FEBRUARY
2018
67AT THE HELM
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/steward-
ess. 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 certifica-
tion, 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.”For more information: Oyster Yacht Charter,
oysteryachts.com From large salon windows
to a swim platform
with shower, Twilight has
superyacht-style features.