Classic Caribbean on Wind Surf

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
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
8118302
|
Dec 23, 2023 through
Dec 30, 2023
Dec 17, 2023
7:00 PM
Category a
Inside
Outside
Balcony
Suite
Amenity Departure Dates
8011397
|
Dec 21, 2025 through
Dec 28, 2025
Dec 15, 2025
7:00 PM
Category b
Inside
Outside
Balcony
Suite
8118303
|

Itinerary
Day | Port | Arrive | Depart |
---|---|---|---|
1 | St. Maarten | 7:00 PM | |
2 | Charlestown | 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 | St. Maarten | 6:00 AM |