A career on the bay

at work

Jennifer Kaye, captain and general manager, Annapolis Sailing Cruises: Schooner Woodwind, Annapolis

April 12, 2009|By Nancy Jones-Bonbrest | Nancy Jones-Bonbrest,Special to The Baltimore Sun

Salary: $55,000

Age: 38

Years on the job: 16

How she got started: A Connecticut native, Jennifer Kaye spent her summers sailing and racing with her parents, Ken and Ellen Kaye, who were both public school teachers with summers off.

As Kaye was graduating from Marist College in New York with a degree in public relations and communications, her father called to tell her that the music program at his elementary school would be discontinued. So the family decided to start a sailing business, something they had always thought about.

Annapolis won out as the best location, and by 1992 they had a contract signed with a boat builder and with the departure site, the Annapolis Marriott Waterfront Hotel.

Typical day: During sailing season, which starts April 11 and runs through October, Kaye finds herself sailing about 35 to 40 hours a week and spending about 10 or 15 hours on administrative work in the office. She works 12-hour days and takes off two days a week.

The company owns two 48-passenger, 74-foot classic wooden schooners, the Woodwind and the Woodwind II. The schooners are used for private parties, corporate team building cruises, overnight boat and breakfast cruises, dinner cruises and wine tastings.

The most popular trip is the two-hour public cruise offered four times a day, seven days a week from the Marriott.

Kaye captains the boat and has three crew members. For the public cruises, she'll start her day at 9:45 a.m. getting the boat cleaned up, stocked and ready for passengers. They have a half-hour turnaround time in between and finish for the day about 9:30 p.m.

During the cruises, they offer information about the schooner, the Chesapeake Bay and surroundings, but keep it conversational so passengers feel as if they are taking a trip with friends and family. The job is a physical one, but passengers get to help sail the boat if they wish.

"I get to spend my day sharing something I love, which is sailing on the Chesapeake Bay, with up to 200 people [a day]."

During the off season, she works a more typical 40-hour week, which is spent planning for the next season, lining up advertising and other office work. This year, she also took off one month to sail, including racing in a regatta in Key West, Fla.

Film work: Kaye got to rub elbows with the Hollywood elite in 2004 when the boat was used for the film Wedding Crashers. "The coolest thing was that boat on the big screen," she said.

New this year: Kaye and her father will take passengers out for the Wednesday night Annapolis race series. Both boats will race against each other as well as more than 130 other boats.

Mishaps: It's usually smooth sailing, says Kaye, who has never had a guest fall overboard.

The good: Turning someone on to sailing, the beauty of the Chesapeake Bay or the history of Annapolis, Kaye says. "We do it all."

The bad: "Not the perfect weather."

Destination of the two-hour cruise: "That's the beauty of sailing. Some days we can get to the Bay Bridge and back or out to Thomas Point Lighthouse, and sometimes we stay in the Severn River." No matter what the weather, they always sail past the Naval Academy.

Philosophy: "Always staying positive."

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