Movies Like Sailor's Holiday

If you liked Sailor's Holiday (1929), a comedy movie directed by Fred C. Newmeyer, 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
Monkey Business (1931)
★ 6.9/10Also comedy
Four stowaways get mixed up with gangsters while running riot on an ocean liner.
2
Cadet Kelly (2002)
★ 6.2/10Also comedy
Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.
3
Beau Hunks (1931)
★ 6.8/10Also comedy
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
4
Airborne (1993)
★ 6.1/10Also comedy
Good-natured teen surfer Mitchell Goosen finds himself staying with his aunt and uncle in Cincinnati, Ohio when his parents head to Australia for work. There he meets his cousin, Wiley, and together they try to…
5
Finding ʻOhana (2021)
★ 6.2/10Also comedy
Two Brooklyn siblings' summer in a rural Oahu town takes an exciting turn when a journal pointing to long-lost treasure sets them on an adventure, leading them to reconnect with their Hawaiian heritage.
6
Scooby-Doo! Pirates Ahoy! (2006)
★ 7.4/10Also comedy
It's horror on the high seas when Scooby-Doo and the gang take a creepy cruise into one of the world's most mysterious places, the Bermuda Triangle! If Scooby, Shaggy and the gang can't solve this mystery, they may…
7
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…
8
The Lizzie McGuire Movie (2003)
★ 6.3/10Also comedy
Lizzie McGuire has graduated from middle school and takes a trip to Rome, Italy with her class. And what was supposed to be only a normal trip, becomes a teenager's dream come true.
9
Beat the Devil (1953)
★ 6.1/10Also comedy
A group of con artists stake their claim on a bogus uranium mine.
10
The Fixer Uppers (1935)
★ 6.8/10Also comedy
Stan and Ollie are greeting card salesmen who agree to help a woman put a spark in her loveless marriage by making her husband jealous.
11
Ron's Gone Wrong (2021)
★ 7.8/10Also comedy
In a world where walking, talking, digitally connected bots have become children's best friends, an 11-year-old finds that his robot buddy doesn't quite work the same as the others do.
12
Mr. Bones (2001)
★ 6/10Also comedy
A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament.
13
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
14
The Trouble with Angels (1966)
★ 6.7/10Also comedy
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and…
15
Wake Up, Ron Burgundy: The Lost Movie (2004)
★ 6/10Also comedy
While Ron Burgundy's rivalry with Veronica Corningstone escalates quickly, a group of unprofessional thieves better known as 'The Alarm Clock' try to make the truth known, whatever that may mean...
16
Moana (2026)
★ 7.5/10Also comedy
Teenage Moana answers the Ocean's call and, for the first time, voyages beyond the reef of her island of Motunui with infamous demigod Maui on an unforgettable journey to restore prosperity to her people.
17
Two Tars (1928)
★ 6.8/10Also comedy
Two sailors on shore leave rent a car and go on a drive with their dates, but soon get involved in a huge traffic jam with dozens of ill-tempered motorists. A minor collision sets off an escalating series of…
18
Towed in a Hole (1932)
★ 7/10Also comedy
Although they are successful fishmongers, Stan convinces Ollie that they should become fishermen too, but making a boat seaworthy isn't an easy task.
19
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
20
The Air Up There (1994)
★ 6.1/10Also comedy
Jimmy Dolan is a college basketball coach who wants a big promotion. To get it, he needs to make a dramatic find. He ends up deep in Africa, hoping to recruit Saleh, a huge basketball prodigy Jimmy glimpsed in a home…