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@MickeyFinns - OcUK's resident global cyclist and storyteller extraordinaire.
Hello
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OP, West coast or East coast? I'd go for east, but once you hit Cairo it's tricky to get to Europe. I've been to Libya, and about to go to Syria, and the visas are super tough. I think there's boats from Alexandria to Turkey/Greece though.
If you go for east I can give you a good amount of advice, I've been to Sudan, Ethiopia, Kenya, Uganda, Rwanda, DR Congo, Burundi and Somalia. West coast I can't give as much advice, but if you're on a UK passport, Equatorial Guinea is going to be your pain point (you can blame Thatcher's son for that one).
If you mention what countries you are going through I'm probably in a good spot to advise on visas, the company I'm a partner in (Lupine Travel) specialize in holidays in places with difficult to get visas (Saudi Arabia, Libya, Afghanistan, North Korea, Turkmenistan, etc.).