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
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:
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?