The vibrant community of the Caribbean is already on the mend, re-opening more hotels, restaurants, and shops every day and getting ready to welcome back travelers. And with our reduced Single Supplements, it's never been a better time to visit these beautiful islands as a single traveler or odd-numbered group. Fly solo, tracing your way through the tropics, visiting each Caribbean gem along the way.
Soak up some sun on the black-sand beaches of St. Lucia, glimpse the breathtaking peaks of the Pitons and snorkel in impossibly blue waters in Les Saintes, admire an eerie underwater sculpture park in Grenada, or stroll the treetop walkway of the Jardin de Balata Botanical Gardens with exotic plants from around the world.
For travelers, not tourists
San Juan to San Juan
7 Days | Star Pride | from $1,499 per guest Waived Single Supplement
Historic San Juan, with more than 400 restored Spanish colonial buildings, Gustavia's chic French boutiques, snorkeling near Guadeloupe. Discover less-visited places in relaxed Caribbean style.
7 Days | Star Breeze | from $1,802 per guest Reduced Single Supplement
Discover the expansive botanical gardens on Deshaies' deep bay, and an eerie underwater sculpture park in Grenada. Experience the perfect mix of traditional Caribbean charms and the delightfully unexpected.
An intimate and welcoming ambiance makes it easy to connect with your fellow travelers and crew
Leave the crowds and clichés behind on small, elegant ships that carry less than 310 travelers
Taste the essence of the culture you just explored with the Official Cruise Line of the James Beard Foundation
Our personalized and immersive approach brings you closer to each destination and every port
Enjoy unfailingly attentive service that delights in bringing you just the right thing at just the right time
Windstar Cruises Awarded Top Honors
Condé Nast Traveler 2017 Gold List Award
Travel + Leisure 2017 World's Best Awards
Condé Nast Traveler 2016 Reader's Choice
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