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BEACH FUN & SUN: A REMOTE CARIBBEAN GETAWAY 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
Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from Windstar’s onboard Watersports Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar takes you to the secret beaches and invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
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.
 

Dec 14, 2025 through
Dec 21, 2025
Dec 8, 2025 7:00 PM
7 Nights from CALL
Category b
Mar 22, 2025 through
Mar 29, 2025
Mar 16, 2025 7:00 PM
7 Nights from CALL
Category b
Dec 28, 2025 through
Jan 04, 2026
Dec 22, 2025 7:00 PM
7 Nights from CALL
Category b

Itinerary

Day Port Arrive Depart
1 Philipsburg, St. Maarten 7:00 PM
2 Falmouth Harbour 8:00 AM 6:00 PM
3 Road Bay 8:00 AM 6:00 PM
4 Jost Van Dyke, Great Harbour 7:00 PM
4 Soper's Hole 8:00 AM 6:00 PM
5 Jost Van Dyke, Great Harbour 10:00 PM
6 Virgin Gorda / Prickly Pear, British Virgin Islands 8:00 AM 5:00 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.