"Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did do.

                   So throw off the bowlines, sail away from the safe harbor. Catch the trade winds in your sails."

                                                                                       - Mark Twain 

 

        Explore.    Dream.    Discover.

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 08, 2025 through
Mar 22, 2025
Mar 2, 2025 7:00 PM
14 Nights from CALL
Category b
Inside
CALL
Outside
CALL
Balcony
CALL
Suite
CALL
8416225
Feb 01, 2025 through
Feb 15, 2025
Jan 26, 2025 7:00 PM
14 Nights from CALL
Category b
Inside
CALL
Outside
CALL
Balcony
CALL
Suite
CALL
8416224

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 7:00 PM
9 Charlestown 8:00 AM 5:00 PM
10 Roseau 8:00 AM 5:00 PM
11 Pigeon Island 8:00 AM 5:00 PM
12 Les Saintes 8:00 AM 6:00 PM
13 Basseterre 8:00 AM 10:00 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.