A beautiful loop with lots of worthwhile stops in tiny medieval towns. From San Quirico, take Old Cassia road to Torrenieri. Go on to San Giovanni D’Asso, a charming tiny town with an old section and a small Romanesque church. Head back down the hill, then turn left to Montisi. After a bit of a climb, you’re on a gorgeous ridge with views on both sides. From Montisi, go to Castelmuzio (great lunch in town’s piazza). From here, you can take an eight-kilometer side trip to another medieval town, Petroio and back, or go towards Pienza, with a stop at the monastery of Sant’Anna in Camprena. From Sant’Anna, on to Pienza, and from Pienza, back to San Quirico.