STARS OF THE GREATER ANTILLES on Wind Surf

Exterior view of Wind Surf sailing near Capri, Italy
Photo Credit: Roger Paperno
Cruise through the Greater Antilles discovering magical places that fell off the map and tiny gems that were never on it in the first place. Skip the crowds of Montego Bay and Ocho Rios and head instead for the silver screen beauty of Port Antonio, "discovered" by Errol Flynn and then long forgotten. Enjoy the retro-Caribbean vibe of Grand Cayman and the undersea wonderland of La Romana. Sink into the sand on perfect white beaches, dive to pirate shipwrecks, swim beneath waterfalls wrapped in jungle and fall in love with a Caribbean you didn’t know still existed.
About Wind Surf
About Windstar Cruises

THE WORLD'S BEST SMALL SHIP CRUISE LINE
NO ONE ELSE GOES SO FAR TO GET TRAVELERS SO CLOSE …
You’re closer to secluded coves, tiny villages, misty fjords. To ancient ruins, medieval alleyways, quaint marinas. To unspoiled beaches, unfamiliar cultures, undiscovered atolls. To enlivening your curiosity and awakening your sense of wonder. You’re closer than ever to the kind of authentic and unforgettable exper
Feb 17, 2026 through
Feb 28, 2026
Feb 11, 2026
7:00 PM
Category b
Inside
Outside
Balcony
Suite

Exclusive Benefits
8812368
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Itinerary
Day | Port | Arrive | Depart |
---|---|---|---|
1 | Cozumel | 6:00 PM | |
2 | At Sea | ||
3 | Grand Cayman | 8:00 AM | 6:00 PM |
4 | Cayman Brac | 7:00 AM | 1:00 PM |
5 | Ocho Rios, Jamaica | 8:30 AM | 2:00 PM |
6 | At Sea | ||
7 | Santo Domingo | 1:00 PM | 10:00 PM |
8 | La Romana | 7:00 AM | 5:00 PM |
9 | At Sea | ||
10 | Jost Van Dyke, Great Harbour | 8:00 AM | 10:00 PM |
11 | Virgin Gorda / Prickly Pear, British Virgin Islands | 8:00 AM | 5:00 PM |
12 | Philipsburg, St. Maarten | 6:00 AM |