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When choosing a vacation in the Caribbean, a lot of variables come into play. All of these areas are well known tourist destinations and the resorts will generally have good security precautions to keep guests safe. If you do book flights separately, just make sure to alert the resort to your flight itinerary if they provide airport transfers. Note that you can also easily book your resort stay and get your flights separately. People often combine airfare with Sandals all-inclusive resorts in Jamaica and St. Lucia.