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EURAIL OR CHEAP FLIGHTS?

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I want to go to europe this summer with a friend and we are considering getting an EURAIL pass but a lot of people seem to advise against this, they say that it costs money to make reservations and you need to book way in advance. We plan on going in may which we heard is just before peak season, We also would like to know if it is better to book hostels/hotels far in advance or just wing it and book when we get to the city. We want to visit Madrid Barcelona Paris Verona Florence Rome and then fly from Rome to London and London home. What is the best way to go about this?

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