Best Vacation Movies of All Time

From sun-drenched beach escapes to chaotic family road trips, vacation movies capture the thrill—and occasional mishaps—of getting away from everyday life. This list spans comedies, romances, and adventures set in resorts, on islands, and across iconic cities, highlighting who made them, where they go, and what makes each getaway tick. Whether it’s a cross-country drive, a spontaneous road trip, or a resort stay gone sideways, these stories pack itineraries full of memorable characters, scenic locations, and travel-sized life changes.

‘National Lampoon’s Vacation’ (1983)

Directed by Harold Ramis, this comedy follows the Griswold family’s cross-country drive to the theme park Walley World. Chevy Chase and Beverly D’Angelo lead the cast, with memorable stops that include desert stretches and small-town detours. The screenplay by John Hughes draws on a magazine short story about a disastrous road trip. Several scenes were filmed across the American Southwest and Midwest, grounding the mayhem in real roadside Americana.

‘Vacation’ (2015)

Ed Helms and Christina Applegate star as the next generation of Griswolds heading to Walley World. The film revisits the franchise’s road-trip structure with new waypoints, mishaps, and modern roadside attractions. It was shot in multiple U.S. states to capture interstates, quirky stops, and theme-park thrills. Cameos from original cast members tie the trip to the earlier adventures.

‘The Hangover’ (2009)

Set in Las Vegas, this comedy centers on a bachelor-party weekend that goes wildly off-script. Bradley Cooper, Ed Helms, Zach Galifianakis, and Justin Bartha lead a search through casinos, rooftops, and the desert outskirts. The production used several real Strip locations, including hotel suites and iconic marquees. Its success launched a franchise that continued the travel-chaos formula in new cities.

‘Mamma Mia!’ (2008)

Adapted from the stage musical, this story is set on a picturesque Greek island where a wedding draws past and present together. Meryl Streep, Amanda Seyfried, and Pierce Brosnan headline, with ABBA songs woven into seaside celebrations. Filming took place on locations in Greece and also on soundstages that recreated sun-washed vistas. The island setting drives the plot’s ferry rides, cliff paths, and taverna gatherings.

‘Dirty Dancing’ (1987)

This coming-of-age romance unfolds at a Catskills summer resort, where vacationers take dance classes, swim, and attend club nights. Jennifer Grey and Patrick Swayze star as guests and staff navigating rules and rehearsal halls. Lake lifts, talent shows, and cabins create a detailed portrait of resort culture. Filming used mountain-lodge locations that stand in for the region’s once-thriving getaway scene.

‘Roman Holiday’ (1953)

Audrey Hepburn and Gregory Peck roam Rome’s landmarks in a tale of a princess sneaking away for a day. Vespas, cafés, and plazas become story beats as the pair weave through the city. Director William Wyler staged key sequences around sites like the Spanish Steps and the Colosseum. The film showcases on-location shooting that doubles as a travelogue of the Eternal City.

‘Forgetting Sarah Marshall’ (2008)

A heartbroken composer flees to a Hawaiian resort, only to find his celebrity ex staying there as well. Jason Segel, Kristen Bell, Mila Kunis, and Russell Brand anchor the ensemble within beach bars, luaus, and cliffside hikes. Production shot at an O‘ahu resort and along coastal trails, folding real amenities into the plot. The setting fuels surfing lessons, ukulele nights, and awkward encounters by the pool.

‘The Way Way Back’ (2013)

A shy teen spends summer at a New England beach town, finding confidence at a local water park. Liam James stars alongside Sam Rockwell, Toni Collette, and Steve Carell, with scenes spread across boardwalks, rentals, and snack shacks. Filming used an actual seasonal water park that informs the work-crew camaraderie. The coastal community sets the rhythm of bike rides, clam shacks, and beach days.

‘The Darjeeling Limited’ (2007)

Three brothers reunite on a train journey across India that winds through temples, markets, and desert towns. Owen Wilson, Adrien Brody, and Jason Schwartzman lead, with production design placing detailed luggage, compartments, and station platforms. Director Wes Anderson shot extensively on location, building a functional train set for interior scenes. The itinerary moves from bustling streets to remote villages, mirroring the siblings’ detours.

‘Y Tu Mamá También’ (2001)

Two friends and an older companion set off on a spontaneous drive to a remote beach in Mexico. Gael García Bernal, Diego Luna, and Maribel Verdú travel through toll roads, ranchlands, and coastal towns. The film pairs road-trip intimacy with documentary-style glimpses of the regions they pass. Beaches, roadside eateries, and guesthouses shape the journey’s shifting dynamics.

‘The Beach’ (2000)

A backpacker follows a rumored map to a hidden island community in Thailand. Leonardo DiCaprio stars, with sequences set in hostels, Bangkok night streets, and long-tail boat rides. Production filmed on Maya Bay and other locations, presenting turquoise waters and jungle footpaths as both lure and obstacle. The story explores the logistics of off-grid living, from fishing routines to guarded secrecy.

‘The Talented Mr. Ripley’ (1999)

A young American insinuates himself into an expatriate circle along Italy’s coast, moving between jazz clubs, harbors, and seaside villas. Matt Damon, Jude Law, and Gwyneth Paltrow headline, with filming in cities such as Rome and on islands known for pastel harbors. Tailored wardrobes, sailboats, and piazzas contribute to an elegant travel atmosphere. The Mediterranean settings frame ferry crossings, café terraces, and shoreline hideaways.

‘The Holiday’ (2006)

Two strangers swap homes across the Atlantic and discover new routines in countryside cottages and Los Angeles neighborhoods. Kate Winslet, Cameron Diaz, Jude Law, and Jack Black split time between cozy villages and sunny drives. Filming combined English lanes, pub interiors, and Southern California homes to contrast different styles of break. The premise leans on house-swap logistics, from key exchanges to adapting to a local commute.

‘Weekend at Bernie’s’ (1989)

Two office workers head to their boss’s Hamptons beach house, only to manage a bizarre predicament during a party-filled weekend. Andrew McCarthy and Jonathan Silverman navigate marinas, decks, and boardwalk crowds. The coastal setting provides speedboat chases, beach volleyball, and porch gatherings. Shoreline mansions and yacht clubs set the comedic stage for mistaken identities.

‘The Great Outdoors’ (1988)

A Chicago family heads to a lakeside cabin for fishing, water-skiing, and campfire nights. John Candy and Dan Aykroyd share the screen as relatives with dueling vacation styles. Filming used a Northwoods resort town with docks, lodges, and trailheads that structure the activities. The setting brings in local diners, wildlife encounters, and rain-day arcade runs.

‘Mr. Bean’s Holiday’ (2007)

Mr. Bean wins a trip to the French Riviera and bumbles from Paris to the Mediterranean coast. Rowan Atkinson’s character navigates trains, village squares, and film-festival crowds. The production showcases coastal drives, open-air cafés, and sandy beaches that become set pieces for visual gags. A camcorder thread ties together the stops like a tourist’s home video.

‘EuroTrip’ (2004)

After a messaging mishap, friends backpack across multiple European cities, hopping trains and budget flights. The ensemble visits landmarks, hostels, and clubs, with rapid-fire detours through plazas and riverbanks. The film stitches together famous sights and lesser-known streets to mimic a whirlwind itinerary. Border crossings, language mix-ups, and night trains fuel the momentum.

‘Before Sunrise’ (1995)

Two travelers meet on a train and decide to wander Vienna together until morning. Ethan Hawke and Julie Delpy walk through bookstores, parks, and quiet neighborhoods, letting conversations follow tram lines and river paths. Filming uses real cafés and alleys that lend a lived-in feel to the city. The structure mirrors a single layover that becomes a nightlong tour.

‘Eat Pray Love’ (2010)

A writer takes a months-long journey through Italy, India, and Bali in search of balance and new habits. Julia Roberts anchors chapters that move from cooking lessons to ashram routines to tropical scooters. The production highlights local cuisines, spiritual practices, and rice-terrace landscapes. Visas, rentals, and language lessons appear as practical waypoints along the way.

‘Couples Retreat’ (2009)

Four pairs visit a tropical resort for what they think is a leisure getaway, only to face mandatory workshops. Vince Vaughn, Jason Bateman, and Kristen Bell lead the ensemble among lagoons, bungalows, and overwater platforms. Filming took place at a real island resort, using kayaks, reef shallows, and spa spaces as recurring backdrops. Group excursions and scheduled activities structure the days like a brochure come to life.

‘Monte Carlo’ (2011)

A mistaken identity whisks three friends from Paris sightseeing to high-society events on the Riviera. Selena Gomez, Leighton Meester, and Katie Cassidy tour museums, boutiques, and seaside hotels. The shoot spans European landmarks and hotel ballrooms to frame both backpacking and luxury travel. Trains, borrowed gowns, and balcony views mark the shift in their itinerary.

‘A Bigger Splash’ (2015)

On an Italian island retreat, a rock star’s quiet holiday is interrupted by uninvited guests. Tilda Swinton, Matthias Schoenaerts, Ralph Fiennes, and Dakota Johnson circle a modern villa, tidal pools, and winding roads. The production uses volcanic terrain, cliff coves, and sun-bleached courtyards to shape tensions. Poolside dinners and island drives form the rhythm of the stay.

‘Blue Hawaii’ (1961)

Elvis Presley stars as a returning serviceman enjoying island life with surfing, ukulele nights, and floral-print pageantry. The film uses O‘ahu scenery, including beaches, lookouts, and hotel lawns, to frame musical numbers. Tourist excursions—pineapple tours, catamaran rides, and shoreline picnics—dot the plot. Costumes and choreography lean into island hospitality and resort entertainment.

‘Captain Ron’ (1992)

A family inherits a sailboat and hires a free-spirited skipper to help them cruise the Caribbean. Kurt Russell and Martin Short helm the voyage through marinas, customs offices, and turquoise anchorages. The film features hands-on sailing sequences, chart talk, and dinghy trips to beach bars. Tropical storms, reef navigation, and port calls structure the nautical route.

‘The Inbetweeners Movie’ (2011)

A group of recent school leavers heads to a party-centric Mediterranean resort for their first big lads’ holiday. Simon Bird, James Buckley, Blake Harrison, and Joe Thomas wend through package-tour hotels, neon strips, and crowded beaches. Filming captures club queues, budget breakfasts, and poolside antics familiar to holiday hubs. The itinerary includes bar crawls, boat cruises, and awkward resort romances.

‘Under the Tuscan Sun’ (2003)

After a divorce, a writer impulsively buys a villa in rural Italy and sets about rebuilding her life. Diane Lane leads the cast, with scenes moving between village markets, hillside vineyards, and renovation crews. The production filmed at real Tuscan locations, incorporating local festivals and countryside towns. The story tracks practical challenges like property paperwork, home repairs, and adapting to neighborhood customs.

‘How Stella Got Her Groove Back’ (1998)

A high-powered stockbroker takes a long-overdue Caribbean break and meets a younger local while navigating family expectations. Angela Bassett and Taye Diggs star, with resort backdrops, beachfront scenes, and island excursions framing the trip. Filming showcases hotel amenities, coastal drives, and daytime markets common to tourist hubs. The plot includes itinerary shifts between leisure activities and phone calls home that keep responsibilities in view.

‘Barb & Star Go to Vista Del Mar’ (2021)

Two best friends leave their Midwestern routine for a Florida resort town filled with cocktails, cabanas, and lounge acts. Kristen Wiig and Annie Mumolo headline, with sequences set at beachfront hotels, pool decks, and tourist shops. Production uses pastel interiors and boardwalk spaces to emphasize a classic sunshine-getaway vibe. The vacation framework features package deals, group activities, and sunset events.

‘Vicky Cristina Barcelona’ (2008)

Two American visitors spend a summer in Spain exploring art, architecture, and complicated relationships. Scarlett Johansson, Rebecca Hall, Javier Bardem, and Penélope Cruz move through Gaudí landmarks, galleries, and Catalan neighborhoods. The film was shot on location across Barcelona and surrounding regions, emphasizing open-air cafés and museum stops. Travel logistics include rented apartments, weekend trips, and seasonal cultural festivals.

‘Last Holiday’ (2006)

A department-store worker splurges on a dream European getaway after a health scare, checking into a grand hotel in the Alps. Queen Latifah stars alongside Gérard Depardieu, with scenes set in gourmet restaurants, spa facilities, and snowy mountain pistes. The production highlights fine-dining rituals, concierge services, and winter-sports amenities. Itineraries include cooking demonstrations, boutique shopping, and scheduled resort excursions.

‘Girls Trip’ (2017)

A longtime friend group reunites for a high-energy weekend at a major festival in New Orleans. Regina Hall, Queen Latifah, Jada Pinkett Smith, and Tiffany Haddish navigate parades, Bourbon Street, and convention venues. Filming captures street performances, hotel conference spaces, and riverfront walks typical of city getaways. The travel setup weaves in flight arrivals, shared accommodations, and packed event schedules.

‘Wine Country’ (2019)

Friends gather in Napa Valley for a milestone birthday weekend that unfolds across tastings, vineyard tours, and rental-house dinners. Amy Poehler directs and stars with Maya Rudolph, Rachel Dratch, and others, moving between wineries and scenic overlooks. The production uses real tasting rooms, hillside roads, and picnic spots to map the route. Transport details include designated drivers, reservation windows, and tour-booking quirks.

‘A Perfect Getaway’ (2009)

Newlyweds honeymooning in Hawaii cross paths with fellow hikers as they trek remote coastal trails. Milla Jovovich, Steve Zahn, Timothy Olyphant, and Kiele Sanchez star, with jungle paths, cliff vistas, and secluded beaches as primary locations. The film features practical gear, trail maps, and campsite logistics common to backcountry trips. Waterfalls, sea caves, and narrow ridgelines structure the route’s checkpoints.

‘Ibiza’ (2018)

A quick work trip expands into a spontaneous European getaway centered on nightlife and coastal scenery. Gillian Jacobs, Vanessa Bayer, and Phoebe Robinson travel through Barcelona and the Balearic Islands, visiting clubs, tapas bars, and seaside promenades. Production leans on real venues and harbor districts to trace the itinerary. The journey includes budget flights, hotel switches, and last-minute ticket hunts.

‘Ticket to Paradise’ (2022)

Divorced parents fly to Southeast Asia to intervene in their daughter’s sudden wedding plans, finding themselves navigating local customs and island life. George Clooney and Julia Roberts lead, with resort villas, rice fields, and snorkeling spots anchoring the setting. The shoot uses tropical beaches, ferry docks, and village ceremonies to mark the trip’s phases. Travel beats include group excursions, family meet-ups, and cultural celebrations.

‘The Sisterhood of the Traveling Pants’ (2005)

Four friends spend a summer apart, each on different trips that range from island villages to soccer camps and art classes. Amber Tamblyn, America Ferrera, Blake Lively, and Alexis Bledel share a narrative that moves among seaside towns and suburban programs. The production intercuts distinct settings—coastal lanes, practice fields, and studios—to keep each itinerary clear. Letters, packages, and shared mementos connect the separate vacations.

‘Summer Holiday’ (1963)

A London bus mechanic converts a double-decker into a camper and sets off across Europe with friends. Cliff Richard stars in a musical road adventure that stops at beaches, rustic inns, and festival stages. Filming uses Continental highways, rural byways, and seafront promenades to map the route. The trip logistics include roadside repairs, campsite setups, and performance bookings.

‘The Endless Summer’ (1966)

Two surfers travel the globe chasing ideal waves, turning beaches into a moving checklist of conditions and seasons. Directed and narrated by Bruce Brown, the documentary visits multiple countries and shorelines. The film records local surf communities, board types, and wind patterns encountered at each stop. Travel segments showcase visas, gear transport, and timing strategy to match swells.

‘Grown Ups’ (2010)

Childhood friends reunite with their families at a lakeside rental, filling a long weekend with classic camp-town activities. Adam Sandler, Kevin James, Chris Rock, David Spade, and Rob Schneider lead scenes around docks, cabins, and picnic areas. Production centers on water-skiing, rope swings, and small-town diners to sketch the setting. Group logistics include shared bedrooms, backyard games, and return-to-town errands.

‘Midsommar’ (2019)

A group of students travels to a remote Scandinavian commune during a rare seasonal festival. Florence Pugh, Jack Reynor, and Will Poulter lead the ensemble through village greens, ceremonial halls, and surrounding meadows. The production builds an immersive rural set with detailed costumes, runic décor, and daylight-heavy exteriors. The trip unfolds through guest accommodations, guided rituals, and meticulously timed celebrations.

Share your favorite getaway flicks in the comments and tell us which vacation movies we should add to the list!