Wind Surf sails alternating seven-day northbound and southbound itineraries roundtrip from Bridgetown, Barbados. Combined, they offer an ideal opportunity to sail for 14-days visiting islands in the windward and leeward chain. The northbound itinerary visits Nevis; St. Martin; St. BarthÃ©lemy; Basse-Terre and Les Saintes, Guadeloupe; and St. Lucia. The southbound itinerary visits Bequia, Dominica, St. Lucia, The Grenadines, Grenada and Tobago. Both itineraries offer a mix of attractions – white sand beaches for sunning and swimming, tropical forests for nature hikes, quaint towns for a peek at how the locals live, and parks and historic sites to explore. On 14-day cruises, part of Windstar’s Connoisseurs’ Collection, guests receive up to 10% off the total cost of the cruise depending on date and itinerary.