Posted October 4, 2012 by in Backpackology 101

The Art of Trip Planning

I’m writing this article for my younger brother, who, with all due respect, is about to make a terrible mistake.

“Steve!” he exclaimed over the phone. “I’m coming to visit you in Thailand for New Years! I’m booking my flight now. I’m gonna stay for two months.”

(That part’s not the mistake).

“Awesome!” I said. “How much money do you have saved?”

“Well… None, really,” he replied nonchalantly. He explained that his friend had loaned him just enough cash for the plane ticket, and that even though he didn’t have a consistent source of income, he was hoping he’d somehow amass several thousand dollars in the couple months before his flight date rolled around.

(That’s not the mistake either. In fact, I admire his adventurous risk-tasking). (Perhaps recklessness is a hereditary trait).

What Sean said next though was completely crazy.

“I’ve got eight weeks to see Thailand, Cambodia, Vietnam, and Laos. What do you recommend? I’m making my itinerary now.”

Itinerary. I cringed.

Itinerary. The dark word seemed to echo over the phone.


Five years ago, I charted out my first backpacking trip—a three-month dash across the Middle East; a blitzkrieg tour-de-force taking in seven countries and three continents. Like most first-time travelers, I was naïve and terrified that everything would go wrong. And, like most first-time travelers do, I attempted to quell my anxiety by over-stuffing my trip with as much structure and meticulous planning as possible. The resulting itinerary was a neurotic, twenty-six page tome, replete with inspirational pictures, strict daily timetables, and even—I admit it—dinner recommendations for all ninety-four days. I was proud of my ‘Trip Bible.’ It was as impressive as it was misguided and laughably sad.

Needless to say, the trip was a stressful and exhausting experience.

Burned from my mistakes, I attacked my next backpacking adventure with a radically opposite approach: I booked a flight to India, and then didn’t open my guidebook until I was on the plane… at which point I learned that I had perfectly timed my trip to coincide with the height of India’s monsoon season. Surprise! Arriving in Delhi at midnight, the temperature soared at 97 degrees Fahrenheit, with 94% humidity and constant torrential thunderstorms. Later, when I woke up in the middle of the night because the heat was so intense, I found that my pillow completely soaked through in my own sweat.

The first day of my trip was spent in the booking office of the Delhi Railway Station, my face pressed firmly in front of their floor-fan, weeping inconsolably.

In the years that followed, I’ve learned that effective trip planning is a delicate art form—one of balance and moderation. It is also deeply personal, and preferences of pace and rhythm are sure to change from one individual to the next. In this week’s blurb of Backpackology, I want to stop any first-time backpackers from sufferings the same rookie mistakes that I did. I’m going to offer a stress-free, fool-proof, simple, and easy formula for plotting out your next backpacking adventure.

The first step to mapping your next trip—even if you forego drafting an itinerary—is to research, research, research your destination. Remember to think in terms of macro instead of micro; instead of looking up famous beaches and top museums, focus on the broader picture. Read up on visa requirements, suggested vaccinations, safety advisories, travel costs, cultural etiquette, language, weather forecasts, what to pack, and other special travel considerations. The trick to effectively researching your destination is to really actually go and research it instead of scanning the WikiTravel page, you lazy asshole. Fun Fact: That newfangled Google internet website isn’t just for finding porn. The internet is rife with information, and it’s never been easier to find practical, relevant advice on the most far-flung destinations. Without proper research, even the most polished itinerary can crumble to pieces:

Thought it would be fun to take a Foodie Tour of Morocco this July? Surprise! It’s Ramadan, have fun fasting.

Thought you’d escape the winter holidays for a peaceful meditation retreat in Thailand? Surprise! You can’t hear yourself think during the height of the tourist season and a drunk chick just puked up a condom on your yoga mat.

Thought you’d sail up the Nile and check out the fabled and forgotten pyramids of Sudan? Surprise! You just died.

Once you’ve researched your destination, it’s time to consider which places to visit. My general rule of thumb is that, if the duration of your trip is two weeks or shorter and there are five or more sights/places that you’re absolutely dying to see, then (and only then) is an itinerary necessary. Otherwise, it’s important to remember that the only benefit of an itinerary is, supposedly, peace of mind; you know you’ll get to see all the sites, you know your time will be carefully managed; you always know exactly what to anticipate. Unfortunately, this peace of mind is a false promise, and instead, following a rigid timetable burdens you with stress, hassle, and the set-up for disappointment.

Far worse, a full itinerary changes the nature of your trip at an elemental level—it robs you of spontaneity, and accordingly, countless potential experiences. By reducing your trip to a checklist of attractions, you lose the ability to seize life’s surprise opportunities. You never know when a friendly cab driver will invite you to a cousin’s wedding, or when you’ll be asked to play a part in a Bollywood movie. You never know when you might fall ill. You never know when you might fall in love. The best approach to travel planning is one of minimalism and elasticity. You needn’t try to visit every single attraction—travel is about so much more than sightseeing.

My planning strategy is to schedule only one activity per week, and then play the rest by ear: Tomorrow, I’m planning to explore Beijing’s Forbidden City Palace in the morning. After that, I think I might take a break from China, simply because it’s too hot and sweaty and I don’t like it when my balls stick to the side of my leg.

Maybe in the afternoon, I’ll catch the train south to Tibet. Or perhaps I’ll board the ferry east to Korea. At this exact moment, I think I might hitch a ride north to Mongolia, though perhaps I’ll be too hot to move and sit in the hostel all day getting drunk instead.

The only thing I’m certain of is that tomorrow I’m going to pack my bag and go somewhere. I’m not sure where yet; there’s no ‘peace of mind,’ I don’t know what to anticipate—but I love that. I love the excitement. I love the suspense. I love the rush of flipping through guidebook photos, then spreading out my map, taking a step back, and asking, “Where do I want to go today?

It’s simply one of the greatest feelings in the world.


Backpackology has a Facebook Page and YOU WILL LIKE IT. Or else.

For more backpacking tips and tricks, click the Backpackology 101 tab at the top of the page.

For more travel philosophy, read The Backpacker’s Manifesto.

The bit about getting picked to play a part in a Bollywood movie was a true example! Check it out in the story Steve McDonald: Bollywood Extra(ordinaire).

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