Once, not so long ago, a passage around Cape Horn was a necessary evil for the crews of clipper ships on trade routes between Atlantic and Pacific ports of call. Today, a rocky promontory on a windswept island at the very bottom of the world commemorates the sailors’ lives lost making that passage. While the sine qua non of the voyage has long since been supplanted by the Panama Canal, the thrill remains for the adventurous few willing to face the unpredictability of the Southern Ocean, with gale-force winds, icebergs, and unrelenting seas. Maybe that’s why a rounding of the Horn is still considered to be the boating equivalent of climbing Mount Everest. True, gyro and fin stabilizers have made the journey more comfortable. But as Jeff Druek, president and CEO of Outer Reef Yachts, learned when he joined a good friend and client aboard an 880 Cockpit Motoryacht to make the journey of a lifetime, having the right boat for the excursion is everything. With Southern Patagonia’s dramatic landscapes, snow-topped peaks, azure glaciers, and far-flung cities to explore, this doable trip (with the right planning) should move up a couple notches on your bucket list. —S.M.