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Touring Tuscany by car

We would like to rent in Siena and return the car in Florence. The plan is to drive “Rick’s” Crete Senesi Drive, stay at an Agro near Volterra, and drive a Volterra San Gimignano loop before returning the car to Florence. What is a good company to look at for car rentals? Is it better to book from Canada before leaving or wait till we arrive in Italy. We plan to start in Rome then travel train/bus to Siena so we would be in Italy about a week prior to wanting to rent. Couple from Canada.
Thanks
Karen

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