How to Travel Like a Pro

You’ve spent fifteen long years saving for that once-in-a-lifetime trip to Europe. You dreamed about it. You talked about it. And you finally flew over and lived it — only to be left thinking, “Was that it?”

Or maybe you’re a frequent business traveler, and despite the many exotic cities you have visited, all you’ve ever really seen is snooty restaurants and shopping plazas.

There’s more to travel than that stuff…. isn’t there?

That’s what I want to talk to you about today. You’re going to learn how to immerse yourself in another culture so you come away with those incredibly deep experiences that shake up your worldview, change your perspective and stay with you forever.

There are as many different travel styles as there are travelers. But I think those “deep travel” experiences contain a few common elements.

The Power of One

If you want to understand a place, travel alone.

When you go with others, the trip is about the dynamics of the group. You seldom interact with the world you’re passing through. And the effect is magnified for couples. A couple travels in a self-contained bubble that others are reluctant to breach.

All of that changes when you travel alone. Your attention is focused on your surroundings. If you’re an introvert, you’ll have to speak up and engage the world around you. You’ll fall into random conversations with strangers, in cafes and on buses. And you’ll be completely drawn into the rhythm of that place.

One of the best parts of solo travel is the memories and associations each new place calls up. When I look back at my notebooks, those are the real gems. As I go deeply into a place, that place in turn causes me to look deeply within myself.

If you truly want those walls to fall down, it’s important to practice non-judgement. Don’t hold that place up against the standards of your home country or city, or you’ll never see beyond your own preconceived opinions. The world’s a big place, and cultures subscribe to many different standards of behavior, cleanliness, morality and personal space. Embrace this and enjoy it. And while you’re there, try to immerse yourself in your host culture’s way of life, even if only for a couple weeks.

Learn to Use the Guidebook in Reverse

When I first started backpacking in Central America, I quickly realized that everyone carried identical guidebooks so they could circle identical passages and mark identical maps. They compared notes on places to see, places to avoid, and cheap hotels where they would be sure to meet others of their kind. And sure enough, they all ended up in exactly the same places.

What’s the point of going abroad to do what everyone else is doing, and to hang out with other foreigners?

Escaping the crowds was simply a matter of learning to read the guidebook in reverse, avoiding the places it recommended, searching the bottom of the accommodation list rather than the top, and scouring the maps for places that weren’t written up.

The other thing I did was to avoid the hotels listed in the guidebook. Sure, there were probably some fun people hanging around those places, but talking with them taught me nothing about that country. And so I looked for smaller local hotels instead. Places that didn’t have English signs or menus.

It’s even easier to find unique accommodations today. Try searching for furnished apartments on sites like AirBnB.com or TripAdvisor. Eat your lunch outside on the go, either by brown bagging from a supermarket deli counter or taking advantage of excellent set menu lunches at local cafes. And then self-cater in your apartment for supper. The only difference between lunch and supper at a lot of those restaurants is the portion size — and the price.

Next, let’s figure out what you’re going to do with your time.

Don’t Cram the Schedule — You’re Not at Work

You can’t immerse yourself in a place if you’re busy forcing it to fit the mold of life back home.

Got a rigid morning routine that you stick to no matter what? Drop it completely and disorient yourself by doing what the locals do, whether that’s cafe au lait and a pain chocolat by the Seine, or just a quick shot of espresso at the counter.

Bring along that detailed itinerary you made for yourself. The one where every moment of every day is accounted for. Take a good long look at it over your coffee. And then rip it up.

Walk around aimlessly instead. Take your time. Sit in cafes and watch the flow of life. Pop into a grocery store and have a wander through the aisles, just to see what sort of things people eat.

And don’t let language barriers get in your way, either. Pick up a little phrasebook or dictionary that you can flip through to point out words or common phrases. And rely on gestures, a sketchpad and a bit of creative acting for the rest.

You’ll quickly discover that a smile, non-judgement and a willingness to learn opens most doors. Curiosity does the rest. People love to teach you about how they live if you simply express a bit of curiosity. “What’s that thing?” is one of the most useful questions in your toolbox.

But what about all those postcard things you’re supposed to be doing?

Should You Do “Sites”?

When I first started traveling, I visited all the historical sites, saw all the natural wonders, and dutifully checked off every item my guidebook recommended — because they must know, right?

Much to my surprise, I was always disappointed.

Now don’t get me wrong. Some sites — like Petra in Jordan, or the Grand Canyon in Arizona — are incredibly overhyped. But they live up to it, and even exceed it. Those places are absolutely worth a visit.

Other sites are not.

Think about it. Some guy visited those places and wrote them down because he either thought they were interesting, or he had several pages to fill. And then all the other guidebooks followed suit.

It took me a few years to get it, but I finally realized that experience is the key: finding an interesting place, meeting interesting people and just hanging around soaking it up. When you do this, you’ll find your own “sites” around which you’ll build your own mythology, one that grows organically from your travels.

I’m more interested in the mundane aspects of everyday life. And I learn an awful lot more about a place by just walking around some neighbourhoods to see how people live.

So do your research. Mark down those sites that really are worth the effort. And spend the rest of your time in free exploration, guided by your instincts and curiosity.

You’ll find that process a heck of a lot easier if you’ve done your prep…

Go Deep — Do Your Homework

I usually end up writing magazine articles about my journeys, so I do a lot of research before a trip. I read a couple volumes of history about that place or region. And then I read early travel accounts and old explorer’s journals, to get a sense of which aspects of life remained constant and which changed with the times. That helps you identify those deep continuities that are at the heart of a culture or worldview.

I also read fiction and poetry by local writers, because fiction reveals a person’s intimate thoughts in a way no history book ever could. And that tells me a great deal about the hopes and dreams, the struggles and joys, of the people I’m traveling among.

Why go to all this trouble?

Because you’ll find a theme to orient your trip. You might end up searching out sites related to a specific time period, person or series of events — Baroque architecture, landmarks from the novels of a favorite author or locations from the Great Siege of Malta, for example. Or you might decide to explore cafe culture, riverside life, wine regions or specific schools of art.

All that pre-trip reading makes your journey a personal one, shaped by your interests rather than the generic checklists of a tourist guidebook.

And what about drawing on local knowledge?

Should You Hire a Local Guide?

Guided trips can be informative, but they also isolate you from the place you’re traveling through. Your interactions with the people around you are moderated by a gatekeeper. You’re eating in “approved” places and talking to people who are used to dealing with foreigners. There’s no spontaneity, no independent discovery, and no opportunities for misadventure. And those are often the things that make the trip.

It’s up to you to decide. A great guide can open up a whole new world. And a bad or incompetent guide can color your entire trip in shades of misery.

Oh yeah, and one last point. It’s probably obvious to you by now, but I still have to say it…

Don’t Be “That Guy”

You know him. The one who walks through the Louvre with a video camera held out at eye level, because he desperately wants to capture the memories of places he never experienced.

You’re never going to watch those tapes. And I certainly hope you won’t torture your friends and family with them either.

Open your eyes, experience that place with all your senses, and capture memories instead.

And don’t let setbacks or “disasters” get you down. Sometimes the worst experiences make the very best travel stories.