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Oct 2000 itinerary - Zurich to Rome in two weeks - help?

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My husband and I are taking my parents to Italy in October and need help with an itinerary. None of us have been before. We are thinking of flying into Zurich (and taking the train through the Alps) and flying out of Rome. The only mandatory stop is Sassoferato (in the Ancona region) which is where my grandparents are from. Any suggestions would be great! Thank you.

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