Movies like My Sweetheart Wants to Go Sailing on Sunday (1961)
The best movies like My Sweetheart Wants to Go Sailing on Sunday (1961) are A Cinderella Story: Starstruck (2021), Find Me Falling (2024) and Hollywood Stargirl (2022). If My Sweetheart Wants to Go Sailing on Sunday hooked you with its romance and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedNational Lampoon's Vacation (1983)7.1/10 from 1,841 votes
- NewestYoh! Bestie (2026)Released 2026
- In GermanWhere Is Fred? (2006)Also in German
A Cinderella Story: Starstruck (2021)
Finley Tremaine, a small-town farm girl, longs to spread her wings and soar as an aspiring performer. When a Hollywood film crew arrives in her sleepy town, she is determined to land a role in the production and capture the attention of handsome lead actor Jackson Stone. Unfortunately, a botched audition forces her to change course. Now, disguised as cowboy “Huck,” Finley finally gets her big break. But can she keep the charade a secret from everyone, including her evil stepmother and devious step-siblings?
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisFind Me Falling (2024)
After a failed comeback album, a rock star retreats to a cliffside home on Cyprus, only to find his new life complicated by visitors — and an old flame.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisHollywood Stargirl (2022)
When Stargirl's mother is hired as the costume designer on a movie, they relocate to L.A., where Stargirl quickly becomes involved with an eclectic assortment of characters.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Fighting Temptations (2003)
Darrin Hill, a slick-talking but down-on- his-luck NYC advertising exec, returns to his hometown in Georgia to claim the inheritance his aunt left him. But before Darrin can collect the money, he must fulfill his aunt's final wish -- to create a local choir.
Why it matches: Recommended by TMDB viewers · both comedy & music
SnoozefestMovies 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 thisFalling for Christmas (2022)
An engaged, spoiled hotel heiress finds herself in the care of a handsome, blue-collar lodge owner and his precocious daughter after getting amnesia in a skiing accident.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisPeople We Meet on Vacation (2026)
Poppy's a free spirit. Alex loves a plan. After years of summer vacations, these polar-opposite pals wonder if they could be a perfect romantic match.
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 thisSilk Stockings (1957)
After three bumbling Soviet agents fail in their mission to retrieve a straying Soviet composer from Paris, the beautiful, ultra-serious Ninotchka is sent to complete their mission and to retrieve them. She starts out condemning the decadent West, but gradually falls under its spell—with the help of an American movie producer. A remake of Ninotchka (1939).
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 thisLittle Italy (2018)
Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?
Why it matches: Recommended by TMDB viewers · both comedy & romance
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 thisYoh! Bestie (2026)
Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies 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 thisThe Wrong Paris (2025)
Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
Why it matches: Recommended by TMDB viewers · both romance & comedy
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 thisChasing Papi (2003)
Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisWhere Is Fred? (2006)
In order to catch a basketball from the favorite team of his girlfriend's spoiled son, Fred poses as a numb, wheelchair-bound fan. But when he catches the ball, he also catches the attention of young, attractive filmmaker Denise, who wants to feature an invalid fan in an image film for the team. Fred has to keep playing his role, while real invalid and really furious fan Ronny might call his bluff at any moment. Worse, still, love sets in...
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe 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 thisBoot Camp (2024)
Unathletic Whitney Carmichael signs up for an intense summer boot camp to reinvent herself and falls for her personal trainer. She then finds the strength to embrace her true self and ignore the others' expectations.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisI Often Think of Piroschka (1955)
Andreas, a young German student comes to Hungary on an exchange programme. In the Hungarian village he falls in love with the stationmaster's daughter Piroschka and spends much of his time with her. They have an enchanting summer until Andreas gets an invitation to join another young woman at a nearby resort. Piroschka is jealous and follows him there, causing trouble. It takes a long time for Andreas and Piroschka to even talk to each other again. When Andreas has to leave Hungary at the end of his holiday, he is determined to return some day.
Why it matches: Similar story and style · both romance & comedy
Come September (1961)
Robert Talbot, an American millionaire, arrives early for his annual vacation at his luxurious Italian villa. His long-time girlfriend Lisa has given up waiting for him and has decided to marry another man. Meanwhile, his sneaky business associate Maurice secretly misappropriates the villa as a hotel while Talbot is away. The current guests of the "hotel" are a group of young American girls.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisHow Stella Got Her Groove Back (1998)
Through good times and bad, Stella and Delilah have always had each other. Now, Stella's so busy building a life that she's forgotten how to really live. But Delilah is about to change all that. What starts as a quick trip to Jamaica, ends as an exhilarating voyage of self discovery as Stella learns to open her heart and find love – even if it's with a man 20 years her junior.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisSex and the City 2 (2010)
Carrie, Charlotte, and Miranda are all married now, but they're still up for a little fun in the sun. When Samantha gets the chance to visit one of the most extravagant vacation destinations on the planet and offers to bring them all along, they surmise that a women-only retreat may be the perfect excuse to eschew their responsibilities and remember what life was like before they decided to settle down.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisBerangkat! (2017)
Three friends decide to take vacation together where they test the meaning of friendship and a journey of self-discovery.
Why it matches: Similar story and style · both comedy
National Lampoon's Vacation (1983)
Clark Griswold is on a quest to take his family to the Walley World theme park for a vacation, but things don't go exactly as planned.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisHead Above Water (1996)
Judge George brings his young wife, Nathalie, to a remote island for a vacation. But while George accompanies their only neighbor -- Nathalie's childhood friend Lance -- on a fishing trip, Nathalie spends time with her ex, Kent. When Kent ends up dead the next morning, Nathalie tries to hide the evidence before her husband gets home. After the body is found, the events of the previous night unravel, with unexpected revelations.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisMother's Elling (2003)
Elling has lived with his mother all his life. Mom is the practical one, while Elling ponders the more theoretical aspects of life. He spends his time in their apartment reading books and looking at the neighbours through the living room window. Elling doesn't seem to need to be around others like most people. That's why Elling is less than enthusiastic when his mother suddenly decides to take her son on a beach vacation to Spain. Reluctantly, Elling agrees. After all, a lady at her age needs a good man by her side. But what Elling refuses to realize is that Mom is not only old, but also sick. Very sick. On her last vacation she tries to get Elling to see that life is bigger than their living room.
Why it matches: Similar story and style · both comedy
Carry On Cruising (1962)
Captain Crowther's lot is not a happy one! Five of his crew have to be replaced and at such short notice before the voyage begins there isn't much to choose from. Not only does he get the five most incompetent shipmates ever to sail the seven seas, but the passengers turn out to be a rather strange bunch too. The SS Happy Wanderer will never be the same.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisEnchanted April (1991)
When married British women Rose Arbuthnot and Lottie Wilkins decide to take a break from their respective spouses, they stay at a castle in Italy for a quiet holiday. Joining the ladies is Caroline Dester, a young socialite, and Mrs. Fisher, an older aristocrat. Liberated from their daily routines, the four women ease into life in rural Italy, and each finds herself transformed by the experience.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like My Sweetheart Wants to Go Sailing on Sunday?
The closest matches to My Sweetheart Wants to Go Sailing on Sunday are A Cinderella Story: Starstruck (2021), Find Me Falling (2024) and Hollywood Stargirl (2022). Below are 27 more, each with the reason it matches.
What should I watch after My Sweetheart Wants to Go Sailing on Sunday?
Start with A Cinderella Story: Starstruck (2021), the closest match to My Sweetheart Wants to Go Sailing on Sunday.
What is the highest-rated movie like My Sweetheart Wants to Go Sailing on Sunday?
National Lampoon's Vacation (1983), rated 7.1/10 by 1,841 TMDB users.
What is the newest movie like My Sweetheart Wants to Go Sailing on Sunday?
Yoh! Bestie (2026) is the most recent release on this list.
Are there German movies like My Sweetheart Wants to Go Sailing on Sunday?
Yes: Where Is Fred? (2006) and I Often Think of Piroschka (1955).
How are movies similar to My Sweetheart Wants to Go Sailing on Sunday chosen?
First come films that Trakt’s viewers watch alongside My Sweetheart Wants to Go Sailing on Sunday, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.