Rome to San Gimignano

You can rent a car in Rome, Orvieto (Hertz only), Chiusi-Chianciano (Avis-Budget only), and just after Cortona also Arezzo (Avis-Budget in front of station but Hertz and Europcar also present a little farther. Orvieto and Chiusi have very small franchises with limited fleet. If you need automatic transmission I would rent in Rome, to make sure you get one with auto transmission. I don’t see a reason to go to Florence and backtrack in your case. My choice would be to rent in Rome.

Yes, I noticed Orvieto had only 3 cars available on my date. Availability and hours of operation have got us in minor binds in the past. Thank you for reply.

I would only say that returning the car to FCO after our part-week in Tuscany added nothing to our sightseeing experience. Controlled access highway hours were unfulfilling. I have the luxury of being able to drive a standard shift, but I would not particularly care to drive from Rome. I admit that we did rent a car in Civitavecchia after a cruise, but we stopped in both Viterbo and Orvieto that day, before arriving for dinner in Sinalunga, Tuscany.

Is this on your air arrival day in Rome? BTW, it is always wise to give the month and year of travel when asking a question here. San G is an incredibly crowded destination in season, although you sort of suggest that your stay is out of town, with guaranteed parking.