I imagine you refer to my list of the most beautiful smaller hill villages of Tuscany, including, Volterra, San Gimignano, Monteriggioni, Cortona, Montepuciano, Pienza, Montalcino and Pitigliano.
My suggestion is you visit 2 or maximum 3 villages per day so to take your time while visiting them. I would start by visiting Volterra, San Gimignano, and the tiny Monteriggioni the first day, then I’d go with Cortona and Montepulciano the second day, then Pienza and Montalcino the third day and I would finally direct south toward Pitigliano by the end of the day. Near Pitigliano are other stunning hill towns like Sorano and Sovana.
So I would say you would require at least 4 days to visit all of them.
Feel free to ask any other question,