“I create parties I would like to throw, and people come to be part of it,” says Captain Jennifer Kaye. Across the Bay in Annapolis, the 74-foot, two-masted staysail schooners Woodwind and Woodwind II have had White House fellows, Girl Scouts, and actors and film crews among their passengers since launching operations in 1993. A scene from the 2005 movie, “The Wedding Crashers,” was filmed aboard the 48-passenger Woodwind II, and the schooner recently hosted photo shoots for the Vineyard Vines line of clothing. Guests choose from regular two-hour sails, special brunches, cocktail cruises, “Wine in the Wind” cruises, “Everything Local” dinner party cruises, sunset sails, lighthouse cruises, and fireworks cruises as well as race night, beer-tasting, and local music and history cruises. “I create parties I would like to throw, and people come to be part of it,” says Captain Jennifer Kaye. One of those parties, which happens only once every three or four years, is planned for mid-August when Hugh Sisson, owner of Heavy Seas Brewery, will lead a “Crafty Brews on the Heavy Seas Dinner Cruise” featuring a four-course dinner pairing beer with names like Small Craft Warning, Loose Cannon, Peg Leg, and Red Sky at Night with sailing. Another party is the annual Mother’s Day brunch cruise. A couple of years ago, it was scheduled for a day the wind was blowing 30 mph and gusting to 40 mph. “We sail in all conditions unless we are pinned to the dock,” Kaye explains. But how were they going to serve the food? “We put one sail up, went downwind, and served brunch,” Kaye says.
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“As soon as everyone got food, we told them to prepare for a fun ride.” It took a nine-year-old fearlessly taking a turn at the wheel under the tutelage of the captain to put some whiteknuckled passengers at ease. But probably the ultimate party experience is participating in the Wednesday night match racing between father (Captain Ken Kaye) and daughter (Jennifer), each at the helm of a Woodwind, followed by a “Party Like a Sailor” experience at The Boatyard Bar & Grill. “We used to go out and just watch the (Annapolis YC) Wednesday night races,” Jennifer Kaye says, “but a couple of years ago, we came up with the match racing idea… It gives the experience of being on a race boat without having to work.” One thing all cruises have in common, Kaye says, is the magic moment. “In the first 15 minutes we are away from the dock, we raise the sails and turn off the engine. I say to the passengers, ‘Do you know what is the best part of sailing? When you turn off the engine. It’s magic when you realize it’s all wind.’” About the Author: Jean Korten Moser is a journalist and USCG-licensed captain who sails out of Rock Hall on a Caliber 38.
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