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Portugal, Spain, France, Netherlands, England - Itinerary and Rail Travel ?

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My 24-year-old son has rather suddenly decided to spend a month in May-June exploring some of Europe - his first trip there on his own (he did a family trip 12 years ago). He's a graduate student and teaching assistant (Spanish) and has little time to do much planning for the trip, so I have volunteered to gather some information for him since he's visiting some places I haven't been. His primary interest is meeting native Spanish speakers, experiencing Spanish culture, and "hanging out." He plans to visit some major sites but that isn't his primary aim. He will likely stay in hostels and hopes he might meet some people with whom he can do some traveling. He currently plans to get a Eurail global pass so he will have flexibility to change plans on the fly but needs to figure out how many days he will be traveling.

His tentative itinerary includes spending 15 days in Portugal and Spain, then 2 1/2 - 3 weeks hitting a few places in France, the Netherlands, and England. Does this itinerary sound workable or should he do things in a different order? Will all of the legs of his trip be covered by a Eurail global pass (except Eurostar and travel in England)? He knows he still needs to make reservations for many of these connections. When France is added to the Eurail Select Pass on April 1st, could he cover Spain, Portugal, France, and the Benelux on a 4-country pass?

15 days for
Fly into Lisbon (2 -3 full days there)
Sevilla
Cadiz
Cordoba
Madrid
Barcelona

Paris - 5 days
Amsterdam - 2 - 3 days
Brussels to catch Eurostar to London
London - 5 days
Depart London
(doesn't add up to a month as some days will be taken up with travel)

Would it make more sense to fly from Barcelona to Amsterdam (or take the train from Barcelona to Amsterdam), then do Paris, and take Eurostar from Paris? Is Paris or Brussels more easily booked or are they about equally in demand?

All information is greatly appreciated!

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