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With so many alluring ports of call at your disposal, planning an extended Caribbean cruising itinerary can seem intimidating. The relatively close proximity of the islands that comprise the Windward and Leeward island chains makes the region well situated for island-hopping. For example, you can go from snorkeling off Anguilla one day to enjoying French cuisine on St. Barts the next.

We asked dozens of experienced cruisers about their favorite Caribbean destinations. From iconic, paradisiacal backdrops to far-flung secret anchorages, here’s the Passagemaker-approved 2019 Caribbean wanderlist.

ST. LUCIA

Few Caribbean islands are as photogenic as St.

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