We would like to rent a car and drive from Rome to Florence. We are interested in medieval villages and authentic italian towns. We roughly have in mind:
From Rome - Hadrian's Villa, Tivoli - Villa D'Este. Had thought about going to Bracciano but I'm not sure.
Then to Orvieto
Then to Cortuna
Then to Montepulciano, Penza, eventually to Siena
Then to Volterra, San Gimignano
Finally to Florence.
Any advice? Shall we skip Bracciano? Where should we go the first night after Tivoli?
Grazi!
I don't know that you actually have much extra time there. Certainly Orvieto isn't tiny and has quite a lot to see, and Siena is typically considered a full-day trip from Florence. If you do need another stop, consider the lovely Assisi. Via Michelin (perhaps optimistically) estimates it at about 95 minutes' driving time from both Orvieto and Montepulciano. Assisi is not a quick stop, though.
Have you considered taking a local train up to Orvieto--70 minutes? It's a very popular place to see and spend the night.
Then pickup a Hertz car across the street from the train station and head north.
It would be good to find an agriturismo north and west of Siena to do your day trips out of. They sure beat wasting time every day trying to find a place to spend the night. The distances between towns in the area mentioned are just not that far apart.
Go through with your plans as you have designed them and you will either accomplish those or subtract from them as you go. No one here can tell you definitively what you will like. You will have a car so you may arrive somewhere where you will not want to spend much time seeing. You may need to base yourself in lodging in one town and make day trips to the others.
Considering you have three nights, you could take almost a full day in Tivoli on your way out of Roma and then go to Orvieto for the night. .
Cortona is a very popular (= lots of tourists) town. I would substitute Assisi, with a stop in Spello and/or Trevi, towns that get less tourist traffic and are lovely, small towns.
