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CLASSIC CARIBBEAN on Wind Surf

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

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
7 Nights from
$2,299.00 (USD)
Per Person
+ $52.00 taxes/fees
Category b
Inside
N/A
Outside
$2,299.00
Cat:B
$328.43 per night
Balcony
N/A
Suite
$5,399.00
Cat:OS
$771.29 per night
8494147
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
Inside
N/A
Outside
$2,299.00
Cat:B
$328.43 per night
Balcony
N/A
Suite
$5,399.00
Cat:OS
$771.29 per night
8493349
Dec 21, 2025 through
Dec 28, 2025
Dec 15, 2025 7:00 PM
7 Nights from
$2,699.00 (USD)
Per Person
+ $52.00 taxes/fees
Category b
Inside
N/A
Outside
$2,699.00
Cat:B
$385.57 per night
Balcony
N/A
Suite
$5,799.00
Cat:OS
$828.43 per night
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
Prices are per-person based on double occupancy, unless otherwise noted.