The best sailing movies and shows, and where to watch them

The America's Cup, sailed on 12 Metres, by people who clearly loved the boats.

Matthew Modine plays a young helmsman who loses the America's Cup and sets out to win it back, in a story loosely inspired by the US losing the Cup in 1983 and winning it back in 1987. The plot is thin; the sailing is the best ever put on film for racers — real boats, real crews, and tacking duels that look like the real thing. If you only watch one film from this list for the racing, make it this.

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The first all-female crew in the Whitbread Round the World Race.

Tracy Edwards bought a battered old boat, put together a crew nobody believed in, and took on the 1989–90 Whitbread — and the sailing establishment that expected them to fail. Told largely through footage from the time, it's one of the best sailing documentaries ever made, and one of the best sports documentaries of any kind.

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Donald Crowhurst and the 1968 Golden Globe race: the darkest story in ocean racing.

The first single-handed, non-stop race around the world drew nine starters. Crowhurst, an amateur in an unfinished trimaran, fell behind, began reporting false positions, and never came home. This documentary tells it with his own logbooks and tapes. Haunting, and a lesson in the pressure a race can put on a sailor.

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The same Crowhurst story as a feature film, with Colin Firth.

Colin Firth plays Crowhurst and Rachel Weisz his wife, waiting at home. Watch it after Deep Water: the documentary tells you what happened, and the film tries to show what it was like.

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Laura Dekker sails alone around the world, starting at fourteen, and films it herself.

Dekker's own footage of her solo circumnavigation, after a Dutch court fight over whether she should be allowed to go. Quiet, funny and completely unlike a racing film — the story of a teenager who simply wanted to be at sea.

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Matt Rutherford sails solo, non-stop around the Americas in a 27-foot boat.

Rutherford went through the Northwest Passage and around Cape Horn in a small, old fiberglass sloop, and this documentary follows the voyage and the life that led to it. Inspiring proof that a big voyage doesn't need a big boat.

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Thor Heyerdahl crosses the Pacific on a balsa raft, in 1947.

Watch both. The 1950 documentary is Heyerdahl's own footage from the raft and won an Oscar; the 2012 drama tells the same voyage as a film and was nominated for one. Together they're the best evening of adventure on this list.

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Frank Hurley's own film of Shackleton's Endurance expedition.

Hurley was the expedition's photographer, and this is his footage: the ship trapped and crushed by the ice, the men on the floe. Silent and over a hundred years old, and still astonishing.

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Shackleton's expedition told in full, with Hurley's photographs and footage.

George Butler's documentary, The Endurance: Shackleton's Legendary Antarctic Expedition, narrated by Liam Neeson. The open-boat voyage to South Georgia is as good a lesson in seamanship as anything in this guide.

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Robert Redford, alone, on a sinking yacht in the Indian Ocean.

A yacht holed by a drifting shipping container, one sailor, and almost no dialogue. The seamanship is mostly right, which is rare in films, and Redford is extraordinary. Hard to watch if you've ever been alone on a boat at night.

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Tami Oldham's survival after a hurricane, with Shailene Woodley.

The film of the book in our gift guide: a yacht delivery from Tahiti caught by a hurricane in 1983, and a young sailor bringing the wreck to Hawaii alone. Read the book too — it's even better.

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A sailing school ship, a crew of teenagers, and a sudden storm.

Ridley Scott's film of the 1961 loss of the school ship Albatross, with Jeff Bridges as the captain. Part coming-of-age story, part disaster film, with some of the best tall-ship sailing on screen.

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A swordfishing boat caught in the storm of 1991.

George Clooney and Mark Wahlberg as the crew of the Andrea Gail. Not a sailing film, but the most famous picture of the sea at its worst — and the reason a generation of sailors started checking the forecast twice.

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Tom Hanks and the 2009 hijacking of the Maersk Alabama.

Paul Greengrass's film of Somali pirates seizing a container ship. A thriller rather than a sailing film, but gripping from start to finish.

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Square-rigged sailing in the Napoleonic wars, done properly.

Russell Crowe as Captain Jack Aubrey, from Patrick O'Brian's novels. The most authentic age-of-sail film ever made, from the rigging to the weather to the way a ship is actually sailed. The film sailors argue about least.

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Spencer Tracy in Hemingway's story of an old fisherman and a great fish.

A small boat, one man and the sea, in a faithful version of the novel. Slow and beautiful, and it won an Oscar for its score.

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The film of Robin Lee Graham's voyage around the world as a teenager.

Joseph Bottoms plays Graham, the sixteen-year-old who sailed around the world alone in the 1960s; Gregory Peck produced it. It isn't sold on Amazon or streaming that we can find, so look for a used DVD — and read the book, which is in our gift guide.

Johnny Depp, the Black Pearl, and five films of swashbuckling.

Nobody watches these for the seamanship. Start with The Curse of the Black Pearl, the best of them; the Blu-ray box set has all five.

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Four seasons of pirates, set before Treasure Island.

Starz's series follows Captain Flint and a young Long John Silver in the Caribbean. Darker and smarter than Pirates of the Caribbean, and the ship scenes are good. The complete series is on Blu-ray.

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Kurt Russell as the worst delivery skipper in the Caribbean.

A family inherits a yacht and hires Captain Ron to sail it home. Every sailor has met a Captain Ron, which is why this is the most quoted film at any yacht club bar. Pure fun.

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Tom Hanks, a desert island, and a volleyball named Wilson.

Not a sailing film until the end, when he builds a raft to get off the island — and that sequence alone earns it a place here.

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Two survival thrillers that will make you count heads before leaving a dive site.

The first leaves two divers behind in the open ocean; the second strands a group of friends who jump off a yacht without lowering the ladder. Not for everyone, and the second one is a lesson every boat owner should take seriously.

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Two surfers chase summer around the world.

Bruce Brown's surf documentary isn't about sailing, but it's about why anyone goes to sea in the first place — the search for the perfect day on the water.

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