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Naples to Cortona

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Trying to decide where to rent a car for our time in the Cortona area. One option is to take the high speed train directly to Florence and then rent a car there, driving to Cortona directly. No transfers on the train, and I understand it is a new train line. We will spend 5 days in Florence after Cortona and can return the car there, not needing it in Florence. I'm concerned about the fines for pedestrian-only areas. Would it be best to try to rent a car from the airport or an area on the outskirts of the city if we do rent the car there?

Another option is to take the high speed train to Rome, transfer there to a train line to Arrezo or another town, rent the car there, return it before training to Florence. Longer train ride and we would need to transfer trains....

Any advice as to our best option? Thanks in advance!

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