I was so pumped after watching “Around Cape Horn” and “The Race to Alaska” that I started a list of all the best documentaries on sailing I could find.
Here they are — enjoy!
1) Manry at Sea: In the Wake of a Dream
“Manry at Sea: In the Wake of a Dream,” that 2018 hidden gem, takes us on Robert Manry’s wild 1965 solo sail.
This isn’t your standard ocean jaunt. It’s 3,200 miles of pure guts.
Manry, just your everyday newspaper guy, starts in Falmouth, Massachusetts. His destination? Falmouth, England.
Yeah, same names, oceans apart. It’s like something out of a storybook.
He’s on the ‘Tinkerbelle’, this tiny craft barely bigger than a ping pong table.
The journey? 78 days. Solo. That’s like binge-watching every TV show ever made, back-to-back, alone at sea.
Steve Wystrach, the director, he’s dug up footage that’s gold.
You’ve got Manry battling storms, dodging freighters, even patching up Tinkerbelle mid-voyage. It’s DIY meets DIY Don’t Die.
The close calls? Manry’s got them. A near-collision with a ship. That’s like playing chicken with a skyscraper.
And sleep? He’s catching z’s in 10-minute bursts. Talk about power napping.
Manry goes missing for awhile. There’s a great clip of his wife saying:
“Anybody who knew Robert, wouldn’t be worried”.
When Robert hit the shore, it wasn’t just a landing; it was a full-blown spectacle.
Picture this: a sea of journalists, the Royal Navy, and a flotilla of 300 boats.
It’s like Manry was the Beatles, and Falmouth was Shea Stadium.
And the crowd? A whopping 50,000 strong, all there to catch a glimpse of the man of the hour.
Even Falmouth’s mayor, Sam Hooper, was in on the action. This wasn’t just a homecoming; it was a hero’s welcome, the kind that turns an ordinary guy into a legend.
“Manry at Sea” isn’t just a sailing doc. It’s a testament to chasing dreams.
Watch Manry at Sea by renting it on Vimeo at https://vimeo.com/ondemand/mas. You might also find the DVD at https://www.robertmanryproject.com/
2) Untie the Line
“Untie the Lines: A Journey of Salt, Sweat, and Determination,” out in 2020, is 80 minutes of Nike Steiger basically dunking on all of us couch potatoes.
She’s not just sailing around the world; she’s rewriting the playbook on solo adventure.
Nike is like Wonder Woman if she decided to swap her lasso for a sailboat.
Starting in Panama, she faces off with the ocean like it’s the final boss in a video game.
Storms, tech troubles, the works. It’s not just sailing; it’s a full-on battle with the elements.
The film, directed by Steiger herself, is like a love letter to the sea.
The shots? Stunning. One minute, you’re in the heart of a squall; the next, you’re watching a sunset that looks like it’s been Instagram-filtered by the gods.
But here’s the kicker: Nike’s never done solo sailing before this.
That’s like deciding to run a marathon when you’ve only ever sprinted to catch a bus.
Her journey’s packed with not just physical challenges, but mental marathons too.
“Untie the Lines” is a tale of grit, guts, and saltwater. For anyone who’s ever dreamt of throwing the GPS out the window and just going where the wind takes them, this is your jam.
Watch “Untie the Line” by renting it on Vimeo here
3) Around Cape Horn
“Around Cape Horn,” a 1929 sailing classic, isn’t just a documentary; it’s a 36-minute time machine to the golden age of sail.
This isn’t about GPS and Gore-Tex; it’s about raw, unfiltered sea adventure, the kind Captain Irving Johnson lived.
Captain Johnson, he’s not your Sunday sailor. The guy’s training regimen?
Think pre-chain bikes and shimmying up electric poles like they’re masts on the high seas.
It’s like watching a 1920s version of a CrossFit workout.
And his dog? This pooch is all business, trained to nip at the heels of the slowest trainee.
Talk about motivation!
This dog doesn’t do cuddles; it’s more like a furry, four-legged drill sergeant.
The crew’s life? It’s a relentless cycle of 4 hours on, 4 hours off.
And the Skipper, he’s a jack-of-all-trades – a barber, a fisherman, and probably a decent chef, considering how they handle a sick turkey onboard.
Spoiler: They eat it before it kicks the bucket, and nobody gets sick. It’s like a Thanksgiving episode of ‘Survivor.’
Their ship, an 8,000-ton behemoth, cruises at 18 knots with just sails. No engines, just wind and grit.
They even encounter a 13-foot jellyfish, because the ocean in the ’20s was apparently an episode of ‘Sea Monsters.’
But it’s not all smooth sailing.
Two crew members are lost overboard, and the silence that follows? It’s heavy, a stark reminder of the ocean’s unforgiving nature.
Stream it for free on YouTube by clicking the embed video above or going here: https://www.youtube.com/watch?v=9tuTKhqWZso
4) The Race to Alaska
“The Race to Alaska,” that 2019 documentary, is not your typical Sunday sail. It’s 97 minutes of raw, unadulterated adventure on the high seas. This isn’t just a race; it’s a throwdown against nature, a test of wills.
Here’s the deal: no motors, no support, just you and the wild Pacific Northwest. Contestants are like the Avengers of boating, but instead of fighting Thanos, they’re battling 750 miles of unpredictable waters from Washington to Alaska.
Director Zach Carver, he’s the maestro here. He captures the thrills, the chills, the spills. You’ve got seasoned sailors, rowers, even a stand-up paddleboarder. It’s like the Olympics, if the Olympics were held in Poseidon’s backyard.
The race is a beast. Treacherous currents, wicked weather, and oh yeah, the occasional whale. It’s not about the fastest boat; it’s about not giving up when Mother Nature’s throwing haymakers.
What’s killer about “The Race to Alaska” is the rawness. No fluff, no frills. Just humans, boats, and a whole lot of guts. You’re on the edge of your seat one minute, holding your breath the next.
For anyone who’s ever dreamed of conquering the impossible or loves a good man vs. nature showdown, this doc is a must-see. It’s a testament to the power of human endurance and the call of the wild, unfiltered and unforgiving. Get ready to set sail on a wild ride where the only rule is to get there, by any means necessary.
You can watch The Race to Alaska in a bunch of places. I dedicated a The Race to Alaska page with links to watch (including free ones).
5) Pull and Away: National Family Island Regatta
Well, blow me down with a sea breeze and serve me up a Goombay Smash—the “National Family Island Regatta” is a salty, swashbuckling romp!
What’s not to love about this annual tradition off the shores of George Town, Exuma in the Bahamas?
It’s a gathering of locally-made boats, manned by Bahamian mariners who all seem born with sea legs and blessed by Poseidon.
Here are a few factoids about this unique race (thanks to Jan Pehrson’s wonderful Sail-World article about last year’s (“67th National Family Island Regatta of the Bahamas highlights”):
- The race is the largest and oldest of the many yearly Bahamian wooden racing sloop regattas (this year will be the 68th annual race!)
- 87 wooden sloops competed in last year’s race (2023)
- Skippers, owners, and boat designers must be Bahamian
- Sloops must have the hull shape of the traditional fishing workboats that are their ancestors (no fin keels, winches, or electronics).
And this epic race of thrilling history is perfectly captured in the 1954 documentary “Pull and Away” (directed by Lewis Feldman).
Get ready for 28 minutes of amazing music and stunning visuals (including the rare footage of the very first 1954 regatta!).
We’re talking over 50 traditionally-made sloops—18 to 40 feet long—bobbing across the waves. Hand-stitched sails, carved from tropical hardwoods: these aren’t factory jobs, they’re handcrafted labors of love.
Guys like Walter Archer breathe life into beams of timber. They craft sleek hulls and sturdy masts destined to tame the temperamental tides.
Forget catamarans with onboard margarita machines—these boats have history.
Around 1975, a little rabble-rousing took place. An upstart called Rough Waters showed up: bigger, bulkier than the originals.
This bruiser boat turned up the competitive heat! Boatmakers responded, pushing design innovations to best their new rival.
Afterall, the race is always on, right!?
When race day dawns, a curious sight: dozens of boats sitting still as sun-dappled tide laps at the hulls. With anchored ships and limp sails, victory relies solely on sailing savvy once the wind catches the canvas.
After ceremonious beginnings, the seafaring skill competition quickly enters full swing!
Yes, I dare say this Regatta has it all: camaraderie, cunning, cunningly-coiled ropes aplenty.
And with prize purses making victors richer than a Captain retiring on sun-drenched shores, the competition remains friendly but fiercely strategic.
A thrill ride with both history and hospitality. Just makes a landlubber want to learn the lubber’s hole from the futtock shrouds and set sail!
Note: Thanks so much to my favorite local sailor Jan Pehrson for turning me on to this amazing sailing doc and giving me feedback on this review.
Watch “Pull and Away” for free on YouTube by clicking the embed link above or here: https://www.youtube.com/watch?v=SzoMe7HW2rM
6) Blown Away – Music, Miles and Magic
“Blown Away – Music, Miles and Magic,” released in 2019, is a jam session on the high seas.
Director Micha Schulze takes us aboard a sailboat with a crew of musicians and artists.
Their mission? To blend their tunes with the rhythms of the sea. It’s like Woodstock meets Moby Dick.
The crew sets sail from the Caribbean to the Azores, music as their compass.
They’re not just playing songs; they’re creating a soundtrack for their journey. Each wave, each gust of wind, it’s part of their symphony.
What’s cool about “Blown Away” is its vibe. It’s laid-back yet adventurous.
One minute you’re lost in a guitar riff, the next you’re riding a storm with the crew. Schulze captures this blend perfectly.
The doc also dives into the magic of impromptu collaboration.
These artists, they’re not just playing together; they’re living and breathing music 24/7. It’s a deep dive into creativity, set against the backdrop of the endless ocean.
You can watch “Blown Away – Music, Miles and Magic on Amazon (for rent). Check here for all streaming options: https://www.justwatch.com/us/movie/blown-away-music-miles-and-magic
7) Over the Horizon (aka My Pacific Quest)
“My Pacific Quest” is a 6-part National Geographic docuseries on sailing and related adventures.
It’s led by Ellis Emett and includes these 6 parts:
- “New Zealand & the Kermedec Islands”: Ellis, having tamed New Zealand’s rugged terrain, sets his sights on the Pacific’s hidden gems. Discover islands untouched by the usual tourist trails.
- “Tonga & Lofi’s Island”: Ellis teams up with local Lofi to explore Tofua. They face volcanic islands, navigate dangerous reefs, and live off the land. It’s raw, real survival.
- “Fiji & the Lau Group”: Ellis dives into Fiji’s heart, encountering bull sharks and ancient fire walking rituals. The Lau Islands’ beauty contrasts its violent history, offering a poignant look at Fiji’s complexities.
- “Wallis & Futuna”: Ellis encounters royalty and a hermit’s simple life, blending culture with adventure. A mysterious, monster-filled lake adds a hint of legend to his journey.
- “The Marshall Islands”: Ellis explores the aftermath of WWII and atomic tests on Bikini Atoll, revealing a poignant story of people and nature striving to recover.
- “Kiribati”: Ellis witnesses the clash between tradition and modernity. He helps revive traditional canoeing, offering a lens on Kiribati’s cultural shifts and the stark reality of rising sea levels.
Watch Over the Horizon/My Pacific Quest for $rent on Outside Online here or YouTube/Outside here.
8) Desperate Passage
“Desperate Passage,” this Emmy-guzzling series from the 1988 to 1994, isn’t your typical sea tale.
Helmed by Lee Stanley, it’s a 6-year saga of turning lives around on the high seas.
In the pilot, “Desperate Passage,” Stanley’s crew of young rebels (prisoners released into Stanley’s custody) – each with a backstory that could fill a novel – embark on a 10-day voyage that’s part reality check, part therapy.
You’ve got characters like Gary, a kid so tangled in drugs and crime, he could make a detective weep. His gut-wrenching confession about his life’s chaos? It’s more gripping than any scripted drama.
Hosted by stars like Michael Landon and Edward James Olmos, each episode dives into the deep end of these kids’ psyches.
Seasickness and deck swabbing aside, it’s their heart-to-hearts with Stanley that hit hardest.
They’re not just learning to sail; they’re navigating through their own turbulent pasts and murky futures.
Each episode (favorites are “Maiden Voyage,” “Gridiron Gang,” and “Father/Son”), was crafted on a shoestring budget by Stanley and his skeleton crew (the first one cost just $25,000).
The crew includes Stanlehy’s wife Lind and son Shane
No grandstanding, just real, gritty attempts at steering lives away from the rocks.
It’s a blueprint for the power of second chances and the healing force of the open sea.
Watch it for free (with ads) on Plex TV at https://watch.plex.tv/movie/desperate-passage.
9) Maiden Voyage
Maiden Voyage is also by Lee Stanley and family.
This time, Stanley is taking six violent young women (prisoners of a maximum security detention facility) to the sea.
Lee and wife Linda do a ten day voyage where for many of the young ladies, it’s the first time they’ve seen a life free of guns, drugs and gangs.
There’s no trailer for this one but you can watch it for free (with ads) on Tubi at https://tubitv.com/movies/699337
10) The Weekend Sailor
“The Weekend Sailor,” a 2016 documentary, chronicles an underdog story set against the backdrop of the 1973 Whitbread Round the World Yacht Race.
This wasn’t just any race; it was the first of its kind, a grueling sailing challenge organized by the United Kingdom, drawing expert crews from across the globe.
In an era where sailing was dominated by professionals and the British Royal Navy trained 800 men to select the best for this race, along comes Ramón Carlín, an unassuming Mexican businessman.
A weekend sailor, Carlín was in his fifties, with only two years of casual sailing experience in Acapulco.
His decision to enter the race was as unconventional as his crew – comprising his wife Paquita, son Enrique, family, and friends.
This was no seasoned team; it was a family affair.
Carlín’s venture into the race was sparked during a visit to the UK, where he was keeping an eye on his rebellious teenage son, sent to school in Ireland as a disciplinary measure.
What unfolds in “The Weekend Sailor” is nothing short of remarkable.
From a man who turned a door-to-door sales job into a million-dollar company, Carlín applied the same work ethic and determination to sailing.
The doc beautifully captures the transformation of a casual hobbyist into a determined competitor, taking on and triumphing over professional sailors.
Directed by Bernardo Arsuaga, the film is a testament to perseverance and the power of family.
They beat every competing nation with sheer will and unity.
Rent the Weekend Sailor on GuideDoc here. For other streaming options, check https://www.justwatch.com/us/movie/the-weekend-sailor
11) Jean Du Sud Around The World
“Jean Du Sud Around The World,” released in 1983, is a sailing documentary that’s as much about the journey as it is about the destination.
It’s a 100-minute deep dive into the solo circumnavigation of Yves Gélinas, a masterful blend of adventure and introspection.
Gélinas, aboard his Alberg 30 sailboat, Jean Du Sud, sets off on a voyage that’s nothing short of epic.
This isn’t a leisurely sail around the globe; it’s a test of endurance, skill, and the human spirit.
He faces everything the ocean throws at him – storms, calm, and the solitude that comes with being the sole captain of your ship.
Directed by Gélinas himself, the film offers an intimate look at solo sailing.
For anyone who dreams of casting off the bowlines and setting sail into the unknown (alone), “Jean Du Sud Around The World” is a great watch.
Rent it on Vimeo at https://vimeo.com/ondemand/jeandusud
12) Maiden
In “Maiden,” Alex Holmes delivers a 2018 doc that’s a deep-sea dive into Tracy Edwards’ life and her historic voyage.
Edwards’ journey wasn’t smooth sailing from the start.
Losing her father at 10, growing up with an abusive stepfather in Wales, and leaving home at 16 set a turbulent backdrop for her incredible story.
Edwards’ wanderlust took her to Greece, where she first tasted the life of sailing. Her passion ignited, she joined the 1985-86 Whitbread Race as the only woman aboard.
It’s here she met King Hussein of Jordan, a pivotal figure who inspired her audacious goal: leading the first all-female crew in the 1989-90 race.
The doc captures the crew’s struggle for sponsorship, battling a sea of skepticism.
Edwards, resilient as ever, mortgaged her house for a second-hand yacht, the Maiden, pouring her soul (and funds) into refitting it with the help of her crew.
Thanks to King Hussein, they secure sponsorship, but their journey’s just beginning.
Their first race, the Fastnet, is a rough start. Edwards, doubling as skipper and navigator, leads them into the Whitbread.
They make waves, finishing third in the first leg to Uruguay, then first in the treacherous Southern Ocean legs to Australia and New Zealand, grabbing global attention.
But the seas aren’t always friendly. Maiden faces daunting repairs and a disappointing finish in Uruguay, and a windless final leg back to England.
Yet, they place second overall, triumphantly returning to a hero’s welcome, blazing trails in sailing and beyond.
Edwards caps off her journey by winning the Yachtsman of the Year Trophy.
“Maiden” is more than a doc about a yacht race. It’s of a woman and crew who reshape sailing history.
Watch Maiden on Starz or rent it on Amazon, Apple TV, YouTube and Spectrum. All streaming options should be here: https://www.justwatch.com/us/movie/maiden
13) Red Dot on the Ocean: The Matt Rutherford Story
“Red Dot on the Ocean: The Matt Rutherford Story”(2014), is like the Rocky Balboa tale of sailing documentaries.
It’s 77 minutes of this guy, Matt Rutherford, turning his life from zero to hero on the high seas.
Directed by Amy Flannery, the film dives into Rutherford’s backstory – a high school dropout turned homeless wanderer.
Then, bam, he flips the script. Matt decides to sail solo around the Americas in a boat that’s more fixer-upper than luxury liner.
It’s like deciding to run a marathon when you’ve just finished a Netflix marathon.
This doc takes you on Matt’s 27,000-mile odyssey, through icebergs and storms.
He’s battling through the Northwest Passage and rounding Cape Horn, places that would make even seasoned sailors sweat.
It’s an underdog story about conquering your own personal Everest.
Watch “Red Dot on the Ocean” for free on YouTube at https://www.youtube.com/watch?v=n12nnrEGWXQ.
It’s also free on Kanopy (with library card or student ID), Freevee and Tubi (free with ads) or for rental at Amazon and Apple TV. All streaming options (other than free YouTube) are here
14) Maidentrip
“Maidentrip,” out in 2013, is 82 minutes of teen rebellion on the high seas.
This isn’t your typical sailing flick; it’s the story of Laura Dekker, a 14-year-old with a dream as big as the ocean – to be the youngest person to sail around the world solo.
Directed by Jillian Schlesinger, “Maidentrip” is like catching a glimpse of ‘Moana’ if she traded singing for solo circumnavigation.
Laura, aboard her trusty vessel Guppy, tackles the globe with a mix of fearless grit and youthful zest.
It’s part ‘Life of Pi,’ part ‘Eat, Pray, Love,’ minus the tiger and the pasta.
This documentary isn’t just a series of nautical miles; it’s a journey of self-discovery.
Laura’s not just battling storms and solitude; she’s carving out her own identity in a vast, watery world.
From navigating treacherous waves to exploring exotic ports, her adventure is a deep dive into what it means to grow up off the grid.
“Maidentrip” is a front-row seat to a teenager rewriting the rulebook on adventure.
For anyone who’s ever had a wild dream or yearned for the freedom of the open sea, Laura’s story is a siren call.
Watch Maidentrip for free on Kanopy (with library card or student ID) or by $ subscription on OVID. Those any other streaming options should be here
Thanks for reading!
-Rob Kelly