Set Sail: 5 Epic Sailing Stories
Five essential nautical stories to get you ready for regatta season.
Whether you’re planning to dominate the yacht club’s Wednesday night regatta this year or just want a good book to read on the dock, we’ve assembled a few favourite pieces of maritime lore (and a curated selection of stylish gear) to get you into the nautical spirit.
The Timeless Memoir
There are countless stories about epic ocean voyages, but even after more than a century Joshua Slocum’s account of his three-year 74,000-kilometre solo journey remains required reading for anyone with a yen for open water. Slocum grew up in Nova Scotia and in 1895, after an adventure-filled career as a merchant sailor, set out in a 36-foot sloop to become the first person to circumnavigate the world solo. Sailing Alone Around the World, which made Slocum a celebrity when it was published in 1899, chronicles his adventures, and remains as entertaining in 2023 as it was in Slocum’s day.
The Great Underdog Story
Like all of the best sports documentaries, you don’t need to know anything about competitive sailing to be enthralled by the historic upset of the 1983 America’s Cup race as told in this gripping film. Untold: The Race of the Century details how a group of scrappy Australians in short shorts broke the snooty New York Yacht Club’s 132-year winning streak to win sailing’s most prestigious trophy.
The Cult Classic
Captain Jack Sparrow has nothing on this swashbuckling tale of high-seas adventure based on Patrick O’Brien’s novels and directed by Peter Weir. Twenty years after its original theatrical release this story of friendship and courage aboard a British navy frigate remains as unapologetically enjoyable as ever, as much for its battle scenes as for the bromance between Russell Crow’s Captain Jack Aubrey and his trusty ship’s surgeon played by Paul Bettany. They don’t make ‘em like this anymore.
The Cautionary Tale
In 1968, ten yachts set out to circumnavigate the world in the Sunday Times Golden Globe Race, the first-ever non-stop solo sailing race around the world. The skippers ranged from seasoned sailors to complete amateurs, and only one would cross the finish line more than 300 days later. This meticulously researched book tells the story of what happened in between, including the bizarre tale of Donald Crowhurst, whose empty boat was discovered adrift in the Atlantic, and Bernard Moitessier, who was favoured to win before abandoning the race and sailing to Tahiti.
The Obligatory Castaway Story
What’s a list of classic sailing tales without a shipwreck? In the tradition of stranger-than-fiction stories like Endurance and In the Heart of the Sea, this is the grisly story of a doomed ocean voyage and the men who survived. Told by David Grann (whose previous bestseller, Killers of the Flower Moon, is currently being adapted into a film by Martin Scorsese), The Wager has all of the elements of a classic sea tale, including a Spanish galleon loaded with treasure, a drifting lifeboat, and allegations of cannibalism.