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CLASSIC CARIBBEAN on Wind Surf

Cruise, Ocean cruise, Small Ship/Yacht
Wind Surf Capri
Exterior view of Wind Surf sailing near Capri, Italy
Photo Credit: Roger Paperno
  • Exterior view of Wind Surf sailing near Capri, Italy - Photo Credit: Roger Paperno
  • Exterior view of Wind Surf
  • Exterior view of Wind Surf - Photo Credit: Jeff Zaruba
  • Close-up exterior view of Wind Surf bow - Photo Credit: Roger Paperno
  • Exterior view of 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
Windstar Cruises logo

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
7 Nights from
$2,299.00 (USD)
Per Person
+ $52.00 taxes/fees
Category b
Dec 21, 2025 through
Dec 28, 2025
Dec 15, 2025 7:00 PM
7 Nights from
$2,899.00 (USD)
Per Person
+ $52.00 taxes/fees
Category b
Mar 21, 2026 through
Mar 28, 2026
Mar 15, 2026 7:00 PM
7 Nights from
$2,399.00 (USD)
Per Person
+ $52.00 taxes/fees
Category b

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
Prices are per-person based on double occupancy, unless otherwise noted.