Movies like Christmas Sail (2021)
The best movies like Christmas Sail (2021) are Picture a Perfect Christmas (2019), Ghosts of Christmas Always (2022) and Haul Out the Holly (2022). If Christmas Sail 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
- NewestChristmas on Windmill Way (2023)Released 2023
Picture a Perfect Christmas (2019)
An extreme-sports photographer returns home for the holiday to take care of her grandmother, only to have a neighbor grab her attention as he needs assistance watching his young nephew.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisGhosts of Christmas Always (2022)
Katherine is a Ghost of Christmas Present and she must help one soul, Peter, rediscover his Christmas spirit. But this year has something unusual in store.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisHaul Out the Holly (2022)
Emily arrives home, hoping to visit her parents, only to discover that they are leaving on a trip of their own. As she stays at their house for the holidays, their HOA is determined to get Emily to participate in the neighborhood’s many Christmas festivities.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisNext Stop, Christmas (2021)
Angie wonders what her life would be like if she had married a former boyfriend who became a famous sportscaster. She takes the train home to spend Christmas with her family and inexplicably finds herself 10 years in the past. With the advice of the train's enigmatic conductor, Angie has the chance to revisit that Christmas and learn what — and who — is truly important to her.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like this'Tis the Season to be Merry (2021)
Looking for a fresh angle to her book on relationships, Merry heads to snow-covered Vermont. She finds a new perspective and Christmas cheer with charismatic aid worker Chris.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Royal Nanny (2022)
Claire is an MI5 agent who goes undercover as the royal nanny. She must overcome the challenges of her assignment, like resisting the charms of Prince Colin, while keeping the family safe at Christmas.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisChristmas in Evergreen (2017)
Allie, a veterinarian in Evergreen, reluctantly will spend Christmas with her long-distance boyfriend. Bound for the airport, she has engine trouble, and Ryan, headed to Florida with his daughter Zoe, stops to help. Sure they won’t meet again, they ignore their attraction, and part ways. At the diner, Zoe wishes on a snow globe, and a storm seems to grant her wish.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisCatering Christmas (2022)
A fledgling caterer, Molly Frost, is hired by Jean Harrison, the perfectionistic director of the renowned Harrison Foundation, to cater this year’s annual Christmas Gala dinner. Things get complicated when Molly falls for Jean’s nephew, Carson, 30s, a travel photographer with no desire to take over the family’s foundation… until his aunt assigns him to the task of making sure the catered dinner goes perfectly.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA Merry Christmas Wish (2022)
Janie, a rising marketing executive living in The Big Apple, returns to her hometown of Woodland Falls when her Great-Uncle Randall passes away. Randall has even arranged for his farmhand, Dylan to help at the event, which is being held in the farm’s sprawling barn. Aware that her Manhattan boyfriend is anxious for her to return to the city so the pair can jet off to a previously planned holiday on the beach, Janie begins to feel an unexpected emotional tug about living life in a more authentic, meaningful way.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisChristmas at the Drive-In (2022)
Sadie Walker is starting over in her hometown of Chesterfield, New York, following a series of major life disruptions that include leaving her law practice after losing her biggest case and no longer being engaged.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisAn Unexpected Christmas (2021)
Jamie hasn’t told his family that he and his now ex-girlfriend Emily broke up. After an inopportune run-in with Emily at the train station in his hometown, Jamie convinces her to pretend they’re still a couple to avoid ruining Christmas for his family.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisNever Kiss a Man in a Christmas Sweater (2020)
Single mom Maggie is facing Christmas alone until Lucas crashes into her life and becomes an unexpected house guest. Together they overcome Christmas while finding comfort in their growing bond.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisJolly Good Christmas (2022)
David is an American architect who relocates across the pond to take up a job at a prestigious London firm. As the clock counts down to Christmas Day, David is running out of time to buy his girlfriend – who also happens to be his boss’s daughter – a thoughtful present so he resorts to buying her a somewhat uninspired gift card.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisToo Close for Christmas (2020)
When Hayley accepts an invitation to spend Christmas with her sister’s new in-laws, her seemingly perfect holiday takes a turn when Paul, Hayley's brother-in-law's brother, unexpectedly shows up. Still harboring a grudge against Paul for ending her last relationship, Hayley reluctantly spends time with Paul and slowly realizes she may have been too quick a judge on Paul
Why it matches: Recommended by TMDB viewers · both romance & drama
SnoozefestMovies like thisThree Wise Men and a Baby (2022)
Three brothers get the surprise of their lives when they are forced to work together to care for a baby over the holidays. As they slowly get the hang of things, they find themselves on unexpected journeys of self-discovery and begin to rebuild their relationships as brothers, as well as the damaged romantic and professional relationships in their respective lives…all while rediscovering their love of Christmas.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisChristmas on Windmill Way (2023)
Mia Meijer gets ready for the Christmas Market Dutch Bake-Off and suspects that her grandmother, Ann, will walk away with the cherished Golden Rolling Pin thanks to her Kerststol, a traditional Dutch fruited Christmas bread. But Mia's world is rocked when she learns that Ann was having financial troubles and had to sell the land deed to the Windmill Way property in her family for generations. Making matters worse, the buyer is Mia's former boyfriend, property developer Brady Schaltz, who must let Mia and Ann know the Meijer family-owned heritage Dutch sawmill, renowned for the past 90 years for its fine millwork and beautiful wooden furniture, will be torn down to put up a luxurious resort.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisA California Christmas: City Lights (2021)
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisA Kindhearted Christmas (2021)
Jamie owns a sightseeing and tour company in the small town of Cooperville, New York. Navigating the holidays with enthusiasm is trickier for Jamie since her husband Matt passed. Matt loved Christmas and found unparalleled joy in giving to others. While reminiscing with family, Jamie realizes the town desperately needs someone with Matt’s genius for thinking of the small gestures that bring genuine happiness to the holidays.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA Very Country Christmas (2017)
Jeanette Williams is a busy single parent, trying to make the best life for her and her daughter. With no time to follow current celebrity gossip, Jeanette is unaware of when a Country superstar returns to their small town to escape the intrusive paparazzi and the chaos of fame. A chance meeting between the two have them both letting their guards down and opening their hearts to the possibility of romance.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisA Merry Christmas Match (2019)
Corey Calvin lives in a ski village where she works at her late father's local antique shop, having sidelined her her big city dreams of becoming a theater director. When Los Angeles hunk Ryder Donnelly comes into her shop, sparks fly and she starts to wonder what could be.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisThe Christmas Secret (2014)
While her life is falling apart, single mother Christine finds a magical family heirloom that leads to love and good fortune during Christmas.
Why it matches: Similar story and style · both romance & drama
Popcorn FlickMovies like thisA Christmas Wedding (2006)
Emily (Sarah Paulson) and Ben (Eric Mabius) find their plans to marry on Christmas day coming apart at the seams when Ben is left to plan the wedding details after Emily is forced to go on a business trip. Though Emily, a perfectionist, is determined to have a fairytale wedding, she realizes that love is all that really matters when a freak storm threatens to keep her from making it home in time for the big day.
Why it matches: Similar story and style · both comedy & romance
A Christmas Miracle for Daisy (2021)
Whitney Alder owns interior design firm Marietta Designs, which she runs with her friend Andi in the small town of Marietta, Montana. Whitney is designing Santa’s float for the annual Marietta Christmas Parade when a potential job opportunity comes her way: the full redesign of a landmark home by Christmas Eve.
Why it matches: Similar story and style · both romance & comedy
SnoozefestMovies like thisKirk Franklin's A Gospel Christmas (2021)
When Olivia, a young assistant pastor, gets assigned to be a lead pastor at a new church a month before Christmas, she's fearful she can't manage the transition, including getting the choir ready to open the town's annual Winter Jamboree. Banding together with her new congregation, Olivia discovers a new home for herself, and even finds a little Christmas romance along the way!
Why it matches: Similar story and style · both drama & romance
My Favorite Christmas Melody (2021)
Once a promising singer-songwriter, Abby now finds herself writing uninspired jingles for commercials. As she heads home for the holidays, she's enlisted by the local high school music teacher to help save the school arts program. In the process, Abby rediscovers her voice and regains the confidence to go after her dreams and lets the possibility of love in too.
Why it matches: Similar story and style · both comedy & romance
A Christmas Proposal (2008)
Two lawyers dueling over a proposal to turn a quaint mountain town into a ski resort discover they are former childhood sweethearts. Lisa is fighting to protect the hamlet, big city attorney Rick represents the developer who wants to plow it under. But when a car accident forces Rick to stick around, the small town, and his former beloved, begin to work their magic on him.
Why it matches: Similar story and style · both comedy & romance
Santa Baby 2 (2009)
Santa's in the midst of a late-life crisis -- he's tired of the responsibilities of the job and is ready to pass on the reins to Mary, who feels torn between the family business and running her own high stakes firm in New York City, along with balancing a relationship with the love of her life, Luke (Dean McDermott). The situation gets increasingly dire when Teri, an ambitious new arrival to the North Pole, sows dissension at the workshop in an effort to take over Christmas.
Why it matches: Similar story and style · both comedy
Christmas with a Prince: The Royal Baby (2021)
Things get complicated for the expecting Prince Alexander and Dr. Tasha when a Royal State Visit is planned abroad, passing through her hometown. The couple must struggle with defying tradition and delivering, literally, on expectations.
Why it matches: Similar story and style · both romance
Christmas Vacation '90 (1990)
Several characters coincide during the Christmas holidays in the winter season of Saint Moritz.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisElmo's Christmas Countdown (2007)
There's a miracle on Sesame Street in this special holiday tale. Elmo, Abby Cadabby, and their new friend Stiller the Elf are going to count down to Christmas with the Christmas Counter-Downer. But all the counting boxes have gone missing and Christmas may never come again!
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like Christmas Sail?
The closest matches to Christmas Sail are Picture a Perfect Christmas (2019), Ghosts of Christmas Always (2022) and Haul Out the Holly (2022). Below are 27 more, each with the reason it matches.
What should I watch after Christmas Sail?
Start with Picture a Perfect Christmas (2019), the closest match to Christmas Sail.
What is the newest movie like Christmas Sail?
Christmas on Windmill Way (2023) is the most recent release on this list.
Are there English movies like Christmas Sail?
Yes: Picture a Perfect Christmas (2019), Ghosts of Christmas Always (2022) and Haul Out the Holly (2022).
How are movies similar to Christmas Sail chosen?
First come films that Trakt’s viewers watch alongside Christmas Sail, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.