The story of a couple with a crazy dream and two schooners.

The story of a couple with a crazy dream and two schooners.
by Laura Boycourt


In 1992, a door closed and a porthole opened for Ken and Ellen Kaye. In that auspicious year, they left their jobs for a new adventure and set in motion a series of events that would change the Annapolis waterfront. The Woodwind story is one about family and living the dream. It’s about being under sail on a boat that moves so beautifully it just might be magic. Perhaps best of all, it’s a story that belongs to anyone who steps aboard.

The Dream

For the Kayes, it’s a steadfast love of sailing. During the early years, the two Connecticut school teachers and their daughter Jennifer enjoyed cruising and racing a variety of boats throughout New England, including a 12-foot dinghy, a Venture 21, a Sunflower, an Ericson 25, and a Niagara 31. The Kayes became smitten with the beauty of the Downeast schooners in Maine whenever they were cruising through. When they learned that Ken’s position as an instrumental music teacher was to be eliminated, he and Ellen decided it was time to go big or go home. After mulling over a handful of ideas about what their next chapter might hold, Jennifer, who was just finishing college, offered her two cents: “Dad, do the thing that you enjoy.” Ken and Ellen quit their jobs, sold everything, and took the leap. They’d build a schooner and invite the public to fall in love, just as they had in Maine. 

They had their work cut out for them, and they knew it. They were determined to get it right. “If you can’t do it better, why bother doing it?” Ellen says.

Doing Their Homework

By early 1992, the family was all in. Ellen gave herself a crash course in business. The pair traveled to research every piece of the endeavor. What were the Coast Guard regulations for a vessel offering sailing cruises? What was a prime, untapped port where locals and tourists could easily join in the fun? What did the numbers look like? One of Ken’s old-school spreadsheets proved that they could, in fact, make a profit.

 Jennifer made a trip to Annapolis and approached then-harbormaster Ric Dahlgren to ask his recommendation for a local excursion boat that could accommodate a large group of people interested in a sail. She knew that Baltimore had Clipper City and Norfolk the American Rover, but Annapolis had zip, nothing, no options. “So you’re telling me that in America’s sailing capital there’s no way that more than six people could go sailing on the same boat?” Jennifer asked, dumbfounded. Simply put, no other commercial Annapolis vessel had a Coast Guard certification of inspection allowing them to accommodate more than six passengers. Jennifer showed Dahlgren a photo of Madeleine, an inspirational double-masted schooner in Newport that sailed beautifully and met all the parameters of the Coast Guard—just what the Kayes had in mind. Dahlgren showed interest and pointed her in the direction of the aldermen to talk Annapolis code and get the ball rolling. She then spoke with the folks at the Annapolis Waterfront Hotel, and the rest is history. 

Woodwind Comes Home

In December, the Kayes were under contract with John Scarano of Scarano Boat Building in Albany to build a 74-foot, two-masted, staysail schooner. Her hull would be built of Port Orford cedar, her beams, Alaskan cedar, and the decks to support many happy passengers would be Douglas fir. Like expectant parents perusing baby name books, they worked their way through boat name guides for possibilities. Jennifer recalls many phone conversations with less-than-appealing suggestions from her folks. When her parents got to “W,” Woodwind appeared. A nod to Ken’s previous career, it had been in the back of their minds and was suddenly the clear choice. By May of 1993, Woodwind had come to life and was launched, bound for Annapolis. She was Coast Guard certified on July 2, enjoyed her first sail the following day, and hosted a packed house with just under 50 passengers on the Fourth of July. 

The team was doing something right. Robust demand inspired plans for a second vessel, and a sister ship, Woodwind II, arrived in Annapolis from Scarano in July of 1998. “The original boat was such a great design, why not keep it?” says Ellen. 

Memories Aplenty

From navigating the boat back into port during daunting storms to assisting actor Christopher Walken at the helm during the filming of “Wedding Crashers,” the Kayes have quite the collection of anecdotes from which to pull, and you’d think the experiences had very recently happened by the excitement and fondness that bubbles up each time they tell a story. 

Woodwind has been the setting for “some powerful stuff” over the years, Ellen says. Time on the schooner is a bit of magic, whether gaining a sailor’s on-the-water confidence, as a source of inspiration, or as a catalyst for emotional onboard experiences. For one passenger, a cruise was a treasured memory of time spent with a loved one. For others, a chance meeting aboard led to marriage. A gentleman with one leg was celebrating his birthday, threw his crutches below, and took control of the schooner, as thrilled “as if it was his own boat,” says Ken. A passenger suffering from dementia took the Woodwind’s helm, and, “as she she steered the boat, all the memories flooded back,” Jennifer says of another outing. Powerful stuff, indeed.

When you love what you do, and love who you’ve got along with you for the ride, it shows. The Kayes are head over heels for each other and both schooners, and for that, downtown Annapolis and the many guests who’ve been part of the Woodwind story over the past 25 years are no-doubt thankful. “It’s been a lot of fun,” says Ken. “I’ve always liked my office. There’s a lot of sailors, and so many of them think about this kind of thing. We did it. We actually did it. And not only that, the boats, to me, they’re magic.” 

Laura Boycourt is a freelance writer, mom to two little pirates, and lifelong boater from Annapolis who’s perpetually in need of a large coffee and a salty breeze.