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Ya, the 3 months for Thailand will probably include the other surrounding countries. After reading some of the ask degen thread I was considering getting an apartment there, then making a 2-3 week trip out sometime during my stay there. My thinking is that the neighbouring countries will be fairly similar to Thailand, so I won't be missing to much by staying mostly in Thailand.

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I disagree, but to each his own.

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For Saudi Arabia, I just assumed I could get in hassle free. Guess I will just skip over that place.

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No, no, no. Very hard/nearly impossible visa to get, especially if you're American.

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I have Israel on my passport. Will that be a problem for other countries in the region?

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Yes. This will be a problem for all countries in the region except Turkey, Jordan, and Egypt. Most muslim African countries included.

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I will be getting a new passport before I leave, so I think I could show the new one to Israel hostile countries, and the Israel stamped one from Israel friendly countries.

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Once you get a new passport, your old one is void. Also, you can't do that as they look for exit/entrance stamps...

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I have about $20K of my own money, and my dad has said he is going to help out. He is very generous and wealthy, so I don't see money being a huge issue. I do intend to spend a lot more time in places that are cheaper. Though I thought Greece, Italy, and Spain would be fairly cost friendly.

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Sweet on the money deal. Spain and Greece CAN be cost friendly, but can also be very expensive. None of your European countries will compare to somethig like Thailand, which is way more expensive than somewhere like India. Really matters where you go/what you do. Italy is very expensive (of course, depending on what you do... but generally speaking).

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With Africa, part of the reason I am scrapping it goes back to the jumping around. If I start straight from Thailand I can just make my way more or less west across Asia/Europe. Adding in Africa makes that a lot more difficult. It also seems like disease/crime are a much larger threat, and my traveling experience so far is minimal. Unless it fits very well into my plans for weather, it is almost surely cut.

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Meh, fair enough. You seem to be very un-educated about the places that you're going. Realize that in Africa you'll need visa's for a lot of the countries, same goes with Asia. Some are available at the border, some arn't. Some you should get while you're at home (some you HAVE to get while you're at home)... i would definitley start to do a lot of research in regards to all of this...