STAR COLLECTOR: IVORY BEACHES & SAPPHIRE SEAS OF THE CARIBBEAN on Wind Surf
Cruise, Ocean cruise, Small Ship/Yacht

Exterior view of Wind Surf sailing near Capri, Italy
Photo Credit: Roger Paperno
Escape on an extraordinary tropical vacation on this twelve-day cruise to hidden harbors and secluded beaches throughout the Lesser Antilles in the Caribbean. Board a catamaran bound for Norman Island off Tortola and listen to pirate legends and treasure tales prior to your secluded snorkeling excursion among pristine reefs and tropical fish. Set a course in your own rigid inflatable boat (RIB) across bays and inlets near Jost Van Dyke before hopping off for swimming and snorkeling near Great Harbour's scenic coastline. Cast deep lines for tuna, mahi-mahi, barracudas, and other delicious blue-water trophies off Nevis. Sample the sweetest of amber island ingredients in the thoughtful company of eco-minded beekeepers on St. Lucia. Admire sweeping harbor views as you sip local island rum with sweet cakes on a tasting tour of Fort Napoleon above Les Saintes. Sip Dominica’s Sea Moss non-alcoholic seaweed drink. Indulge your senses in classic Cuban cigars paired with spirits, wines, and cocktails at Basseterre, on St. Kitts.
About Wind Surf
About Windstar Cruises

THE WORLD'S BEST SMALL SHIP CRUISE LINE
All cruise ships let you see the world. Only Windstar’s private yacht style cruises brings you close enough so you can truly experience it. Each of our Windstar Cruises yachts serves between 148 and 342 guests. This intimacy provides you with the luxuries of time, space, and freedom to immerse yourself in both the journey and the destination — in ways you may never have imagined possible.
Dec 02, 2025 through
Dec 14, 2025
Nov 26, 2025
7:00 PM
Category b
8860574
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Itinerary
Day | Port | Arrive | Depart |
---|---|---|---|
1 | Philipsburg, St. Maarten | 7:00 PM | |
2 | Jost Van Dyke, Great Harbour | 7:00 PM | |
2 | Soper's Hole | 8:00 AM | 6:00 PM |
3 | Jost Van Dyke, Great Harbour | 10:00 PM | |
4 | Virgin Gorda / Prickly Pear, British Virgin Islands | 8:00 AM | 5:00 PM |
5 | Gustavia | 8:00 AM | 10:00 PM |
6 | Philipsburg, St. Maarten | 6:00 AM | 7:00 PM |
7 | Charlestown | 8:00 AM | 5:00 PM |
8 | Roseau | 8:00 AM | 4:00 PM |
9 | Mayreau | 8:00 AM | 5:00 PM |
10 | Les Saintes | 6:00 PM | |
11 | Basseterre | 8:00 AM | 10:00 PM |
12 | Gustavia | 8:00 AM | 10:00 PM |
13 | Philipsburg, St. Maarten | 6:00 AM |