Best sailing films

My picks for the best movies with a sailboat

Old timey engraving of pirates about to cut a person’s arm off
His buyer’s remorse was twofold. A 50% discount on an arm and a leg is still an arm. And now it would take twice as long to apply his new bottom paint.

I’m an expert on film:


My list of best movies for sailors

Here’s my list of the best movies where sailboats play a role. We’re talking great stories told by excellent, some even legendary, writers, directors, and casts.

More importantly, with one oddball, these films realistically portray sailboats and sailors. Few things in this world break my heart more than trying to suspend disbelief while choking down the urge to yell “That’s not how boats work!” at the screen.

Master and Commander: The Far Side of the World

Respectable on-screen versions of Captain Aubrey and Dr. Maturin.

Movie poster for Master and Commander

Genre: Historical adventure

Director: Peter Weir

Starring: Russell Crowe, Paul Bettany

Year: 2003

Studio: 20th Century Fox

Despite the popularity of Patrick O’Brian’s Captain Jack Aubrey and Dr. Stephen Maturin among nerds and sailors, or maybe because of it, this is the only film adaptation. Like the novels, the film doesn’t insult your intelligence and has plenty of adventure. The film’s title is only coincidental to the novel. The former draws from a few of Aubrey-Maturin’s adventures.

Like the books, the look and feel of the movie convinces you that this could have really taken place in the early 19th century. They say things like larboard and starboard, not port and starboard. Even the way they dress is convincing. Captain Aubrey has an enormous hat. Like huge.

The themes won’t shake your world view. This is more about good guys, bad guys, and adventure. The protagonist is torn between friendship and duty. The antagonist is mysterious and constantly threatening. The battle scenes kick ass.

Moby Dick

Sympathize with the need to prove a point at any cost.

Movie poster for Moby Dick

Genre: Historical adventure

Director: John Huston

Starring: Gregory Peck, Richard Basehart, a great white whale

Year: 1956

Studio: Warner Bros

The literal and figurative Moby Dick of movies. The director and the cast are legends, including a cameo from Orson Welles. Hell, even the screenplay is by Huston and Ray Bradbury, the legendary sci-fi author.

Maybe back in the day Moby Dick was about defying God. Today we can spin it as a resonant story about shareholder value vs climate change.

Probably not intentionally, this movie induces cringes of political incorrectness. But that makes it feel historically accurate. And yet the crew is ethnically diverse, including prominent Quaker, Polynesian, African, and Native American characters.

The production quality holds up. The Pequod looks as close to a mid-19th century working whaling ship as I can imagine. The sailors are grubby and malnourished from toiling with wood, iron, and canvas. Interiors are dim and cramped. You can almost smell the salt, dampness, and rendering whale blubber.

Sixty years later, the special effects hold up too. The whale hunting scenes include footage of a real whale hunt. That’s real water that Moby Dick kicks up to tear the Pequod a new one.

The story, man, that story. Huston and Bradbury distill 135 chapters into a fine whiskey of less than 2 hours. Telling the story from Ishmael’s point of view instead of Ahab’s immerses you deeper. No sane human can empathize with Ahab’s manic charisma but we sure can sympathize with his victims/adherents.

Spoiler: the money shot is fantastic. Moby Dick shows up only at the end. But he ends it like a boss, in a gruesome whirlpool of mayhem, literally. Moby Dick 1, humanity 0.

Mutiny on the Bounty

They’re mad as hell and aren’t going to take it anymore.

Movie poster for Mutiny on the Bounty

Genre: Historical drama

Director: Lewis Milestone

Starring: Marlon Brando, Trevor Howard, Richard Harris

Year: 1962

Studio: MGM

I’m not sure why I’m bothering with this review. With Brando what more kick in the ass do you need to watch?

I wouldn’t believe it until I saw it, but here’s the Marlon Brando playing Fletcher Christian as a full on fop, complete with the upper class British accent and a bigger, shinier wardrobe than Beyonce and Madonna combined. At one point he even says “Oh dear”. The Godfather. Oh dear.

And you know what? He pulls it off. In this take on the Bounty’s salacious story, Christian has more humanity than his tyrant Captain. But as an officer Christian still has to maintain order among the crew. Brando strolls that line between Captain Bligh and the crew. Well, until he can’t take it anymore.

Trevor Howard plays Bligh. And he pulls it off too, you almost feel bad for Bligh. Almost. Bligh’s devotion to King and country are admirable, but he has the people skills of, well, a Captain Bligh. Even a dick with good intentions is still a dick.

Richard Harris plays a secondary part, but this was before his heyday. You can see greatness about to happen, but either he isn’t ready or isn’t given a chance in this role.

White Squall

Can a rag-tag crew pull through a bad situation?

Movie poster for White Squall

Genre: Disaster survival

Director: Ridley Scott

Starring: Jeff Bridges, Caroline Goodall, John Savage

Year: 1996

Studio: Buena Vista

Not the classic heavyweight of the previous movies, but still solid entertainment. A 19th century ship crewed by 20th century kids. What could go wrong? Based loosely on the true story of the Albatross.

Dead Calm

A frightening premise and nail-biting suspense.

Movie poster for Dead Calm

Genre: Psychological thriller

Director: Philip Noyce

Starring: Nicole Kidman, Sam Neill, Billy Zane

Year: 1989

Studio: Warner Bros

A fun thriller and a great cast. Things start badly, get better, then get weird and scary. (Spoiler alert?)

Kidman, Neill, and Zane all do excellent work. At this point in their careers they have just reached stardom. Zane is more of newcomer, fame-wise, but he holds up his end of the movie.

The story is based on a novel of the same name by Charles Williams. George Miller, the creator of the Mad Max franchise, produced it. Callback to Orson Welles: he tried to adapt it but never finished it.

Knife in the Water

Gotta love love triangles and mind games.

Movie poster for Knife in the Water

Genre: Psychological drama

Director: Roman Polanski

Starring: Leon Niemczyk, Jolanta Umecka, Zygmunt Malanowicz

Year: 1962

Studio: Zespół Filmowy

The original Polish title is Nóż w wodzie.

Yes, I know that it’s an understatement that Roman Polanski is... problematic. But his films are still compelling with their tight stories, great acting, and brilliant direction. This is his first feature length film, in Polish. A version with English subtitles isn’t easy to find. But if you can find a copy, it’s worth it.

Three characters, one boat, one knife, and 24 hours. Oh, and neverending, tense power shifts as each character wins and loses the upper hand.

Captain Ron

More laughs, less murder and mayhem.

Movie poster for Captain Ron

Genre: Comedy

Director: Thom Eberhardt

Starring: Martin Short, Kurt Russell, Mary Kay Place

Year: 1992

Studio: Buena Vista

This is the oddball of the list. Sorry, there's little that you can call realistic about the boat, or the water. It jettisons technical accuracy in favor of laughs. Kurt Russell reaches Martin Short’s high comedic bar in this one. Watch this movie with your crew if they aren’t passionate about cinéma nautique like you are.

At your service

Humbly yours,

Marc, Supreme Purser