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Two Weeks in and around Italy

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I am visiting my boyfriend stationed in Aviano, Italy for two weeks in March. He has been to Switzerland, Berlin, and Barcelona so far. I've been to Paris and London.

Except for spending a day in Venice he hasn't really explored Italy. I'm trying to plan places to go that are a must see and how long we should stay in each place. He has a car but I'd like to use the rail so he isn't stuck driving the whole time.

We are thinking about a flight to Dublin for St. Patrick's Day so that throws in a whole other country. Just looking for advice. Thanks for your help!!!

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