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When Maggie Shipstead set out to report on women-only expedition travel, she was driven by a desire to learn new skills in a low-bro-factor environment. But six days exploring Alaska with the state’s first woman-owned adventure outfitter turned out to be regenerative in ways she didn’t expect.

The first Golden Globe Race, a solo, nonstop, around-the-world sailing event held in 1968, was a mixture of triumph, tragedy, and madness—all chronicled in a classic bestselling book and recent BBC movie. Fifty years later, 17 sailors are once again setting out for the most ambitious—and loneliest—regatta on the planet.