Movies Like Milton

If you liked Milton (2023), a movie directed by Kevin Machate, 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
I'll See You in My Dreams (2015)
★ 6.3/10
A sudden loss disrupts Carol’s orderly life, propelling her into the dating world for the first time in 20 years. Finally living in the present tense, she finds herself swept up in not one, but two unexpected…
2
Some Kind of Heaven (2021)
★ 7/10
Behind the gates of a palm-tree-lined fantasyland, three residents and one interloper at America's largest retirement community strive to find happiness.
3
The Sisterhood of the Traveling Pants 2 (2008)
★ 6.3/10
Four young women continue the journey toward adulthood that began with "The Sisterhood of the Traveling Pants." Now three years later, these lifelong friends embark on separate paths for their first year of college and…
4
Love in the Villa (2022)
★ 6/10
A young woman takes a trip to romantic Verona, Italy, after a breakup, only to find that the villa she reserved was double-booked, and she'll have to share her vacation with a cynical British man.
5
Grumpy Old Men (1993)
★ 6.7/10
For decades, next-door neighbors and former friends John and Max have feuded, trading insults and wicked pranks. When an attractive widow moves in nearby, their bad blood erupts into a high-stakes rivalry full of…
6
Happiness for Beginners (2023)
★ 6.2/10
At a crossroads after her divorce, a schoolteacher ventures toward a fresh start in life — and love — when she signs up for a grueling group hiking trip.
7
People We Meet on Vacation (2026)
★ 6.9/10
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.
8
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…
9
The Four Seasons (1981)
★ 6.3/10
Three middle-aged wealthy couples take vacations together in Spring, Summer, Autumn and Winter. Along the way we are treated to mid-life, marital, parental and other crises.
10
Before Midnight (2013)
★ 7.5/10
It has been nine years since we last met Jesse and Celine, the French-American couple who once met on a train in Vienna. They now live in Paris with twin daughters but have spent a summer in Greece at the invitation of…
11
Book Club: The Next Chapter (2023)
★ 6.3/10
Four best friends take their book club to Italy for the fun girls' trip they never had. When things go off the rails and secrets are revealed, their relaxing vacation turns into a once-in-a-lifetime cross-country…
12
Spa Weekend (2026)
★ 6.5/10
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break…
13
Aftersun (2022)
★ 7.7/10
Sophie reflects on the shared joy and private melancholy of a holiday she took with her father twenty years earlier. Memories fill the gaps between camcorder footages as she tries to reconcile the father she knew with…
14
Solo Mio (2026)
★ 7.5/10
After Matt's dreams of a picturesque Italian wedding are shattered when his fiancée leaves him at the altar, he embarks on his planned honeymoon across Italy alone, immersing himself in the country's vibrant culture…
15
Dreamchild (1985)
★ 6.6/10
80-year-old Alice Hargreaves is about to visit Columbia University to attend a reception in honour of author Lewis Carroll. As a child, Alice's close friendship with the writer was the creative catalyst for Carroll's…
16
Eat Pray Love (2010)
★ 6.2/10
A married woman realizes how unhappy her marriage really is, and that her life needs to go in a different direction. After a painful divorce, she takes off on a round-the-world journey to "find herself".
17
Elsa & Fred (2014)
★ 6/10
After his daughter persuades him to move into a new apartment, aged widower Fred strikes up a friendship with his eccentric 74-year-old neighbour Elsa, who convinces him it's never too late to keep enjoying life…
18
The Whales of August (1987)
★ 7/10
Two aged sisters reflect on life and the past during a late summer day in Maine.
19
A Nice Girl Like You (2020)
★ 5.8/10
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey…
20
Now and Then (1995)
★ 6.9/10
Waxing nostalgic about the bittersweet passage from childhood to puberty, four childhood girlfriends — Teeny, Chrissy, Samantha and Roberta — recall the magical summer of 1970. During their walk down memory lane, they…