STAR COLLECTOR: LOVELY LEEWARDS on Star Pride
Cruise, Ocean cruise, Small Ship/Yacht
Exterior view of Star Pride sailing near Manhattan, New York
Whether you’re passionate about swimming among rarely seen undersea wildlife or the intricate cultures and intertwined European histories of the Windward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands normally associated with places like Madison Avenue, but displayed in an ambiance that’s anything but intimidating. Master the art of cooking with distinct spices like nutmeg, cloves, and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg. This Caribbean getaway is the perfect duration for lovers of island life and those who want to spend more time exploring the Windward Islands overlooked by other cruise lines.
About Star Pride
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.
Nov 29, 2026 through
Dec 13, 2026
Nov 23, 2026
7:00 PM
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Dec 13, 2026 through
Dec 27, 2026
Dec 7, 2026
7:00 PM
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Dec 27, 2026 through
Jan 10, 2027
Dec 21, 2026
7:00 PM
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Itinerary
| Day | Port | Arrive | Depart |
|---|---|---|---|
| 1 | San Juan | 7:00 PM | |
| 2 | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | 8:00 AM | 6:00 PM |
| 3 | Gustavia | 8:00 AM | 10:00 PM |
| 4 | Basseterre | 8:00 AM | 5:00 PM |
| 5 | Philipsburg, St. Maarten | 8:00 AM | 10:00 PM |
| 6 | Jost Van Dyke, Great Harbour | 9:00 AM | 10:00 PM |
| 7 | Virgin Gorda / Prickly Pear, British Virgin Islands | 8:00 AM | 5:00 PM |
| 8 | San Juan | 7:00 AM | 7:00 PM |
| 9 | At Sea | ||
| 10 | St. George's | 9:00 AM | 10:00 PM |
| 11 | Bequia | 8:00 AM | 10:00 PM |
| 12 | Mayreau | 8:00 AM | 5:00 PM |
| 13 | Les Saintes | 10:00 AM | 5:00 PM |
| 14 | Marigot, St. Martin | 8:00 AM | 3:00 PM |
| 15 | San Juan | 7:00 AM |
