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Driving from Milan to Tuscany

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We are celebrating out honeymoon by traveling to Italy. We arrive in Milan at around 9 am early May. We are picking up a rental car and driving the A1 to Tuscany for a few days then to Rome. We want to know if there are great stops off the highway on our way down to Tuscany. Our check in times at our villa isnt until 4pm. Also we wanted to know if its worth it to take backroads down instead of the highway.

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