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Car rental pick up/drop off in Florence, Italy

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Hi-

My fiance and I are planning a trip to Italy for our honeymoon in mid-May. We are flying into Milan and then heading to Venice/Verona then to the Tuscany region via train. Then we are off to Rome for a few days.

We are looking to rent a car while in Tuscany since our villa is in San Donato, outside of San Gimignano. There is no easy way to get there other than renting a car and we would also like to drive to the different towns in Tuscany. My question is:

Is it better to rent a car at the Florence airport or in the city? I know that gettiing in and out of Florence can be hassle so what would be our best course of action? Should we do drop off in Siena and take the train down to Rome?

Any information would be helpful. Thank you in advance!

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