15 Solo Journeys Inspired by Film and Literature, Itineraries and All

Ready to go full ‘Into the Wild’?

August 10, 2018 9:00 am

Best thing about solo travel? You have to make exactly zero compromises.

No endless flight-coordination email chains. No sleeping on the cot with the bars poking through because the hotel ran out of doubles. No fighting over the complimentary shower cap.

It’s why we love books and films with protagonists who strike out on their own: they’re taking the trip we all dream of, blissfully unfettered by the plans, schedules or departure times of others.

So today, we’re rounding up 15 such literary sojourns, from an Alaska-bound naturalist to an Irishman lost within his own head.

All with detailed itineraries to help you replicate their trips in real life — not that you need to heed them.

Into the Wild by Jon Krakauer
In the summer of 1990, college grad Christopher McCandless abandons all his worldly possessions, adopts the name “Alexander Supertramp” and spends the next two years vagabonding across the North American continent, with the ultimate dream of living alone off of the land. A dream that, tragically, results in his untimely death at the age of 24.

Estimated Travel Time: Depending on how close one wishes to hew to McCandless’s itinerant worldview, anywhere from two years to the rest of your life.
Your Marching Orders: Begin by destroying your credit cards and identification and donating your life savings to Oxfam. Then drive aimlessly around the American Southwest before abandoning your car near Lake Mead and continuing on foot/kayak/train around North America, occasionally making a temporary life for yourself in surroundings that suit you. Then head to Alaska and set off along the Stampede Trail, stopping when you reach abandoned Fairbanks City Transit System Bus 142.
What to Pack: As little as humanly possible aside from a journal. Once you reach Alaska, procure a 10-lb. bag of rice, a Remington semi-automatic rifle with 400 rounds of ammunition, several books, camping gear and a pair of Wellington boots. (Note: in reality, any trip into the Alaskan Bush should include both plenty of supplies and a seasoned guide familiar with the area.)
Pit Stops: Sleep in your car along the shores of Lake Mead; camp along the shores of Big Sur; wander the California Redwoods; kayak illegally down the Colorado River into Mexico; make friends in Slab City, California and visit Salvation Mountain; enjoy the soul-stirring solitude of Denali National Park.
If You Take One Picture: Recreating the iconic self portrait of a kid who died tragically at the location of said self portrait is pretty morbid, but you certainly wouldn’t be the first person to do it.
The Quote to Have in Your Back Pocket: “So many people live within unhappy circumstances and yet will not take the initiative to change their situation because they are conditioned to a life of security, conformity, and conservatism, all of which may appear to give one peace of mind, but in reality nothing is more dangerous to the adventurous spirit within a man than a secure future. The very basic core of a man’s living spirit is his passion for adventure. The joy of life comes from our encounters with new experiences, and hence there is no greater joy than to have an endlessly changing horizon, for each day to have a new and different sun.”

Travels with Charley in Search of America by John Steinbeck
The aging Monterey-born scribe feels disconnected from the nation he’s written about for decades, and thus sets out in a custom camper with his French poodle Charley.

Estimated Travel Time: Three months-ish
Your Marching Orders: Get yourself a camper. Steinbeck labored to outfit his properly, but you’ll have almost too many options. Drive the States’ outer ring: Long Island, New England, Heartland, Montana, California, Texas, the South, back up the East Coast.
What to Pack: Journals, canned sardines, dozens of downloaded podcasts, a portable grill, dog treats, bourbon, scotch, gin, vermouth, vodka, a medium good brandy, aged applejack and a case of beer (Steinbeck staunchly supports the nightcap)
Pit Stops: Sample Carr Valley Cheese in the Wisconsin Dells; head for some Walleye fishing in North Dakota; visit the new Mississippi Civil Rights Museum (honoring a period Steinbeck witnessed firsthand)
If You Take One Picture: Big Sky. See above.
The Quote to Have in Your Back Pocket: “Montana seems to me to be what a small boy would think Texas is like from hearing Texans … Montana has a spell on me. It is grandeur and warmth. If Montana had a seacoast, or if I could live away from the sea, I would instantly move there and petition for admission. Of all the states it is my favorite and my love.”

The Beach by Alex Garland
Richard, a young British post-grad in Thailand, strikes backpacking gold when a fellow traveler draws him a treasure map that leads to an idyllic beach commune. He recruits a French couple for company and they set out, eventually arriving at what amounts to an intimate, weirdly bureaucratic tropical Burning Man.

Estimated Travel Time: 3-6 months oughta get you properly enlightened, although the rules of the tribe call for lifetime membership
Your Marching Orders: Fly to Bangkok; from there head to Kho Samui and hire a private boat. Hopefully your captain knows where the fabled beach is.
What to Pack: Loose-fitting knit garb and a good pair of sandals. The look you’re going for is hostel chic.
Pit Stops: In Bangkok, stay in cheap backpacker’s hotel on Khao San Road like this one to gather some partners in crime; in Kho Samui, head to the town of Thong Krut and haggle with a longboat captain who knows of a secret beach; if you can’t find one, you can always head to the beach in Ko Phi Phi Leh where they shot the movie — it’s set to reopen in September after some rehabilitation.
If You Take One Picture: This will pretty much be your view for the entirety of the trip, but take Richard’s lead and leave your camera at home.
The Quote to Have in Your Back Pocket: “If I’d learnt one thing from travelling, it was that the way to get things done was to go ahead and do them. Don’t talk about going to Borneo. Book a ticket, get a visa, pack a bag, and it just happens.”

The Straight Story (1999)
WWII veteran Alvin Straight, 73, can’t see well enough to get a driver’s license. But he’s damn well gonna visit his older brother Henry, who’s suffered a stroke … but lives 240 miles away.

Estimated Travel Time: Six weeks
Your Marching Orders: A not-so-straight shot from Laurens, Iowa, to Mount Zion, Wisconsin. No driver’s license needed, because you’ll be atop a John Deere 110 Lawn Tractor. Top speed: 5 MPH.
What to Pack: Gasoline, camping gear, clothes, canned food, wieners and replacement parts for your riding mower (condenser, plugs, generator and a starter).
Pit Stops: Head to the R Campground in Charles City and tell your story to other travelers. (Though not a part of Straight’s sojourn, the campground is just down the road from the area’s first whitewater park.) While you’re getting repairs in West Bend, IA, head to the Grotto of Redemption, nine grottos depicting the life of Jesus (and the largest grotto in the world). Reflect on his journey, if you wish. Oh, and stop and admire the wildlife before the passing cars run them down.
If You Take One Picture: Separate the wheat from the chaff, as Alvin would say. Bring a drone and grab endless panoramic shots of the amber waves of grain that dot the Midwestern landscape.
The Quote to Have in Your Back Pocket: “Anger, vanity, you mix that together with liquor, you’ve got two brothers that haven’t spoken in ten years. Ah, whatever it was that made me and Lyle so mad … don’t matter anymore. I want to make peace, I want to sit with him, look up at the stars … like we used to do, so long ago.”

Trout Fishing in America by Richard Brautigan
A conceptual 1967 novella circling San Francisco and the Pacific Northwest, at different periods of the author’s life. Things culminate in a 1961 camping trip with his wife and child to Stanley, Idaho, where they go to about a jillion creeks (and where he wrote the book). Fun fact: the book has reportedly spawned at least two people named Trout Fishing in America (one goes by Trout).

Estimated Travel Time: A month or a lifetime. At least one marriage.
Your Marching Orders: If we’re staying on-script, you’ll find a 10-year-old station wagon in San Francisco and buy it with your $350 dollar tax return check. Then it’s east to Idaho’s Stanley Basin, camping and fishing where you will. Since it’s a time-spanning road story with more creek names than street names, at a certain point it’s dealer’s choice where you wet your waders. An abridged list of the author’s favored creeks between SF, the PNW and Idaho, which he liked for their romantic names: Tom Martin, Graveyard, Hayman, Owl Snuff, Carrie, Paradise, and Salt, to name a fraction. Godspeed.
What to Pack: A fishing pole (a seven-foot, two-section RA Special #240 bamboo fly rod and an Olympus reel, if possible), fishing vest, a Coleman camp set (chapter “A Note on the Camping Craze That Is Currently Sweeping America” spins a surprisingly compelling yarn around Coleman camping gear), a childlike reverie for nature, Karo and peanut butter sandwiches
Pit Stops: Salmon-Challis National Forest in Idaho; Big Smoky Creek in the Sawtooth National Forest; Silver Creek campgrounds; the Klamath River in Oregon (Grider Creek, specifically); Mill Valley, California
If You Take One Picture: It must be a portrait of you and your favorite travel companion in front of the Benjamin Franklin statue in Washington Square Park in San Francisco, because this is the backdrop of the cover photo of he and his muse Michaela Le Grand. The first chapter of the book is a meditation on the photo.
The Quote to Have in Your Back Pocket:
“As a child, when did I first hear about trout fishing in America? From whom? I guess it was a stepfather of mine. Summer of 1942. The old drunk told me about trout fishing. When he could talk, he had a way of describing trout as if they were a precious and intelligent metal.”

Hidalgo (2004)
At the end of the 19th century, a half-white, half-Native American cowboy named Frank Hopkins and his mustang Hidalgo defend their title as “the world’s greatest endurance horse and rider” in a 3,000-mile race across the Arabian Desert. Based very, very loosely on the real Hopkins.

Estimated Travel Time: 68 days
Your Marching Orders: Fly with your horse to Yemen then ride across the Arabian Desert, ending in Damascus. [Ed. note: Don’t actually do this. If you’re looking to seriously test your Hidalgo chops, the 620-mile Mongol Derby is currently the “longest and toughest horse race in the world.”]
What to Pack: A painted mustang, sand-colored cowboy hat, giant red bandana, Colt Single Action Army pistol, as well as dates, water and camel butter for provisions
Pit Stops: The coastal city of Aden, Yemen; the Persian Gulf coast from Yemen to Kuwait; Damascus. But don’t stop until you hit the Mediterranean Sea in Lebanon.
If You Take One Picture: After the locust swarm, when they’re all dead on the sand, take a selfie while you eat them for sustenance.
The Quote to Have in Your Back Pocket: “Most of the riders do not even get halfway. Last year, 40 men perished, roasted alive before reaching Iraq. The fortunate few cross Allah’s Frying Pot, then must pray they do not bear witness to the jinni of the West … where the old ones speak of the sand devil who guards the secrets of the passage to the sea. Those who reach the gulf waters travel west across Syria where the sands shift. East becomes west. West becomes south. What looks like sand to you soon becomes the poison pits. Men and horses fall through the air and are boiled thus. This is not possible.”

Dharma Bums by Jack Kerouac
Follow the footsteps of Kerouac’s self-modeled protagonist Ray in this post-On the Road narrative, which asks more questions than it answers as Ray travels between mountains and jazz clubs, three-day parties and remote wildernesses, hoping to achieve zen or something like it.

Estimated Travel Time: Until enlightenment is achieved or approx. three months. Whichever comes first.
Your Marching Orders: Centered on and around the Pacific Coast, you’ll start in the Bay, ideally at party overlooking the city, loaf about absolutely wine-drunk for a few weeks before embarking for 60 days alone on Desolation Peak in Skagit County, Washington.
What to Pack: An open, calm mind, a depiction of Yab-yum, and a sh*t-ton of wine
Pit Stops: Desolation Peak in Washington (near Hozomeen Mountain), where Kerouac was stationed alone as a fire lookout during the summer he wrote the book; Matterhorn Peak in California, where a few characters have a climb; 3119 Fillmore Street in San Francisco, the site of the infamous Six Gallery reading, which is recounted in an episode in the book.
If You Take One Picture: What’s the point? Just enjoy it.
The Quote to Have in Your Back Pocket: “Who were all these strange ghosts rooted to the silly little adventure of earth with me? And who was I?”

Leaving The Atocha Station by Ben Lerner
A young American poet is on a poetry fellowship in Madrid to research the effects of the Spanish Civil War on the literature of Spain. In reality, he spends his time getting high, chasing Spanish women and having existential crises about self-worth and the value of art.

Estimated Travel Time: At least nine months
Your Marching Orders: Fly to Barajas Airport in Madrid and find a nice Airbnb in Plaza Santa Ana. Take a weekend trip with one love interest to Granada as well as an impromptu trip on the AVE to Barcelona with a different love interest.
What to Pack: Lorca’s Collected Poems, a book of John Ashbery Poems and maybe a little Tolstoy. (He reads a lot.) Also some rolling papers.
Pit Stops: Go to Museo Del Prado and contemplate Roger Van der Weyden’s Descent from the Cross; head out for drinks in the Chueca neighborhood of Madrid; eat at Alkimia in Barcelona near La Sagrada Familia; stay in the Albaicín neighborhood of Granada at Rosa de Comares; run up a foolishly large bill at Restaurante Horcher in an ill-advised effort to impress one of the love interests.
If You Take One Picture: It’s gotta be in the colossal and verdant train station for which the novel is named.
The Quote to Have in Your Back Pocket: “I told the waiter I was looking for a hotel whose name I didn’t know on a street whose name I didn’t know and could he help me; we both laughed and he said: Aren’t we all.”

Less by Andrew Sean Greer
A washed-up novelist named Arthur Less on the verge of turning 50 doesn’t want to attend his ex-lover’s wedding. Naturally, he embarks on an impromptu global sojourn.

Estimated Travel Time: One year
Your Marching Orders: Fly to New York (Less starts in SF), then head to, in order: Mexico City, Northern Italy, Berlin, Paris (layover), Morocco, India, Japan, back to SF
What to Pack: This book, a blue linen suit, stretching straps and a cosmonaut helmet
Pit Stops: Visit the ski resort Oukaimeden in Ifrane, Morocco’s “Little Switzerland”; walk the Temple of the Sun and the Temple of the Moon outside Mexico City; sit down for a seven-course kaiseki meal at Gion Karyo in Kyoto.
If You Take One Picture: Less finds time for everything, from clubby Berlin dungeons to Edo-period Japanese dwellings. But your go-to shot’s gotta be in Morocco, right around the time when the night slowly blankets the desert.
The Quote to Have in Your Back Pocket: “New York is a city of eight million people, approximately seven million of whom will be furious when they hear you were in town and didn’t meet them for an expensive dinner, five million furious you didn’t visit their new baby, three million furious you didn’t see their new show, one million furious you didn’t call for sex, but only five actually available to meet you. It is completely reasonable to call none of them.”

Master of None “The Thief” S2E1
Thirty-something New Yorker Dev (Aziz Ansari) tables his acting dreams and heads to Italy to learn the culinary arts of handmade pasta.

Estimated Travel Time: 3-4 months
Your Marching Orders: Book a one way flight for Rome; take a three-hour bus up to Modena in northern Italy and find yourself a nice little studio on the cheap, preferably just off a piazza
What to Pack: Dev’s biking-Italy style is off the chain, and you’ll want to look the part. Think linen trousers, mid-century polos and sockless footwear. Aaand wouldn’t hurt to download Find My iPhone in case any pickpockets get grand ideas.
Pit Stops: Menomoka for coffee and a chat; Boutique del Tortellino for crafting your own tortellini, Hosteria Giusti for a world-class birthday meal (it’s reservation-only, houses just four tables)
If You Take One Picture: Your plate at Hosteria Giusti. This is one of the very, very few times it is acceptable to take a picture of your food before tucking-in.
The Quote to Have in Your Back Pocket: Allora!”

Pee-Wee’s Big Adventure (1985)
A tricked-out bike owned by man-child Pee-Wee Herman is stolen. He must travel cross-country to get it back. Hilarity ensues (Aghhh heh heh!).

Estimated Travel Time: Hitchhiking, it might take you anywhere from 1-5 weeks. Biking? Up to 7 weeks. Your Marching Orders: Start at the ranch at 26800 Mulholland Highway in Calabasas, CA. Head over to South Pasadena, ride through North Hollywood Park, shop at the Santa Monica Mall … then make multiple stops (see below) on your way to the Alamo. Head back to California when you can’t find the basement.
What to Pack: Some Mr. T cereal. Assorted Rube Goldberg devices. Bow ties.
Pit Stops: Assorted truck stops (maybe don’t accept a ride). A Texas rodeo. Put “Tequila” on the jukebox at the Steel Horse Saloon in Phoenix and dance among the biker crowd. Take a leisurely ride within Malibu Creek State Park (which filled in for the film’s Tour de France dream sequence). Enjoy the VIP backlot tour of Warner Bros. Studios. And while Twisted Sister is no longer around for a cameo, frontman Dee Snider could very well be filming a music video during his domestic tour dates. Oh, and remember the Alamo.
If You Take One Picture: Take it at night, overlooking the the T-Rexes of the Cabazon Dinosaurs museum (and ignore the museum’s more recent creationist propaganda).
The Quote to Have in Your Back Pocket: “You don’t wanna get mixed up with a guy like me. I’m a loner, Dottie. A rebel.”

All the Pretty Horses by Cormac McCarthy
After the death of his grandfather and imminent sale of his ranch, 16-year-old John Grady Cole rides his horse into Mexico to work as a horse trainer and live as a true cowboy.

Estimated Travel Time: One year
Your Marching Orders: Begin in Texas. Ride your horse south across the border into Mexico and pick up work as a ranch hand wherever they’ll have you. Fall in love with the ranch owner’s daughter, get picked up by Mexican authorities and thrown in prison, escape, meet back up with the ranch owner’s daughter, then head back to Texas.
What to Pack: Horse, tobacco, rolling papers, Colt Bisley .32-20 revolver and a Spanish-English dictionary (or language-learning app)
Pit Stops: Find work in the city of Cuatro Ciénegas in the Coahuila region. After getting out of prison, meet the ranch owner’s daughter in the city of Zacatecas. John Grady and Alejandra stay at an “old colonial hotel” called the “Reina Cristina.” None such hotel exists, so stay at the Quinta Real Zacatecas. Visit the Plaza de Armas, see the angel in the Jardin Independencia.
If You Take One Picture: Take one outside the hotel in Zacatecas with the ranch owner’s daughter before she breaks your heart and leaves you forever.
The Quote to Have in Your Back Pocket: “If one were to be a person of value that value could not be a condition subject to the hazards of fortune. It had to be a quality that could not change. No matter what. Long before morning I knew that what I was seeking to discover was a thing I’d always known. That all courage was a form of constancy. That it was always himself that the coward abandoned first. After this all other betrayals came easily.”

The Old Man and the Sea by Ernest Hemingway
Old timer and down-on-his-luck fisherman Santiago has gone 84 days without catching a fish. On the 85th, he sails out from Cuba into the Gulf Stream, snags a giant marlin, fights it for two days and nights, and kills it on the third. Spoiler: sharks attack and eat it on his way back to shore.

Estimated Travel Time: Three days
Your Marching Orders: Fly to Havana, Cuba and rent a sail-equipped skiff
What to Pack: Pencil-thick fishing lines, sticks to tie them to, gaff, club, harpoon, bait box (with albacore, blue runners, yellow jack and sardine for scent). Water and food for yourself.
Pit Stops: Make sure to fish for 84 days with no bait to ensure you don’t catch anything. Then enroll solo in the Ernest Hemingway International Billfish Tournament and wait for the fish that will become your brother.
If You Take One Picture: Get that marlin in all its glory before the sharks dig in
The Quote to Have in Your Back Pocket: “Then he was sorry for the great fish that had nothing to eat and his determination to kill him never relaxed in his sorrow for him. How many people will he feed, he thought. But are they worthy to eat him? No, of course not. There is no one worthy of eating him from the manner of his behaviour and his great dignity.”

On the Road by Jack Kerouac
The one without the punctuation. A young iconoclast hitchhikes his way all over the Lower 48 and Mexico, working odd jobs and crashing on friends’ floors as often as possible to help fund his journey.

Estimated Travel Time: Kerouac’s “research” lasted four years, but a single, deliberate transcontinental drive should suffice — plan on 2-3 weeks.
Your Marching Orders: Start in New York City with $573 dollars in your pocket (that’s Kerouac’s $50 adjusted for inflation). Take a bus to Chicago and then hitchhike to Denver. When you run out of money, call a generous aunt for a wire. Then proceed to San Francisco (again via bus), before hitchhiking the final leg of the journey down Highway 1 to L.A. Eventually, you’ll hop on a bus to Pittsburgh, and then hitch a ride back to NYC from there.
What to Pack: Apple pie, books, road maps and enough journals to write a publishable beat novel.
Pit Stops: In Chicago, visit a jazz club; catch the opera in Central City, Colorado; hike the Lands End trail when you reach San Francisco; pick some grapes at a winery outside of Bakersfield.
If You Take One Picture: Pull over in Davenport, Iowa, for a Mississippi River selfie.
The Quote To Have in Your Back Pocket: “‘I just won’t sleep,’ I decided. There were so many other interesting things to do.”

Ulysses by James Joyce
The other one without the punctuation. A humble man with a big appetite wanders around Dublin on June 16, 1904, interacting with local bystanders and merchants before eventually returning home to his wife in a single-day approximation of Homer’s Odyssey.

Estimated Travel Time: Sunup to sundown.
Your Marching Orders: From the city center, head south to Westland Row; wander west along the river, admiring all the National institutions; in early evening, head north, crossing the River Liffey onto Talbot street, site of Dublin’s now-defunct Red Light District.
What to Pack: Inscrutable opinions on modernity and Irish nationalism, a good mackintosh (raincoat), stationery, a large appetite.
Pit Stops: Davy Byrne’s pub for lunch, where you’ll nosh a gorgonzola sandwich with a glass of red; the National Museum and Library; any pub you pass that looks inviting; a brothel (you’re on your own there).
If You Take One Picture: Snap a candid shot of your beloved wife upon returning to your hotel room.
The Quote to Have in Your Back Pocket: “Every life is in many days, day after day. We walk through ourselves, meeting robbers, ghosts, giants, old men, young men, wives, widows, brothers-in-love, but always meeting

Additional reporting by Kirk Miller, Alex Lauer, Walker Loetscher, Athena Wisotsky, Danny Agnew and Eli London.
Images from Wikimedia Commons, IMDB


Join America's Fastest Growing Spirits Newsletter THE SPILL. Unlock all the reviews, recipes and revelry — and get 15% off award-winning La Tierra de Acre Mezcal.