You sense it the second you step off the waterfront and into the pulse of the street, when the Caribbean shifts from its familiar coastline to a routine built on markets, galleries, rum shops, town squares and cultural crossroads. The region’s cities hold an entirely different kind of escape, one shaped by history and architecture, by neighborhoods and harborfronts, by the quiet thrill of discovery that comes when the Caribbean reveals itself away from the shoreline. This is where you walk into bakeries just after sunrise, where you follow the sound of a steel pan echoing from a courtyard,...

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