CLASSIC CARIBBEAN on Wind Surf
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
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
Mar 21, 2026 through
Mar 28, 2026
Mar 15, 2026
7:00 PM
Category b
Inside
Outside
Balcony
Suite
Exclusive Benefits
8494147
|
Dec 07, 2025 through
Dec 14, 2025
Dec 1, 2025
7:00 PM
Category b
Inside
Outside
Balcony
Suite
Exclusive Benefits
8493349
|
Dec 21, 2025 through
Dec 28, 2025
Dec 15, 2025
7:00 PM
Category b
Inside
Outside
Balcony
Suite
8533875
|
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 | 5:00 PM |
5 | Les Saintes | 6:00 PM | |
6 | Basseterre | 8:00 AM | 10:00 PM |
7 | Gustavia | 8:00 AM | 10:00 PM |
8 | Philipsburg, St. Maarten | 6:00 AM |