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Travel between Venice and San Gimignano - train or rental

We will be flying late May to Venice, staying a couple days, then traveling to San Gimignano and staying outside the town in a villa 3 or 4 days. We will want a rental car in San Gim for our travels in the hill towns. We will be going to Florence for a couple days following our time at the Villa. We then go on to Cinque Terre and Rome...

We are trying to decide if we should rent a car when we leave Venice and drive to San Gimignano or take the train. If we take the train should we stop someplace along the way for the car? We know we will need a rental car while we are in the San Gim area. It doesn't look like Poggibonsi (where the train ends from Venice) has much for rental cars.

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If it were my trip, I would take the train to Florence and visit Florence first for a couple of days, then rent a car in Florence on my way out, go to San Gimignano by car, and lastly drive the car to La Spezia, next to the Cinque Terre, where I would return my car before staying at the Cinque Terre.

If this change in your plan is not possible then the choices are 2:
1-train to Florence, rent a car in Florence, drive to S.G. then return the car in Florence.
2-rent the car in Venice, drive directly to SG, then return the car in Florence, before your two day visit there.

Between these last two options, I would take no. 2. Your call.