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Time to Watch, Then Go! My Favorite Travel Movies & Where to Stream Them

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Favorite Travel Movies

My Favorite Travel Movies to Enjoy as I Prepare to Hit the Road, Skies & Rails

Things are looking up.  Many out there have been traveling, or busied themselves with planning, over the last year.  I’ve largely sat on the travel bench this last year, figuring that I’ll let the game come to me.  I like planning a bit, maybe just a future Disney World trip, but I’ve mostly preferred the wait and see approach during the pandemic.  Well, I’m now getting closer to the “see” portion.  But first, I’m more able to make concrete plans.  As I do so, I’m rewatching some of my favorite travel movies.  Some are just on in the background, keeping me company as I plan.  Here are a few of my favorite travel movies, why I like the films, and where you can stream them!

Planes, Trains, and Automobiles

Okay, so I’ll get an obvious one out of the way first.  Steve Martin and John Candy star in this John Hughes comedy about one man (Martin) trying to get home to his family for Thanksgiving while the other one (Candy) keeps appearing.  There’s something for everyone in this film, particularly involving travel frustrations.  Unfortunately, behavior on airplanes has gotten even worse since this film was released in 1987.  And I love the surprisingly poignant ending.  I’ve heard some describe this movie as the “Best Thanksgiving Movie ever made.”  I’m not sure enough Thanksgiving movies exist to warrant a stand-alone category.  I just know this one’s quite a ride.

Where to Stream:  Fubo TV, Sling, Starz

Favorite Travel Movies
Montana from Amtrak’s Empire Builder route.


Alexander Payne filmed this masterpiece in Montana, Wyoming, South Dakota, and, yes, Nebraska.  The black and white presentation makes the desolate, beautiful scenery pop even more.  The story revolves around Bruce Dern’s character, Woody, and his son, David (Will Forte) driving to Nebraska to pick up a million dollar prize Woody is convinced he won.  Plenty of hilarity, surprises, and melancholy ensue.  Similar to Payne’s Election, About Schmidt, Sideways, and The Descendants, the writing and filmmaking of Nebraska strike an immaculate balance between drama and comedy.

Where to Stream:  Amazon Prime, YouTube TV


Probably one of Cameron Crowe’s most critically-panned creations, I enjoy this comedy-drama for lots of little reasons, many of which I can relate to.  Here are just a few, in no particular order:

  • Staying in a hotel that a wedding party is currently dominating.
  • Driving solo in an unnecessarily large rental car.
  • Orlando Bloom’s redeye flight as the sole passenger.
  • Ruckus, a longtime local band that probably should have broken up years earlier.
  • The development of the Orlando Bloom/Kirsten Dunst relationship over the phone (pre-smart phone era).
  • Rediscovering the warmth of long-forgotten family roots.

Yeah, this one probably gets too cutesy here and there, and it may overly rely on road trip montages.  But hey, I’m a sucker for this movie.  Speaking of road trip montages…

Where to Stream:  Amazon Prime

Dumb and Dumber/Kingpin/Me, Myself & Irene

Why am I grouping these three comedies together?  One, because they’re all Farrelly Brothers movies.  Two, because their plots don’t really matter.  Three, because road trip montages are central to the telling of each quasi-story and much of the humor.  As I write this, I’m wearing a cardigan and am taken back to this Dumb & Dumber scene:

  • Cop:  “Pull Over!”
  • Harry Dunne (Jeff Bridges):  “No, it’s a cardigan, but thanks for noticing.”
  • Lloyd Christmas (Jim Carrey), to Cop:  “Killer boots, man!”

Quite honestly, simply watching other people fake-travel in movies brings on my travel urges.  As Trey Parker famously exclaimed, “I need a montage!”

Where to Stream:  Sling (Dumb and Dumber), Fubo TV (Kingpin and Me, Myself & Irene) 

Favorite Travel Movies


This film directed by Sofia Coppola tells the story of an actor (Stephen Dorff) reconnecting with his daughter (Elle Fanning), often in beautiful locales.  We get to view the Chateau Marmont in Los Angeles and beautiful surroundings throughout Italy.  Apparently, some scenes of the movie are inspired by the director’s own relationship with her real-life father, famed filmmaker Francis Ford Coppola.

Speaking of Sofia Coppola, some may prefer another of her films, Lost in Translation.  I do enjoy that movie and the window into Japan which it provides.  Indeed, it has turned the Tokyo Park Hyatt into an important travel destination for many.  Both movies are subtle studies where the settings are characters just as much as the actors.  The soundtracks for each film are excellent.

Where to Stream:  Apple TV, Amazon Prime, Google Play Store, YouTube TV

Ferris Bueller’s Day Off – My Favorite Travel Movie Without the Travel

Okay, so Ferris Bueller’s Day Off isn’t exactly a travel movie.  But Ferris, Sloan, and Cameron exploring Chicago is one huge trip in itself.  I was a grade schooler when this one came out, and it immediately became one of my favorites.  Decades later, I watch it, pick up small bits, and find other messages that I can relate to more now.  These days, Jennifer Grey’s character, Ferris’s sister Jeanie, is who I enjoy most in the movie.

Not coincidentally, Chicago is my favorite big city in the States.  Indeed, it’s going to be my first trip after vaccination.  The fictional Shermer, Illinois of many John Hughes films appears, as well.  One of the many reasons I love Chicago is because of this movie.  Or maybe it’s the other way around.  Probably both.

Where to Stream:  Amazon Prime, Google Play Store, YouTube TV 

The Way Way Back

A teenager, Duncan, is coaxed into a trip with his mother and her unpleasant boyfriend to a small town near Cape Cod, Massachusetts.  Duncan eventually starts working at a local water park and forms a friendship with Owen, played by Sam Rockwell.  Owen ends up becoming an unlikely mentor for Duncan.  I grew up going to water parks, and the filmmakers nail the summer vibe in this one.  Steve Carell is impressive as the bad guy.

Where to Stream:  Apple TV, Amazon Prime, Google Play Store, YouTube TV

Favorite Travel Movies


Again, I shall admit that this is not a travel movie at all.  Rather, it’s the beautiful San Francisco setting for this cop movie that sucks me in.  This 1968 film just gets better with age, in my opinion.  Steve McQueen’s Mustang is quite a looker, and so is the film’s big car chase.  Each time I see this, I tell myself that’s it’s been too long since my last San Francisco trip.  It’s a close second to Chicago as my favorite big city in the States.

Where to Stream:  HBO Max

The Straight Story – My #1 Favorite Travel Movie

A G-rated David Lynch movie released by Disney?  Yes, such a film exists, and it’s a true story.  The movie tells the story of Alvin Straight (Richard Farnsworth), who drove a lawn mower across Iowa and Wisconsin to visit his estranged, ailing brother.  The simple plot is peppered with excellent characters throughout.  During production, Richard Farnsworth’s prostate cancer spread to his bones.  His paralyzed legs in the film were the real deal.  He took his own life the next year at age 80.

While I love the film, Mark couldn’t get through five minutes of it.  Even a G-rated David Lynch film is polarizing, apparently.  The film’s soundtrack by Angelo Badalamenti, a frequent Lynch collaborator, is another one of my favorites.

Where to Stream:  Disney+

My Favorite Travel Movies – Conclusion

Surely, I’ve missed plenty of great travel movies.  But if I insisted on seeing them all, I probably wouldn’t have much time to actually travel.  I’m pleasantly surprised at how different films bring on my urge to travel from different angles.  Regardless, I’m glad I’m closer to real travel rather than simply relying on films, books, or local experiences for those escapes.  What are your favorite travel movies?

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Benjy Harmon
Benjy Harmon
Benjy focuses on the intersection of points, travel, and financial independence (FI). An experienced world traveler, husband, and father, he currently roams throughout the USA close to expense-free. Benjy enjoys helping others achieve their FI and travel goals.

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    • Maria,

      Good call on Due Date – another great road trip movie. I never thought of Titanic as a travel movie, but it definitely fits the category!

  1. Testosterone-filled list!

    Out of Africa; Under the Tuscan Sun; Eat, Pray, Love; & Roman Holiday capture Africa & Italy pretty well.

  2. The Way – Martin Sheen’s son dies on Camino de Santiago and he decides to walk it. Adventure, the different people you meet when traveling, and a lot more. Great movie
    The Secret Life of Walter Mitty – fun adventure has him in some beautiful places. A “live your life to the fullest” type movie.

  3. Fun list. I’ll need to check some of these out, thanks for compiling it.

    PLANES, TRAINS AND AUTOMOBILES, is an annual November watch for me. But the one ‘travel’ film in my collection that speaks to me the most is UP IN THE AIR (2009). It’s probably too on-the-nose for many that are part of the points and miles game, but I always envied folks like the films main character, Ryan Bingham, who got to travel and rack up points as a part of their career path. Though, his actual job seemed like it would be soul-crushing, so it’s a kind of Faustian bargain.

    Outside of this, my preferences delve into locale-specific films about places that I love to live/visit (Hong Kong, Singapore, etc.). But one sort of outlier is from YouTube video maker JeffHK, who does time-lapse videos of cargo ship voyages. This 30-day video he did is a personal favorite.

    • Paul,

      Thanks for chiming in! A fun activity during Up in the Air is to consider which references have and haven’t aged well. I miss the old design of the Hilton Honors elite membership card Ryan used to get into his old grade school. I still have mine!


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