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Capt. Kathy Pennington and I are chatting in the cockpit aboard the Oyster 125 Twilight. The yacht is the British builder’s flagship, a study in Dubois naval architecture with a new sparkle in her spinnaker, fresh from a hull paint job and interior updates following an ownership change.

We would discuss all that, of course, but Pennington is one among so few female charter-yacht captains that I can count them on one hand. So we first talked about the treatment she typically receives as she sails throughout the Caribbean and Mediterranean.

“Men,” she says with an eye roll. “You know, you call them on the radio and they say, ‘Can I speak to the captain?’ And I say, ‘I am the captain.’ And there is just shock.”

Capt. Kathy Pennington, S/Y Twilight

Capt. Kathy Pennington, S/Y Twilight

Pennington decided to address the lack of respect a few years ago, just before the start of the summer season in Spain’s Balearic Isles. At the time, she was captain aboard the 118-foot (36-meter) Abeking & Rasmussen Tiziana, a sailing yacht built in 1963.

She brought the classic hull into a marina slip in Palma de Mallorca while standing on deck wearing a pair of Crocs, a bikini and her hair in pigtails.  

“I just wanted to show them that it could be done,” she says with a beaming smile. “It was hilarious.”

Now in her late 30s, Pennington is combining her playful nature with years’ worth of experience to create Twilight’s new charter program. I can guess by the mischievous look in her eyes that she still has that bikini somewhere on board, but professionalism and the maturity forged by one particularly tough life lesson have pushed it to the back of a cedar-lined closet.

She was born and raised in South Africa, where she sailed with her father. Unlike many captains, she didn’t follow a straight path from that upbringing to a life on the water; after high school, she lived with extended family in London, where she became a hairdresser.

But then, in 2001, her 24-year-old brother died. The cause was melanoma of the bones. She was 23, and she thought the disease might be genetic.

“I said, ‘Okay, is this going to be me?’” she recalls.

All of a sudden, trimming bangs seemed a waste of what might be exceptionally precious time.

“Dad and I bought a boat, a Lavranos 37,” she says. They sailed from England to France, Spain, Portugal and Gibraltar. She became a PADI scuba instructor. She did deliveries to earn her Yachtmaster certificate.

And she considered going back ashore. Once.

“The guy I was dating was talking about marriage and kids,” she says, “so I got on the first boat I could and sailed away across the Atlantic.”

At 28, she landed in Antigua and fast realized she had more skills and experience than a lot of the guys working aboard bigger yachts as mates. She walked the marina docks and came upon Tiziana, whose captain and stewardess were on the aft deck. By 10 a.m., she had a job as a deckhand/stewardess. Six months later, she was first mate. A year after that, she was captain. She remained on board for nine years, until October 2016, when she took Twilight’s helm.

When I met her last spring, Pennington was one test away from her Master of Yachts 3000GT certification, a goal she hoped to achieve during the off-season.

“I just have to do my oral exam,” she says, “but everybody wants to charter Twilight, so I have no time.”

The plan is to set a course that follows charter demand, taking guests wherever they want to cruise in the Mediterranean and Caribbean. During winter 2016-17, her first aboard Twilight, the yacht spent a good deal of time in the Grenadines. Pennington says she’d be happy to return.

She expects to do further upgrades under the new ownership, too, including a five-year survey that was scheduled to begin this past October.

“It’s having the time to really go and nitpick,” she says, thinking about more ways to enhance the charter experience. “That’s what we’re doing now.”

Pennington hired a favorite chef, Jean Matthee, as part of Twilight’s new crew. He’s also South African and, she says, “is amazing. Sushi, Thai, pastas—pastas that are the proper al dente—he’s just excellent.”

She barely pauses before adding, with a cheeky smile, “And he’s lovely to look at.”

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