Iolaire: The Last Chapter

The end has come for Don Street's legendary yawl, Iolaire.

Iolaire in her glory in happier days, powered up with full sail and a full crew racing off Antigua in the early 1990s.Beken Of Cowes

For legendary ­sailor and cruising-guide ­author Don Street, this past July 26 should've been a ­happy day: his 89th birthday. ­Instead, it will be a day Street remembers for all the wrong ­reasons—the day his beloved 46-footer, Iolaire, aboard which he roamed the Atlantic and the Caribbean with his family and friends over a half-century of ownership, was lost in heavy weather under the command of her latest owner off the coast of the Spanish island of Ibiza.

The boat’s rich history reads like a riveting maritime novel. What happened off Ibiza was just the sad, final chapter.

Street sold Iolaire in 2009. Before that, for five decades, the engineless red yawl was a ubiquitous presence in both Europe and the Eastern Caribbean, on both sides of the Atlantic, which she crossed seven times under Street's command. It's hard to imagine a sailor and his vessel being more intertwined than Street was with Iolaire. Street used the boat as his base to cruise, race, charter, explore and write, and his adventures spawned hundreds of magazine articles, the Imray-Iolaire charts of the Caribbean and Atlantic islands, three books, and his series of all-inclusive cruising guides.

Street has long maintained that, aboard Iolaire, through his own stories and travels, he demonstrated how accessible the Caribbean was, and that he played a huge role in opening up the islands to the throngs of cruising sailors and charterers that followed. And he’s absolutely correct.

The 114-year-old Iolaire already had a long legacy when Street acquired the shipwrecked boat, for $100, off a beach in St. Thomas, USVI, in 1959 after she'd washed ashore when an anchor shackle failed. "I resurrected her from the dead," he said.

Street has often said that if Iolaire's gimballed dining table could talk, "oh, the tales it would tell." Built in 1905, she was immediately commissioned for racing, as she was every year (except from 1940 through 1945, during World War II), right up to 2019. Among her distinguished owners were Rose Richards and Bobby Somerset, both of whom were founders of the venerable Royal Ocean Racing Club and served as its commodores. Over the years, countless great sailors crewed aboard Iolaire, including high-latitude explorer Bill Tilman, America's Cup legend C. Sherman Hoyt, and former submarine skipper Bill King, who became famous for his round-the-world voyage on Galway Blazer.

Iolaire's second life, with Street as captain, was nothing less than extraordinary. She survived three hurricanes: a pair in 1961 and Hurricane Klaus in 1984. There was a dismasting in the Anegada Passage in 1962, and the time she lost 10 feet off the top of the spar off Dominica in 1984. In that instance, Street sailed the boat home to Grenada with his 4-year-old daughter, Dory (who later sailed as a navigator while a member of Dennis Conner's America's Cup squad), and a Grenadian boat boy. And Street counts another half-dozen near disasters, "three of which were avoided by the skillful work of crew and skipper, and three by her own lucky streak."

Alas, Iolaire's luck ran out this past July, reportedly when she jibed accidentally while sailing dead-downwind, and then hit the bricks on the rocky shores of Ibiza. The crew managed to scramble into a life raft and made it ashore safely.

Street always believed Iolaire's massive main boom, left over from her days as a gaff-rigger, "could be a real widow-maker in an inadvertent jibe." For that reason, he spent years rigging, testing and perfecting various preventer systems to head off such a possibility. "This was obviously not rigged on July 26," he said.

Street, of course, was devastated by the loss, but has wonderful memories of "the long-lived and long-loved" Iolaire. "For 50 years, I lived on Iolaire," Street said, with an emphasis on lived. "I camped out when I came ashore!"

And there is a silver lining to this dark cloud, an epilogue to the grand story. Perhaps the best thing of all about Iolaire: Her skipper Don Street—who loved her more than everybody else—is not only as feisty as ever, he's still racing Dragons off the coast of Ireland, the oldest (and still most capable) in the fleet. Yes, Iolaire is gone. But Street sails on.

Herb McCormick is CW's executive editor.