Nothing can inspire dreamers quicker than an evening of streaming old sailor movies. Sailing adventure movies can be terrifying survival stories or inspirational documentaries about sailors pushing their limits. Unfortunately, Hollywood blockbusters are rarely sailing-related, but there are a few examples out there that will get the seawater in your veins pumping.
Feature Films and Big Productions – Best Sailing Films of All Time
In no particular order, here are my top picks for the best sailboat movies. Good sailing movies can be divided into two categories. Most are about survival at sea, less a sailing movie and more of a drama set on a sailboat. Others are feature films, sailor movies complete with sailing action and exploration. Let’s start with those.
It’s the year 2500, and the ice caps have melted, and sea level rise has claimed the world. The Mariner (Kevin Costner) lives as a wandering nomad on the oceans in his custom-built trimaran. Chased by thugs on jet skis, he leads a search for a mystical place called the “Dryland.”
Ok, it’s ridiculous, and it was a complete flop at the box office when it was released. But Costner’s trimaran is pretty cool. And what cruising sailor doesn’t envy him, with his sad little tomato plant and total freedom?
White Squall (1996)
Based on a true story, White Squall is the story of the brigantine Albatross and her crew of college-aged men. Directed by Ridley Scott and staring Jeff Bridges as the salty Skipper, the movie is captivating and authentic.
The Albatross was a teaching vessel, and Skipper was there to teach the men discipline and how to survive as a team. Drama unfolds as the crew gets to know one another, and even more drama ensues when the brigantine encounters a freakish white squall offshore.
Wind (1992) – The Story of the World’s Biggest Sailing Prize
Even cruising sailors will love this inspirational story of an underdog attempt to take back the America’s Cup. For the uninitiated, the America’s Cup is the most prestigious trophy in sailing and the oldest trophy in competitive sports.
The movie features incidents taken from real competitions and fictionalized into the plot. Peter Gilmour, who sailed in the 1987 America’s Cup, was the “Sailing Master” for the film. Many of the yachts used in filming were actual boats from America’s Cup races. Best brush up on those points of sail and sailing terms before watching–this movie is as authentic as it gets!
Overall, the movie has the over-the-top romanticism of movies of the era, like Top Gun but set on the water. But just like Top Gun, this movie is as entertaining today as it was back then.
Captain Ron (1992)
Absolutely no list of sailing movies is complete without including Captain Ron. And love it or hate it, it deserves to be in top place. Sure, it’s goofy, silly, and a bit dated. But this story of a straight-laced midwestern family throwing in the towel to live on a sailboat in the Caribbean resonates with dreamers and sailors like no other film does.
What makes the movie so special is Kurt Douglas’s portrayal of the singular Captain Ron Rico. Who else could’ve given us these quotes, which will live on, quoted repeatedly on sailboats everywhere?
“If anything is going to happen, it’s going to happen out there!”Captain Ron Rico
“A diesel loves her oil like a sailor loves his rum.”
“If we get lost, we’ll just pull in somewhere and ask directions!”
“Yeah, incentives are important. I learned that in rehab.”
And then there’s the boat. The Formosa 51 ketch Wanderer was the perfect boat for this movie. Its dilapidated condition and lack of seaworthiness are sure to make every boat owner laugh out loud. But, like any good boat, with a little elbow grease, she got them through it.
There are tons of rumors and fables surrounding this film in sailing circles. But consider this. It accurately details two real types of characters. The Harvey family, led by the indomitable Martin Short, is like many starry-eyed Americans who fled to the Caribbean for a life afloat. And Captain Ron? He’s based on a real person. The real one even had a peg leg, but the movie producers thought that would be too over the top!
Pirates of the Caribbean (2003-2017)
For a movie series based on a hokey 1960’s Disney Land ride, the Pirates of the Caribbean films have made a name for themselves. It’s the 15th highest-grossing film series of all time, and two movies have grossed more than $1 billion. There have been five films to date, but rumors are a sixth may be in the works.
So, Pirates is a fun series of movies, but how’s the sailing connection? Well, the Black Pearl is a sailing ship, sort of. It’s more of a ghost ship. And it’s all set at sea or on pirate-plagued islands in the Caribbean, so that’s neat. Overall, I wouldn’t rate these films as sailing ship movies, but they certainly are fun to watch.
Black Sails (2014-2017) – A Series with Great Sailing Scenes
It’s not a movie per se, but who doesn’t like a binge-worthy series? Combine Game of Thrones with a realistic pirate story, and you get the idea. It’s dirty, gritty, and historically accurate. Black Sails aired on Starz Network for four seasons and can be streamed on Hulu, Amazon Prime, and others.
The series is a prequel to Treasure Island and provides a backstory for pirates Long John Silver and Captain Flint. Unfortunately, Robert Louis Stevenson didn’t go into much detail about the notorious Flint, so the show used some artistic license to combine these fictional characters with the real pirates of the Caribbean.
More specifically, the stories are set in Nassau during its period as the “Pirate Republic” before England sent Woods Rogers to govern the island in 1718 and drive the pirates out. Yes, this is all there, and many real-life pirates are depicted in the show. The story tells the tales of Anne Bonny, Jack Rackham, Charles Vane, Israel Hands, and even Blackbeard. What a show!
And, of course, the ships and the action packed battle scenes are amazing to watch.
Master and Commander – Far Side of the World (2003)
This movie is based on the novels by Patrick O’Brian about Captain Jack Aubrey (Russell Crowe), commander of the British man-of-war HMS Surprise during the Napoleonic Wars. The story follows the chase and battle with the French privateer Acheron, who they follow around Cape Horn to the Galapagos Islands, where drama ensues.
The characters in the movie and novels are fictionalized, as are the precise events. But the author drew from real events that occurred during the Napoleonic Wars. The film draws from three different novels in O’Brian’s series.
The film is exceedingly accurate, with all shooting taking place on real ships. Ten days of filming were done at sea, while the rest was shot in the same 20-million-gallon seawater tank in Baja California where Titanic was shot.
Kon Tiki (2012)
The Kon-Tiki Expedition was a 1947 raft journey to prove people from South America could have populated the Polynesian Islands. At the time, most theories believed that the Polynesian people settled from west to east, not east to west. The expedition was led by Norwegian writer Thor Heyerdahl, who wrote the book about it. There was also an Academy Award-winning documentary made by the same name in 1950.
The 2012 version is dramatized but follows the events closely. Heyerdahl’s opponents, at the time, countered that no expedition would likely be successful in reaching Polynesia from Chile. To prove them wrong, he builds a balsawood raft with the same materials and techniques that people would have 1,500 years prior. The 4,300 nautical miles journey doesn’t go smoothly, as you might imagine. But then, I don’t want to give away the movie!
The Bounty (1984)
You can’t talk about sea stories without including a good mutiny. And while there are plenty of good tails, few stand the test of time better than the character-driven plot of William Bligh and Fletcher Christian of the HMS Bounty. The story was portrayed in the 1962 MGM film Mutiny on the Bounty and again in 1984 in The Bounty starring Mel Gibson and Anthony Hopkins. Both films used extremely accurate replica ships.
Sailing Movie Stories of Survival at Sea
It can’t be denied that many good sea stories revolve around the conflict of man against the elements. The sea is the ultimate element, so many movies about sailing turn toward a darker survival story.
All is Lost (2013)
Most sailors dislike this movie immensely. It has so many flaws that the story takes on more water than the boat in the movie does. But putting those facts aside, it’s a gripping tale of one man (Robert Redford), alone on a sinking cruising boat in the middle of the ocean, struggling to survive.
In 1983, a young couple was asked to ferry a yacht from the South Sea islands, through the sailing routes across the Pacific, to the US. But things go poorly when they run head-first into Hurricane Raymond, a late-season Category 4 storm.
The boat is knocked down and dismasted, and the man is washed overboard. The movie is based on the 2002 book Red Sky in Mourning by Tami Oldham Ashcraft, the sole survivor. In other words, it’s a true story.
The Mercy (2018)
Another true story follows amateur sailor Donald Crowhurst (Colin Firth), a dreamer who sets out to enter the 1968 Golden Globe single-hand around-the-world race. The only problem? He doesn’t own a boat or know how to sail. So he gets some sponsors, builds a trimaran, and leaves his home and family behind. Then, as you might suspect, drama ensues.
Documentary Sailing Movies
Sailing documentary films aren’t for everyone and seldom make for a light-hearted date night. But there are some great sailing movies in this genre for those looking for inspiring true stories without all the big-movie hubbub.
This movie tells the tale of the all-woman crew in the 1989-1990 Whitbread Round the World Race. It features interviews with Captain Tracy Edwards, who formed the team.
Chasing Bubbles (2016)
This YouTube documentary is about the true story of the (self-described) worst sailor to ever sail around the world. At 25, Alex Rust left his life as a day trader in Chicago to sail the world. With a sailboat he buys on Craigslist, Rust finds adventure during his four-year journey.
Sea Gypsies: The Far Side of the World (2017)
Sea Gypsies is the story of the sailing ketch Infinity, a 120-foot hand-built vessel on a never-ending nomadic voyage. The crew of 16 “wandering miscreants” set out from New Zealand in 2014 during one of the worst winters on record. They stopped in Antarctica on the way to Patagonia, 8,000 miles away. The film has won numerous awards at global film festivals.
You can rent Sea Gypsies: The Far Side of the World on Venmo or Amazon Prime in the US.
Red Dot on the Ocean (2014)
Another story about a young man risking it all to find freedom on the ocean, Red Dot on the Ocean tells the story of Matt Rutherford. At age 17 and in jail, Rutherford became inspired and turned his life around. He bought a pocket cruiser sailboat on the internet and cruised from the US to Europe, West Africa, and back to the Caribbean.
He was then inspired by Artic explorers like Shackleton and set out to transit the Northwest Passage by boat. That led to his desire to become the first sailor to circumnavigate the American continents, a 27,000-mile journey.
You can purchase Red Dot on the Ocean on Venmo, Amazon Prime, or Apple TV. You can also hear some great interviews with Rutherford on the On the Wind podcast from 59 North Sailing.
Maidentrip is a movie about sailing around the world, as done by Laura Dekker. In 2009, Dekker decided she would become the youngest person to circumnavigate single-handedly. At one point, the Dutch courts stepped in and prohibited her from leaving. But with legal hurdles cleared, she departed in 2010 for the 518-day voyage.
Dekker sailed the 40-foot ketch Guppy on her trip. She was inspired by Tania Aebi, author of Maiden Voyage and person who previously held the record as the first American woman and youngest person to circumnavigate solo.
Which Are Your Favorite Top Sailing Movies?
Whether you’re in the mood for hardcore action binging Black Sails or a light-hearted escape to the Caribbean with Captain Ron, there’s a little something for everyone. From docs to laughs, there’s a sailing movie to make everyone in your crew happy.
But the best is Captain Ron, seriously.