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Europe Itinerary and Hotel Booking Help

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Hi, I am traveling with my Partner to Europe for the first time. We are flying to London on
Sept 15 and flying out of Madrid on Oct 7th 2012. We all ready purchased flights as we got a good deal on airline tickets. I have researched for a while several itineraries which we are doing on our own, but need advice.

We have an aggressive itinerary planned. Staying maybe 2 nights in London, taking the train to Paris for 3 nights.....the middle of the trip is still in the works...maybe heading from Paris to Amsterdam, 2 nights, then Frankfurt or straight to Munich, don't mind the overnight train to not loose time, but being Oktober Fest don't know if we can get rooms.....or maybe from Paris taking the overnight train to Zurich or Lucerne......the last part of the trip would be 2 days in Venice, 3 nights in Rome, Florence along the way (not staying) and finishing 2 nights in Barcelona and 3 or 4 nights in Madrid......I know it seems like alot, but I added the stays, overnight trains, and it add ups to the 23 days (or 21 without lost flight days in and out)......

Would I get a better deal purchasing a Eurorail Global Pass (expensive!) or just purchasing train tickets on site???

I want to purchase hotels prior to flying in for London, maybe Paris, and Madrid....is it safe to purchase the remaining on site...researching beforehand of course....safe for late september? just to add some sense of adventure and being free to change itinerary as we are there....we are in early 30's and late 30's so we don't mind walking and some adventure. we want to stay in centrally located hotels or B&B's, mainly budget, not so much hostels, as we do not want to sacrifice comfort given the intensity of the trip.

I am traveling very light, carry-on convertible backpack....

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