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Car rental questions for Italy

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1) I would like to rent automatic transmission (NO MANUAL) car for 4-5 days, perhaps from Florence to Venice traversing several hill towns in between, will I pay through the nose for one way drop off charges or should I do round trip rental?

2) Can my 22 yo DD legally drive the car if I am the primary renter? I need her help, can you recommend any car rental companies that might allow this?

Any tips/tricks on finding best discount rental car? We want to visit some hill towns between Florence and Venice. We are starting in Rome, visiting Florence, hill towns and flying home from Venice. Want to minimize driving time, maximize value. Any suggestions would be helpful.

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