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Every Caribbean packing list online looks perfect. Flowy dresses. Straw hats. Matching sets laid out on crisp white sheets. Everything styled for the photo—and very little designed for the kind of day you’re actually about to have. We used to pack that way too. And while nothing went wrong exactly, small things kept chipping away at how relaxed the trip felt. Clothes that clung by midday. Swimsuits that never quite dried. Bags that looked great but were annoying the second w