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Train Travel in Italy

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I'm a little intimidated! We will be in Venice in late May and will be taking a train to Florence. Is it safe to wait until we are there to book our tickets? Is Rail Europe a good spot to get tickets if we want to get them beforehand? Later in our trip, we will rent a car in Siena and want to return it before heading to Rome. We will be staying 30 miles south of Siena, but was thinking to return our car back in Siena and taking the train into Rome. Does this make sense and does anyone know if there is a car rental that is near the train station?

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