1. On the Road – Jack Kerouac
Jack Kerouac was a leader of the Beat Movement, an artistic grouping that analysed the culture and politics of the USA after World War II. ‘On the Road’, famously typewritten on one long scroll of paper over three weeks, fuelled by coffee and amphetamines, was among the most iconic works to emerge from the period. It’s a searing, poetic and raw account of two young men journeying repeatedly across the country by car, to a background of jazz and drugs. Semi-autobiographical, ‘On the Road’ is an electric read that’s difficult to put down once you get into the rhythms of Kerouac’s writing, that rarely stops for breath and is considered by many to have captured the voice of a generation.
2. The Art of Travel – Alain de Botton
One of the modern era’s greatest thinkers addresses the hows and whys of travel across a series of essays covering Departure, Motives, Landscapes, Art and Return. The philosopher focuses less on the experiences a person might have in a particular destination, and more on what inspires humans to explore the world beyond their immediate backyards, and what the effects can be on them by doing so. The book is essentially a collection of meditations on various aspects of travel intertwined with reflections on particular incidents, and the works of other intellectuals and artists related to the subject at hand. It’s a lot more accessible and engaging than you might think, and will open your eyes not just to the places you’re going, but prompts you to reflect on how to really experience every aspect of your trip.
3. Endurance: Shackleton’s Incredible Voyage – Alfred Lansing
Endurance was the name of explorer Sir Ernest Shackleton’s ship, that departed from Norway in 2012 and became hopelessly stuck in the Antarctica ice in early 1915. Legend has it that when looking for crew, Shackleton produced a newspaper ad reading: “Men wanted for hazardous journey. Small wages, bitter cold, long months of complete darkness, constant danger, safe return doubtful. Honour and recognition in case of success. Sir Ernest Shackleton.” Lansing’s book is a riveting account of the crew’s fight for survival in the face of crushing odds. Heroism, resilience and leadership are constant themes of this amazing story that has made Shackleton’s one of history’s great adventurers.
4. Notes from a Small Island – Bill Bryson
Bill Bryson lived in England for over 20 years, and before returning to his native Iowa for a spell, he decided to embark on a marathon journey around Great Britain from tip to tail. ‘Notes from a Small Island’ is a wry, heartfelt and honest account of his life and experiences in the country, covering heritage, nature, and the idiosyncrasies of the British along the way. Many people would say there has never been a better travel book written about Great Britain.
5. The Motorcycle Diaries – Ernesto Guevara
Before Ernesto ‘Che’ Guevara became a figurehead of the Cuban Revolution and a countercultural icon, he travelled the length of South America, mostly by motorbike, keeping a travel diary as he went that shows how his Marxist leanings were formed and solidified. Although many of the experiences Che and his friend Alberto encountered were humorous, it is his accounts of oppression, poverty and disenfranchisement that are the most riveting, and by the end we are left with an avowed champion of the poor, an opponent of American imperialism, and a budding revolutionary.
6. Seven Years in Tibet – Heinrich Harrer
Harrer was an Austrian mountaineer who escaped a British prison camp in India during World War II and reached Tibet, eventually arriving in Lhasa where he became a trusted personal tutor to the 14th Dalai Lama. The author gives a gripping account of China’s invasion of Tibet in 1950, and also a fascinating glimpse of a then-unknown and mysterious world when describing the Dalai Lama’s life and court. 
7. The Great Railway Bazaar – Paul Theroux
This 1975 travelogue is thought to be Paul Theroux’s finest work, which given the span of his writing is really saying something. It recounts an epic journey, from England to Southeast Asia through India and the Middle East aboard the Trans-Siberian Railway. During the journey, Theroux encounters a colourful band of fellow passengers, from rogues to business people. It’s a vivid paean to the romance of train travel, and an undisputed classic of the genre. 