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Help with itinerary, Italy, Salzburg, Amsterdam, Portugal

This will be my second trip to Europe. Will be going May 4-25. The first week, my mom will be with me and is already reserved. Realize Rome gets a little rushed, but this was the only way she could see Venice as well. I have a million guide books that I am pouring through, but still trying to narrow down a plan. Just looking for any suggestions and input. I enjoy moving through different cities, but don't want to be too rushed. Will be travelling by myself the last 2 weeks and staying in hostels Fri May 4 fly to Rome day 2 Land in Rome 10am 3 Rome 4 Rome 5 Orvietto 6 Venice 7 Venice 8 Venice, mom leaves 9 Salzburg 10 overnight train to Amsterdam (have gone before and am also considering areas in Switzerland instead) Have aslo taken ON train before and am fine with it. Didn't see any discount airlines with this route. 11 Amsterdam 12 Amsterdam 13 fly to Porto
14 Porto Have 7 more nights. Am thinking my last 4 in Lisbon and fly out from there. One of those days would be a day trip to Sintra. So that leaves 3 nights. I would like some beach time. I live in Florida and have seen lots of gorgeous beaches. Would Navarre be a good choice or the Algarave? Also wondering if end of May will be too cold for the beach. There just seems to be so many great cities in Portugal, having a difficult time deciding.

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