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Sitting on your butt beachside with a piña colada and ordering room service doesn’t take a lot of planning; discovering the eclectic beauty and otherworldly treasures of Jamaica, however, does. Truly drinking in the culture and flavors of this Caribbean destination is more for the temerarious, not the timid. Every hairpin twist and turn reveals either a natural wonder or a colossal blunder, depending on whose directions you take.

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