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I was in Hawaii last spring and Jamaica last winter. Hawaii is great. But it is a deep water, long period wave sort of place. Jamaica is the shallow, warm, nearly waveless Caribbean during winter. The sand is soft, the weather perfect and the people much like they are in any less weathly corner of the globe.
Much of the advice here sounds like Walter Huston in the Treasure of the Sierra Madre. Yes, Jamaica is poor. No, it would not be a good idea to flash a Rolex while drunk after midnight at a local bar while loudly proclaiming your 1st world superiority. But act with humanity and common decency, and don't do things you wouldn't do in the US and you'll be fine. It is a beautiful place, and planeloads of Americans return safely every day.
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