SAIL

First Times the Charm

It happens in a moment of weakness. Perhaps my wife is distracted, perhaps she buckles under the gray of the winter sky. Even though Danielle’s idea of a Caribbean vacation features white sandy beaches, a comfortable hotel room, and dinner at a seaside restaurant, she says yes. Two days later I book a sailboat charter in the Caribbean for the spring.

Our son, Owen, grins when I tell him it’s an Oceanis series Beneteau, and our daughter, Avery, jumps up and down and asks whether there will be sea turtles. Daughter Hannah does a ballet twirl, her whole face alight. Then Avery asks, “Will there be sharks?” and shudders, and Danielle says, “We’ll be on the open ocean?”

I try to convince them the sharks are in the deep water away from the islands and that it’s like sailing on the lake—we’ll always be able to see land.

If there ever was a more anticipated vacation, I can’t remember it. Over the next six months, I spend hours at the kitchen table calculating distances between islands, researching anchorages, and routing and rerouting itineraries. I watch Sailing Virgins YouTube videos, re-read John Rousmaniere’s , listen to 59 North podcasts, and devour John Kretschmer’s As the trip draws near, the Amazon deliveries grow exponentially: Sea-Bands, reef-safe sunscreen, UPF shirts, snorkel equipment, duffle bags, and bathing suits. We talk about the trip every night at

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