DESTINATION GPS
The Long Way Home
Stay a while when exploring the Caribbean aboard Windstar.
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.
Make your own rum in Antigua
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
Under the sea in St. Barts
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.
Race an America’s Cup sailing yacht
in St. Maarten
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.
Unspoiled nature in Dominica
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.
Nutmeg and chocolate in Grenada
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.
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.
Make your own rum in Antigua
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
Under the sea in St. Barts
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.
Race an America’s Cup sailing yacht
in St. Maarten
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.
Unspoiled nature in Dominica
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.
Nutmeg and chocolate in Grenada
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.
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Rachael Brusseau, CTA,MCC, has been helping the most discerning travelers see the world since 1999. That’s last century but who’s counting?! Highly efficient, intuitive, and well organized, she is truly a professional at planning dream vacations. Her long list of loyal clients consistently sing her praises about how well she prepares them for each and every trip. Rachael’s secret to success is high touch service, working as a team with her clients throughout the whole planning process. Rachael has lived and studied abroad so she has a unique understanding of how to make the very most of a destination. Great Britain, Germany, Israel, and Alaska are her favorites, with extensive experience planning memorable, upscale river and ocean cruises to these regions and beyond.