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Where to pick up rental car Rome to San Gimignano

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We are heading from Rome to San Gimignano to spend a few nights in Tuscany. It will be my husband, myself and 3 kids. We are trying to figure out the best place to pick up a car. Do we pick it up in Orvieta and drive to San Gimi or take the train somewhere closer to San Gimi and pick it up there? Suggestions?

We are also heading to Levanto after our time in San Gimi. We may or may not need the car in Levanto, but will then head to the Holiday Inn express at Milan MXP airport the night before our flight. Do I drop the car off near Levanto and take a train to the airport and shuttle to the hotel, or just drive the car to the airport hotel, then to the airport in the am?

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