DESTINATION GPS

The Long Way Home

Stay a while when exploring the Caribbean aboard Windstar.

Anyone who has ever been to the Caribbean has most likely contemplated extending their stay. While Windstar doesn’t offer residency, it gets pretty close with its 55-night Grand Caribbean Adventure cruise on Windstar’s flagship, 342 guest, 5-masted sailing ship, Wind Surf. Setting sail in January of 2026, the itinerary covers 28 sun-soaked islands, 39 ports, and 100-plus optional shore excursions that are fully vetted, authentically local, and truly unforgettable. With so many options, there’s truly something for everyone, and with such a lengthy voyage, there’s plenty of time to foster new and amazing friendships.

Rum takes credit for some of the best cocktails—pina coladas, daiquiris, mojitos, and of course an island favorite, the mai tai. But who takes credit for rum? During an expert led rum master class, learn the art of tasting prior to creating, distilling, and labeling your personalized bottle of rum to take home

Explore the vast underwater world without getting wet on this semi-submersible yellow submarine. The vessel’s glass bottom and viewing windows provide a rare glimpse into the life of tropical fish, green sea turtles, and even sharks. While underwater, you’ll also float over the remains of an old shipwreck before drifting towards St. Barts Marine Park.

Considered one of the top thrills in the Caribbean, this exhilarating excursion allows you to experience the oldest international competition still operating in any sport. After a quick tutorial, you’ll board an America’s Cup winning sailboat as a crew member, then head for the racecourse, where you can grind a winch, trim a sail, punch a stopwatch, or just sit back and enjoy the ride.

Aptly dubbed “The Nature Island,” Dominica is one of the Caribbean’s best-kept secrets. Hike among exotic flora and fauna to Trafalgar Waterfalls, twin waterfalls that plunge 125 and 75 feet, one into a cold-water pool and the other a hot spring. Later, relax in a natural sanctuary of hot sulfur springs, tropical flowers, and exotic birdsong.

A visit to the Gouyave Nutmeg Processing Station will give you a new appreciation for this precious spice. Here, nutmegs are harvested, processed, and exported the old-school way (no conveyor belts or machines, only nimble fingers and diligent workers). Then, head to the Diamond Chocolate Plant, where jouvay organic chocolate—considered one of the 10 best chocolates in the world—is made. Learn about the quality of beans and the country’s rich history of cocoa production before sampling some for yourself.

Discover all the flavors of the Caribbean.