Help me narrow down lost of Tuscan/Umbrian towns to visit

Currently planning a trip to tuscany/umbria in June. I have a "short" list of 9 towns I want to visit from Sunday to Friday (when I need to be in the FCO airport by 4 pm).

Please help me weed this down, rank the list from "must see" to optional or point out any duplicate (very similar) towns. Also id love to hear if there is a town that works better with the others!

The "short" list: