Once left San Gimignano, we reach Poggibonsi through some ups and downs. Hence begins an uphill stretch leading us to Colle Val d’Elsa, Gracciano d’Elsa and Strove, with the beautiful Romanic Pieve.We pass the beautiful complex of Abbadia a Isola before reaching Monteriggioni, with the unique crown of towers.

Once left the old town center of Monteriggioni, we travel across the dirt roads of the Siena mount towards Crbaia, an ancient medieval hamlet that is currently abandoned. Shortly before reaching Cerbaia we descend towards the Cassia, which we take to reach Siena.

Water and resting points are only available in villages.