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I don't know baraka: I know that summers up there can get pretty warm, but when I was down in Puerto Rico last fall (September), there were times the heat was really stifling. I'm a Southern boy, born and bred in South Carolina, and it gets plenty hot down here. 100F, humidity in the 85% - 90% range...and still. As for the base tan, I think of it more like developing callouses when playing guitar. Sure, you can still burn your fingers up if you're a regular player and you play too long, but you do get some level of increased protection by breaking yourself in slowly. You can get sunburns down there even with clothes on, and the people around you won't be hardly affected. It will also be likely that most places won't have central air conditioning; most rooms have their own AC on the window, but when you're out and about there's a good chance there won't be any AC. I know you already mentioned it, but make sure you watch out for your head. I believe your hair is rather sparse up top - sunburn on the head sucks.
Regardless, have a blast. I love it down in that part of the world, then again I'm a beach bum at heart. If you don't speak Spanish, I'd put some time in on that front, or at least hopefully someone you're traveling with speaks Spanish. My girlfriend is latina, so I've got a built in tour guide and translator. Some latin dance lessons wouldn't hurt either.
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