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For five grand I'd probably do luxury in Goa, Penang or Thailand as you get weather beach and culture. The most interesting place in the Caribbean an is also too dangerous (Jamaica), smaller Islands are safer if you want to wander about and see local life. Some of the diving is spectacular and the West sides of the islands have great swimming. The Caymans are very nice and also safe.
The Garden Route in Soth Africa is spectacular and you can finish with a Safari (I'd recommend Shamwari estates). Cape Town is awesome and once there it is cheap as fuck. (A wine that would cost 400 in a UK restaurant is around 50 quid their).
I'm a little the worse for beer right now, but already I've seen myself hurtling round the Namibian desert in a Series 1 Land Rover fighting off tribesmen and searching for diamonds in amongst the shipwrecks on the Skeleton Coast. What a cracking site that is, I shall definitely be giving that some airtime.
There's a similar company called Exodus that a friend of mine uses, she's out in Rwanda with them at the moment, watching gorillas. Looks friggin amazing from her Facebook posts.
I've travelled with Exodus - very good - and Explore - really good.