13 Of the Best Sailing Movies, You Can Watch Again and Again

I’m a recreational sailor. I’ve been sailing on Saginaw Bay since I was a little kid. We started off sailing Snarks and Sunfish. Our family loved sailing movies, and we watched them all. In the early 1970s, my dad took advantage of a marketing campaign by Kool cigarettes where we could purchase a Snark with the white and green KOOL logo on the sail. We still have this old boat and manage to bring her out to play with from time to time. One of the things that irk me is the lack of movie entertainment that revolves around my favorite pastime. I’ve managed to collect a few examples of movies with sailboats here.

Sometimes you can find these sailing movies streaming on Netflix, Amazon Prime, or Hulu.

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White Squall (1999)

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The true story of a bunch of boys, a ship, and the sea.

The movie White Squall is based on the 1961 sinking of a brigantine named the Albatross—a two-masted sailing vessel with a fully square-rigged foremast—White Squall is an exciting tale of adventure, friendship, and tragedy. This sailing movie stars Jeff Bridges as Captain Christopher “Skipper” Sheldon, who takes his charges on an epic voyage around the world on the Albatross.

Along the way, the boys learn how to sail and how to work together as a team. They also develop life-long friendships and forge incredibly tight bonds that they can only get from being in such close quarters with each other.

But then tragedy strikes: A white squall appears out of nowhere, sending massive waves crashing down upon their beloved ship. With their lives on the line and all hope of survival seeming lost, Skipper urges his boys to keep fighting for their lives—and trust each other above all else, no matter what happens next.


Wind (1992)

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Wind is a 1992 film directed by Carroll Ballard that follows Will Parker, played by Matthew Modine as he loses America’s Cup, the world’s biggest sailing prize, to the Australians and decides to form his own syndicate to win it back. Will hires Kate Bass, played by Jennifer Grey, to help him with his PR campaign.

The film co-stars Cliff Robertson as Morgan Weld, a businessman who offers to sponsor the team and pays for their yacht. Rounding out the cast is Jack Thompson as Michael “Brue” Brindley, a sailor who found success in racing and now manages an Australian team; Stellan Skarsgård as Bjorn Ericson, a Swedish sailor who sails for an American syndicate; and John McGlinn as Frank Hennessy, an Australian businessman who is investing in the Australian team.


All is Lost (2013)

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All is Lost is one of the most harrowing survival stories ever committed to film, All is Lost is a minimalist exploration of a man’s struggle for survival in the face of adversity. In this case, “adversity” means “the Indian Ocean.”

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The story begins with Robert Redford waking up halfway through a solo voyage across the Pacific. He finds that he has struck a floating shipping container, and his boat is filling with water.

Redford’s character is never given a name, but we do get to know him through his actions. He doesn’t panic when he discovers the leak; instead, he sets about repairing it as best he can. He rigs a jury-rigged sail to help him stay afloat while he waits out a storm. When the radio fails, there’s no bemoaning his fate; instead, he puts on his best poker face and keeps going. Each time he faces down yet another crisis and finds a solution, we learn more about him—and the stakes just keep getting higher.


Dead Calm (1989)

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A young couple on a yacht trip in the South Pacific encounters a damaged ship and its only living inhabitant. He is looking for a ride home, so he can return to his wife and kids. The captain is suspicious and refuses to take him on board. As the story unfolds, it becomes apparent that the stranger was responsible for slaughtering the other crew members and that his wife may not be waiting for him at all.

The director depicts this story in an original way, shot completely on a boat, as it sails through the Pacific Ocean. Although the story is fictitious, it still gives us some real sailing skills and challenges of open water navigation.

This movie Dead Calm stars Nicole Kidman, Sam Neill, and Billy Zane.


Morning Light (2008)

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Morning Light is a documentary that follows the youngest crew ever to compete in the Transpac sailing race. All crew members were between 18 and 23. The film follows the development of the Morning Light sailing team, their six months of sea training, and finally, the weeklong race across the Pacific between Los Angeles to Honolulu.

The film follows the young sailors as they develop their teamwork and learn to navigate under pressure and in high winds. The film also gives viewers a glimpse of the athletes’ personal lives: one woman struggles to find childcare so she can attend training while several others struggle with homesickness or the physical and emotional toll of leaving their families behind for months at a time.

The young sailors operate under incredible pressure: they are working hard to impress their sponsors (who have provided them with $2 million worth of equipment), they have only six months to learn how to sail, and they are constantly being compared to more experienced crews. They also must contend with a strict coach who pushes them harder than they’ve ever been pushed before.


Adrift (2018)

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When you’re out on the open sea, you never know what fate may bring.

For Tami and Richard, it was a once-in-a-lifetime adventure—and one they’ll never forget.

Adrift is the true story of their journey to love and their battle with Hurricane Raymond in 1983, considered one of the most destructive storms ever recorded. Tami wakes up in the aftermath of the storm to find Richard seriously injured and their sailboat in shreds and sinking. Now, Tami must summon all her will and strength to save herself… and Richard, with no possibility of rescue.

Starring Shailene Woodley and Sam Claflin, Adrift is an incredible tale for anyone who’s ever felt like they were fighting against the world.


Kon-Tiki (2012)

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It’s not often that you can come away from a movie with a new appreciation for the world around you—but that’s precisely what happened when I watched Kon-Tiki!

The movie is based on an actual expedition led by Thor Heyerdahl, a famous Norwegian explorer, and ethnographer, in 1947. Thor theorized that South Americans had settled parts of the South Sea Islands, and he wanted to prove his point. So, after months of preparation, he and five other guys set sail from Peru on a balsa-wood raft. They planned to use natural elements (like stars and ocean currents) to navigate their way through the sea.

It sounds impossible, right? But they did it! And they didn’t even have modern equipment like GPS or maps—just a radio. It’s one of the most incredible things I’ve ever seen. You should watch this movie; it leaves you feeling inspired about what you can accomplish if you believe in your aspirations.


Maidentrip (2013)

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The documentary, Maidentrip, chronicles the two-year journey of Laura Dekker as she attempts to become the youngest person to sail around the world. The video, directed by Jillian Schlesinger, is a testament to the human spirit and what can be accomplished when one pursues one’s ambition and works hard to attain it.

Dekker is depicted as a free-spirited outsider who finds her utopia in a never-ending sea. She is shown spending time with friends, getting tattoos, and enjoying life on her boat. While she does occasionally use bad language in the video, it never interferes with her message that you can accomplish anything you set your mind to if you are willing to work hard and overcome obstacles that may arise along the way.


The Endurance (2000)

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The Endurance tells the story of Sir Ernest Shackleton’s 1914-1916 journey to Antarctica, which is considered one of history’s greatest survival stories. Following the terrible death of legendary English polar explorer Robert Falcon Scott on his journey to the South Pole, Shackleton embarked on his third voyage.

Shackleton assembled a 27-man crew aboard his ship, Endurance, and set out in search of a new route across Antarctica from the Weddell Sea to the Ross Sea. The expedition was thwarted by ice near the Weddell Sea, and Endurance was trapped for nearly a year before being crushed by the ice and sinking. The men escaped with their lives onto the floes, where they remained for another five months before reaching Elephant Island. Five men stayed behind at the site of their camp as Shackleton sailed in a small boat with five others in search of help. He sailed 800 miles through dangerous seas to reach South Georgia Island, where he arranged for a rescue ship to save his stranded crew members. All 27 men survived this ordeal, which is considered an epic feat in polar exploration history.


Sea Gypsies: Far Side of the World (2017)

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Picture this: a gang of roving miscreants, with no licenses or insurance and an almost non-existent budget, is bound towards the most perilous seas on the planet.

This is almost the polar opposite of what you may have learned in your sailing classes. But for the crew of “Sea Gypsies: The Far Side of the World,” their story is one of adventure, courage, and determination.

In this heart-pounding documentary, a group of friends takes on the challenge of a lifetime: sailing from New York to Japan without any formal training, using only an old wooden boat that they built themselves.

“We knew it was crazy,” says Timmy Sniffles, one of the participants. “But we threw ourselves at it anyway.”

With three cameras on board to capture every moment and a host of experts who explain the dangers, they faced along the way, “Sea Gypsies” is a real-life thriller that will keep you glued to your seat.


The Old Man and The Sea Return to Cuba (2018)

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Finbar Gittleman is a 75-year-old master sailor. He has a mythical position among sailors in Key West and the Caribbean after living a rough and perilous life at sea. As he returns to Havana, Cuba for the first time since Castro’s revolution, this is his narrative.

The Old Man and The Sea Return to Cuba: Finbar Gittleman takes you on an adventure of sailing, perseverance, and self-discovery.

In this video, Finbar recounts his life at sea and how he came to be in Florida. He also shares some of the hardships he faced along the way as he struggled to make a living in the harsh environment of Key West.

He then describes the day when he decided to sail back home – through the dangerous reefs of Cuba – with nothing but his old boat, a compass, and some provisions.


The Mercy (2018)

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Featured on the Today Show and in the New York Times, this extraordinary narrative of amateur sailor Donald Crowhurst’s effort to solo around the world in the first race of its type, the 1968 Sunday Times Golden Globe Race, is told in “The Mercy.”

Crowhurst was an amateur sailor who dreamed of winning the race. Struggling with his business and family life, he decided to enter the race. He convinced a local businessman to support him and set about building a boat for the race.

The race was ill-fated from the start: one competitor died at sea and another disappeared without a trace. Crowhurst became increasingly unstable as he sailed around the world; radio transmissions from him became more erratic as he sailed on.

He finally returned to England, where he was declared the winner of the race due to his competitors’ fates. However, it was discovered that he had never made it past the Cape of Good Hope in South Africa and had falsified his log entries. He returned home in disgrace and committed suicide shortly after his return


The Weekend Sailor (2016)

It’s not often that a story like this comes along. “The Weekend Sailor” is a documentary about Ramon Carln, a Mexican man who, in 1974, wins the first crewed around-the-world sailing race on his boat Sayula II. The race is now known as The Volvo Ocean Race, and it takes place every three years.

The reason this story is so captivating? Carln wasn’t your typical sailor. He had very little experience with sailing, and he won the race with a crew of family and friends.

The film follows Carln’s journey: from his humble beginnings as a young boy when he began to dream of being a sailor, to his later years when he competed in the race and then won it (overcoming many obstacles along the way). It’s an inspiring story of determination and drive that you’ll want to watch with your whole family!


Upper Thumb Boating and Sailing – Here is another wonderfully produced video from LIVE Huron. This one focuses on Huron County boating and sailing opportunities with some great shots of Caseville harbor and breakwall

Interview with Author Jacki Howard – I reached out to Jacki Howard to see what she has done since the book was published 10 years ago. She is still involved with the book, but life has moved on. Like so many in the Thumb region, we are distant cousins. While we have never personally met, we found common ground with our interest in the “Dying Sparlings” Here is our exchange.

Boat Names – Transom Charm – The boat name you select may not seem like an important thing, but most of us feel that selecting the right name for our boat is important.

A Kool Little Cigarette Sailboat – In 1971 KOOL Cigarettes ran a unique marketing campaign. Magazines around the country ran an ad that if you sent in $88 and one box end from a carton of Kool cigarettes that this fully functional sailboat would be shipped to your door.

Michigan Monday – Saginaw Poet Theodore Roethke – Regarded as one of the most accomplished and influential poets of his generation, Roethke won the Pulitzer Prize for poetry in 1954 for his book The Waking.

The Amazing Michigan Photography of Steven Donahue – Steven was born and grew up on his family farm near Port Hope. He moved away and started studying the arts, including photography, in Chicago. He was in the military during the Vietnam War and became an MP. Part of his job was to photograph deaths and burials. A job I’m sure was not pleasant.

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