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Spontaneous solo backpacking trip

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Hello!

So I'm in a bit of a unique situation that is allowing for some spontaneous traveling. The basics: I have about 4-6 weeks to travel solo, about $5,000 outside of airfare to and from the U.S, and a loose list of things I want to do. I can come back pretty much whenever I want in August, so I'm thinking I'll just buy my return ticket home when I'm ready to come home.

I've been told that holding off on my return flight will be very expensive, but when I look at flights from Barcelona to JFK for next week, the prices aren't bad. I don't mind spending $100 extra to have the freedom to return when i want from where i want. Thoughts on this?

I have a one-way flight out of JFK into Tel Aviv on July 13th. Tel Aviv is like home to me, so I will be staying with friends there for about a week. After that, I'm pretty flexible. I want to be sure to plan ahead as much as necessary so that I don't waste a ton of money, but I'm also relying on meeting other fun backpackers to bounce around with.

I would really like to go to Istanbul and Olympus for a few days, so I'm thinking I'll head there after Israel. BUT the week that I'm there is going to be a great time to meet other travelers and make some concrete plans, so that is subject to change.

Places that are non-negotiable are Berlin, Prague, and Ibiza. I would also like to go to Dubrovnik (Croatia in general), Sarajevo, Budapest, Munich, and Amsterdam. Again though, I'm going to be alone so I need to just go with the flow depending on my social situation. I'm very independent, but I am not going to be hitting up clubs or hiking up mountains by myself.

I want to do lots of dancing and partying (because I'm 23 and need it in my life right now) but I also want to see as much nature as possible and have adventures. Hiking, camping, rafting, things like that would be great (and that is why I want to go to Olympus).

Basically, I'm just looking for advice as to how to do this right. Is it okay to just wait until I'm in Israel to set the game plan? I'm familiar with flights, but know nothing about trains so I don't know if it would be a bad idea to make purchases last minute or what.

I work for a travel company so I talk about travel all day long, but backpacking spontaneously is a whole different animal. Please help!

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