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Two Weeks in Italy

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Just planning a trip. My expected dates are depart Boston on June 23rd, arrive in Italy Saturday am. Would like to fly back on Friday 7th. Tickets are not booked yet, but I would like to book tickets in the next two weeks. Its my 50th birthday celebration so we are not 20, but we are young 50 year olds and fairly active. Not cross fitters, but not couch potatoes either.

First trip to Italy and I want to visit several cities and move about, but don't want to make it so hectic that we don't enjoy what we see. Are there any sites out there that I could see proposed travel routes? Also, are there any passes similar to what Paris has to see attractions?

Thanks for your help!

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