Summer Escapes on Screen: The Best Vacation Movies to Watch Year-Round

These films will take you on perpetual summer vacation

Vacations in movies go hand in hand. There are few better settings than an away-from-home or away-from-routine scenario for characters to get out of their comfort zone and drama to ensue—something that we can all relate to. Whether it’s staying home during the summer months as a teen, heading to camp, or finding yourself in an exotic paradise (or the familiar paradise you routinely travel to every year), vacations are where some of the best stories happen. We put together a list of some of our favorite getaway-themed movies that will keep you thinking of summer well into September.

Forgetting Sarah Marshall

What are the odds that you end up on vacation with your recent ex? In Forgetting Sarah Marshall, composer Peter Bretter (Jason Segel), after being dumped by his famous girlfriend, actress Sarah Marshall (Kristen Bell), escapes to Hawaii for some solace. But to his dismay, Sarah is also at the same resort, flaunting her new relationship with rock star Aldous Snow (Russell Brand). As Peter wallows in his misery, he gradually finds unexpected support and a potential new romance with Rachel (Mila Kunis), a kind and witty hotel employee. Through a series of hilarious and awkward encounters, Peter begins to let go of his past, rediscover his self-worth, and realize that moving on means embracing new beginnings. The perfect blend of sharp humor and heart, this movie proves you CAN find love–but more importantly yourself–after heartbreak.

Fire Island

Joel Kim Booster, writer and star of this movie, reimagines Jane Austen’s Pride and Prejudice in the modern rom com Fire Island. Set on the iconic LGBTQ+ vacation spot, Fire Island, off the south shore of Long Island NY, a close-knit group of friends embark on their annual summer trip to a summer cottage owned by a close lesbian friend (played by Margaret Cho). The island is historically a haven for queer culture and community, and the film does a fantastic job of showcasing the island’s beauty and cultural history while delivering side-splitting laughs and sweet moments between friends and love interests. Booster plays Noah, who has dedicated his week to getting his friend Howie (played by Bowen Yang) in a love connection–but in the process might be finding his own. Amidst parties, beach days, and personal revelations, the friends learn about love, self-worth, and the importance of chosen family. Fire Island offers a fresh, inclusive take on a classic story, celebrating queer joy and the complexities of modern relationships.

Ticket to Paradise

One vacation turns into another in Ticket to Paradise starring Julia Roberts and George Clooney–two actors we love to watch playing formerly married couples (Ocean’s Eleven gives us this thrill as well). Ex-spouses David and Georgia have managed to keep their lives separate except in their full support of their daughter, Lily. While on a post-collegiate vacation in Bali with friends, Lily meets a Balinese seaweed farmer and…they fall in love. They decide to get married quickly, and David and Georgia must reunite in Bali to team up and stop her from making the same mistake they believe they did: getting married too young. They put aside their long-standing animosity in a shared mission to sabotage the wedding, and as they scheme and bicker, they find themselves unexpectedly reconnecting with each other and questioning their own past choices. This movie will have you wondering about past loves, hoping you might meet the love of your life on your next adventure, and….wanting to book the next flight to Bali, as it is a stunning setting for the film.

The Sisterhood of the Traveling Pants

Based on the novel of the same name, The Sisterhood of the Traveling Pants is a coming-of-age movie about four lifelong friends—Lena, Tibby, Bridget, and Carmen—who are spending their first summer vacation from school apart. But before they go their separate ways, they discover a pair of jeans that magically fits each of them perfectly, despite their different body types. To keep themselves connected throughout the summer, the girls decide to share the pants, sending them to each other along with letters about their individual experiences. Thus, the jeans become the “traveling pants.” As the summer unfolds, the pants become a symbol of their unbreakable bond, helping each girl navigate personal challenges, from first loves and family issues to self-discovery and grief. The pants keep them connected, but really it’s their relationships to one another that prove to be magical.

Wine Country

You can’t get better than this cast of legendary women of comedy. Wine Country stars Amy Poehler, Tina Fey, Maya Rudolph, Rachel Dratch, Paula Pell, and Ana Gasteyer, just to name some. In this girls’ trip vacation movie, a group of longtime friends reunite for a weekend getaway in Napa Valley to celebrate one of their 50th birthdays. They expect a relaxing and fun-filled trip, but as they indulge in wine tastings and vineyard tours, old tensions and unresolved issues start to surface. The weekend turns into a rollercoaster of laughs, awkward moments, and heartfelt conversations as the friends confront insecurities, aging, and the changes in their lives. The film humorously explores the complexities of friendship and the importance of reconnecting with those who know you best, even as time and life pull you in different directions.

Dirty Dancing

A classic summer vacation movie with one of the best soundtracks of all time, Dirty Dancing set the standard for all family vacation movies. Set in the summer of 1963 at a resort in the Catskill Mountains, 17-year-old Frances “Baby” Houseman is on her annual summer family trip and lamenting never having a real adventure. Baby’s world is turned upside down when she discovers the resort's secret after-hours dance scene, where she meets the charismatic and rebellious dance instructor, Johnny Castle. Drawn to the sultry world of dance and Johnny’s magnetic presence, Baby steps in as his new dance partner when his usual partner, Penny, is unable to perform. As Baby and Johnny rehearse for a crucial performance, their connection deepens, leading to a passionate romance that defies societal expectations and family disapproval. Through their relationship and the power of dance, Baby transforms from an innocent girl into a confident young woman, and a thrilling final dance at the end of the movie embodies her newfound freedom and independence–and has fans all over the world trying to do that lift at weddings and parties when someone plays the iconic “(I’ve Had) The Time of My Life.”

Theater Camp

You don’t have to love theater to love Theater Camp (but it helps). It is a comedic mockumentary written by self-proclaimed theater kids themselves Ben Platt, Noah Galvin, and Molly Gordon, with Nick Lieberman. (Platt and Gordon grew up together and as children performed in many shows with one another, which gives this movie tons of realistic levity.) The film follows the eccentric and passionate staff and campers of AdirondACTS, a rundown summer theater camp in upstate New York. When the camp’s beloved founder, Joan, falls into a coma, her clueless but well-meaning son, Troy, steps in to manage the camp despite having no experience in theater (or in business). As the counselors scramble to keep the camp afloat and prepare for their final big show, they face a series of hilarious challenges, from outrageous camper antics to financial crises. The film hilariously captures the quirks, drama, and camaraderie of theater kids and their mentors, celebrating the chaotic yet magical world of summer camp where creativity and friendship take center stage. 

The Sandlot

This film put “You’re killing me, Smalls” into pop culture lexicon and we couldn’t be happier about it. In the coming-of-age nostalgic sports comedy The Sandlot, young Scotty Smalls moves to a new neighborhood and struggles to make friends until he discovers a local sandlot where a group of boys play baseball every day. Under the guidance of the charismatic Benny “The Jet” Rodriguez, Scotty learns the game and becomes part of the team. The boys embark on a series of summer adventuresL they face off against rival teams, endure humorous and humiliating mishaps, and confront the legendary Beast, a ferocious dog guarding a stash of lost baseballs. You know, normal kid stuff. Through their experiences on and off the field, the boys forge lasting friendships and create memories that define their childhood.

Now and Then

If The Sandlot was a movie about boys coming of age during a summer, Now and Then is the female equivalent. A fateful summer solidifies a preteen friend group in this nostalgic coming-of-age film. Four childhood friends—Roberta, Teeny, Samantha, and Chrissy—reunite as adults to fulfill a promise made during their youth during the summer of 1970. The story is told from the perspectives of their present-day lives and flashbacks to that summer, a pivotal time when the girls navigated the challenges of growing up in their small suburban town. As they reminisce, the women confront their pasts, revisiting old secrets, enduring friendships, and the bittersweet moments that shaped their lives. The movie is a cult favorite as it captures the essence of childhood innocence, the bonds of friendship, and the journey from adolescence to adulthood.

What’s your favorite vacation-themed movie? We want to hear all about it in the comments!

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