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Car rental in Tuscany

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We've been exploring Tuscany locations and found so many things we wished to see that I just managed to change our flight to come in a day earlier. This will make our proposed plan as following: This is part of a larger trip in May.

Wednesday - leave from Venice to determined Tuscany base
Thursday - explore hill towns
Friday - hill towns
Saturday - hill towns
Sunday - drive to Civita Bagnoregio, then hotel in Orvieto
Monday - Orvieto underground tour, train to Rome

We would like to stay at one base while in Tuscany. We want to drive in Tuscany. My husband is asking for an option of not driving from Venice, but taking train to Tuscany and obtaining car rental.

Per some wonderful advice from Fodorites, we are looking at San Quirico or Pienza as
a base. Would you advise taking train to Florence , getting rental there ? or take another train to Chiusi ? or any other ideas are welcome. Thanks

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