A still from the film based on Hunter S. Thompson's classic novel

Ask any Dreamy Poet or Bearded Wannabe Novelist to name their favourite book of travel writing, and they’ll no doubt give you an impressively literary title like Steinbeck’s ‘A Russian Journal’ or ‘The Sheltering Sky’ by Paul Bowles.

Like broccoli, these books are no doubt high in mental vitamins. But they also bore me to tears.

Personally, I’d rather read adventures with bite, wit, danger, and stakes. So in the hopes of helping you inspire someone you love this Christmas, I give you:

5 books that inspired me to become a travel writer

#5) ON THE ROAD

Author: Jack Kerouac

A road map for the Beat Generation, the novel’s characters (based on Kerouac and his friends) speed from New York to Denver, San Francisco, LA, and Mexico, fuelled by cheap gas and youthful energy.

When I read this novel at 21, I didn’t just quit my job so I could travel … I convinced two other employees to quit with me. Then I gobbled caffeine pills, and drove across the USA to become a lifeguard on the Pacific coast.

Most inspirational moment: when Kerouac’s narrator, Sal Paradise, describes the perfect travel buddy: “the only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones that never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars and in the middle you see the blue centerlight pop and everybody goes “Awww!”

WARNING: this book will make you want to hitchhike. Also, people who never yawn or say a commonplace thing are on drugs.

#4) THE RAZOR’S EDGE

Author: W. Somerset Maugham

A novel about the post-World War I wanderings of a wounded pilot, Larry Darrell. Traumatized by the death of a comrade during the Great War, he puts the brakes on his impending marriage, loafs in Paris for two years, and then travels through India on a spiritual search for meaning and happiness.

Most inspirational moment: when Larry arrives in Bombay, he quits his deckhand job on a luxury ocean liner. “My heart began to beat like mad, because I’d suddenly become aware of an intense conviction that India had something to give me that I had to have. It seemed to me that a chance was offered to me and I must take it there and then or it would never be offered me again,” he says.

More than anything I’ve read, this sums up why I need to travel.

WARNING: avoid the 1984 movie. Featuring a badly miscast Bill Murray in the lead, this film was so slow and lifeless, Murray didn’t star in another movie for four years.

#3) THE WORST DATE EVER

Author: Jane Bussmann

Hilarious, informative, and heartbreaking, this is the true story of how a celebrity interviewer blithely quit her job to follow a handsome humanitarian to Africa.

But when the guy doesn’t show up for weeks, she decides to stop an African warlord whom she describes as “the most evil man in the world.”

Bussmann’s chapter titles are fantastic: Chapter 6 is called “I’ve got a six-foot rubber vagina and you’re using it,” Chapter 23 is “Dragged into the bushes and machete,” and Chapter 59 is “Whoreobics.”

Most inspirational moment: the opening, when she realizes while interviewing Ashton Kutcher that she has to flee Hollywood’s ‘Golden Age of Stupid’ and pursue her higher African calling.

WARNING: you’ll be inspired to stop African warlords, too, which ain’t all fun and games.

#2) FEAR AND LOATHING IN LAS VEGAS: A SAVAGE JOURNEY TO THE HEART OF THE AMERICAN DREAM 

Author: Hunter S. Thompson

The paperback that made me want to hit the open road with a quart of tequila, a quart of rum, a case of Ballantine ale, and a pint of raw ether. This is HST’s hilariously debauched recounting of his epic late ‘60s road trip to Las Vegas with his “300-lb Samoan attorney” in a great red shark of a convertible. HST was supposed to be on an assignment for a sports magazine, covering the Mint 400 desert rally. But HST ditched that story for a deeper quest of finding the elusive American Dream.

Most inspirational moment: the narrator’s famous Wave Speech where he describes riding his motorcycle through southern California in the mid-‘60s at the peak of the counterculture dream.

WARNING: don’t try to recreate this book in real life, or you’ll electrocute yourself with a live toaster in a hotel bathtub.

#1) HOLIDAYS IN HELL

Author: P.J. O’Rourke

A compilation of P.J’s best articles published in magazines like Rolling Stone and Playboy, Holidays in Hell is the funniest book about a war correspondent ducking bullets in countries ravaged by war, earthquakes, and corruption.

Each chapter, P.J. lifted the lid on another pot of foreign ‘80s trouble, whether it was brewing in El Salvador, the Philippines, Panama, or Lebanon. His first-person mission was to explain — in hysterically sharp similes — why people are drawn to trouble in some of the world’s most beautiful settings.

Most inspirational moment: P.J.’s pithy primer on how to survive on an Indian highway

WARNING: don’t confuse this 1988 classic with his recent sequel, ‘ Holidays in Heck’, a collection of sadly tepid essays about travelling with his family.

So those are my 5 faves. What book makes you want to quit your job and sail to India?

— Ken Hegan

Read all of Ken’s MSN travel stories here and follow Ken to victory on Twitter 

Photo: CP Images

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