Cruise the Caribbean and Save up to 70% Windstar Cruises
Ready to unplug? At the top of your can't-miss list is the seductive Caribbean and Windstar can make it happen, private yacht style. Wake up where the water is the bluest blue and tourists are nowhere to be found.
Off the Grid in the Caribbean
Ready to unplug? At the top of your can't-miss list is the seductive Caribbean and Windstar can make it happen, private yacht style. Wake up where the water is the bluest blue and tourists are nowhere to be found. Island hop from one island paradise to another. If rainforests are your thing, take a hike in Montserrat. Dive into the blue and snorkel alongside the most colorful sea life and breathtaking underwater scenery you've ever imagined. Discover hidden coves that only our small ships can reach, find deep calm on the deserted beaches of Culebra and enjoy overnight stays in Virgin Gorda and St. Lucia. Want to get up close and personal with the local flavor? Enjoy a Private Event at Prickly Pear Beach, St. Lucia or Mayreau. For a limited time, Windstar will transform your imagination into one of our Caribbean packages with fares from $1,499 pp.
SAVE UP TO 68%
YACHTSMAN'S CARIBBEAN Philipsburg to Philipsburg 7 DAYS / FROM $1,599 PP Let us take you into hidden coves and tiny harbors no one else can reach as you fully experience the Caribbean's private yachting scene.
SAVE UP TO 70%
CLASSIC CARIBBEAN Philipsburg to Philipsburg 7 DAYS / FROM $1,499 PP From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Here's the best of the Caribbean in one single voyage.
» SAVE UP TO 64%
SAN JUAN & THE VIRGIN ISLANDS San Juan to San Juan 7 DAYS / FROM $1,899 PP Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. Then explore Puerto Rico's best-kept secret: the island of Culebra.