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Yankee in a Che Shirt: How To Travel to Cuba Independently and Illegally as an American

Published December 30, 2009 Being American , Budget , Cuba , Independent , Offbeat , Places , Safety , Tips , Transit 38 Comments
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Americans you're likely to encounter in Cuba

Si, se puede!

Three years ago, I traveled to Cuba. I didn’t get a visa, didn’t book a tour, didn’t go with a dance troupe or salsa band (though that would have been killer). I did it the way I do everything, independently.

Fear mongers, nay sayers and foreign travel agencies would lead you to believe that independent travel to Cuba is dangerous and impossible. They’re the same people that make full and complete stops at every stop sign, and are too scared to ride the subway in NYC. Or else they’re trying to sell you something—the hustling taxi driver outside of the airport. They clamor cowardly behind the embargo.

Here’s the legality deal: as an American, you’re technically not banned from traveling to Cuba; you’re prohibited from spending money there. Whatever. If you didn’t obey your parents’ curfew as a teenager, are you really gonna start heeding authority now?

The fun thing about traveling to Cuba as an American is that it requires more effort, more digging. You can’t buy your plane tickets online; most worthwhile advice won’t come from guidebooks but fellow travelers, via forums like Thorn Tree. Basically, you have to work a little harder. But the reward is getting to go to one of the most un-Americanized countries in the world—remarkably only 90 miles from Florida.

I’m pretty sure it’s technically illegal to give Cuban travel advice to Americans. But eff that too. Here’s how I did it, how it worked and the gems of wisdom I smuggled back (along with the cigars):

Before You Go: Money and Packing

Your most important pre-travel preparation as an American is money. Your ATM and credit cards won’t work in Cuba, meaning you’ve pretty much got to bring everything you plan on spending with you. Travelers checks are a pain in the ass and have a hefty commission tacked on—which means you’ll be bringing cash. Lots and lots of cash.

If you’re like me, you’re not too thrilled at the idea of walking around with $1300 on your person. But keep in mind Cuba’s remarkably low crime rate, the absence of desperate drug addicts and your own street sense—you’re gonna be fine.

Another consideration is which type of currency to bring in. The greenback gets an extra 10% penalty fee on top of the standard 8% exchange commission, so most travelers opt to bring in Canadian dollars or Euros. It pays to do the math on conversions and figure out how much you’ll be hit by commissions and fees for dual exchange (changing from dollars into Euros into CUCs).

Another pre-trip consideration is what to bring, and what not to bring. This is for everyone, not just Americans. Charitable donations like medical supplies and clothes are greatly needed and appreciated, but check out regulations on what and how much to bring. Cuban Customs has some unusual regulations regarding the import of electronics and pornography, and is super strict about narcotics. Of particular concern to Americans is the prohibition of anti-revolutionary literature—make sure you don’t have any crazy right-wing, Miami ex-pat ramblings with you. Not that you would anyway.

Getting In: Booking a Flight

The easiest, most popular and often cheapest way for an American to get into Cuba is through Mexico, namely Cancun. Of course, Cancun is the #1 most suspicious transfer point, and word around the chat rooms is that you’re singled out by US Customs most often when arriving from Cancun. But it’s also an insanely popular destination, and I think the Mexican- to Cuban-vacationer ratio still works in your favor.

American travel agencies and airlines are prohibited from booking flights or giving any kind of assistance to Cuban travelers. But foreign airlines and agencies aren’t. So instead of shelling out big bucks to some Canadian company that’ll orchestrate the whole thing (for a mere 300% mark-up), do what I did: call a foreign airline at one of their international offices. I called Mexicana in Mexico City (52 55 2881 0000), requested to speak to an agent that spoke English (not a bad idea when purchasing something as expensive as plane tickets), and bought tickets from Mexico to Havana. Not as easy as Orbitz, but pretty damn close.

The way the flight times worked out, we ended up bookending our Cuban travels with overnight stays in Mexico. I thought I’d be smart and fly through Merida, whose Sunday night dance parties sounded infinitely preferable to Cancun’s binge-drinking co-eds. Turns out that you can’t fly directly from Merida to Havana, so we had to transfer in Cancun anyway. Ah well, better than a spending a night in Cancun.

Arriving: Surviving Customs

Passing through Cuban Customs is the most intimidating border crossing I’ve ever done. But, as I reminded my then-boyfriend and travel companion, Cuba wants to let you in. They need tourists’ money. They just wanna make sure you’re not there on an anti-revolution espionage mission. Fair enough.

Expect to stand in an impossibly long line. You’ll be instructed to approach the Customs booth by yourself. They’ll scowl at you, tell you to take off your glasses and look into the camera. They’ll photograph you, record you, enter every last bit of info on your passport into their computer. They’ll then stamp your tourist card, your golden ticket. Cuba doesn’t stamp passports, but $20 purchased tourist cards. Mexicana provided mine, but it’s a good idea to check your airline or prepurchase your card at a Cuban Embassy, as getting ahold of one at the airport sucks. And hang on to that baby—losing it is an expensive, bureaucratic hassle.

Once your passport is handed back to you, you’ll get directed through the floor-to-ceiling solid door that the travelers before you disappeared behind. It may seem like you’re being funneled into an interrogation room, but most likely, you’ll be headed off for a quick frisking and x-raying of your baggage. Drug sniffing dogs will accompany female agents in ridiculously short skin-tight mini-skirts—the most amusing part of your Customs experience.

While You’re There

Really? Couldn't have left the Confederate swim trunks at home?

Once you’re in Cuba, there’s not a lot in your day-to-day travels that’ll set you apart as American. You’ll have to deal with the money issue, but the good news is that everyone will guess you’re from somewhere other than the US. It’s a nice change of pace from the Frenchman breaking into sudden English with, “And where in the States are you from?”

Getting Out: Playing Dumb and Looking Innocent

The trickiest and most anxiety-inducing part of any American’s trip to Cuba is coming home. I’ve heard of Americans getting hassled by Cuban customs agents, but it’s pretty rare. The folks you have to worry about are the good ole’ boys (and girls) back home.

But first you have to worry about a double-entry stamp back in Mexico. This means that you’ll have a stamp for arriving in Mexico, no stamps for Cuba, but then another entry stamp for your return to Mexico; there’s a void in there, signaling nefarious activity.

You can handle this one of two ways: bribing the Mexican Customs agent to not stamp your passport (trickier at Cancun, where they’re more vigilant, but still possible), or by hoping for the best with a doubly stamped passport. We opted to bribe the Mexican Customs agent. We tucked a sizable peso note into our passports and softly asked not to be stamped. The agent grunted and handed us back our passports, unstamped. If you’ve got a heavily stamped passport to begin with, it might be worth saving the money and relying on the slim odds that the US Customs agent will bother to inspect your passport closely. I’ve never had an agent more than glance at my stamps.

Aside from the extensive, albeit poorly edited, advice by eco-hippies International Bike Fund (I mean that in a good way), any American who’s ever traveled to Cuba will be eager to give you plenty of tips and first-hand accounts on how to elude US Customs—whether you want to hear it or not. So here’s my two centavos:

Revolution anniversary poster I stole and smuggled back home

Reports vary, but up to 100,000 Americans are claimed to have visited Cuba last year. Most of them breeze through US Customs without a problem. There’s nothing that should single you out as particularly suspicious. Be respectful; don’t roll up to the counter smoking a cigar and wearing a Che hat. But don’t sweat it too much. Customs agents are doing their job, and you’re doing yours. They really don’t want to write out lengthy reports anyway. I truly regarded my traveling to Cuba as not too dissimilar from jay-walking—not supposed to really do it, but no big deal. Folks’ll tell you not to bring anything incriminating and obviously Cuban back with you, but eff that—I brought cigars and stolen street posters.

We arrived at SFO disheveled and tired with a horde of sunburnt vacationers. I of course did not write on my Immigration Card that I’d traveled to Cuba, nor did I list the goods I was smuggling back (why you gonna rat yourself out?). I smiled nicely at the agent, told her yes, I’d had a great time in Mexico, picked up my bags, passed em through the x-ray machine without incident, and headed home.

But enough out of me. Any Americans out there wanna share their Cuban travel experiences?

The French Won’t Save You: Recklessness, Fear and Safety Abroad

Published November 10, 2009 Bay Area , Being American , California , Colombia , Oakland , Places , Safety , South America , USA 8 Comments
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Military chillin in central Bogota

Military, chillin in central Bogota

We’d taken refuge from the soggy Bogota afternoon in the hostel’s dank kitchen, sat drinking coffee and swapping tales. Only my third trip out of the country, I sat quietly, listening to the boys one-up each other. No one could beat the Swede in zip-off pants.

He sat smugly, like a guru, doling out morsels of his tales in titillating tidbits. He’d dyed his hair brown, donned dark contacts, and backpacked through Iran, Iraq, Pakistan. He’d ridden buses rarely, walked mostly, and had almost been killed (purportedly) by an anti-American lynch mob. Sparks of awe and admiration flew from the enthralled eyes of other travelers.

One of the boys in his rapt audience turned to me, suddenly aware of my presence. He quizzed me on my basics: where was I from, how long was I traveling, did I speak Spanish. “What’s your itinerary?” was his final question. I bit my lip as he looked me over, sizing me up for what I was: an early-twenties American girl, not terribly well-traveled, with a mediocre accent and a minimal vocabulary. I recited my basic plan: Bogota, Medellin, Cartegena, Santa Marta and La Ciudad Perdida.

“Hmph,” he snorted. “Typical.” And with that, he turned his attention back to the blond god before him.

Fast forward several years and a couple thousand miles to this afternoon, as I rattled down the uneven pavement of Interstate 880, windows down and blasting NPR (yo, turn it up so it bumps). I’d just caught the beginning of a story on France’s proposal to charge tourists for rescues from risky spots while abroad. The hotly debated bill came about several months ago, prompted by a much-publicized rescue of French citizens who were captured by Somali pirates while pleasure-yachting around the Indian Ocean. Reportedly, public outrage at the travelers’ perceived irresponsibility was intense enough to inspire a bill that would require tourists rescued from dangerous situations abroad to repay rescue costs (aid workers and journalists excluded). A coordinating author from Lonely Planet was on hand to discuss the proposal and its implications, a discussion that centered around issues of travel safety, and real versus perceived dangers abroad.

Here’s something most independent travelers, including myself, rarely check before going abroad: the Department of State’s Current Travel Warnings. When you grow up amid a culture of fear mongering, it’s easy to get desensitized. Yeah, yeah, yeah, you think, the world’s sooo dangerous and I’ll get kidnapped and killed the moment I leave the US. Fear is one of three reasons discussed in Nomadic Matt’s article, Why American Don’t Travel Overseas. Once certain travelers step outside the country and see the rest of the world isn’t the depraved war zone it’s often portrayed to be, they get cocky. And brazen. And sometimes stupid.

Take that to the extreme: extreme tourism. I haven’t heard this term in awhile, but it was tossed around the hostel table in Bogota that afternoon. It refers to a type of off-the-beaten-path thrill-seeking travel that prides itself in brushes with danger. Real danger. As in, I’m-gonna-walk-through-Baghdad-just-to-prove-I-can danger. Implicit in this type of travel, I would argue, are entitlement and bragging rights.

Fresh stencil in Bogota

Fresh stencil in Bogota

Which begs the question: should risk-taking travelers enjoy the luxury of being rescued, at the expense of their countrymen? The French don’t seem to think so. Nor do the Germans. The United States—well, we don’t really need to worry about it, since so few of us travel to begin with. Reportedly vague and insufficient, the French bill also opens the door to a lot of loaded issues—namely, who decides what countries and regions are dangerous, and whether travelers are behaving recklessly?

I’ve been to three gasp-evoking places often deemed too dangerous for travelers (let alone a solo white girl): Caracas, Mexico City, the entire country of Colombia. I didn’t go to any of these places because they were considered dangerous, but despite them being considered dangerous. One I ended up in circumstantially, but the other two I sought out—I’d heard too many good things from other travelers. I did my research. Street sense and good luck got me through unscathed. But there’s certainly people who would have regarded my traveling in these places as reckless, stupid and asking for trouble.

I remember thinking Colombia was a lot like Oakland. Which isn’t true: armed military don’t roll through city streets, and you can’t smoke cigarettes inside shopping malls (not even Eastmont). But both places have a sort of infamy to them, a danger that either lures or deters. As in Oakland, many parts of Colombia feel totally safe; as in Oakland, other parts of Colombia continue to feed the unsafe reputation. To stay safe in Colombia, I did everything I already do in Oakland: don’t go out at night alone, stick to main streets in safe neighborhoods, don’t ride buses at night, check my back like a motherfuck.

The Swedish guy in the Colombian hostel reminded of suburban kids that move into Oakland warehouses (snark alert). They proudly tell you they live in the Lower Bottoms, Murder Dubs, Dirty 30s, Ghost Town. “The thugs aren’t that bad, really,” they tell you. Then, knowingly, as though they’re imparting some great gem of karmic street ethics upon you—“If you don’t bother them, they don’t bother you.” Then they mugged/assaulted/held at gunpoint, and they leave, go back to their suburbs bruised and bitter and hating the town they so recklessly glamorized.

There’s a certain romance with violence and danger that people who have no real experience with violence and danger have. It’s exciting, enlivening, visceral and real. It’s the wild-eyed rapture of Futurists (which for all of their sexism, fascism and idiocy still created some good art). It’s as easy to write off as the uninformed fear that keeps some folks away from Oakland, away from traveling, and comfortably cocooned in familiarity.

But neither side is right, neither view complete. They’re just two sides of the same coin—exoticizing someone else’s world, treating it as the Other, instead of attempting (however falteringly) to meet it, understand it and experience it as it is. Can I claim to have traveled so honorably? Not really. But I can claim to have tried.

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Good times with the Colombian military

Which could all be an elaborate rationalization for why the rules don’t apply to me—why I haven’t gotten into any real trouble while traveling, and why I would surely be rescued in the event of any dire incidents. And not expected to pay for it. (Because, after all, I’m not French.) But I suspect the truth lays somewhere muddled between all this, between embassies and travelers, the frightened and the intrepid, the streets of East Oakland, the seas of Somalia and hostel kitchen tables around the world.

Top 5 Things That Make Me American

Published October 29, 2009 Being American , Home , Lonely Girl Loves 15 Comments
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That is totally mine.

“The more I travel, the more I realize how American I really am.”

This was Matt, leaning on a pole in a Madrid metro car, observing the raucous teenagers and stylishly dressed adults of an average Spanish evening. I nodded in sad agreement.

I’d like to say that traveling has made me more cultured, sophisticated and worldly. Maybe it has. But it’s also made me acutely aware of my incurable Americanness.

I didn’t really know what it meant to be an American before I started traveling; it’s hard to know if you have nothing to compare it to. I’ve now caught on to plenty of red-flag characteristics that will immediately identify one as hopelessly American. I’m guilty of many of them: holding my fork like a shovel, having obscenely straight teeth, living on my own before marriage, maintaining a staunch belief in the importance of a hearty breakfast. There’s also some attributes I don’t share with my countrymen: I don’t own a TV, I’m not overweight, and I can find Australia on a map. And I travel.

Being as though I travel, and have had the luxury to mingle with other cultures, I’ve been made aware of my grosser American offenses. Here’s the top 5 off my American rap sheet:

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From the human race, I'd like to extend my apologies, little fellow.

5. I walk fast.

I didn’t know this was an American characteristic until someone pointed it out to me. It makes perfect sense. We don’t stroll in America. Walking is not a leisure activity; it’s the lowliest form of transportation. We do it briskly to conceal our shame. Or else we construe it as exercise (as in, office workers powerwalking their lunch breaks away).

Our avoidance of walking manifests in everything from drive-thrus to elevators to Segways. Remember when MacDonald’s had step counters as a meal prize? Exactly.

4. I shake hands.

Now, this isn’t exclusively American; many cultures shake hands. But Americans place special importance on the handshake, measure relative grip and firmness to construct deep insights into another’s character and psyche. “I like that young man; he’s got a good handshake.” And I was just in Europe, where nothing announces your Americanness like jabbing someone in the chest with your outstretched hand as they lean in for a check kiss. (Sorry, Pierre, hope that doesn’t bruise.)

3. I call myself American.

America isn’t a country, it’s a continent. Two continents, actually. Filled with many, many countries. In our utterly naive narcissism, we seem to forget this (read: title of this post). Numerous travels through Latin America have taught me to say that I’m from “Estados Unidos,” not “America.” But I still have trouble pronouncing “Estadounidense,” which basically means United-States-ian. Doesn’t flow off the tongue as easily, but it is more correct.

2. I don’t speak another language.

I mean, really. It’s just ridiculous at this point.

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And the rockets red glare...

1. I have a deep and abiding love of peanut butter.

Protein, healthy fat, delicious taste: the American love affair with the peanut culminates when we grind it, jar it and spread it on stuff. Or eat it by the spoonful.

Trying to find peanut butter outside of the United States is a depressing, frustrating and often futile effort. If you can find a jar, on a lonesome dusty shelf hidden behind the Nutella and marmalades, it’s bound to be sugared to hell, rife with hydrogenated oils and staggeringly expensive. I’m not sure why the rest of the world is sleeping on the PB tip; with great taste, nutritional value and versatility, they’re really missing out.

There’s plenty of things I could change about myself to become more international, a “citizen of the world” as the obnoxious call it. Sure, I could learn 7 languages, use military time and metrics, and school myself in the finer points of kissing cheeks. I could disregard my reverence for the orderliness of lines, become a football fan (not American football, silly), even slow my roll to a smooth swagger. But I will never give up my passionate fervor for peanut butter.

Lauren Quinn is a writer and traveler currently living in Hanoi. Lonely Girl Travels was a blog of her sola travels and expat living from 2009 to 2012. She resides elsewhere on the internet now.

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