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These 10 Caribbean Islands Are Small, Quietly Cool, and Full of Personality
Riding a flats boat through the mangroves, the engine cut low, water so clear you can see the bottom slide past. Walking a beach long enough that the footprints behind you disappear before you reach the next bend. Standing at the edge of a dock while a resident grouper circles below, close enough that you can make out the markings along its side.
This is what small-island travel looks like when it’s done right. It’s swimming until your shoulders feel tired, then drying off on the sand because there’s nowhere else you need to be. It’s driving a short road that ends at the water, parking, and realizing you’re alone. It’s a reef close enough to shore that you don’t need a schedule, just a mask and a few quiet hours.
The bartender remembers your order on the second night. Someone on the dock waves because they saw you there yesterday. You take the same path to the water each morning, and by the third time it feels familiar instead of new. The best part is how personal it feels. You don’t disappear into a crowd. You don’t spend the whole trip moving. You spend it returning—back to the same shoreline, the same barstool, the same stretch of road that leads to the water.
These 10 Caribbean islands all deliver that feeling in different ways. Some are best for reef time and days on the water. Some are best for harbors and villages where daily life shapes the trip. Others offer long beaches and quiet nights where the loudest sound is the surf. Each one points to a different kind of vacation, and each one still feels like an island with a personality. Here are 10 small islands for your next Caribbean getaway, including tips on where to stay.
Bimini, The Bahamas
Bimini is close to Florida, but it feels far once you step off the plane. The island’s story runs through Prohibition-era smuggling, sportfishing, and the long shadow of Ernest Hemingway and Dr Martin Luther King Jr. In 2026, getting here becomes even easier with a new American Airlines nonstop, tightening the link between South Florida and Bimini. On the ground, the experience stays simple: shallow turquoise water, bonefishing flats, and a village where the marina is still the center of daily life. Bimini Big Game Club fits naturally into that setting, sitting right on the harbor with a front-row seat to the island’s fishing culture.
