Happy 30th to the Schooner Woodwind Sailing Family!
This summer an institution in the Annapolis waterfront community marks 30 years of sailing. The Schooner Woodwind, docked in downtown Annapolis, has for three decades welcomed aboard tourists and locals alike to experience joy of casting off from an Annapolis bulkhead and plying into the brackish waters of the Chesapeake.
Over the years, the Kaye family, Ken, Ellen, and daughter Jennifer Kaye—who own and operate the business—have introduced thousands of people to sailing. Along the way they’ve become an important part of the fabric of this historic waterfront town.
The story of how it all began goes like this: when the instrumental elementary school music program that Ken taught for 25 years was cut from the curriculum, he and Ellen retired from their teaching jobs in New England. At the time, Jen was about to graduate from college, during which she had spent a semester at sea aboard a schooner. All three were active sailors and ready for a new adventure.
They looked at many similar businesses that took guests out on boats, and they methodically researched the idea, riding as guests aboard other head boats, taking notes, and developing their business plan. They selected Annapolis as their home port, commissioned a new, 74-foot schooner, and began welcoming customers in June of 1993. To meet the demand for their popular group and private sails, five years later they added a second, identical boat, Woodwind II.
Captain Jen says, “We wanted to take our business to a higher level than the other head boats we had seen. We were advused to became involved in the Annapolis community, which we did, and whenever we were on the boat with customers we made it a point to share our knowledge and enthusiasm about sailing and the local area.”
Captain Ken, who generally speaks in measured tones, gushes with pride when asked about Jen’s role in the business. He says, “Jen is the center of it all. She sails the boats, organizes the business, and makes sure everything works properly. She has this wonderful ability to know where she is in the world and what’s happening around her. When she’s captaining a race, she can keep track of the crew, the water, the wind, the other boats, and the racing strategy. She always pays attention to whether the guests are enjoying themselves and how we can improve their experience. She has high ideals and has done a phenomenal job.”
For her part Jen says, “We’ve always treated everyone like friends and family. My biggest pleasure has been to see my family’s impact on others. We’ve been mentors to so many young people that we’ve hired, and lots of them have gone on to live their own big dreams, in marine careers and other fields too. We keep in touch and are so proud of all of them. Their successes show what can happen when you hire people who are passionate and enthusiastic and create a space in which you can tell them, ‘Go, do this with guts!’”
For more about the Woodwind boats and business, including tickets, sail times, fun facts, videos, photos, private cruises, and more, go to schoonerwoodwind.com.
