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Where to Pick Up Rental Car for 4 days in Tuscany?

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My fiance and I are traveling all over Italy during the month of August and are so excited! We are in our late 20s and very energetic. :) During one part of the trip we will be leaving Sorrento and heading towards Tuscany, where we will be staying for the next few days. Our home base will be in Montepulciano, but we'd like to rent a car and explore the region. At this point, we aren't sure where we should pick up the car. Would it better to get the car in the South (e.g. Naples, Sorrento?) or take the train farther north and then pick up the car?
We'd really appreciate any advice and/or information :)

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