Movies like The Cayman Triangle (1977)
The best movies like The Cayman Triangle (1977) are Swashbuckler (1976), The Retirement Plan (2023) and The Crimson Pirate (1952). If The Cayman Triangle hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
The Cayman Triangle
Quick picks
- Highest ratedMoana (2016)7.6/10 from 14,169 votes
- NewestCats from the Crow’s Nest: The Bottle (2026)Released 2026
Swashbuckler (1976)
A pirate and a hot-tempered noblewoman join forces to protect Jamaica from a tyrant.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Retirement Plan (2023)
When Ashley and her young daughter Sarah get caught up in a criminal enterprise that puts their lives at risk, she turns to the only person who can help: her estranged father Matt, currently living the life of a retired beach bum in the Cayman Islands. Their reunion is fleeting as they are soon tracked down on the island by crime boss Donnie and his lieutenant Bobo. As Ashley, Sarah, and Matt become entangled in an increasingly dangerous web, Ashley quickly learns her father had a secret past that she knew nothing about and that there is more to her father than meets the eye.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisThe Crimson Pirate (1952)
Burt Lancaster plays a pirate with a taste for intrigue and acrobatics who involves himself in the goings on of a revolution in the Caribbean in the late 1700s. A light hearted adventure involving prison breaks, an oddball scientist, sailing ships, naval fights and tons of swordplay.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Pirates! In an Adventure with Scientists! (2012)
The enthusiastic Pirate Captain, along with his rag-tag crew, sets out to beat his bitter rivals. The chaotic adventure takes them from exotic shores to Victorian London, and from a haplessly smitten scientist to a diabolical queen.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisPirates (1986)
The adventures of pirate Captain Red and his first mate Frog.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisKnight and Day (2010)
A fugitive couple goes on a glamorous and sometimes deadly adventure where nothing and no one – even themselves – are what they seem. Amid shifting alliances and unexpected betrayals, they race across the globe, with their survival ultimately hinging on the battle of truth vs. trust.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisTop Secret! (1984)
Popular and dashing American singer Nick Rivers travels to East Germany to perform in a music festival. When he loses his heart to the gorgeous Hillary Flammond, he finds himself caught up in an underground resistance movement. Rivers joins forces with Agent Cedric and Flammond to attempt the rescue of her father, Dr. Paul, from the Germans, who have captured the scientist in hopes of coercing him into building a new naval mine.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisBad Boys II (2003)
Detectives Marcus Burnett and Mike Lowrey of the Miami Narcotics Task Force are tasked with stopping the flow of the drug Ecstasy into Miami. They track the drugs to the whacked-out Cuban drug lord Johnny Tapia, who is also involved in a bloody war with Russian and Haitian mobsters. If that isn't bad enough, there's tension between the two detectives when Marcus discovers that playboy Mike is secretly romancing Marcus’ sister, Syd.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisTom and Jerry: Shiver Me Whiskers (2006)
Dueling cat-and-mouse team Tom and Jerry hit the high seas on a hunt for buried treasure in this pirate adventure. The tale begins when crew member Tom sets sail with an infamous pirate and finds a treasure map along with stowaway Jerry. The furry swashbucklers race to a deserted island where X marks the spot, but along with battling each other, they must outwit ruthless buccaneers, angry monkeys and a giant octopus to strike it rich.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMoana (2016)
In Ancient Polynesia, when a terrible curse incurred by Maui reaches an impetuous Chieftain's daughter's island, she answers the Ocean's call to seek out the demigod to set things right.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe SpongeBob Movie: Search for SquarePants (2025)
Desperate to be a big guy, SpongeBob sets out to prove his bravery to Mr. Krabs by following The Flying Dutchman – a mysterious swashbuckling ghost pirate – on a seafaring adventure that takes him to the deepest depths of the deep sea, where no Sponge has gone before.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMoana 2 (2024)
After receiving an unexpected call from her wayfinding ancestors, Moana journeys alongside Maui and a new crew to the far seas of Oceania and into dangerous, long-lost waters for an adventure unlike anything she's ever faced.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisBarb & Star Go to Vista Del Mar (2021)
The story of best friends Barb and Star, who leave their small midwestern town for the first time to go on vacation in Vista Del Mar, Florida, where they soon find themselves tangled up in adventure, love, and a villain’s evil plot to kill everyone in town.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe SpongeBob Movie: Sponge Out of Water (2015)
Evil pirate Burger Beard is in search of the final page of a magical book that makes any evil plan he writes in it come true, but the final page happens to be the Krabby Patty secret formula. When Burger Beard endangers Bikini Bottom, SpongeBob, Patrick, Mr. Krabs, Squidward, Sandy, and Plankton must embark on a quest to retrieve the recipe and save their city...a quest that takes them to the surface world and transforms them into superheroes.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMike & Nick & Nick & Alice (2026)
Two gangsters and the woman they love try to survive the most dangerous night of their lives. As if that wasn’t enough, there’s one wild ingredient added to the mix: a time machine.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCraig Before the Creek (2023)
Before he was Craig of the Creek, he was just Craig — a new kid in a new town. All Craig wants is to go back to his old friends at his old home. But when he learns that the nearby creek is hiding a lost treasure that could make his wish come true, Craig sets off on a journey to find it — navigating the perilous suburban wilderness, forging new friendships, all while being pursued by a fearsome band of pirates who are bent on destroying the Creek itself.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisBeat the Devil (1953)
A group of con artists stake their claim on a bogus uranium mine.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHarold & Kumar Escape from Guantanamo Bay (2008)
Having satisfied their urge for White Castle, Harold and Kumar jump on a plane to catch up with Harold's love interest, who's headed for the Netherlands. But the pair must change their plans when Kumar is accused of being a terrorist. Rob Corddry also stars in this wild comedy sequel that follows the hapless stoners' misadventures as they try to avoid being captured by the Department of Homeland Security.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisTropic Thunder (2008)
A group of self-absorbed actors set out to make the most expensive war film ever. When budgets skyrocket and schedules fall far behind, the director tries to save the production by leading his cast into the jungles of Southeast Asia, where they inadvertently encounter real danger.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLEGO Scooby-Doo! Blowout Beach Bash (2017)
Mystery, Inc. heads to Blowout Beach for a real swinging beach party when the Ghost Pirates threaten to harsh the good vibes.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Adventures of Timmy the Tooth: Rainy Day Adventure (1995)
During a rainy day, Timmy imagines that he is Captain Good Guy, and Brushbrush is his first mate. They work to save Sunny the Sun from The Cavity Goon and Miss Sweety.
Why it matches: Similar story and style · both comedy
Cats from the Crow’s Nest: The Bottle (2026)
An animated pilot featuring three feline swashbucklers and the silly hijinks that ensue.
Why it matches: Similar story and style · both comedy
Treasure Island (1988)
Young Jim Hawkins finds himself serving with pirate captain Long John Silver in search of a buccaneer's treasure in this Soviet Ukrainian animated adaptation of Robert Louis Stevenson's classic tale.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisKaizoku Sentai Gokaiger: Let's Make an Extremely GOLDEN Show of it! The 36-Stage Gokai Change!! (2011)
Captain Marvelous and Gai are accidentally fused together in one body during Insarn's attempt to put Gai inside Karizorg, the empty shell of Barizorg. Determined to retrieve Insarn's gun and reverse the process, the duo transform into a hybrid form of Gokai Silver with Gokai Red's helmet and boots, and change into the red warriors from the past 34 Super Sentai while battling dozens of Gormin Sailors!
Why it matches: Similar story and style · both comedy
One Piece: The Movie (2000)
There once was a pirate known as the Great Gold Pirate Woonan, who obtained almost one-third of the world's gold. Over the course of a few years, the pirate's existence faded, and a legend grew that he disappeared with his gold to a remote island, an island pirates continue to search for. Aboard the Going Merry, Luffy and his crew, starved and reckless, are robbed of their treasure. In an attempt to get it back, they wreck the getaway ship, guided by a young boy named Tobio, who's a captured part of El Drago's pirate crew. El Drago's love for gold has driven him to look for Woonan's island, and thanks to Woonan's treasure map, he finds it. During this time, Luffy's crew have been split up, and despite their own circumstances, they must find a way to stop El Drago from obtaining Woonan's gold.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisBebe's Kids (1992)
When Robin meets the lovely Jamika he thinks he's in heaven. But when he meets her friend Bebe's children, whom she is looking after, he knows he's in hell.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisRaggedy Ann & Andy: A Musical Adventure (1977)
Raggedy Ann and Andy, along with other toys, reside in the nursery of a little girl named Marcella. During Marcella's seventh birthday, Babette, from France, is introduced as the new doll from a large package. When the lecherous Captain Contagious kidnaps Babette and escapes from the nursery, Ann and Andy must navigate the Deep Deep Woods to save her.
Why it matches: Similar story and style · both comedy
Hook (1991)
The boy who wasn't supposed to grow up—Peter Pan—does just that, becoming a soulless corporate lawyer whose workaholism could cost him his wife and kids. During his trip to see Granny Wendy in London, the vengeful Capt. Hook kidnaps Peter's kids and forces Peter to return to Neverland.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisOne Piece: Baron Omatsuri and the Secret Island (2005)
The Straw Hats visit a recreational island, run by Baron Omatsuri, who asks them to complete a series of ordeals if they wish to stay on the island. Luffy accepts and the Straw Hats work together to complete them, but as the island's mysteries unfold, their lives and friendships are put to the test. It's up to Luffy to stop the Baron's plot and keep his crew together.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like The Cayman Triangle?
The closest matches to The Cayman Triangle are Swashbuckler (1976), The Retirement Plan (2023) and The Crimson Pirate (1952). Below are 27 more, each with the reason it matches.
What should I watch after The Cayman Triangle?
Start with Swashbuckler (1976), the closest match to The Cayman Triangle.
What is the highest-rated movie like The Cayman Triangle?
Moana (2016), rated 7.6/10 by 14,169 TMDB users.
What is the newest movie like The Cayman Triangle?
Cats from the Crow’s Nest: The Bottle (2026) is the most recent release on this list.
Are there English movies like The Cayman Triangle?
Yes: Swashbuckler (1976), The Retirement Plan (2023) and The Crimson Pirate (1952).
How are movies similar to The Cayman Triangle chosen?
First come films that Trakt’s viewers watch alongside The Cayman Triangle, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.