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
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.
Dec 07, 2025 through
Dec 14, 2025
Dec 1, 2025
7:00 PM
Category b
Inside
Outside
Balcony
Suite
8493349
|
Dec 21, 2025 through
Dec 28, 2025
Dec 15, 2025
7:00 PM
Category b
Inside
Outside
Balcony
Suite
8533875
|
Mar 21, 2026 through
Mar 28, 2026
Mar 15, 2026
7:00 PM
Category b
Inside
Outside
Balcony
Suite
Signature Collection
8494147
|
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 |