I will be doing a road trip in Tuscany for 6 days in second of week of September. I have already an itinerary. I just want to know what's your favorite hill towns. My home base is in Pienza and I will visit the towns of Cortona, Montepulciano, San Quirico d'Orcia, Montalcino, and Volterra.
Lucignano, Buonconvento, Radicofani, Monticchiello are nearby.
San Casiano dei Bagni
Murlo. Small but beautiful with a lovely Etruscan museum.
Pienza! My whole family from age 75 to age 12 loved it the best. Check out a tour of Isabella's (of The Isabella Experience) family farm about a two-minute walk outside Pienza. https://www.theisabellaexperience.com/en/experiences-cretaiole. Fantastic!