1. The Darjeeling Limited (2007)
Wes Anderson reimagines the all-American family road trip as a rail journey across India. Set on a cramped train, three brothers, who haven't spoken in the year since their fathers death, reunite for a train trip across India on a spiritual quest to find their mother (Angelica Houston). Set in the busy, colorful aesthetic of India, the movie's most arresting visuals take us across the striking desert and mountain landscape through India.
2. Midnight in Paris (2011)
Gil Pender, played by Owen Wilson, is a wide-eyed screenwriter and aspiring novelist on a trip to Paris with his fiancée (Rachel McAdams). Like many tourists in the City of Light, he retraces the steps of Parisian creatives past, drinking coffee in the same places they once did—until, late one night, a car of these very icons appears, sweeping him back in time to an evening of revelry among the literati of the 1920s.
3. Wild (2014)
Reese Witherspoon plays Cheryl Strayed, a writer who trekked 1,100 miles on the Pacific Crest Trail after the devastating loss of her mother. (The film is based on Strayed’s best-selling 2012 book of the same name.) Strayed crosses the dusty Mojave, crazy forests, snowy fields, and muddy trails, losing toenails but gaining mental clarity—or at least self-acceptance—along the way.
4. Call Me By Your Name (2017)
Consider Luca Guadagnino's Call Be By Your Name a starter guide to the Italian countryside life (specifically in Bergamo, and greater Lombardy) you've always wanted: Riding bikes through hundred-year-old piazzas, fossil-diving in Lake Garda, and waking up to a breakfast of soft-boiled eggs and freshly picked peaches.
5. Crazy Rich Asians (2018)
Crazy Rich Asians tells the story of Rachel Chu, a Chinese-American professor who travels to Singapore to meet her fiancé's wealthy family. The world of Singapore's old-money elite is filled with yacht parties and royal weddings, but between all that extravagance, Rachel—and viewers—get glimpses of the city's greatest hits: Gardens by the Bay, and the infinity pool of Marina Bay Sands.
6. Sideways (2004)
The allure of California’s fantastic vineyards is well known, but wine culture still has a sniff of exclusivity. That’s what makes Sideways, whose wine-touring middle-aged slobby protagonist, so relatable—and hilarious. Aside from telling a great story with great characters, the movie also happens to showcase some of the most beautiful vineyards and tasting rooms in Santa Barbara.
7. Thelma & Louise (1991)
Thelma & Louise reinvented the concept of the buddy movie by putting two women on the road, escaping good-for-nothing men and setting off on an adventure of their own making. For the first time, women were at the center of the picaresque. Ultimately, Thelma and Louise don't get their happy ending, but the best coda is knowing their movie paved the way for countless other women to hit the road on their own.
8. Endless Summer (1966)
Bruce Brown’s 1966 surfer documentary makes us yearn for summer. Brown shadowed buddies Robert August and Mike Hynson on a round-the-world surfing trip, filming their travels to places like Hawaii, New Zealand, and South Africa as they crested waves and met like-minded surf obsessives. The film’s impact on surf culture and tourism was huge, thanks in no small part to Brown’s cinematography, as well as the subjects’ ability to make riding those impossibly large waves seem effortless.
9. National Lampoon’s Vacation (1983)
Vacation was the world’s introduction to the Griswold family, led by accident-prone dad-in-chief Clark (Chevy Chase). The film spoofs the tried-and-true American tradition of the family road trip, taking the Griswold car through at least two real-life national parks—Death Valley and Grand Canyon—on their way to the fictional amusement park, Walley World. Add in an unforgettable cameo from Christie Brinkley and you have a movie every vacationer should watch once in their lifetime.
10. Roman Holiday (1953)
Set in Rome, Audrey Hepburn plays a princess, Gregory Peck a journalist for an American news bureau who helps the young, seemingly drunk woman one night and lets her sleep it off in his apartment. He soon realizes she is the princess and he has a big scoop. What follows is a grand romp, with Peck playing local guide to the princess. Their tour of Rome proves the perfect catalyst for their budding romance.