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STAR COLLECTOR: CARIBBEAN EXPLORATIONS 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
Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.
About Wind Surf
About Windstar Cruises
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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
Apr 04, 2026
Mar 15, 2026 7:00 PM
14 Nights from CALL
Category b
Inside
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Outside
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Balcony
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Suite
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8494253

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 7:00 PM
9 St. John's 8:00 AM 5:00 PM
10 Road Bay 8:00 AM 6:00 PM
11 Jost Van Dyke, Great Harbour 7:00 PM
11 Soper's Hole 8:00 AM 6:00 PM
12 Jost Van Dyke, Great Harbour 10:00 PM
13 Virgin Gorda / Prickly Pear, British Virgin Islands 8:00 AM 5:00 PM
14 Gustavia 8:00 AM 10:00 PM
15 Philipsburg, St. Maarten 6:00 AM
Prices are per-person based on double occupancy, unless otherwise noted.