JEWELS OF THE WINDWARD ISLANDS on Wind Surf
Cruise, Ocean cruise, Small Ship/Yacht

Exterior view of Wind Surf sailing near Capri, Italy
Photo Credit: Roger Paperno
This is the Caribbean of days gone by – deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.
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.
Jan 18, 2026 through
Jan 25, 2026
Jan 12, 2026
7:00 PM
Category b
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Itinerary
Day | Port | Arrive | Depart |
---|---|---|---|
1 | Bridgetown | 6:00 PM | |
2 | Anse Mitan | 9:00 AM | 11:00 PM |
3 | Pigeon Island | 6:00 PM | |
3 | Castries | 8:00 AM | 4:00 PM |
4 | Pigeon Island | 6:00 PM | |
5 | Bequia | 8:00 AM | 10:00 PM |
6 | Mayreau | 8:00 AM | 6:00 PM |
7 | St. George's | 7:00 AM | 2:00 PM |
8 | Bridgetown | 6:00 AM |