Movies like Sailor's Holiday (1944)
The best movies like Sailor's Holiday (1944) are The Prince & Me 4: The Elephant Adventure (2010), I Love You Again (1940) and What's Love Got to Do with It? (2023). If Sailor's Holiday hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest rated5 to 7 (2014)7.1/10 from 428 votes
- NewestChampagne Problems (2025)Released 2025
The Prince & Me 4: The Elephant Adventure (2010)
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged marriage to the brooding and sinister Kah and is secretly in love with a young elephant handler named Alu.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisI Love You Again (1940)
Boring businessman Larry Wilson recovers from amnesia and discovers he's really a con man...and loves his soon-to-be-ex wife.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisWhat's Love Got to Do with It? (2023)
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLet's Make Love (1960)
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLove Is in the Air (2023)
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisEasy Virtue (2008)
A young Englishman marries a glamorous American. When he brings her home to meet the parents, she arrives like a blast from the future - blowing their entrenched British stuffiness out the window.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Disorderly Orderly (1964)
Poor Jerome Littlefield. He wants to be a doctor – but that's not exactly the perfect career choice when you're hopelessly squeamish. So he settles for the job of orderly at the Whitestone Sanitarium, a career move that's guaranteed to keep the patients – and viewers – in stitches!
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Other End of the Line (2007)
An employee at an Indian call-center travels to San Francisco to be with a guy she falls for over the phone.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisHow to Marry a Millionaire (1953)
Three women set out to find eligible millionaires to marry, but find true love in the process.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisChristmas with You (2022)
Feeling career burnout, pop star Angelina escapes to grant a young fan's wish in small-town New York, where she not only finds the inspiration to revitalize her career but also a shot at true love.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisPlatinum Blonde (1931)
Ann Schuyler is an upper-crust socialite who bullies her reporter husband into conforming to her highfalutin ways. The husband chafes at the confinement of high society, though, and yearns for a creative outlet. He decides to write a play and collaborates with a fellow reporter.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThis Little Love of Mine (2021)
Laura Price is a successful San Francisco lawyer on the cusp of promotion – a far cry from her childhood growing up on a tropical island with best friends Chip and Gem. When the firm’s biggest client – Chip’s grandfather – asks Laura to travel to the island and deliver a contract to make Chip his heir, she leaves behind her practice and fiancé Owen to convince her childhood friend to sign a contract that will make him a billionaire.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove, Weddings & Other Disasters (2020)
A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisWhisky Galore (2016)
The story of the inhabitants of the isolated Scottish island of Todday, in the Outer Hebrides, where gloom sets in as their wartime rationing of whisky runs out. When cargo ship the SS Cabinet Minister runs aground the shrewd islanders run rings around the buffoonish English Home Guard commander Captain Waggett and conspire to hide away cases of the precious amber nectar.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisPhffft (1954)
Robert and Nina Tracey resolve to live separate lives when their eight-year marriage dissolves into disagreements and divorce. But their separate attempts to get back out on the dating scene have a funny way of bringing them together.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisGood Advice (2001)
An investment banker loses everything and must discover what's really important in life.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisAll for Love (2017)
When a romance novelist is teamed with a Navy SEAL as research for her book, by a mandate from her publisher, she is less than thrilled and he is more than honest. However, as she works with the SEAL, she has a change of heart and learns to look at her life and writing with a different point of view.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisChampagne Problems (2025)
A driven American exec heads to Paris determined to acquire a champagne brand by Christmas — and accidentally falls for the heir to the bubbly empire.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisWatching the Detectives (2007)
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets turned upside down and the line between reality and the movies quickly begins to blur.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like this5 to 7 (2014)
A young writer begins an affair with an older woman from France whose open marriage to a diplomat dictates that they can meet only between the hours of 5 p.m. to 7 p.m.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisDames Ahoy (1930)
Three sailors go searching for a girl who swindled one of them out of half his pay.
Why it matches: Similar story and style · both comedy & romance
French Leave (1948)
Merchant seaman Skitch Kilroy (Jackie Cooper) and "Pappy" Reagan (Jackie Coogan)arrive in Marseilles, eager to resume their combative rivalry for Mimi. But they are ordered by their skipper Muldoon (Ralph Sanford) to remain on board and guard against theft of foodstuffs by a black market gang.
Why it matches: Similar story and style · both romance & comedy
Gobs of Trouble (1935)
Two sailors decide to settle down and get married, and live to regret it.
Why it matches: Similar story and style · both comedy
Bring on the Girls (1945)
A millionaire joins the Navy hoping to find a girl who'll marry him for himself, not for his money. A beautiful gold-digger who works at a resort hotel sets out to get him.
Why it matches: Similar story and style · both comedy
Back from the Front (1943)
The Stooges join the war effort by enlisting at Merchant Marines. While aboard, they have a brief run-in with (a secret German Nazi officer) Lt. Dungen (Vernon Dent), and then mistake a torpedo for a beached whale. Moe says they have to kill it, and it promptly explodes. After being lost at sea for several days, they come across the SS Schicklgruber and climb aboard. Now with fully grown beards, they come across Lt. Dungen again, who does not recognize them. After realizing they are on a German war ship they eventually overtake the crew and toss them overboard.
Why it matches: Similar story and style · both comedy
Sailor's Holiday (1929)
Sailors Pike and Shorty are on leave when a street woman swindles them out of some money by telling them she is looking for her long-lost brother, a sailor.
Why it matches: Similar story and style · both comedy
In the White City (1983)
Fed up with the sea, Paul, a Swiss mechanic working in the noisy bowels of a merchant ship, lands in Lisbon.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisSailor Beware! (1933)
A pair of sailors are on shore leave - skirt chasing and raising hell. They're targeted and pursued by a gang looking for a sailor with a winning lottery ticket. Mayhem ensues.
Why it matches: Similar story and style · both comedy
A Sailor’s Heart (1912)
A sweetheart at every port has ever characterized the sailor, but it is believed that the sailor in this comedy carries the tradition a trifle further.
Why it matches: Similar story and style · both comedy
Lock Up Your Daughters (1969)
Three sailors on leave turn a British town upside down.
Why it matches: Similar story and style · both comedy
Like Sailor's Holiday and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Sailor's Holiday?
The closest matches to Sailor's Holiday are The Prince & Me 4: The Elephant Adventure (2010), I Love You Again (1940) and What's Love Got to Do with It? (2023). Below are 27 more, each with the reason it matches.
What should I watch after Sailor's Holiday?
Start with The Prince & Me 4: The Elephant Adventure (2010), the closest match to Sailor's Holiday.
What is the highest-rated movie like Sailor's Holiday?
5 to 7 (2014), rated 7.1/10 by 428 TMDB users.
What is the newest movie like Sailor's Holiday?
Champagne Problems (2025) is the most recent release on this list.
Are there English movies like Sailor's Holiday?
Yes: The Prince & Me 4: The Elephant Adventure (2010), I Love You Again (1940) and What's Love Got to Do with It? (2023).
How are movies similar to Sailor's Holiday chosen?
First come films that Trakt’s viewers watch alongside Sailor's Holiday, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.