CLASSIC CARIBBEAN on Wind Surf
Cruise, Ocean cruise, Small Ship/Yacht

Exterior view of Wind Surf sailing near Capri, Italy
Photo Credit: Roger Paperno
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. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
About Wind Surf
About Windstar Cruises

THE WORLD'S BEST SMALL SHIP CRUISE LINE
All cruise ships let you see the world. Only Windstar’s private yacht style cruises brings you close enough so you can truly experience it. Each of our Windstar Cruises yachts serves between 148 and 342 guests. This intimacy provides you with the luxuries of time, space, and freedom to immerse yourself in both the journey and the destination — in ways you may never have imagined possible.
Feb 28, 2026 through
Mar 07, 2026
Feb 22, 2026
7:00 PM
Category b
Amenity Departure Dates
Amenity Departure Dates
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Itinerary
Day | Port | Arrive | Depart |
---|---|---|---|
1 | Philipsburg, St. Maarten | 7:00 PM | |
2 | Charlestown | 8:00 AM | 5:00 PM |
3 | Roseau | 8:00 AM | 4:00 PM |
4 | Mayreau | 8:00 AM | 4:00 PM |
5 | Deshaies | 1:00 PM | 7:00 PM |
6 | Basseterre | 8:00 AM | 10:00 PM |
7 | Gustavia | 8:00 AM | 10:00 PM |
8 | Philipsburg, St. Maarten | 6:00 AM |