May changes how the Caribbean feels in a way you notice almost immediately. Flights are easier to find, restaurants start to open up, and you don’t need to plan your day around what’s already full. What replaces that pressure is something more useful: time and room to move through each place at your own pace. You can land, get to your hotel, and start the trip without waiting for anything.
It’s also a month where timing works differently depending on the island. In some places, it’s about food, with restaurant weeks stretching across entire coastlines and pulling you from one table to the n...
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