From the lush vineyards to the moon-like landscape of the Crete Senesi, the transition is brief but spectacular. Leaving behind the villages along the Via Cassia, you are immersed in the Crete Senesi with its characteristic gullies (calanchi) and clay hills (biancane). Oaks and cypress trees signal the presence of isolated farmhouses, where cheese is produced and tables are adorned with the Crete Senesi’s white truffle, known as the region’s "diamond." Breathtaking and enchanting landscapes lead to Asciano, a treasure trove of history, art, and tradition. Asciano has witnessed both Etruscan and Roman eras and is famous for its culinary delights, such as ribollita. Along this stretch, cyclists in the June NOVA Eroica are captivated by the vibrant colors and scents of the region.

Points of interest: Ancient Walls and Siena Gate (Asciano), Mill Path (Asciano).