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Where should we rent a car? Traveling from Rome to Tuscany.

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Hello seasoned travelers! My husband and I will be traveling to Italy for the first time in June. We will be staying in Rome for a little while and then traveling to the Tuscany region.
We are looking for advice on where to pickup and drop off a car?

In Rome we will be staying in the neighborhood: Esquilino. (It was very hard to find a place hope that area is alright?)

We'll be leaving Rome and going to the Valdonica Winery
Via Dogana 1, 58036 Sassofortino, Italy.

Then heading back to Rome and staying at the Marriott near the airport to get ready for our flight back home.

Where should we pickup and drop off our rental car? We have been told, 1) It is easiest to rent a car to get to Tuscany and it's a nice drive, 2) It is not fun at all driving in Rome. Should we take public transportation someone outside the city and rent a car there. Should we drop off the car somewhere in Tuscany and take the train back to Rome?
Any help would be greatly appreciated!!!

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