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On The Road

The best literary road trips

On The Road
14 March 2011

The epic journey genre inspires the desire to travel in a way a Lonely Planet guide never could. ShortList’s James McMahon revisits the great literary road trips.

Critic Gilbert Millstein wrote, “It is [for] a generation that does not know what it is searching for,” in his New York Times review of Jack Kerouac’s On The Road, “but it is searching.” That review, written in 1957, made reference to a post-war generation that Kerouac had previously prefaced with the word Beat. Yet much like it described Dean Moriarty and Sal Paradise, Beat might also describe anyone who’s ever looked for truth on a road map.

This year the actor Sam Riley embarks on the same journey, in a film adaptation of Kerouac’s book directed by Walter Salles and produced by Francis Ford Coppola. It’s set to inspire yet another generation to head out into the wilds. In tribute, ShortList compiled a selection of literature’s other road-based adventures with tips on how you can recreate them. Though it’s probably best if you leave the industrial-strength amphetamines at home.


by Che Guevara, 1993

Ernesto ‘Che’ Guevara’s diaries from his nine-month trip around South America in 1952 were never meant to see the light of day, but his family pieced together the then 23-year-old’s type-written notes in the Eighties. The result is a tale of how a wealthy medical student found his fledgling calling to become a Marxist revolutionary, marked forever by his experiences on the roads of South America. It ticks all the boxes – historic significance, adventure, incredible scenery, spicy food, the occasional snake - but it’s one hell of a trek, so purists should be prepared for a hard slog. Word to the wise: your kit should include a tool box for a 1939 Norton 500cc motorcycle.

Start out from Buenos Aries (Che and his 29-year-old companion Alberto began in January) moving down to the Argentine seaside town of Miramar and then across to Chile. Once on the Pacific coast, drive north of Santiago via Valparaiso to the copper mine of Chuquicamata, where Che and Alberto met a couple expelled from the complex for their communist beliefs and Che describes the lives of the workers as a “living hell”. From there the pair go north to Peru (motorbike breakdown optional) and travel by truck with native Indians and livestock, eventually coming to the ancient Inca ruins of Machu Picchu, and then on to Lima, where they spend three weeks in the Amazonian leper colony of San Pablo de Loreto.

In the original journey the travelling pair stayed on the doctor’s side of the river, but if you’re committed to retracing Che’s every movement, prepare to swim the two-and-a-half-mile stretch across the river to spend your final night with the ostracised patients (again, aggressive asthma would make it particularly realistic). Time spent pondering the inequalities of life will also come in handy. “I got the impression that Che was saying goodbye to institutional medicine and becoming a doctor of the people,” Alberto once said of their time at the colony.

Once ready to move, a raft – preferably built by the patients – should be procured to float to Leticia in Colombia, the country’s only port on the river. Then fly to Bogota, drive to Caracas, Venezuela, and return to Buenos Aries (via Miami, like Che, if you so choose) to begin a new life fighting injustice.


by Jack Kerouac, 1957

Jack Kerouac often claimed he crafted the semi-autobiographical cross-state adventures of Dean Moriarty (based on fellow Beat, Neal Cassady) and narrator Salvatore Paradise (based on himself) in three weeks in 1951, constantly ingesting amphetamines and typing continuously on to a 120-foot roll of teletype paper. In truth, the writer had been keeping notebook accounts of his cross-country adventures since his first major road trip in 1947, and work on this major tale began just one year later.

You’ll need time on your hands for this one. The trip doesn’t take a particularly linear path. For a crude recreation, begin in New York, head to Chicago, Illinois, then San Francisco, California. Then, to be really authentic, take the bus to Los Angeles. Proceed to Denver, Colorado, before making your way down to Mexico City.

But the odyssey doesn’t end there. Kerouac actually handwrote an itinerary of his 1947 hitchhiking trip (he didn’t get a driving licence until he was 34, in 1956) and drew a map of it in his journal too (it reads “hitchhiking trip July–Oct 1947. And all the great territories…”). It’s this that provides a firmer structure for a planned trip and includes the more obscure towns of Davenport, Cheyenne, Laramie, Selma and Albuquerque, as well as a host

of other backwaters rarely advertised on holiday brochures.


by Robert Byron, 1937

Not an easy one, but there’ll definitely be a book deal at the end of it. Byron shimmied across the globe when a cut-glass English accent would result in begrudging reverence rather than a rifle butt in the face, so his inter-war ‘grand tour’ of Islamic architecture, while taxing in places, benefited greatly from Britain’s colonial power.

Today you’ll need more than an Oxbridge education and a Fortnum & Mason hamper to see you from Venice to Beirut then on to Damascus, Baghdad, Tehran and Oxiana – between the Hindu Kush and Pamir Mountains in northern Afghanistan – all via the remains of the Persian empire and the only excavated Greek city of central Asia.

Byron’s 1937 account is a study in the chaffing superiority of the British ruling classes and a diary of such elegant prose and dry wit, you’ll wish you too had nothing better to do than think up artful verbal snapshots while bumping along on the back of a camel. And he had his fair share of traveller woes too, including “mosquitoes the size of eagles”, revolting hotel rooms and officious border guards. And in 2011, you can just about guarantee the journey will be positively crawling with them.


by Rex Pickett, 2004

You saw the film, you stopped drinking chardonnay in favour of pinot noir, so now you really should do the tour – particularly if, unlike Miles and Jack (Paul Giamatti and Thomas Haden Church), you don’t want a wine-tasting trip to be your last flirtation with youth.

First head to the Santa Ynez Valley in California. Once there, make to Los Olivos Wine Merchant & Café, located at 2879 Grand Avenue in Los Olivos. Good news: the restaurant reportedly offers a $35 (£22) Sideways tasting menu. Bad news: you can’t sit at the same table the characters did in the film because it was set up in the gift shop.

It’s also worth visiting the Fess Parker Winery – called Frass Canyon in the original story – where Miles is told his novel won’t be published. Nearby lies The Hitching Post, which as fans of the film will be aware, does an “excellent” Highliner pinot noir. There you’ll also find the two men’s base for their boozy adventures, the Days Inn Solvang (try room 234 to be really authentic). In fact, the only way to make your trip more like the original is to attempt to sleep with a waitress and/or anyone who is vaguely friendly.


by John Steinbeck, 1962

Find yourself a poodle. Call it Charley. Modify a camper van and name it Rocinante after Don Quixote’s horse. Done? Right, now you’re ready to retrace Steinbeck’s 10,000-mile round trip from New York to the Deep South and back again in search of the spirit of his nation. Start at Long Island, then travel by ferry to Connecticut. Then take Highway 1 to Maine where the writer stayed with his ex-literary agent at Dunham’s Point, stopping at Deer Isle for lobsters – “the best in the world” as he wrote in the book. Whether you then want to spend the night in a field with French potato-pickers is, of course, up to you.

Before you head to Texas and the Deep South, first check into Chicago’s Ambassador East Hotel, scene of Cary Grant and Eva Marie Saint’s tryst in Hitchcock’s North By Northwest. Make sure you ask for an unmade room – as Steinbeck’s was – but don’t bother asking which one he stayed in. “If anyone would know, I would,” sighed the hotel historian, when writer Bill Steigerwald recreated the trip last year. “But I don’t.”

We ate at the Michelin-starred One Market Restaurant in San Francisco