in the Merse could bring unexpected benefits. Stigliano, with its short supply chain store, is hospitable and anticipates the GATE of San Rocco a Pilli that arrives after the well-known "Vidritta" dirt road.

It's hard to resist the beauty that one encounters going up from Bagnaia, turning to Casciano towards the Basso Merse Natural Reserve and then meeting the Ombrone and the ancient railway with the Befa station and the Mines of Murlo. Unique delights up to the Etruscan POINT.

From the area of Murlo, where the features of the inhabitants are those of the ancient Etruscan people, one travels in the direction of Siena without ever encountering it to deviate at the GATE of Sovicille.

From Sovicille, the capital of the municipality with no less than 55 medieval villages, we climb the mysterious Montagnola that hides many treasures to be discovered. The GATE of Casole d'Elsa comes at the end of one of the most beautiful efforts that a cyclist can make in his or her life.