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Greatest Sailing Movies of all Time (and not)

We'll bet there are some here you haven't seen.
And "In no particular Order"

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Charlie St. Cloud

This is a romantic drama starring Zac Efron as a young man who survives an accident that lets him see the world in a unique way. In this emotionally charged story, he begins a romantic journey in which he embraces the dark realities of the past while discovering the transformative power of love. Accomplished sailor Charlie St. Cloud (Efron) has the adoration of mother Claire (Oscar® winner Kim Basinger) and little brother Sam (newcomer Charlie Tahan), as well as a college scholarship that will lead him far from his sleepy Pacific Northwest hometown. But his bright future is cut short when a tragedy strikes and takes his dreams with it. After his high-school classmate Tess (Amanda Crew) returns home unexpectedly, Charlie grows torn between honoring a promise he made four years earlier and moving forward with newfound love. And as he finds the courage to let go of the past for good, Charlie discovers the soul most worth saving is his own.

All is Lost

Are you ready to watch Robert Redford lost at sea in a virtually wordless two-hour film? Or did you already allot all your nervous viewing (and meds, if necessary) to Gravity?

We suppose this belongs on this page purely because it has become a must see for any sailor who wants to experience as many "How not to do its" as possible. This is possibly Redfords worst film (IMHO). Of course, we have already watched it more than once...

Academy Award winner Robert Redford "gives a solo tour-de-force in this awards-caliber adventure" (NY Post) about one man's battle for survival against the elements on the open sea.


Sorry, this is not a sailing movie but it is produced by Jimmy Buffett and a real hoot! Based on the Newbery Honor-winning book by Carl Hiaasen, it is a mystery adventure story about three middle schoolers who take on greedy land developers, currupt politicians, and clueless cops to protect a local population of endangered owls. Hoot revolves around a boy who moves from Montana to Florida, where he discovers a disturbing threat and mobilizes his new friends to prevent the adults from making a big mistake. Filmed in 2005 in Boca Grande and released April 2006, Hoot was produced by Frank Marshall and Jimmy Buffett for Walden Media, the folks who brought us Chronicles of Narnia. And, yes, there is plenty of original music by Jimmy and the Coral Reefers. Buffett also plays a convincing role as the surfing marine biology teacher. Overall the film sends a conservation message and reminds kids that they can make a difference. See for more information.

Captains Courageous

The classic MGM, coming-of-age children's film acquired four Academy Award nominations (Best Picture, Best Film Editing, and Best Screenplay) with Spencer Tracy taking home his very first Best Actor Oscar.  One of cinema's greatest classic adventure stories by director Victor Fleming (1937). It is an adaptation of English novelist Rudyard Kipling's 1897 work of the same name, and advertised: "As Great as Mutiny on the Bounty" with exciting action sequences, and a heart-felt story of the emerging relationship between an over-privileged and bratty young boy and a humble, common fisherman. And who wouldn't like Freddie Bartholomew (The Prince and the Pauper)?

Captain Ron

This is just a fun movie. Yes, it is unbelievable, yes it is a bit dorky, but it's a lot of fun. With Kurt Russell and Martin Short, you’ll be laughing out loud.  A family from Chicago inherits the yacht formerly owned by Clark Gable. Not knowing anything about sailing, they decide to sail it from the island of Ste. Pomme de Terre to Miami . T hey sail with the assistance of Captain Ron and their lives will never be the same again.

Dead Calm

This is a sailing horror movie.  It will keep you from relaxing onboard for ages.  You’ll be suspect of everyone and you’ll never stop to help a disabled vessel.  A mass-murderer (Billy Zane) commandeers a vessel and rapes a young woman after leaving her husband to die on the vessel whose crew he's just slaughtered.  Nichole Kidman and Sam Neill play the happy couple who stumble upon the vessel in apparent distress.  You will be gripping your seat the entire time.  Nicole Kidman reportedly took lessons from the owner of the Storm Vogel on how to operate the ship. During the storm sequences near the end of the film, she is actually piloting the yacht.

Violets are Blue

After fifteen years of traveling around the world Gussie (Sissy Spacek), a famous photographer, returns to the Maryland coastal resort where she grew up. She meets her high school sweetheart Henry (Kevin Kline), now married (to Bonnie Bedelia) and running the local newspaper he's inherited from his father. An awkward and tension-filled but harmless enough love triangle forms with some nice sailing sequences on a traditional day-sailing sloop and a Hobie cat race.  Pleasant mindless fare, especially when there’s a blizzard out and not a boat show in sight.

Mutiny on the Bounty

1935 Charles Laughton and Clark Gable

1962 Marlon Brando, Richard Harris, Trevor Howard

1962 Anthony Hopkins, Mel Gibson, with Daniel Day Lewis, Liam Neeson and Sir Lawrence Olivier in supporting roles

Midshipman Roger Byam joins Captain Bligh and Fletcher Christian aboard the HMS Bounty for a voyage to Tahiti . Bligh proves to be a brutal tyrant and, after six pleasant months on Tahiti , Christian leads the crew to mutiny on the homeward voyage. Even though Byam takes no part in the mutiny, he must defend himself against charges that he supported Christian. 

Of the various film versions of the tale, Mutiny on the Bounty (1935) is one of the best nautical adventure films of all time and one of MGM's greatest classics. The rousing, 18th century story of the Bounty's mutiny, directed by Frank Lloyd, was adapted from the first two volumes of the Charles Nordhoff-James Norman Hall 1932 best seller, The Bounty Trilogy (composed of Mutiny on the Bounty, Men Against the Sea, and Pitcairn Island ). It was the highest grossing movie of the year. The Bounty (1985), starring Anthony Hopkins as Bligh and Mel Gibson as Fletcher Christian, was the most accurate but had a tepid reception by the critics. One remake, starring Marlon Brando and Trevor Howard, the 70 mm Panavision widescreen version of Mutiny on the Bounty (1962), fared poorly.


One needn’t be a sailing afficionado to appreciate Carroll Ballard’s WIND, a thrilling sports drama based on the true story of Dennis Conner, the man who caused national embarrassment in 1983 by becoming the first American to lose the America's Cup trophy in the 140-year history of the race (only to win it back again in the next challenge). Unfortunately, in Ballard’s film, the Cup isn't all Will Parker (Matthew Modine) loses. His girlfriend Kate (Jennifer Grey), also an expert sailor, already walked out on him when she was denied a place on his crew because of her gender and Will failed to protest the decision. Following his defeat, Will heads to Utah to find Kate and convince her to team up with him in building a brand-new, improved yacht that they will sail together in an attempt to win America 's Cup back from the Australians. With the help of the brilliant Joe Heiser (Stellan Skarsgard) and the wealthy Abigail Weld (Rebecca Miller), Will puts everything he has into one last chance at redemption. The sailing scenes are quite spectacular. This movie has everything, including a low-key cast more focused on the story line than their own stardom.

Captain Blood

December, 1935 Cosmopolitan/Warner Bros. Academy Award Nominee for Best Picture.

Errol Flynn, Olivia de Havilland, Lionel Atwill, Basil Rathbone, Ross Alexander, Guy Kibbee. Music by Erich Wolfgang Korngold. 

This irresistible story is about Peter Blood, a medical doctor living in England during the late 1700s. This former soldier of fortune, now living a life of peace, is caught aiding a friend wounded in a rebel uprising. Blood is spared a hanging and condemned to serve as a slave.  He is purchased in Port Royal by Olivia de Havilland on a plantation across the sea in Jamaica . During a raid on the town by Spaniards, the slaves escape, commandeer a Spanish Galleon, and take up a life of buccaneers in the Caribbean under the astute leadership of Captain Blood. The character is based in part on legendary pirate Captain Morgan.  It’s the ultimate swashbuckler. 

The Sea Hawk

August, 1940, WB-FN

Errol Flynn, Brenda Marshall, Claude Rains, Flora Robson, Donald Crisp, Alan Hale, Una O'Connor, Gilbert Roland  Music by Erich Wolfgang Korngold.

Based on Sir Francis Drake and the "Sea Dog" privateers of the 1500s.  The adventures of a piratical sea fighter, Geoffrey Thorpe, commander of a British sailing ship that preys on Spanish commerce in the late 16th century. Also focuses on internal politics within the court of Elizabeth I who secretly condones Thorpe's buccaneering activities. Wonderful sequences with Elizabeth I and trudging across Panama .  Pure Errol Flynn.


Horror/suspense movie about a woman sailing around the world alone. Produced in 2003. Some pretty good sailing scenes, but as with many sailing movies, it might make you not want to go sailing. After six months at sea on a solo trip around the world, Georgia Perry's 44-foot sail boat sits idle with no wind in her sails for several days. Cabin fever sets in, and the border between fact and fantasy begins to trickle away. Are uninvited visitors boarding the vessel, or is her mind deceiving her? But if these are just tricks of the mind, how do these ghostly encounters leave Georgia with bruises and if the visitors are real, is there a bigger danger? It's awful. Don't do it!


Maybe this 1995 epic isn't nearly as bad as it seemed. At the time it was the most expensive Hollywood production in history ($200 million budget), and it arrived in theaters with so much negative publicity that it was an easy target. The movie is a hugely flawed but still somewhat enjoyable post-apocalypse thriller. Waterworld stars Kevin Costner as the flatly portrayed Mariner, a lone maverick with gills and webbed feet who navigates the endless seas of Earth after the complete melting of the polar ice caps. The Mariner has been caged like a criminal when he's freed by Helen (Jeanne Tripplehorn) and enlisted to help her and a young girl (Tina Majorino) escape from the Smokers, a group of renegade terrorists led by Dennis Hopper in yet another memorably villainous role (it's obvious he had a good time). They travel in search of land. The script was not very intelligent, the waterworld didn't have a ripple or a storm, and not one of the characters was particularly likeable. The best part of the movie was near the beginning. Where the guy had boarded the Mariner's boat while he was "fishing" below. When the guy thought he was going to get away, Costner hit the controls and deployed his sails under what anyone might call a rapid furling system.  I sure do wish I could have some of those webbed feet and gills, too.

White Squall

A real sailing movie. Frighteningly realistic, brilliantly acted as only Jeff Bridges can accomplish. (Ever notice that he chooses only intelligent roles. The son of Lloyd Bridges of Sea World TV fame has a great knack for picking interesting roles.)

Perfect Storm

Well once again, this is not exactly a sailing story but there is a sailboat in it, which unfortunately gives sailors a bit of a bad aura.  The sailboat that was abandoned was later found adrift and in seaworthy shape (who knows what it was like out there). The story itself is awesome about the power of the sea (We took mammi to see it just after we told her we were going on a world cruise! Wrong!).  Respect is one thing we all need to have and even then a good prayer may become necessary.  Of course, watching George Clooney is always a pleasure. The coolest thing was meeting the Coasties who were part of the Search and Rescue that night aboard the chopper that went down.  Now the real guys were true heros.  Amazing and I  sure hope these guys are somewhere nearby if we ever need them.

Moby Dick

As Captain Ahab, the bearded, one-legged, insanely obsessed whaler, Gregory Peck has often been called miscast. The volcanic eruptions of Ahab seemed beyond him. Yet his quiet brooding works an intriguing variation on the fiery character. John Huston, the legendary director, had his hands full with the difficult open-water filming in Ireland and the Canary Islands. Since Ahab chases the rare white whale, three model whales had to be constructed, two of which were lost at sea. For all the problems, the film is amazingly visually beautiful. Huston and cinematographer Oswald Morris developed an unusual color process meant to suggest old whaling engravings. Huston wrote the script with the science fiction genius Ray Bradbury. Richard Basehart, whose voice will be familar to many of our age, plays the narrator, Ishmael. Orson Welles provides a wonderful single-scene thundering sermon about the mysteries of the sailor's life as Father Mapple. There are so many great things about this 1956 production.


Okay, so it’s a boat movie not a sailing movie.  But the critical scene that changes everything is about sailing.  Those poor little kids. And, the harbor it was filmed in is Menemsha!

Message in a Bottle

An example of a good sailing movie but with an awful plot (the book was no better).  Kevin Costner has only occasional redeeming qualities, but his character's devotion to his boat is well portrayed, and he really did the sailing himself. The sappy, tragically romantic Hemingwayesque ending does not suit the character nor the overall story.  A man so wise about the sailing life would not risk what he did.  It’s just not plausible. (How is it that Costner managed so many bad performances?)

The Dove

Based on the true story of a 16 year old (Robin Lee Graham, played by Joseph Bottoms) who sailed alone around the world in a 23 foot sloop named "The Dove". On his journey he meets a young woman also traveling the world (Patti Ratteree, played by Deborah Raffin) and falls in love. The story follows Robin around the world to many beautiful locales, as he grows from a boy to a man.

A wonderful movie, but the film deviates from reality so credibly that most people mistake the film for the true story. Graham's boat was a 1960 Lapworth 24, not a Ranger 23 designed 6 years after he departed Long Beach . He did not set fire to the interior, he just cast himself adrift. And he changed boats in the BVI - because of fears the plywood deck of the Lapworth 24 would collapse in a storm. In 1995, the original Dove was still on Tortola where he left it.

In the Line of Fire (1985)

Okay so you can't remember Clint Eastwood as a sailor? That's because he isn't, he's a secret service agent caught in a cat and mouse game. A Cherubini is featured and the film studio even made a mock-up of the interior for the below decks shots. Apparently the boat that blows up right in front of it was handled entirely by computer-generated images!

Riddle of the Sands

Based on the "classic spy thriller of the 20th century" that historians hail as the "tip-off" that saved Britain from invasion. Set in the early 1900s, Carruthers, an Englishman, is rescued from a hot summer at a deserted office in London by an out-of-the-blue invitation to join an acquaintance, Davies, on his yacht , a converted lifeboat he's been sailing around the northern coast of Germany in the Baltic. He arrives to find that Davies needs his help in a spying mission with enormous stakes. The two sailboating Englishmen discover a massive German fleet secretly preparing to attack their nation and set out to do something about it. The Riddle of the Sands created a sensation when it appeared in print in 1903. It is the forerunner of spy novels like those of John Le Carré, and its detail and dry humour have made it a classic for sailors as well as for thriller addicts. Kind of slow moving but a good spy adventure, with gorgeous scenery, historical costumes, and some nice action on traditional wooden sailboats. Also available as an audiobook. Starring the ever delightful Michael York.

Knife in the Water

On their way to a sailing trip, an aging husband and wife invite along an emphatic young hitchhiker.

Roman Polanski's first feature is a brilliant psychological thriller that many critics still consider among his greatest work. The story is simple, yet the implications of its characters' emotions and actions are profound. When a young hitchhiker joins a couple on a weekend yacht trip, psychological warfare breaks out as the two men compete for the woman's attention. A storm forces the small crew below deck, and tension builds to a violent climax. With stinging dialogue and a mercilessly probing camera, Polanski creates a disturbing study of fear, humiliation, sexuality, and aggression. This remarkable directorial debut won Polanski worldwide acclaim, a place on the cover of Time, and his first Oscar¨ nomination.

Pirates of the Caribbean : The Curse of the Black Pearl (2003)

Pirate Jack Sparrow, played refreshingly by Johnny Depp, sets out to save a governor's daughter from fellow pirates, with the hopes that it will give him the opportunity to regain the ship that was stolen from him. `Pirates of the Caribbean ' is worth seeing for its unpretentious Disney-like fun for the family.  “Prepare to be blown out of the water.” You just have to love Jack, even though he isn't always you're typical pirate - or maybe because he isn;t your typical pirate.

Midnight Crossing

Faye Dunaway is featured as the cheated-upon, half-blind wife of a true scoundrel played by Daniel Travanti. The plot is pretty implausible but relies upon the limitations (and assets) of the confines of a yacht at sea.

Master and Commander: The Far Side of the World (2003)

During the Napoleonic Wars, a brash British captain pushes his ship and crew to their limits in pursuit of a formidable French war vessel around South America .  The most realistic and exciting sea saga ever based on the novels by  Patrick O'Brian.   This was what it was really like. One ship, 197 men, 4500 miles from home. Chasing a French ship twice her size. No retreat. And the ship was originally the “Rose” sailing for many years out of Black Rock Harbor in Connecticut ! Russell Crowe with a stunning performance as Captain Jack Aubrey, with Paul Bettany as his trusted friend and ship’s surgeon, Dr Stephen Maturin. Perfectionists will say that it's not true to the O'Brian editions, but I say it's fine with me.

Down to the Sea in Ships

This film centers on the grandfather/grandson relationship on a whaling vessel. Bering Joy the Captain of a Whaling ship wants to take grandson Jed out to follow in "Gramps" footsteps. Unbeknownst to him, the Company that employes him has all but written him off for future voyages due to his poor health and age. Enter Ricard Widmark as Dan Lunceford. The soon to be First Mate (and Captain in waiting) has a Master's Licence, sea experience (despite being quite young) & a wealth of Book-Learning degrees & school taught smarts that makes old Bering very nervous. Still the crafty, crusty old sea dog finds a way to turn everything to his advantage. This is an adventure that you will never forget

1492: Conquest Of Paradise

The controversial 1992 film about Christopher Columbus. Directed by Ridley Scott and starring Gerard Depardieu, Sigourney Weaver, Armand Assante and Frank Langella.

It is a beautiful, and wonderful movie. It is entertaining, and presents to us a fair interpretation of Columbus and what he accomplished through his life.

The film succeeds on four of its noteworthy merits. The first one would be Scott's directing, and his reputation for incorporating vivid & gorgeous images into all his films, the second one would be its historical accuracy, the third one would be its score, composed by Vangelis, who can create gorgeous paintings like Scott can, but only to the music he makes. Finally the fourth one would be the casting of Depardieu, who can add spice to basically any film that he stars in.


The Old Man and the Sea

Ernest Hemingway's Pulitzer Prize story about a fisherman's pursuit of an elusive marlin with Spencer Tracy in a monumental performance.
Year: 1958
Director: John Sturges
Starring: Spencer Tracy, Felipe Pazos, Harry Bellaver.

Spencer Tracy gives a powerful performance as Santiago, the desperate old fisherman who must struggle to subdue and then keep the giant marlin that represents his salvation. Director John Sturges and screenwriter Peter Viertel retain much of Ernest Hemingway's symbolism, making of Santiago a Christ-like figure. A more apt Biblical analog might be Job; like him, Santiago endures the indignities and strife thrust upon him, but perseveres and endures while retaining his appreciation of nature and simple pleasures.

The African Queen

Starring Academy Award® winners HUMPHREY BOGART and KATHARINE HEPBURN, The African Queen tells the timeless tale of two mismatched strangers joining forces in a common cause - and finding love along the way. The story chronicles the burgeoning romance between Bogie's river rat Charlie Allnut and Hepburn's missionary Rose Sayer, as they reluctantly join for ces to torpedo a German gunboat in war-torn East Africa. Directed by Academy Award® winner JOHN HUSTON, and filmed on location in the Belgian Congo, The African Queen is arguably one of the finest films ever made - with one of the most legendary star pairings ever to appear on the screen!

TV Series

Horatio Hornblower

Excellent A&E series that will make you search out the entire series of books. He is the ultimate high-seas hero: a man of unshakeable courage, unwavering principles and extraordinary skill. Joining the Royal Navy at the outset of the bloody Napoleonic Wars, Horatio Hornblower rises quickly from raw recruit to seasoned sailor, and his exploits become the stuff of legend.

This lavish adaptation of C.S. Forester's classic novels charmed millions of viewers with their swashbuckling action, broadside battles and below-decks intrigue. This expansive set brings together the complete, Emmy-winning Hornblower saga for the first time. Ioan Gruffudd (Black Hawk Down, Titanic) gives a star-making performance as the dashing hero, and the stellar supporting cast includes Robert Lindsay (Me & My Girl) Jamie Bamber (Band of Brothers) and Paul Copley (Queer as Folk). Six feature-length Hornblower films: The Duel, The Fire Ships, The Duchess and the Devil, The Wrong War, The Mutiny, Retribution.


Cruising Western Long Island Sound with J.R. Smith

"From the Description:
Mix fantastic cruising waters, sandy beaches, protected bays, hundreds of islands, fun fishing, outstanding near-water dining & you have Long Island Sound. This video profiles major ports from Hell Gate to Branford CT , crossing to Mt. Sinai then following the Long Island coast back to Manhattan . With coverage of charts, navigation advice & safety tips. Minutes: 60 mins"

Sounds good doesn't it? We were excited to find this. And it's expensive. Well, save your money. DO NOT buy this DVD. It is so superficial as to be completely useless as a guide to these waters. There is no imagery of Hell Gate, they flash a chart but then don't show the corresponding area on video, they do not go ashore nor show any useful details. Trust us. This one is just not worth it.

“Around Cape Horn

From the Cover: In 1929 the last great days of commercial sail were passing. During that year Captain Iving Johnson sailed aboard the massive bark PEKING . In this program he narrates the passage in the style that has made him a favorite on the lecture circuit around the world. The most spectacular scenes are filmed during a wild storm as the ship rounds the feared Cape Horn . Photographed 1929 and narrated 1980 by Captain Irving Johnson. 37 Minutes, Black & White.  Available from Mystic Seaport Museum Bookstore 1-800-331-2665 or better sailing bookstores everywhere.  Peking is now berthed at South St. Seaport in NYC.

"Around Alone"

"Around Alone" is about Dodge Morgan's record-breaking single-handed circumnavigation in 1986. Lots of on-board "footage." Excellent. 58 mins. $29.95 from The New Film Co. 617-641-2580 or 800-462-2306

"American Challenge"

"American Challenge" is about the 1980 OSTAR race. Superbly done with  cameras aboard seven American boats. Highly recommended. 58 mins. $29.95 from The New Film Co. (see above).

"The Friendship Sloop,"

"The Friendship Sloop," 28 mins., shows both wooden and fiberglass boats under construction and in the water. This is a traditional gaff-rigged design developed on the Maine coast. Available from New Film Co.

"The Whitbread Round the World Race, 1993-94"

"The Whitbread Round the World Race, 1993-94" is made up of ESPN materials narrated by Gray Jobson and Peter Montgomery. 60 mins. $19.95. Available from The Armchair Sailor in Newport , RI (phone 800-29CHART), my favorite bookstore in the world!

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