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Ken, Ellen and Jen
Schooner Woodwind is a family business

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



Schooner Woodwind was Contracted to be Designed

Schooner Woodwind was commisioned late 1992. This picture was taken in eary 1993.
Schooner Woodwind in construction, early 1993.


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.



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.


Woodwind’s first voyage!

Schooner Woodwind's first sail in Annapolis, Maryland
The first sail for the Schooner Woodwind in Annapolis.


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.


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.




The Great Chesapeake Bay Schooner Race

The start of the Great Chesapeake Bay Schooner Race with 4 schooners in picture

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. 



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.


A Second Identical Boat Was Commissioned

Building of the Schooner Woodwind II for Annapolis, Maryland
Late 1997, the building of Woodwind II


After the first successful Schooner Woodwind, the owners needed another Schooner for increased demand.



“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.


May & June

“The Wedding Crashers“

Christopher Walken at the helm of Schooner Woodwind II in 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



Celebrated 25 Years

Schooner Woodwind 25 Years Merchandise



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. 



Celebrated 30 Years

Schooner Woodwind