Tuscany from 3 Bases - Car or No Car???

How will you get from Orvieto to SG?
That’s going to take all day

There are public parking lots outside each of those towns and there are hotels outside the walls that offer parking as well.
(Orvieto for sure has hotels inside walls that offer parking)

I guess it can be done without a car but buses are infrequent especially on weekends.
No train in SG

I’d start at www.Rome2rio.Com and check options for whichever towns you are interested in.

I know cars are pricey this year. We ended up renting for just 3 days and cut out a few places we would have liked to visit.

I think Orvieto without a car would be sort of OK but SG probably not. You’ll be limited by the bus schedule.

You could pick up car as you leave Orvieto, use it for SG then drop in Florence ( or outside Florence/airport

Try revising your schedule to deal with expensive rental cars: Orvieto & Florence by train; rent a car in Florence for SG and park outside SG walls when not using the car. We rented a car in Sienna and used it for Volterra, SG, Montelcino & Montepulciano. Returned car to Sienna, stayed there for 2 nights and took train to Florence. We’re going to Orvieto by train this year and then to Northern Italy by train. No car on this trip.

I can’t imagine trying to visit Tuscany without a car. We have been there four times and always rented one. If you want to visit Tuscany, rent a car.
Take a train to Venice from Florence..

It depends on your travel style and daily plans. For example, it is difficult even in places with good transit (say, Germany) to visit three or more towns in a single day entirely by public transit. Are you sure you need to change rooms for three places. I personally would allocate three days without a car to Florence and Fiesole, but I like art.

We try to avoid renting a car for most of our European travel. But Tuscany is one exception to that rule. We chose a rural luxury resort (I simply mean, not an Agriturismo, which many here prefer) partly because of the parking convenience. I suppose you could say we simply omitted several important destinations because they were over an hour by car from Sinalunga. I guess I'm sort of admitting that I'm usually "an encylopedic tourist", but I simply decided we could not see "all" of Tuscany in four or five days.

I'm not trying to get you reach any particular solution. I wonder if, even in July, it's correct to say that Orivieto has "unlimited parking", because that is nearly ... true. We had to cruise around (as a daytripper, I mean) the San G lots until we found someone pulling out of a space, like a mall at Christmas. I wonder if it might be helpful to consider sleeping in a town that is NOT a major target in Tuscany. I mean, how many restaurants do you need to have to choose from for three nights? Different visitors would have different answers, of course.

Okay, I bit the bullet and I'm going to rent a car at Naples airport on 7/23 and keep it for the 6 nights we are in Orvieto & San Gimignano, and return it to Florence Peretola Airport for the start of our 3 nights in Florence on 7/29. The cost for a station wagon (cheapest car that will be comfortable for us) is $950 + addt'l $50 on site to drop at different location, so $1,000. That's thru AutoEurope/Europcar. Is that a decent price?

We just paid 460 euros for a smaller automatic car
Actually 4 days picked up Sunday at FLR, dropped Wednesday in Lucca
Avis thru AutoEurope
Plus the 80 euros drop off fee
I booked it in Jan or Feb, can’t remember

So I think your rate is decent
Looks like prices are finally coming down

Did you check pick up in Orvieto or Chiusi?

Returned last week from Italy, and for our Tuscan portion, we rented a small station wagon with manual transmission and full coverage for 460 Euros thru Sicily by Car. Picked up and returned at FCO.

I wonder if it might be helpful to consider sleeping in a town that is NOT a major target in Tuscany. I mean, how many restaurants do you need to have to choose from for three nights?

I agree with Tim’s thought. Both towns are small and it would be an added hassle, expense and time waster to reclaim and return your car to take day trips. I don’t feel that it would be worth it staying in those towns for 3 nights each since both can easily be toured in a day trip. I have stayed in a hotel near the Duomo in Orvieto that provided valet parking (for a fee) but it wasn’t easy to drive to the hotel and then call in advance to get the car back. Add to that the ZTL’s and possibility of getting a fine. Too much stress.