My friends & I (5 total) will be visiting Florence & its surrounding area in the fall. We only have one day set aside for a trip to Siena, SG & Montepulciano. We plan to rent a car the night before so we can have an early start on our driving "tour" of Tuscany. We are also considering keeping the car another night so we can use it to transport us & our bags to the train station the next day. That being said, we have at least 12 hours (maybe as much as 14 as our designated driver says he is not opposed to very long days/drives) to visit those 3 towns. Is our plan to drive feasible or even recommended? What would be the best order to visit these towns? Maybe a picnic lunch along the way (we could pack something from our "home" in Florence) if it means saving time waiting for service at a restaurant so we can have time to visit all 3. We can limit ourselves to Siena & San Gimignano if it will mean that visiting all 3 will be too hectic. I was also thinking that we could have dinner in Siena because I think it looks pretty at night.