It reads like something out of a Thoreau novel: summering on a secluded tropical isle, bone fishing in a mangrove forest and island-hopping in a sailboat. But that’s how Dana Hokin spent her childhood summers on her family’s private retreat in the British Virgin Islands. Luckily, the Hokins’ slice of paradise is no longer exclusive: Over the last 37 years, the family has transformed their hideaway into the Bitter End Yacht Club, a luxe resort and must-visit for sailors and water-sport enthusiasts. “There are no roads that lead to Bitter End,” Hokin explains. “The only way you can get to our part of the world is by boat. It’s all like-minded people.”
Though the resort was started by her grandfather, Hokin, 46, took the reins 20 years ago, overseeing the company from within its Chicago headquarters. Under her guidance, Bitter End has grown to employ nearly one in every five people on the island of Virgin Gorda — and it now boasts one of the most impressive water-based recreational facilities in the Caribbean. For no additional fee, guests of the resort can hop into one of the more than 100 kayaks and high-performance sailboats, spend an afternoon stand-up paddle-boarding or embark on one of 15 snorkeling trips offered by the resort every week. As a result, the Bitter End boasts A-list fans like actress Chloe Sevigny and billionaire tycoon Richard Branson.
While the resort has expanded over time, Hokin has made sure it maintains ties to her childhood. “A lot of the excursions that our guests go on today are the activities I did with my parents and grandparents as a kid,” says Hokin. “That’s why the model has held all these years. We’ve grown organically, and people feel it. It doesn’t feel like we were constructed in a boardroom in Chicago.”
If a quick jaunt to the British Virgin Islands isn’t in your travel budget, fear not: Hokin has found a way to bring a piece of the Bitter End home. This month, she’s launching a line of nautical-inspired bath and beauty products called Captain B’s, in honor of her grandmother, Bernice. Paying homage to Bernice’s spunky sensibility, Hokin gave all of the products playful names, like Scales Belong on the Fish lotion and Zero Knots conditioner. “It’s cute and spirited, [like] my grandmother was,” she says.
Here, the seafaring CEO takes a break from paradise for a serene Sunday in the city she calls home.