7 Must-Watch Films and Books for Fans of 'The Itinerant'

Introduction: Why These 7 Picks Speak to the Itinerant Soul

So you've watched or read 'The Itinerant' and can't shake that feeling. That restless pull. The quiet ache for open roads, unfamiliar faces, and the kind of solitude that forces you to look inward. You're not alone. Stories about wanderers—people who trade stability for uncertainty—have a way of sticking with you long after the credits roll or the last page turns.

But finding the next fix? That's tougher than it sounds. Most travel stories are either too romanticized (every sunset is perfect) or too bleak (the road is a dead end). 'The Itinerant' hit a rare sweet spot: raw, honest, and deeply human. So I've put together a list of 7 films and books that capture that same energy. These aren't just random road trip stories. Each one digs into the psychology of movement—why we leave, what we find, and what we leave behind.

I picked these based on three criteria: thematic resonance with 'The Itinerant', genuine emotional depth, and storytelling that doesn't rely on clichés. Some are documentaries. Some are fictional. One is a 60-year-old surf film. All of them will make you want to pack a bag.

1. 'Nomadland' (2020) – The Modern American Nomad

Chloé Zhao's Oscar-winning portrait of van-dwellers

If 'The Itinerant' is about choosing the road, Nomadland is about being forced onto it—and then choosing to stay. Chloé Zhao's film follows Fern (Frances McDormand in a career-defining role) after her Nevada company town collapses. She throws her belongings into a van and joins a community of modern-day nomads crisscrossing the American West.

What makes this film essential viewing is its refusal to sugarcoat anything. Fern isn't on some Instagram-worthy adventure. She's scrubbing toilets at campgrounds, eating canned beans, and sleeping in parking lots. Yet there's a dignity to her existence that's impossible to fake. Zhao blends fictional scenes with real-life nomads playing themselves, and the result feels less like a movie and more like a documentary from another dimension.

Key features:

• Stunning cinematography of America's national parks and backroads
• A deep exploration of grief, community, and economic displacement
• Frances McDormand's Oscar-winning performance—raw and unflinching

Pros: Authentic portrayal of nomad life; no Hollywood gloss; deeply moving without being manipulative.

Cons: Slow pace might frustrate viewers expecting a traditional plot; some scenes feel repetitive.

Honestly, this is the closest you'll get to the soul of 'The Itinerant' in film form. Watch it alone, late at night, with a good pair of headphones.

2. 'The Motorcycle Diaries' (2004) – A Transformative Journey

Che Guevara's early travels across South America

Before he became a revolutionary icon, Ernesto Guevara was a 23-year-old medical student with a motorcycle and a vague sense of wanderlust. The Motorcycle Diaries charts his 8,000-mile journey across South America with his biochemist friend, Alberto Granado. And here's the thing: it's not really about politics. Not at first.

The film, directed by Walter Salles, is a coming-of-age road movie that slowly transforms into something more profound. Guevara starts out as a privileged young man cracking jokes and chasing girls. But as he witnesses the poverty of leper colonies, the exploitation of mine workers, and the isolation of indigenous communities, his worldview cracks open. The journey literally changes who he is.

Key features:

• Breathtaking landscapes—the Andes, the Atacama Desert, Machu Picchu
• A nuanced performance by Gael García Bernal that captures youthful arrogance and awakening empathy
• Based on Guevara's actual travel diaries, so the authenticity is baked in

Pros: Perfect balance of adventure and introspection; accessible even if you know nothing about Che; incredible soundtrack.

Cons: Some critics argue it sanitizes Guevara's later political actions; pacing drags slightly in the middle.

For fans of 'The Itinerant', this film hits the same note: travel as a catalyst for personal transformation. You don't come back the same person.

3. 'Into the Wild' (2007) – The Ultimate Escape

Sean Penn's adaptation of Jon Krakauer's book

You've probably heard the story. Christopher McCandless graduates from Emory University, donates his savings to charity, burns his cash, and hitchhikes to Alaska to live off the land. He dies alone in an abandoned bus. But Into the Wild isn't a tragedy—it's a question mark.

Sean Penn's film adaptation of Jon Krakauer's book refuses to judge its subject. McCandless (played with magnetic intensity by Emile Hirsch) is both brilliant and naive, inspiring and frustrating. He rejects materialism but relies on the kindness of strangers. He seeks solitude but forms deep connections with people along the way. The tension between his idealism and the harsh reality of survival is what makes this story unforgettable.

Key features:

• Eddie Vedder's soundtrack—haunting and perfect
• Supporting performances from Hal Holbrook, Catherine Keener, and Vince Vaughn (yes, really)
• Filmed on location, including the actual bus where McCandless died

Pros: Emotionally devastating in the best way; raises profound questions about freedom and belonging; visually stunning.

Cons: Some viewers find McCandless reckless rather than heroic; the nonlinear timeline can be confusing.

If 'The Itinerant' made you romanticize the road, Into the Wild will slap you back to reality—but gently. It's a cautionary tale that still celebrates the urge to break free.

4. 'The Alchemist' by Paulo Coelho – The Spiritual Journey

A fable about following your dreams

Let's be honest: The Alchemist is the kind of book people either love or roll their eyes at. But for fans of 'The Itinerant', it's worth revisiting with fresh eyes. The story follows Santiago, a young Andalusian shepherd, who dreams of treasure near the Egyptian pyramids. He sells his sheep and crosses the Sahara, meeting a crystal merchant, an Englishman searching for alchemy, and a mysterious alchemist along the way.

What makes this book work—when it works—is its central idea: the journey itself is the destination. Santiago learns that the treasure he seeks was buried back where he started. But he wouldn't have known that without the journey. It's a paradox that resonates deeply with anyone who's ever felt the pull of 'The Itinerant'.

Key features:

• Short, fable-like chapters that make it a quick read
• Universal themes of destiny, fear, and self-discovery
• Coelho's simple, almost biblical prose

Pros: Inspiring without being preachy; works as both a surface-level adventure story and a deeper allegory; widely translated.

Cons: Critics call it simplistic or repetitive; some find the spiritual messaging too heavy-handed.

Look, this isn't a gritty travelogue. But if 'The Itinerant' spoke to your spiritual side—the part that believes travel has a purpose beyond sightseeing—The Alchemist will hit home.

5. 'Tracks' (2013) – One Woman, One Camel, One Desert

Robyn Davidson's solo trek across Australia

Here's a film that proves you don't need a cast of characters to tell a compelling travel story. Tracks follows Robyn Davidson (Mia Wasikowska) as she walks 1,700 miles across the Australian desert with four camels and a dog. No support team. No GPS. Just her, the animals, and the vast red emptiness.

What makes this film stand out is its quiet intensity. Davidson isn't running from anything specific—she's running toward something she can't name. The journey is brutal: heatstroke, blisters, loneliness, and the constant threat of dehydration. But there's also a strange peace in her solitude. The bond she forms with her camels (especially Dookie and Zeleika) is surprisingly emotional.

Key features:

• Stunning cinematography of the Australian outback
• Based on Davidson's real-life journey and bestselling book
• A minimalist approach that mirrors the isolation of the desert

Pros: Mia Wasikowska delivers a quietly powerful performance; avoids melodrama; celebrates female independence without making it a statement.

Cons: Slow pacing may test impatient viewers; limited dialogue means less character interaction.

For anyone who loved the solitary stretches of 'The Itinerant', Tracks is a perfect companion piece. It asks the same question: what do you find when there's nothing left to distract you?

6. 'The Art of Travel' by Alain de Botton – Why We Wander

A philosophical guide to travel and perception

This isn't a travelogue. It's not a novel either. The Art of Travel is a philosophical exploration of why we travel and how we experience places. Alain de Botton examines everything from airport waiting lounges to the paintings of Edward Hopper to explain the psychology behind our wanderlust.

Why does a place look magical in a postcard but disappointing in person? Why do we romanticize journeys we've never taken? De Botton doesn't just ask these questions—he answers them by drawing on writers like Flaubert, artists like Van Gogh, and his own travel experiences. The result is a book that makes you think differently about every trip you've ever taken.

Key features:

• Short, digestible chapters organized by travel themes (departure, the exotic, the sublime)
• Combines art criticism, literary analysis, and personal narrative
• Beautifully written—de Botton has a gift for making philosophy accessible

Pros: Changes how you see travel; full of "aha" moments; works as both a read-through book and a reference.

Cons: Can feel academic at times; lacks the emotional narrative drive of fiction.

If 'The Itinerant' made you curious about the why behind the wandering, this book is your manual. It's like having a smart friend explain the hidden mechanics of your own restlessness.

7. 'The Endless Summer' (1966) – The Surfing Odyssey

Bruce Brown's classic surf documentary

Okay, this one's a curveball. The Endless Summer is a surf documentary from the 1960s. But stick with me—it captures the spirit of 'The Itinerant' better than most modern films. The premise is simple: two surfers, Mike Hynson and Robert August, travel around the world chasing summer. They surf in Africa, Australia, New Zealand, Tahiti, and Hawaii, always looking for the perfect wave.

What makes this film special is its lighthearted philosophy. These guys aren't searching for meaning or escaping trauma. They're just following a passion with joyful abandon. Bruce Brown's narration is deadpan and witty, and the cinematography (for 1966) is surprisingly beautiful. The film practically invented the modern surf travel genre.

Key features:

• Iconic surf footage from locations that were virtually unknown at the time
• Brown's humorous, self-deprecating narration
• A soundtrack that captures the era's optimism

Pros: Pure, uncomplicated fun; historically significant as the first surf film to go mainstream; gorgeous visuals.

Cons: Dated in its portrayal of local cultures; no deep emotional arc—it's a travelogue, not a drama.

For fans of 'The Itinerant' who want a break from heavy themes, The Endless Summer is a palate cleanser. It reminds us that sometimes the road is just about enjoying the ride.

Conclusion: Your Next Itinerant Adventure Awaits

So there you have it—7 films and books that capture the restless, searching spirit of 'The Itinerant'. Each one approaches the nomadic experience from a different angle: some are gritty and real, others are philosophical, and one is just pure fun. But they all share a core truth that 'The Itinerant' understands deeply: travel isn't about the destinations. It's about who you become along the way.

My top picks for your immediate watch/read list:

• If you want the closest match to 'The Itinerant' in tone and theme: start with Nomadland.
• If you're in the mood for something introspective and philosophical: grab The Art of Travel.
• If you need a lighter, more joyful take on wandering: queue up The Endless Summer.

Honestly, you can't go wrong with any of these. They're all worth your time. So pick one, find a quiet corner, and let the road take you somewhere new. Even if it's just from your couch.