This week’s travel dream: Island-hopping in the Grenadines

Flying in a small prop plane across the Grenadines, you wouldn’t even imagine how varied life can be from island to island, said Gully Wells in Condé Nast Traveler. Not that they all look the same. Some “protrude from the sea like a giant’s rotting molars”; others are little but crescents of sand or isolated volcanic peaks. But after 40 years of occasional visits to Carriacou—the largest of them at just 8 miles long—I only recently found a boat captain willing to help me explore, in one multiday swoop, a few of Carriacou’s closest Caribbean neighbors. The adventure opened my eyes: Each island’s culture is so distinct that “it’s as if you are participating in a different play” each time you set foot on a new shore.

Tiny mountainous Bequia actually harbored two very separate cultures. When the dark-skinned cabdriver who picked me up near the main dock told me that my hotel was where all the “colored” people live, he wasn’t kidding. Just about everybody high above the harbor in Mount Pleasant is a sun-reddened descendent of indentured Scottish servants who arrived on the island centuries ago. My lodging, built from the ruins of a plantation house, was “the kind of hotel you never want to leave,” yet I enjoyed the best meal of the week down by the water at Toko’s Step Down, an open terrace where we watched one of Toko’s assistants behead and debone our fish on a nearby rock.

I never did warm to Mustique, a privately owned island whose many famous homeowners “rarely emerge from their secluded private villas.” So I was happy to jump back into “the messy, complicated real world” when my boat dropped me off at Mayreau, the poorest of the Grenadines. Again, I was swept away by car—one of only six on the island—to a hotel that was “an oasis of serenity and charm.” My host at Dennis’s Hideaway was dressed all in white linen when he greeted me and offered a cool glass of rosé. A table was set for lunch in a tropical garden near a small pool and “a few friendly chickens.” Every Caribbean island needs a few.

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At Dennis’s Hideaway (dennis-hideaway.com), doubles start at $85.