It's not on your list, but if you have any interest in art history, I would recommend Orvieto. Perhaps you want to visit somewhere smaller and more out of the way, but Orvieto is a lovely hilltop town with some beautiful art and scenery.

Posted May 24, 2012

This is also not on your list, but I had an incredible meal at Cum Quibus in San Gimignano. It's in the same area as some of the other towns you mentioned.

Posted May 25, 2012

Sorry to add a third not on your list, but I'd suggest Castiglion Fiorentino, which is not far from Cortona. I had probably the best meal of my life at Muzzicone two weeks ago—fabulous bistecca, salumi, even the spinach was incredible. It made me completely rethink what Tuscan food can be. And the vin santo and cantucci blew my mind (I've had a lot of vin santo and cantucci in my life, it's always fine, this rocked my world). Muzzicone has an old Tuscan feel to it, no menus (so it's nice if you know some Italian), both the antipasti (cheese and salami) and dessert are brought to your table whole and you take what you want. And the town is delightful and definitely off the beaten path. Check for closed days, and remember that with Italians eating dinner late, you won't be hitting the road for Rome until very late. Maybe you can go for lunch, then get coffee in Cortona? I went there for lunch and wasn't hungry for dinner.

http://www.ilbelcentro.com/2013/03/04/tuscany-revisited/

Posted Mar 17, 2013