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 experiences that you travel to find in the first ...
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 experiences that you travel to find in the first ...
Dec 07, 2025 through
Dec 14, 2025
Dec 1, 2025
7:00 PM
Category b
Inside
Outside
Balcony
Suite
8404406
|
Jan 18, 2025 through
Jan 25, 2025
Jan 12, 2025
7:00 PM
Category b
Inside
Outside
Balcony
Suite
8404410
|
Dec 21, 2025 through
Dec 28, 2025
Dec 15, 2025
7:00 PM
Category b
Inside
Outside
Balcony
Suite
8404407
|
Itinerary
Day | Port | Arrive | Depart |
---|---|---|---|
1 | Philipsburg, St. Maarten | 7:00 PM | |
2 | At Sea | 8:00 AM | 5:00 PM |
3 | Roseau | 8:00 AM | 5:00 PM |
4 | Pigeon Island | 8:00 AM | 5:00 PM |
5 | Les Saintes | 8:00 AM | 5:00 PM |
6 | Gustavia | 8:00 AM | 10:00 PM |
7 | Basseterre | 8:00 AM | 9:00 PM |
8 | Philipsburg, St. Maarten | 6:00 AM |