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Europe Trip (4 months)

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Hello,
I'm completely new to traveling abroad. I bringing a backpack and will be jumping around Europe for 4 months by myself and would appreciate any advice or help. Here is the tentative itinerary I made through the bit of research I've done via friends and travel books. Again, any help would be greatly appreciated and I won't take any offense to "This schedule is dumb you stupid naive American boy." Thanks in advance!!!

3/26- 4/8 SFO->London (2 weeks)
4/9-4/25 Fly London-> Berlin (2.5 weeks)
4/25-5/3 bus/train Berlin-> Amsterdam -> Ghent->Brussels (1.5 weeks)
5/4-5/11 euroline bus or rideshare Brussels->Paris, France (1 week)
5/12-5/31 fly or overnight train Paris->Spain--- Barcelona->Madrid->Lisbon (Salamanca/Toledo/Avila if there is time)--3 weeks
6/1-6/13 Fly/ train Lisbon->Rome, Italy, train ->Florence and Milan (2 weeks)
6/13-6/30 fly/ferry ->Greece (2 weeks)
6/30-7/14 Fly Greece->Milan, scenic train -> Vienna->Budapest->Prague (2 wk)
7/15-20 5 extra days for flexibility in travels-maybe back to Berlin.
7/21-7/24 back to London->SFO/Home

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