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Sailing With the Boy

The truth is, at first, she didn’t really consider bringing the boy. In fact, a powerful part of her wasn’t sure she wanted to.

It was the same part that had pushed her multiple times through the WaterTribe Everglades Challenge—300 unsupported nautical miles in a kayak through Florida’s labyrinthine, mangroved wilderness. That had jumped aboard a 6,000-plus-mile, two-month-long yacht race from Auckland, New Zealand, to Fukuoka, Japan, after spotting an ad for an all-women’s entry that needed one more crew. That had convinced the leader of an expedition up Mont Blanc—at 16,000 feet the highest peak in Europe—that she was perfectly capable of making this her first real high-altitude alpine climb.

There is an element of Kristen Greenaway’s character that thrives on pitching herself against the odds and that craves the deeply personal challenge of solo endeavor. And even though her role now as president and CEO of the Chesapeake Bay Maritime Museum—a job demanding the unrelieved navigation of political and social intercourse—seems to proscribe solitude’s pure self-containment, there’s one place she knows she still can find it: sailing Magdalena, her 1986 Cape Dory 32.

And so, when the museum’s board granted her a two-month “seabattical” in the summer of 2022—eight years after she’d started running the museum, two years after guiding it through the shutdowns and economic hardships of the Covid-19 pandemic, six months after the museum launched the new Maryland Dove, its five-million-dollar, first-ever build of a ship from the keel up—she was bloody ready to go sailing alone for a good long while. Two months from the Chesapeake up the East Coast to Maine and back. Bliss.

So, at first, no, she didn’t consider bringing the boy. And anyway, he’d probably be happier pursuing his true passion of playing golf, staying umbilicaled to the internet, hanging with friends.

Also, there was Lori, the boy’s other mother and Kristen’s wife, who wasn’t entirely sold on extended sailing without a shower, truth be told. The thought

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