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Trains & car Rental in Italy

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What is the easiest way to get from Rome to Cortona? I have looked at several options but unsure of details yet. I figured we'd take the train to Orvieto or Chiusi & rent a car at the train station, continue to drive to Cortona, then in three day drive to Siena & eventually dropping the car off in Florence and train to Venice. Or would it make more sense to take the train to either city, then bus to Cortona and then rent a car there on day of departure? I can see it is important to note the rental car agencies hours of operation. Any help would be greatly appreciated!!!! I am helping a friend to put this together. My husband & I are familiar with the are & have traveled to these cities but we always drove and did not take the trains. Thank you!

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