LUSH & LOVELY ISLANDS OF THE LESSER ANTILLES 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
Enjoy the perfect mix of must-see Caribbean towns and harbors off the beaten path as you cruise and sail the royal beauties of the Lesser Antilles islands. Explore colonial history in pastel waterfronts, weathered forts and former sugar plantations. See the Caribbean at its most wild and beautiful on Dominica, St. Lucia and St. Kitts. Join the jetsetters on St. Barts, and everywhere you go, find delicious white beaches that turn rose and orange under Caribbean sunsets.
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 experiences that you travel to find in the first place. You’re about to board Windstar. And you’re closer to all the places that larger ships can’t reach.

SEE A WORLD FEW WILL EVER SEE …
Welcome to a world of understated elegance and uncommon beauty. A world that leaves crowds and commonplace behind to find unique ports of call, and local, exotic cultures that are at once fascinating and wondrous. A world that’s equal parts intimate, indulgent and inspiring. Where the allure and beauty and magic of the places you sail to is equaled only by the ship that takes you there.

Jan 11, 2026 through
Jan 18, 2026
Jan 5, 2026 7:00 PM
7 Nights from
$2,499.00 (USD)
Per Person
+ $131.00 taxes/fees
Category b
Amenity Departure Dates

Itinerary

Day Port Arrive Depart
1 St. Maarten 7:00 PM
2 Basseterre 7:00 AM 10:00 PM
3 Little Bay 8:00 AM 6:00 PM
4 Gustavia 8:00 AM 11:00 PM
5 Deshaies 12:30 AM 10:00 PM
6 Roseau 8:00 AM 5:00 PM
7 Pigeon Island 7:00 AM 4:00 PM
8 Bridgetown 5:00 AM
Prices are per-person based on double occupancy, unless otherwise noted.