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Sydelle Gifford: Jamaica’s First Female Boat Captain

Captain Sydelle Gifford with First Mate Jason Powell
Captain Sydelle Gifford with First Mate Jason Powell

Sydelle Gifford has been a boat captain with Island Routes Caribbean Adventure Tours since 2011, but water has always been part of her life. As a child, her parents owned a water sports business on the beach in Negril. When the business shut down in the 1990s, she became involved in scuba diving, water skiing and parasailing. As a child, she started sailing as a hobby and later this grew into a job opportunity. Now in command of the 65ft catamaran Kool Kat Kelly, Gifford is Jamaica’s first ever female boat captain.

Gifford’s hometown of Negril, a resort on Jamaica’s east coast, is a tourist friendly area that she remembers as “a good place to grow up.” Although there isn’t much yachting in Negril, there are lots of other water sports in which locals and tourists can get involved. Gifford says she wouldn’t be a boat captain today if she hadn’t been raised in Negril.

Like many residents of the town, Gifford worked at various hotels and resorts before joining Island Routes. Her previous resorts had sailing programs and, during her training at Island Routes, she became a regular member of a boat crew. As crew, she assisted the captain with navigation and maintenance.

Later, her manager encouraged her to train as a boat captain and in 2011 she passed the exam and received her letter of acceptance.

As the captain of Kool Katt Kelly, Gifford is in charge of the scores of tourists who sail on the boat and oversees a crew of eight.

Kool Katt Kelly is licensed to carry 120 people and onboard entertainment includes a water slide, open bar, and a live DJ. Crew includes first and second mates, navigational crew, and a bartender. Gifford typically sails for three hours along a seven mile stretch of coast that offers breathtaking views. Sailing twice a day, the afternoon Reggae Catamaran tour is family friendly and for children to enjoy sailing along the coast with stops for snorkeling.

Although she has accomplished so much, Gifford says she is still learning and even though she holds a coxswain license, she takes classes to keep up with changing technology.

Working to a busy schedule, Captain Gifford still finds the time to be a mother – she has a 14-year-old son in eighth grade, and a daughter who is nearly four. One daughter has Down’s syndrome, and Gifford is a member of the non-profit Jamaica Down’s Syndrome Foundation (JDSF), where she has the opportunity to work with parents and therapists. The parents in the foundation work on behavioral challenges and physical and speech therapy. They also work with children with autism.

Juggling life as a yacht captain and her work for the JDSF is not without its challenges, not least of which is the long drive from Nagril to Kingston to support the foundation. She has been fighting to get more resources to her hometown but notes it’s hard to balance work and family. “I don’t know how I do it,” she admits.

Sometimes, she takes her children out on the catamaran. “Being out on the sea with dolphins and sting rays is fun for them,” she says and recommends that children get into water sports.

Gifford says not many women sail but she encourages them to try it. She suggests that women in her area could start by working in water sports and notes that hotels usually have diving, tubing, wind surfing, fishing, and sailing. “The lifeguard exam is given once a year in Negril. I suggest you first take that and then apply for a job at a water sports facility.”

Saba Igbe is a freelance writer based in Kingston, Jamaica. He is a contributor to The Jamaica Observer, Rue Morgue and World War II Magazine.

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