There are five movies that have earned a place in my onboard library. I say they are there to entertain my overnight guests but actually the shared viewings are more like comical sailing lessons and a way to initiate my friends into the lore of the sea—Hollywood style. You really can’t call yourself a sailor if you haven’t seen (and in some cases memorized) these five movies.

Did your favorite film make the list? Dive in to find out...

White Squall

Based on a true story from 1961, this 1996 Ridley Scott classic stars Jeff Bridges and Caroline Goodall. The film is based on the demise of the brigantine Albatross, a training ship captained by Dr. Christopher Sheldon (Bridges). The story opens as a dozen male high school students join the ship for their senior year at sea in what is to become a time of back-to-back lessons on the rigors of sailing, the expectations of discipline and ultimately the need for courage. That each student has a backstory and that there is a rich kid with an embarrassing and overbearing father is a given. Real drama unfolds as the ship is hit by a “white squall” the existence of which was much debated at the captain’s ensuing trial. The appearance of “line squalls” has since been documented and the thought of such a scenario will send chills down the spine of any sailor. It’s not great movie making in terms of character development or plot but it is mesmerizing scenery and exhilarating sailing so the popcorn disappears quickly.



Captain Ron

Hands down, one of the silliest but most entertaining sailing movies ever made – Captain Ron is surprisingly accurate in all the small details. A 1992 romp directed by Thom Eberhard and produced by David Permut for Touchstone Pictures, this is the film that is most memorized and quoted by sailors everywhere. Martin Short and Mary Kay Place become accidental sailors with their two kids when they’re joined by delivery skipper Captain Ron, played by Kurt Russell. The action is all hype and Caribbean guerrillas but the sailing sequences and details are spot on with the exception of Russell’s description of the single diesel engine on a sailboat as having “1200 ponies.” Otherwise, the bungling, irresponsible and generally low-life captain is deftly played by Russell who wins our hearts and our admiration. Get your remote out because it takes a few rewinds to memorize all the gut-busting lines.


Dead Calm

Perfect for a Halloween showing, Dead Calm is a 1989 Australian thriller starring Sam Neill, Billy Zane and a very young Nicole Kidman (frizzy hair and all). The movie is based on a 1963 novel by Charles Williams and it was filmed on the Great Barrier Reef, around the Whitsunday Islands. A couple is sailing their yacht around the Pacific in an attempt to heal from the death of their infant son when they encounter a man on a sinking boat. What happens next is an over-the-top dramatic story of survival and rescue. It’s fantastically ridiculous in its details but the boat shots are beautiful and the story is compelling even if strange. It turns out that Orson Welles initially set about filming the story in the 1960s but the film was never completed and Welles’ estate didn’t part with the book rights until the 1980s. This horror movie on the high sea is good fun as is Kidman’s bizarre hairdo.



For hands-down breathtaking sailing imagery and amazing footage, Wind is a clear winner. The 1992 film stars Mathew Modine, Cliff Robertson and a baby-faced Jennifer Grey (pre-cosmetic reconstruction). For racers, this film is a must as it centers on the 1987 America’s Cup series off Fremantle, Australia. Several real-life events were re-created for the movie and a few of the original 12-meter racing yachts were used in filming. The movie is shot with spectacular vision from on-deck sequences to the beauty of Jennifer Grey’s character sewing “the Whomper” sail, surrounded by yards and yards of billowy fabric. Despite a weak love story and some cheesy dialogue, there are edge-of-your seat thrills and simply gorgeous cinematography that shows that Director of Photography, John Toll, understood the world of competitive sailing. Director Carroll Ballard and Executive Producer Francis Ford Coppola, forged ahead bravely although the film flopped at the box office as it didn’t resonate with a general audience. That said, for racing sailors, this is akin to the Grail of classics.


Deep Water

You might not expect to find a British documentary among great sailing movies but the story of Donald Crowhurst is so compelling and at the same time so ridiculous, that it just couldn’t be ignored. The 1968 Sunday Times Golden Globe Race (the first officially sponsored round-the-world single-handed yacht competition) brought together the likes of Bernard Moitessier, Robin Knox-Johnston and Donald Crowhurst, a deranged and desperate man convinced he could take on the Southern Ocean in a home-built trimaran. Nine sailors started the race and only one completed it but it was Crowhurst’s story that made headlines as he seemingly faked logs and eventually committed suicide, having never left the Atlantic Ocean. In 2006, directors Louise Osmond and Jerry Rothwell called on Tilda Swinton to narrate a film pieced together from original voice recordings as well as 16mm film footage of a story that still makes sailors shake their heads. Watch this so you’re prepared to evaluate the fictionalized version with Colin Firth and Rachel Weisz called The Mercy, which is scheduled to be released in 2018.


Worst Sailing Movie

And now for the absolute worst, hang-your-head-in-shame, piece-of-soggy poo sailing stories ever committed to film: All is Lost. Clearly made by complete non-sailors, this film was directed by J.C. Chandor and stars Robert Redford. The story opens with a nearly-mute man sailing the Indian Ocean on his 39-foot sloop (which turns out to be a very coastal boat that you’d most likely never take on such a voyage). After colliding with a shipping container, a sequence of unbelievably ignorant moves ensues with one ridiculous gaffe after another. It all culminates in our guy setting fire to the only thing that keeps him from death – his life raft. Uh huh. The nonsensical events come at you so fast, it’s hard to find even an ounce of reality in it and frankly, it’s worthy of having vegetables thrown at the screen. I’d have consulted on this for free but clearly, the producers didn’t get any sailors to consult, free or otherwise.


If you want to feel salty, find these classics by downloading or even combing through garage sale memorabilia, then make some popcorn and enjoy. If you want to continue the movie marathon, read Best Boat Movies.