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First time traveler, 1 month Euro trip during June!

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Hi everyone,

To start off, I am a 21 year old male and I will be graduating this May from my University. I am planning a 1 month trip to Europe with my brother, none of us have done any traveling just on our own so as you'd imagine I have plenty of questions and need advice. I have not booked a flight yet but plan to fly in to either Madrid or Lisbon on 6/1/16.

First off, I will list my current itinerary.

Lisbon (2-3 days)

Madrid (2 days)

Granada (1 day)

Barcelona (2-3 days)

Amsterdam (2 days)

Berlin (2 days)

Munich (?)

Prague (3 days)

Venice (2 days)

Florence (3 days)

Rome (3 days)

Naples (??)

Sorrento (??)

Fly out of either Italy?? or make way back to Madrid?

What do you guys think about my current itinerary, I am open to any suggestions or advice! Ideally I would like to keep this trip under $7000 if possible, I plan on staying in hostels the entire time, and maybe try my luck with some couchsurfing.

I have some questions about hostel bookings and rail bookings. How early in advance should I be booking hostels and rail tickets, I know I am going during prime tourist season but I also currently don't know exactly how long I want to stay in each city? Do I need to book all my hostel reservations because I get to Europe?? Also, I heard it is significantly cheaper buying rail tickets ahead of time, should I also purchase these before I arrive in Europe? Also, any thoughts on the Eu rail pass are much appreciated. And with regards to couchsurfing, I have never done it before but would it be easy to find places to stay using couchsurfing, if we are two 21 year old males?

Thank you!

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