If I had one last bike trip to take, this would be it. It’s mostly empty, unpaved roads with unlimited views, and stops at castles, a monastery, and Tuscany’s best medieval town. You can start this loop anywhere but I’ll go from San Quirico d’Orcia. Follow the Old Cassia road north (paved), toward Torrenieri. After 1.86 miles, turn right at the sign for Cosona. The road is unpaved from here for quite a while. After a short climb, you’ll have a breathtaking view on your right of the entire Val D’Orcia (a World Heritage region) with the great volcano beyond. Bike on to Castello di Cosona and feel free to walk around. A couple hundred yards past the castle, turn off and walk out past the ruin and a pond to another ruin with the world’s best view. Back on the main dirt road for a little over 3 miles, you hit paved road. Turn left for about ½ mile to the medieval monastery of Sant’Anna in Camprena where The English Patient was filmed. Ogle. Backtrack on the paved road all the way to Pienza (most beautiful medieval town). Take the back road to the cemetery, join the main road toward San Quirico d’Orcia. Descend beyond the left hairpin turn, then at the bottom of your descent, where the paved road straightens to the right, turn off left onto a dirt road. Follow a dirt road back to San Quirico.