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First Trip to Europe

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We will be visiting Europe for the first time in May. Our first stop will be to Peccioli, Italy, which is close to Florence and a 2 hour train ride to Rome. We plan on staying in that area for 5 days. We were also thinking of taking the train to Germany, Austria, France then back to Italy to depart. We live in Las Vegas, and would be flying to NY or Boston for the connecting flight.

Any ideas of what to see, what to do, and if leaving from the same airport is best? Also, is it better to take the train or to drive. We will be there a total of 2 weeks.

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