Movies Like Cupcakes and Wine

If you liked Cupcakes and Wine (2008), a movie, 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
Sideways (2004)
★ 7.1/10
Two middle-aged men embark on a spiritual journey through Californian wine country. One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.
2
You, Me & Tuscany (2026)
★ 7.3/10
When a woman crashes at an empty Italian villa, posing as the owner's fiancée, she discovers an unexpected romance that could transform her life.
3
Bottle Shock (2008)
★ 6.4/10
Paris-based wine expert Steven Spurrier heads to California in search of cheap wine that he can use for a blind taste test in the French capital. Stumbling upon the Napa Valley, the stuck-up Englishman is shocked to…
4
Autumn in the Vineyard (2016)
★ 6.2/10
When Frankie Baldwin and Nate Deluca both have a claim to ownership of Sorrento Farm, they are forced to divide the vineyard right down the middle and work the fields alongside each other to bring in the harvest…
5
French Girl (2024)
★ 6.2/10
Sweet Gordon, an affable English teacher in Brooklyn, has beaten the odds; a French Girl has fallen in love with him and he’s fallen even harder back. But their future is thrown into limbo when she interviews for an…
6
Sour Grapes (2016)
★ 7.3/10
Controversy erupts when an unassuming young man floods the American wine market with fake vintages valued in the millions, bamboozling the wine world elite, in this humorous and suspenseful tale of an ingenious con on…
7
Beverly Hills Chihuahua 2 (2011)
★ 5.9/10
Puppy mayhem turns the lives of newlywed Chihuahua parents Papi and Chloe upside down when their rambunctious, mischievous puppies present one challenge after another. But when their human owners end up in trouble, the…
8
Herbie Fully Loaded (2005)
★ 5.9/10
Maggie Peyton, the new owner of Number 53 - the free-wheelin' Volkswagen bug with a mind of its own - puts the car through its paces on the road to becoming a NASCAR competitor.
9
Entourage (2015)
★ 6.2/10
Movie star Vincent Chase, together with his boys, Eric, Turtle and Johnny, are back…and back in business with super agent-turned-studio head Ari Gold. Some of their ambitions have changed, but the bond between them…
10
A Walk in the Clouds (1995)
★ 7.4/10
World War II vet Paul Sutton falls for a pregnant and unwed woman who persuades him -- during their first encounter -- to pose as her husband so she can face her family.
11
A Midsummer Night's Sex Comedy (1982)
★ 6.5/10
A nutty inventor, his frustrated wife, a philosopher cousin, his much younger fiancée, a randy doctor, and a free-thinking nurse spend a summer weekend in and around a stunning - and possibly magical - country house.
12
It's Complicated (2009)
★ 6.5/10
Ten years after their divorce, Jane and Jake Adler unite for their son's college graduation and unexpectedly end up sleeping together. But Jake is married, and Jane is embarking on a new romance with her architect…
13
Under the Tuscan Sun (2003)
★ 6.9/10
Frances Mayes, a 35-year-old professor and writer from San Francisco, decides to take a tour of Tuscany following a difficult divorce. After impulsively buying a run-down villa in the Italian countryside, she begins to…
14
All of My Heart: Inn Love (2017)
★ 6.9/10
Brian and Jenny are preparing for the grand opening of their bed and breakfast, Emily's Country Inn, when a big storm hits Buck County. Brian agrees to go back to Wall Street to boost their funds, while Jenny scrambles…
15
The Nanny Diaries (2007)
★ 6.4/10
A college graduate goes to work as a nanny for a rich New York family. Ensconced in their home, she has to juggle their dysfunction, a new romance, and the spoiled brat in her charge.
16
Love Sarah (2020)
★ 6.2/10
A young woman wishes to fulfill her mother's dream of opening her own bakery in Notting Hill, London. To do this, she enlists the help of an old friend and her grandma.
17
The Dink (2026)
★ 6.4/10
Desperate to save a struggling country club and earn his father's respect, a washed-up tennis pro is compelled to break a sacred vow and do the unthinkable: play pickleball.
18
Willy Wonka & the Chocolate Factory (1971)
★ 7.5/10
When eccentric candy man Willy Wonka promises a lifetime supply of sweets and a tour of his chocolate factory to five lucky kids, penniless Charlie Bucket seeks the golden ticket that will make him a winner.
19
Petulia (1968)
★ 6/10
Dr. Archie Bollen is having a midlife crisis. He's just divorced his wife and is establishing a new life for himself. One night, he catches the eye of Petulia Danner, a charming, free-spirited young woman. Petulia's…
20
Fatherhood (2021)
★ 7.5/10
A widowed new dad copes with doubts, fears, heartache and dirty diapers as he sets out to raise his daughter on his own. Inspired by a true story.