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Tuscany/Florence/Positano/Rome

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We will be traveling to Italy next summer (2014) for a family reunion, departing New York City. The trip will be about 17 nights and we are locked in to the first week in Tuscany/Florence. After that my wife and I splinter off on our own. We are planning to stay in two locations: Rome and Positano. But in what order? Which mode of transportation between places? Rented car, train, ferry? (Comfort and ease of connection is important to us.) We have not booked our flights yet, though there is a good chance it may actually be less expensive to fly to Rome and catch a second flight to Florence when we arrive. Any thoughts as to any of these issues would be greatly appreciated. Including, which city to fly home from, and where to from Florence - Rome first, or Positano? Again many thanks in advance.

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