“We’ve gone on holiday by mistake,” laments the melodramatic Withnail in the cult film ‘Withnail and I’ as his escape from his filthy London squat for the fresh country air of the English Lake District turns out to be anything but idyllic.

Withnail and his of out-of-work actor chum “I” are enduring what so many have experienced for real on their own travels: when the pictures on the holiday brochure (or in one’s imagination) turns out be nothing like the real experience.

This all too familiar feeling of traveller’s gloom is one of the many aspects of that great human urge to “go on holiday” that the British philosopher and best-selling author Alain De Botton explores in his highly entertaining and insightful book The Art of Travel.

“We are inundated with advice on where to travel to, [but] we hear little of why and how we should go,” muses De Botton in the first chapter called “On anticipation”.

De Botton recalls his own disappointing experience of a tropical island holiday to Barbados where he went with his partner one year, to escape the London winter.

Prior to traveling he imagined only “a beach with a palm tree against the setting sun”, a “bungalow with views through French doors” and an “azure sky”.

What he didn’t imagine was the “large petrol storage facility” near the airport, the long line of people waiting to have their passports stamped, adverts for rum above the luggage carousel and “a confusion of taxi drivers and tour guides outside the terminal building”.

It’s not just that the holiday ‘looks’ nothing like the brochure. Even when the author does find himself in a place which should be restful and calming – the idyllic sandy beach of his imagination – he struggles to relax, his mind is full of worries about “back home” leading De Botton to the depressing realisation that he has taken ‘himself’, with all its anxieties, fears and frustrations, on holiday with him too.

“…the mind meanwhile revealed a commitment to anxiety, boredom, free-floating sadness and financial alarm.”

This candidness and almost painful honest is one of the great joys of reading De Botton. He is never afraid to draw on his own bitter experiences, failings and annoying habits to illustrate a key point; in this way, he makes himself a very likeable and sincere narrator.

As with the other books of his I have read (The Consolations of PhilosophyThe Consolations of Philosophy and How Proust Can Change Your Life)  De Botton draws on the wisdom of the great thinkers of the past – philosophers, artists, writers, painters and poets – to provide answers to the questions he has about the paradoxes, ironies and mysteries of the travel experience.  (Surely no other writer has managed to make philosophy so interesting and so practical).

These include the American realist painter Edward Hopper whose evocative scenes of lonely travellers waiting in empty motels rooms, gas stations and automats, De Botton relates to the idea of travel as a journey of reflective introspection. The poetry and power of these melancholic scenes De Botton also says explains why we take pleasure and comfort in ugly highway rest stops, where we find kingship with other fellow travellers amid the harsh lighting and plastic furniture.

I particularly enjoyed De Botton’s description of a lacklustre visit to Madrid, where he could barely muster the strength to get out of bed, despite the great Spanish city with its palaces, museums and art galleries beckoning him from below his hotel room. Only the fear of the hotel maid entering his room for a fourth time and exclaiming “Hola, Perdone!” roused him from his depression.

While one’s first reaction is to be annoyed with De Botton for squandering such a great opportunity to see the sights, who on their own travels has not grown lethargic and bored at the prospect of a visit to yet another ancient ruin, art gallery or museum, which our travel guide tells us we should be enthusiastically visiting and gazing at in wonder.

Here De Botton takes his cues from the great German explorer and naturalist Alexander von HumboldtGerman explorer and naturalist Alexander von Humboldt whose curiosity for all the things strange and unusual he discovered and catalogued on his expeditions reminded De Botton that what we find pleasurable or interesting on our travels should not be determined by the latest edition of the Lonely Planet or Rough Guide.

Humboldt did not suffer such intimidation…He could unselfconsciously decide what interested him. He could create his own categories of value…

De Botton’s other guides include Vincent Van Gogh, whose vibrant paintings of bright yellow wheatfields and whirling Cypress trees in Arles reveal the hidden beauty and power in seemingly ordinary places and the poetry of William Wordsworth, which celebrated daffodils, sheep and trees – as an explanation for why we yearn to escape the city for the restorative piers of the countryside.

(It’s just a shame my paperback edition of The Art of Travel reproduced all the artworks and photographs in black and white, though its easy enough, albeit a little disruptive to one’s reading, to look up the full colour version on one’s smartphone or tablet.)

There is of course another message that De Botton is so eager to share: that one does not have to jump on a plane and fly 5000 miles to a remote island to undertake an enlightening journey. Just exploring one’s own neighbourhood with a curious eye and alert mind can reveal wonders, as the author does himself with a meditative walk through his London suburb of Hammersmith.

In fact, one does not even have to leave one’s bedroom to “travel” if one subscribes to the wisdom of French writer Xavier de Maistre whose bizarre book Journey Around My Bedroom, published in 1794 De Botton brings back from obscurity.

While De Botton acknowledges there is clearly something rather silly about de Maistre’s suggestion that rather then go travelling we instead admire the elegance of one’s bedroom furniture,  he also recognises a more profound message that “the pleasure we derive from journeys is perhaps more dependent on the mindset with which we travel then on the destination we travel to”.

It’s one worth remembering the next time we reach for the chunky travel guide wedged in our bookshelf, when the urge to go on holiday hits us again.

(Readers of The Art of Travel, might also enjoy an accompanied documentary Alain De Botton made on the topic, which you can watch for free on YouTube: