I'm overwhelmed with possibilities on where to stay or IF to stay in a town in Umbria/Tuscany. The plan is to rent a car in Rome and take the back roads to Florence. Shall I just do it in a day or spend a night somewhere along the way to make the experience better.
Thanks!!

Depends upon how much time you have. Orvieto would make a nice stop in Umbria. But there are numerous towns in southern Tuscany you might want to stay in: Pienza, Montepulciano, Siena, etc.

Train to Florence in only 90 minutes then decide if you want to day trip from there. You do not want to drive in either city.

Depending on the time of year you are traveling, it may be difficult to rent a car for anything less than 3 days. Presuming you can, you could take the train to Orvieto and drive into the val d'Orcia, looking to spend the night around Pienza, Montepulciano or Montalcino. From there I suggest you head toward Siena or Pisa to drop off the car, or Arezzo if you want to go the other way. Depends on what you want to see, but all are easier than Firenze to navigate and all have train connections into Firenze (that's what the Italians call Florence).

It is possible to take a scenic route in one day from Rome (or Orvieto) through a lot of Tuscany, ending in Florence (or Siena), but you might very much enjoy spending the night.

But sebinah is right: All depends on how much time you have. And bob is right that you don't want to drive into Firenze if you can possibly avoid it.

Many posters on this forum have had mysterious and expensive traffic tickets from Florence sfter they get home because many areas are limited to resident-only cars with special stickers.

The signs are hard to spot, and you will be ticketed from a traffic camera photo of your license plate.

Opinions vary on whether you can blow off the ticket itself -- that is a huge argument here -- but your car rental will charge you $75 or so on your credit card for giving your address to the police. You cannot get out of paying this as it is a valid charge for them to make.

Upshot? Should you drive to Florence, get their early and park in one of the peripheral lots. Do not drive into the city.