Small towns

[mutt]

In order of desirability, how would you rate the small towns we can visit? We’ll be based just east of Florence and will have a car with 4 or 5 days to wander.

 

[Lourdes]

I would suggest heading to Chianti and visiting Greve, Castellina, Panzano, Radda -- then on to San Gimignano and Volterra.
I would also try to make it down to Val d'Orcia and while there visit Montepulciano, Pienza, San Quirico d'Orcia and Montalcino.