How to Plan the Best Trip of Your Life



Wicklow Mountains National Park, Ireland.

Anyone who can travel for fun has a lot of decisions to make about where to go, what to do, see, eat, etc. To help with these decisions, there are innumerable travel apps, addictive instagram feeds, “listicles,” and even good old-fashioned guidebooks. If you still make time for turning paper pages, there are some outstanding travel memoirs. The commonest queries are both practical and capricious. What are the essential sights in Paris? What’s the best way to get around Japan? Do I need an international phone plan? What clothes will help me blend in? Which establishments are authentic, and which are tourist traps? Where will I meet with real locals? Where are the best tacos el pastor in Mexico City? The best coffee in Cairo? What if I lose my way, my phone, my wallet? What if it’s dangerous? What if I miss out?

You can find answers to most of these questions, but that doesn’t mean you should. The wealth of information and misinformation at our fingertips now expands at a dizzying pace. That is potentially powerful, but certainly overwhelming. Worse, it sometimes gives us the illusion that we can engineer our experiences the same way we custom-order our burritos at Chipotle. Maybe this blog will dispel that stagnating, soul-sucking delusion of control. In reading these two paragraphs, you’ve already bested the average attention span of both a human with his smartphone and the slightly more attentive average goldfish. Well done! I haven’t the heart to string you along any further, so here’s the big secret:

To plan the best trip of your life, stop planning. 

This is not a trick. I know some steps are genuinely important. Check visa requirements. Book your flight. Dig your passport out of your underwear drawer. While you’re there, grab some underwear. Alert your bank. Look up the exchange rate. A map or two might be useful. But the truth is that too much planning spoils the fun. There is at least one juncture in every life when a blind date with a new place is just what the doctor ordered. The whole point of leaving home is to meet an uncertain future with all its unfathomable obscurity and luster, peril and promise.

Trip planning is a little like painting. Imagine blending green and blue on the canvas to represent the sea. The deeply saturated colors meld wildly under your brush-strokes, but if you sweep back and forth too much, the whole thing fades irrevocably from captivating movement to a flat, monochrome torpor. It feels like watching a time lapse of a hibiscus flower that blossoms and wilts in the space of seconds. For a moment your heart quickens at the climatic imperfection of tender unfurling petals or surging waves and wind-whipped foam, but if you don’t stop fixing it, you’ll be left in the doldrums, bemoaning your fatal perfectionism.

So it is with adventure. When I look back over my journeys, I recall many highlights, but they weren’t what I had planned. In fact, the very best bits were positively antithetical to any semblance of a plan. Weak and thwarted plans have left me tired, ill-dressed, hungry, dehydrated, sun burnt, sore, painfully embarrassed (again and again,) significantly poorer, exhilarated and profoundly alive. Just imagine what could happen if your plans don’t work.

If you’re lucky, you’ll get lost.

While you’re lost, maybe you’ll stumble upon a family-kitchen-cum-restaurant that serves the best pesto in Genoa. You might also nearly drown on Copacabana beach before being rescued by a lifeguard who’s obviously more Olympian god than man.  Maybe you’ll wind up crashing a French wedding, a Bosnian funeral, a Castilian village barbecue, or the opulent after-party of the Pebble Beach Food and Wine Festival. You might spend a night shivering in a Spanish wheat field under a Milky Way so luminous that you can’t bear to close your eyes. On your long, inconvenient layover, maybe you’ll stumble upon two gifted cellists rehearsing in a hidden corner of the airport. Sit down at their feet and let their sweet, thick music fill you like honey fills a spoon. You might be struck by a torrential monsoon in the remote mountains of northern Thailand and so emerge from the jungle blessedly soaked to the skin, with lungs finally cleansed of Bangkok’s thick smog.  You might stumble into a corner of the world which Google hasn’t explored.  (Yes, such places exist.) You might have to use absurd hand gestures to ask a local for directions, and even then he still might have to lead you step-by-step to your bus-stop.  Your rental car might get vandalized and your handbag stolen. In that case, perhaps you can enjoy the fascinating bureaucratic ordeal of boarding your next flight without any identification whatsoever. Maybe the only truly enjoyable thing you’ll do in a new city is simply to catch some rays and people-watch in a small public square off the beaten path. Maybe you will end up in an overpriced tourist trap, but maybe it will be funny. Maybe wherever it is that you next lose your way is also where you’ll fall in love.  Who knows?

For the record, one of those things didn’t actually happen to me, but you’ll just have to wonder which, because I’m not telling.

The few brief journeys which went according to my plans were comparatively lame. Happily, the wide, wild world—especially the so-called undeveloped parts of it—generally gives not a flying fig for my plans. Adventure has nearly always found me in spite of myself, but wouldn’t it be pleasant to dispense with the adjustment period? Plans can hurt because when they don’t work out, we feel disappointment, frustration, and anxiety which prevent us from enjoying the moment. In my case, those sentiments have sometimes been wildly disproportionate to the inconvenience incurred or the opportunity missed. If you haven’t been that traveler, you’ve at least seen her: tense, grim, losing poise, straining her relationships and beginning to whine. It’s not a pretty sight.  Don’t be her.

If you are a truly incorrigible worry-wart, control-freak or just plain tired, then consider an all-inclusive cruise or resort vacation. These don’t require much planning either, because the saintly staff have already planned to accommodate their guests’ fickle whims. At least, that’s what I’ve heard.  I have yet to sample such an experience, but I imagine its like mental bubble-wrap. Honestly, day-to-day life is often difficult and sometimes downright scary, so a bit of luxury and a lot of cushioning are perfectly in order, especially on vacation.

However, if you seek adventure above relaxation, then it’s even more important to stop with your silly plans. Just let adventure happen to you. Let the world be big at you. Feel your own tiny insignificance in its vastness.  Trust strangers, because what other choice do you really have? Laugh at your absurd predicaments. Always remember that even the best tourist is still nothing more than a clueless, curious fool. Get humble. Let your powerlessness sink into your bones and set you free.

As explained by Andrew Collins of Humane Pursuits, “Adventure requires an embodied engagement with the unknown.” In common  speak, I say it like this: Take a chance. If you’re trying to plan the best trip of your life, then give up early.

The best laid plans of mice and men are as nothing to the inscrutable dreams of God.

So what can you plan for? Well, I don’t always quote Steve Carell, but when I do, it’s only from Dan in Real Life.  His final words of wisdom in that charming flick are just these: Plan to be surprised.

May we all remain curious about the uncertain future ahead of us.  I don’t know what tomorrow brings, or where my feet or my pen will lead me. I only hope to enjoy getting there. Red cabbage

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