How to Make Friends With Locals in a Foreign Country

It’s dusk, and I’m hanging on a rooftop with a family I just met on the east coast of Cuba. Another power outage has blackened the streets, the shark-finned cars parked on cracked concrete, the one-story pastel houses washed yellow by the full moonlight. Four generations are here, and all of us save the baby are drinking rum and Cokes.

I’ve provided the libations and smokes (Cubans earn less per month than the average American does in two hours) but it’s their roof, candles, and red plastic chairs facing out toward the Bay of Honey.

A pair of floodlights shines inland from the maritime horizon and sweeps the shoreline. “It’s cat and mouse,” someone on our rooftop says. I’m confused until I see what he’s talking about: On the shoreline, a group of five push a motorboat into the bay. They jump in -- first the women, then the men -- paddle out to sea. “They’ll start the engine once they know they can beat the coast guard,” my friend continues. “The family pays $5,000 up front, then another $15,000 when they reach Miami.” They row until their boat is enveloped by the distant blackness.

I’ll never forget Baracoa. Watching those people flee (with their countrymen providing honest commentary) was so dissimilar from everything I knew at home. It was an intimate encounter with the vastness of the world -- a reminder of why I started traveling in the first place.

Why is it so tricky to find moments like these when we travel? So often on a trip, we only interact with locals when we’re buying drinks or haggling over a souvenir. We get tripped up by language barriers, fear of straying from our guidebooks, the inhibiting comfort of the hostel scene.

Luck plays a part in meeting real people on your trip, sure. But you can push the odds to your favor. And if you do, locals reward you with a side of their country that puts the best guidebook to shame.

It’s great to travel somewhere with a favorable exchange rate. For some, taking cabs and eating out every night is a huge part of the trip’s appeal: a vacation from your limited means back home.

The downside to living it up? You won’t run into locals if your lifestyle insulates you from them. Money is a barrier everywhere -- even in communist countries that have strived to eliminate class.

In Cuba, the government’s unique approach to money illustrates that point. They’ve created two different currencies: one for tourists (the convertible peso) and one for locals (the national peso). The former buys everything a tourist could want: hotel rooms, booze, taxi rides, food. The latter buys the daily staples that Cubans need: fruits and vegetables, the municipal bus fare.

When I arrived at the airport in Havana, I converted about $20 into the locals’ money, enough bills to fill a small plastic bag. Leaning on the national peso meant foregoing great Cuban cuisine for stark, uninspiring diners. It meant waiting hours for local share taxis to carry me a few miles. But it also got me on an intercity bus (that -- obligatory side note -- was illegal for me to take), which was how I met the Cubans who would show me Baracoa.

In Thailand, I met a shoestring traveller who’d chatted with literally hundreds of locals. That’s because he’d lost thousands of dollars to scam artists two weeks into a six-month trip. Then, his girlfriend dumped him. He began wandering the country alone. Along the way he’d somehow gotten his hands on a bulk supply of condoms, which he sold one by one for his daily sustenance while awaiting his return flight.

His Thai, he told me, was really coming along. When I asked if he’d met many other tourists on his trip, he laughed. “Very few,” he said. “Nothing gets you off the beaten track quicker than going broke.”

The traveler who wants to avoid the tourist scene without becoming a door-to-door condom salesman faces a conundrum: nearly everything in the guidebook caters to tourists. As such, following a guidebook keeps you on a path.

At the risk of marginalizing myself: You’re better off widening your scope of research beyond travel writing. Local English-language publications are a great place to start.

On a trip to Calcutta, India, I went to a bookstore and picked up a copy of Cal Calling, a magazine for the city’s arts scene. Listed there was a rooftop poetry reading hosted by students from Jadavpur University. I was the only Westerner who went. Afterward, I chatted with the writers, exchanging numbers. They invited me to a party on their campus the following evening. I rolled with that crew for a week.

For those who haven’t aged out of this move, it’s a great shortcut. College kids have more free time for you, a welcome distraction, than people with full-time jobs. They also tend to be young, open-minded, and speak more English than those without the benefit of higher education. And colleges host free events worthy of attention in their own right.

Some seasoned travelers play the minimalist packing game, claiming bragging rights by the extent they cut bulk. By all means, save space with that 33-tool Swiss Army knife. But the most worthwhile item I ever traveled with was a pocket trumpet, which I carried on a long solo trip to Colombia. It wasn’t light or cheap (about $200), and I hadn’t played the horn since high school, but I wanted to play music on the road and the piano wasn’t fitting in my carry-on.

At first, the trumpet was more companion than social tool. I’d go to parks and play along to my headphones until my lips tuckered out. Eventually, I started meeting street musicians, and before I knew it I was in an Andean folk group, playing with a guitarist and quena player at lunch counters and city buses throughout Bogota.

A harmonica’s even more packable. If you’re an artist, draw portraits. Juggle. Play soccer, basketball, baseball. Bring a shareable passion, and the meetings will manifest.

If you’re staying somewhere more than a few weeks, consider getting a job. I spent years teaching English in Latin America (here are some other great countries for English teachers). Many of my best friends from the road started as students.

Trip not long enough to merit printing resumes? Call a local charity and offer free labor. The same social benefits apply. Besides, the nonstop indulgence of vacation can get boring. This’ll give you a “work day” that makes the partying feel earned.

You don’t have to take a college course: a few hours with an app or MP3s will demonstrate a lot of respect. And even if you procrastinate until after your arrival, and you should be able to say “hello,” “thank you,” “please,” and some sort of polite apology by the end of an afternoon of study. Throw in “bathroom,” “hotel,” “how much,” and the numbers 1-10, and you’re quasi-independent.

Going somewhere where the language is so obscure -- Macedonia, say, or Finland -- that learning it feels like a wasted effort? Remember that other travelers have made that same calculus. Making the effort will make you stand out all the more.

Couchsurfing.com changed the landscape of independent travel. Behold, a social media platform that connected travelers with local hosts. Personally, it’s saved me hundreds of dollars on hotel rooms and introduced me to some very fine folks.

But when it’s a miss -- oh, boy. I once booked a trip through Central America that overlapped with my birthday. Spending the day alone sounded depressing, so I found a host to take me in in San Salvador, El Salvador. Luis was a young man who -- by his profile -- seemed nice enough. Then, back at his modest one-bedroom in a walk-up apartment, he revealed to me, in turn, that he liked to draw swastikas; that “Hitler is a really interesting guy;” and that, rather than a couch, I was to sleep on a bare of linoleum kitchen floor with an undressed pillow. “Sorry I don’t have a couch,” he told me.

There was no air conditioning, and so I tossed and turned on that sticky floor all night, ruminating on how -- no matter how far off the beaten path you go -- locals aren’t all magical unicorns. Some are genuinely assholes, same as back home.

Service industry workers -- who tend to keep late hours and who stay plugged-in -- can be invaluable impromptu guides. When I was traveling in Prague with a friend, we were harangued all night with fliers advertising topless bars. Seeking something a little less seedy, we asked our bartender where he went on his nights off. That led to a name on a napkin, which in turn led to a killer dance party.

You may find, too, that they serve as guides to otherwise inaccessible parts of town. I found out as much in the Brazilian city of Salvador do Bahia. I stayed there in the Historic Center, a beautifully compact UNESCO World Heritage Site of cathedrals and cobblestones. Cute, yes, but aloof. I needed something more lively.

My hotel receptionist, Washington, agreed to take me out after his shift. We left together, him leading us half a block before turning down an alleyway. I’d noticed the city’s alleys when I arrived, but the dangers of Brazil -- beaten into my head at every turn -- meant I’d assumed them off-limits. Now, as we walked the alleyways, they intersected and multiplied.

We came to an opening where a group of young men gathering on a bench, beneath crisscrossing clotheslines and a grape-dark sky. One of the men sized me up and stumbled over, clearly inebriated. He stuck his hands in my pockets: half-mugging me, his nonchalance indicating that I didn’t merit discretion. Washington said a few words to him that I didn’t understand. The meaning was clear enough when dude left me alone.

Someone opened a bottle of liquor. Someone else lit a joint. That’s when I noticed the music. Brazilian hip-hop played from a tinny boom-box: the languid lilt of Portuguese swaggering over a walking bass line and a trumpet, soloing through a Harmon mute. Behind it, I could still hear the muffled sounds of street life a few blocks away. The town had layers, I realized -- the promenades and plazas like skin, the darkened alleyways inky veins. And I’d successfully gotten below the surface.

Sign up here for our daily Thrillist email and subscribe here for our YouTube channel to get your fix of the best in food/drink/fun.