Thanks a ton for your response Dingeryote! We'll be driving

Hopefully though, driving a manual car on steep and winding roads is lesser of a challenge than I am anticipating.
As a Suggestion.
Opt for the compact or larger car, and NOT the Fiat 500 or little Peugot, unless they are automatic.
If you are a typical American that is awkward with a manual, the winding roads, switchbacks, off camber and blind turns, and wonderful 12% grades found in Tuscany, might be really awkward.
The Italian car market and rentals are geared towards fuel economy, and smaller motors that are taxed less, so they take some fairly aggressive inputs as well as finesse.
The little Fiat 500 can BARELY get out of it's own way, and needs it's little motor wound up to an uncomfortable level, before making any power.
I own several Manual vehicles by choice, and a manual truck or two, but none so hopelessly underpowered, so it took some adjustment. I can see why so many pay extra for the automatic.
Stops on severe grades, and some parking garages in basements for that matter, are "Sporty" even if you are an enthusiast or drive a manual by choice. The hand brake is an essential tool, that we ignore here, so don't forget that it's there.
If you like to drive, and live for the corners and challenge of off camber and steep, you'll LOVE the Tuscan back roads.

Go easy at first though.
One other thing.
Make sure your credit card that will be used for the rental, has RAISED embossed numbers, and is not just printed like many of the new cards are in the states.
We ran into a hassle over the issue.
Over there, credit cards have raised numbers and name.
The debit cards and bank cards, have printed numbers and name.
Some rental car office employees wont risk the difference, or have a company policy against using the new printed number Credit cards.
One agency we tried, used the old carbon copy slider, so it was just a no go.