Movies Like The Cayman Triangle

If you liked The Cayman Triangle (1977), a comedy movie directed by Anderson Humphreys and Ralph Clemente, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Swashbuckler (1976)
★ 6.2/10Also comedy
A pirate and a hot-tempered noblewoman join forces to protect Jamaica from a tyrant.
2
The Retirement Plan (2023)
★ 5.8/10Also comedy
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…
3
The Pirates! In an Adventure with Scientists! (2012)
★ 6.5/10Also comedy
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…
4
The Crimson Pirate (1952)
★ 7/10Also comedy
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…
5
Pirates (1986)
★ 6.3/10Also comedy
The adventures of pirate Captain Red and his first mate Frog.
6
Knight and Day (2010)
★ 6.2/10Also comedy
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…
7
Top Secret! (1984)
★ 7.1/10Also comedy
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…
8
Bad Boys II (2003)
★ 6.7/10Also comedy
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…
9
Tom and Jerry: Shiver Me Whiskers (2006)
★ 6.9/10Also comedy
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…
10
Moana (2016)
★ 7.6/10Also comedy
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.
11
The SpongeBob Movie: Search for SquarePants (2025)
★ 6.8/10Also comedy
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…
12
Moana 2 (2024)
★ 7/10Also comedy
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…
13
The SpongeBob Movie: Sponge Out of Water (2015)
★ 6.1/10Also comedy
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…
14
Barb & Star Go to Vista Del Mar (2021)
★ 6/10Also comedy
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…
15
Tropic Thunder (2008)
★ 6.7/10Also comedy
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…
16
Mike & Nick & Nick & Alice (2026)
★ 6.7/10Also comedy
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.
17
Harold & Kumar Escape from Guantanamo Bay (2008)
★ 6.3/10Also comedy
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…
18
The Road to El Dorado (2000)
★ 7.3/10Also comedy
Stowing away after a failed con, a pair of swindlers end up on El Dorado, the fabled "city of gold", where they quickly get in over their heads when they are mistaken as gods by the inhabitants.
19
Shrek the Third (2007)
★ 6.3/10Also comedy
After the King of Far Far Away dies, Shrek and Fiona are to succede. However, Shrek wants to return to his cozy swamp and live in peace and quiet, so when he finds out there is another heir to the throne, he and Donkey…
20
Baywatch (2017)
★ 6.1/10Also comedy
Devoted lifeguard Mitch Buchannon butts heads with a brash new recruit. Together, they uncover a local criminal plot that threatens the future of the Bay.