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Best Literary Road Trips

Best Literary Road Trips & Travel Adventures

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9 December 2015 by Alison Nicolle

The highways and byways of the USA offer some classic routes, but follow in the tracks of these authors for an authentic adventure – including journeys through Latin America, the Middle East and Asia.

Jack Kerouac

On the Road book jacket On the Road image

Kerouac claimed that he crafted this semi-autobiographical cross-state odyssey in three weeks in 1951, typing continuously on a great roll of teletype paper and ingesting amphetamines.

In truth, he kept detailed notebooks of his cross-country adventure since his first road trip in 1947. The book, based on the adventures of Dean Moriarty (based on fellow beat Neal Cassady) and narrator Salvatore Paradise (based on Kerouac) swings with the rhythms of underground 50s America.

It doesn't follow a linear path though and consists of three separate trips, so recreating the route is difficult. To get a sense of the journey, hop in a '49 Hudson in New York, drive to Chicago, then head south to San Francisco. Visit Los Angeles, motor to Denver and ultimately make your way to Mexico City. All the while, look and listen out for the sights and rhythms of America that so inspired the original Beat combo.

John Steinbeck

Travels with Charley book jacket Rocinante, Steinbeck travels with Charley

In 1960 John Steinbeck and his gregarious French poodle Charley set out from New York in a converted pick up truck nicknamed Rocinante, after Don Quixote's horse, to tour the USA, in search of the spirit of the nation he'd written so widely about.

10,000 miles and some 40 states later, the result was Travels with Charley in Search of America, an absorbing and beautifully written account of the landscapes and people he encountered along the way.

Start at Long Island, then travel by ferry to Connecticut. Take Highway 1 to Maine, stay at Dunham Point, and eat lobster at Deer Isle. Avoid sleeping in a field with French potato-pickers if possible then continue on to Texas and the Deep South.

Steinbeck's bleak evocation of events and attitudes in the Deep South reveal just how much America has changed in the past 60 years. Other observations on America make Steinbeck proud, angry, sympathetic and elated, all of which he records with remarkable honesty and insight.

Hunter S. Thompson

Fear and Loathing in Las Vegas book jacket Las Vegas

Surreal, sharp and consistently funny, Hunter S. Thompson's "Savage Journey to the Heart of the American Dream" follows Raoul Duke and his attorney Dr Gonzo on a drug-addled trip to Las Vegas.

The novel is said to owe its origins to two genuine journeys to Sin City made by Hunter S. Thompson while covering stories for Rolling Stone magazine.

Follow in the freewheeling pairs tracks and roar down the desert highway from Los Angeles in an apple-red Chevrolet Impala convertible, the Red Shark, although it's probably best if you leave the industrial-strength drugs at home.

Bill Bryson

Lost Continent book jacket Small town USA

Prolific travel writer Bill Bryson returns to the United States after two decades in England to search for the perfect American small town. But Bryson finds an America unlike the place he idealizes.

In a Chevy Chevette he borrows from his mother, Bryson leaves Des Moines, Iowa and drives aimlessly through 38 states, eschewing the big city and luxury hotels befitting his celebrity. He doesn't find the idyllic small town but does gain a great understanding of rural America.

Rex Pickett

Sideways book jacket California vineyards

If you saw the film and subsequently stopped drinking chardonnay for pinot noir, you ought to read the book or better still take the tour.

Head to the Santa Ynez Valley in California and follow Miles and Jack as they drink, carouse and attempt to hang on to their youth.

Make your way to Los Olivos Wine Merchant & Café, visit the Fees Parker Winery, called Frass Canyon in the original story, eat and drink at the Hitching Post and stay at the Days Inn Solvang, where the boys base themselves for their boozy adventure; ask for room 234 to be truly authentic. Just don't get caught up with a waitress on your way.

William Least Heat Moon

Blue Highways book jacket Back country road

Blue Highways is an unforgettable circular journey along America's backroads. William Least Heat-Moon lost his job so jumped in a half-ton Ford van he christened Ghost Dancing, with a few necessities and set out with little more than the need to put home behind him and a sense of curiosity about "those little towns that get on the map-if they get on at all-only because some cartographer has a blank space to fill.'

Follow in his wake from Missouri, on the roads that used to be coloured blue in the Rand McNally atlas, and discover unlikely destinations including Remote, Oregon, Simplicity, Virginia New Freedom, Pennsylvania, New Hope, Tennessee, Why, Arizona, Whynot, Mississippi, Igo, California and nearby Ono.

His adventures, his discoveries, and his recollections of the extraordinary people he encountered along the way amount to a revelation of the true American experience.

And by motorbike...

Ernesto Che Guevara

Motorcycle Diaries book jacket Argentina road trip

Guevara recorded his nine-month trip around South America in 1952 but the diaries weren't ever intended to be released; his family pieced together and published the type-written notes some 30 years later.

The result is an extraordinary story of how the road trip experiences of a young, wealthy medical student shaped the thoughts and ideology of the man who became a Marxist revolutionary and global icon.

The epic journey boasts adventure, dramatic landscapes, great food and historic resonance but if you're following the route be prepared for a hard slog, especially if attempting it on a 1939 Norton motorbike, even one nicknamed La Pedorosa, the Powerful One.

Set out from Buenos Aires, motor south to Miramar then cross over into Chile. Hit the Pacific coast and turn north via Santiago to Valparaiso and then the copper mine of Chuquicamata. Enter Peru, explore Machu Picchu and pitch up in Lima, although you may want to pass on the weeks spent in a leper colony here.

To be totally authentic, float to Leticia in Colombia, fly to Bogota, drive to Caracas in Venezuela and finally return to Buenos Aires, ready to fight injustice.

Or by train...

Paul Theroux

Great Railway Bazaar book jacket Trans-Siberian railway

Paul Theroux's first and arguably finest book, The Great Railway Bazaar recounts a four-month journey through Europe, Asia and the Middle East that sees him go from London to Tokyo and back again.

An essential for any enthusiast of train travel, the book features some of the world's greatest lines. Kick off on the platform at Victoria, London and hop onto every train that hoves into view, including the the Khyber Pass Local, the Delhi Mail from Jaipur, the Golden Arrow to Kuala Lumpur, the Hikari Super Express to Kyoto and the Trans-Siberian Express.

Along the way, do as Theroux did, listen in on snippets of chat and allow yourself to be drawn into conversations with fellow passengers. The result is a travelogue that pays tribute to the joys of long distance train travel.

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