The Woodwind Family
The owners of Woodwind, Captain Ken and Ellen Kaye, were public school teachers, who decided to retire while still young (after teaching for 25 years).
They dreamed of someday owning a schooner to introduce people to sailing. After their daughter, Jennifer, returned from a semester at sea aboard a 125′ schooner, the family pursued their dream in earnest. They had their handsome vessel custom designed and built based on their knowledge gained from more than 20 years of sailing. They fell in love with Annapolis and moved here after spending all their lives in Connecticut.
Jennifer became a Captain in 1996 and joined them full time. A second, identical “Woodwind“- named “Woodwind II” was the latest addition to the family in 1998.
The extended “family” of crew members are chosen for their sailing knowledge, friendliness and enthusiasm. These are the qualities that make your on board experience a special one.
History of the Two, Identical 74-foot Schooners
1992
December
Schooner Woodwind was Contracted to be Designed
Schooner Woodwind was contracted to be designed by John Scarano for Ken and Ellen Kaye, from Wallingford, CT. The schooner was specifically designed to provide a fun sailing experience for guests.
1993
May
The schooner was finished!
The schooner was finished at the Scarano Boat Builder’s Yard in Albany, NY. Her hull was made of Port Orford Cedar ribs and then strip planked with the same material, her decks Douglas Fir, and a thin sheathing of fiberglass on the outside of the hull.
June
Woodwind’s first voyage!
Woodwind’s first voyage! She was sailed down the Hudson River, up the Delaware Bay, through the C & D Canal, and down the Chesapeake Bay to Annapolis.
July
Certification of Inspection
The U.S. Coast Guard gave Woodwind the Certification of Inspection for 49 passengers, and our kick off sail was on July 3. Schooner Woodwind was now sailing the Bay four times a day with as many as 48 passengers. The dream became a reality.
1996
October
Our First TRIFECTA RACE WIN
The Great Chesapeake Bay Schooner Race
1995: The first time we won the TRIFECTA of the Great Chesapeake Bay Schooner Race! TRIFECTA means First over the Finish Line, First in Corrected Time in our Class AND First Overall! This was the first of 8 Trifecta wins of the race (as of 2022). This one was extra special because it was our first big win and we only had the boat for 2 seasons. We had a fine crew of guests and our professional crew. We had a finish time of 23 hours, 3 minutes, 59 seconds.
1997
July
The Dream Became a Reality
Woodwind was very busy with many private charters and public cruises. We realized, in order to keep up with the demand for both private charters and public cruises, a second, identical Woodwind would be needed. The same boat builder was called to construct the new one.
July
A Second Identical Boat Was Commissioned
After the first successful Schooner Woodwind, the owners needed another Schooner for increased demand.
1998
July
“Woodwind II“ was Completed
“Woodwind II” was completed and sailed down to Annapolis the same way Woodwind was delivered. After three short weeks, we were up and running with both schooners.
2004
May & June
“The Wedding Crashers“
Christopher Walken at the helm of Schooner Woodwind II in Wedding Crashers
“Woodwind II” was selected to be the sailing yacht of Christopher Walken’s character in the movie, “The Wedding Crashers”. The filming took place in Oxford, Cambridge, St. Michael’s and on the Choptank and Miles Rivers. New Line Cinemas booked the boat for 9 days to film the scenes for the movie starring Vince Vaughn, Owen Wilson, Rachel McAdams, Jane Seymour, and Christopher Walken. The name of the boat was kept the same for the movie
2018
July
Celebrated 25 Years
2021
October
WON THE TRIFECTA of the Schooner Race
1st in class, 1st over the finish line and 1st overall
The year we won the TRIFECTA of the Great Chesapeake Bay Schooner Race with the biggest lead!
TRIFECTA means First over the Finish Line, First in Corrected Time in our Class, AND First Overall! On corrected time (applying a handicap) the difference was 5 hrs: 39 min: 28 seconds. It may have been our largest win over our competitors, and we have been doing the race since 1993!
The crew consisted of Captain Mickey Lawlor, Captain Jen Kaye, Captain Ken Kaye, Rai Muhlbauer, Delaney Vorwick, Chris Garau, Courtney Boucher, and Dallas Elms. Guest Crew of Gene McCollum, Brett Harrison, Chris Lundberg, and Susan Brannigan worked hard for this amazing victory.
2023
March
Celebrated 30 Years
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