On Wednesday my social media feeds lit up like a Christmas tree in the happy prospect of travel, soon, to Cuba.

Why, we might ask, does Cuba so capture our imaginations? Is it the forbidden fruit of isolation and prohibition? A glimpse into the amber-preserved past of Rat Pack decadence? A peek into a system that purportedly privileges the welfare of people over the welfare of profits? Or maybe it is just the prospect of a new vacation target in the nearby Caribbean with a lower pricetag than any other island in the region.

Whatever draws you to Cuba, President Obama has dangled that delicious prospect in front of all us. As someone who regularly visits the island for research, let me help prepare you for inevitable disappointment.
 

1. Despite the Change, You Still Probably Can’t Go.

“With the changes I'm announcing today, it will be easier for Americans to travel to Cuba…”

Your first disappointment will come from the fact that regular tourism, in the official eyes of the U.S. Treasury (which oversees and authorizes U.S. travel to Cuba) is not in the works. At present, U.S. citizens need one of twelve licenses from the Treasury Department (in the Office of Foreign Assets Control, or OFAC) to travel legally to Cuba. No license permits bread-and-butter (or, better said, rum-and-Coke) tourism in Cuba. 

They do however permit research, humanitarian outreach, arts exchanges, education, family unification, and some commercial initiatives (news flash: we’ll do close to $350 million worth of export business in Cuba this year alone).

Still tourism happens. The people-to-people study tours that the Obama administration has encouraged since 2011 have helped more than double the number of Americans traveling to Cuba since the last year of the George W. Bush administration. But to the loudest voices in Miami opposing any warmth toward the Castro government, it is all tourism. Recall Marco Rubio’s outrage last spring, over Beyoncé and Jay Z’s trip to Havana.

When the pair appeared in photographs frolicking there, on their wedding anniversary, Cuban-American politicians accused them of breaking the law. But the Treasury Department countered, saying the trip was perfectly legal under a license granted for education and arts. Senator Rubio declared that nothing educational happens in such study-tours and that their nakedly self-indulgent tourism puts American dollars in the hands of a “cruel, repressive and murderous regime.”

I’m not sure whose hands those American dollars wind up in, but study tours don’t come cheap (you can expect to pay at least $3,000 a person and up to $6,000, all-inclusive). And despite the uptick in both study tours and family visits (a reported 350,000 a year), increased travel has not yet stimulated the growth in transportation infrastructure that would make Cuban travel, even with a license, easy. 

Most travel from the United States to Cuba takes place on charter flights, arranged by small Miami-based agencies that cannot really promise, for sure, that your plane will leave or return on the days you thought you had booked. A researcher friend from Boston had the nasty experience, not long ago, of finding herself stranded in Miami when her charter changed its plans.

Bear in mind that the charters do most of their business for and with the Cuban American population who, thanks to relaxed rules in recent years, can regularly visit the island. Close to 60 percent of the 2,000,000 Cuban Americans in the United States were born there, so—understandably—they seek to remain close contact with family. Thus, the flight that gets rerouted or rescheduled at your great inconvenience was never really about you, as a tourist, in the first place. And it won’t be with these changes, anytime soon, at least until regular tourism returns. 
 

2. If You Do Go, You Should Still Probably Pack All the Cash You’ll Need.

“…and Americans will be able to use American credit and debit cards on the island.”

Have you ever been anywhere that you can’t get easy access to cash or credit because you can’t use your plastic? Cuba, right now, is that place for Americans, the nearly 100,000 of us a year who look longingly upon the little Visa and MasterCard decals in Cuban shop windows, and wish for a connection. All that is supposed to change!

But I wouldn’t count on it happening overnight. And there are many reasons to hedge your bets against the arrival of American plastic to grease the commerce of your life on your short trip to Cuba.

First there are effectively three currencies in Cuba (although one of them is slated to disappear this year): There is the national Cuban currency, (called the Moneda Nacional, or “M.N.”, and often referred to simply as “pesos”) in which Cubans receive their meager salaries, pay for bulk, basic foodstuffs, and surrender in mandatory expenses (for things like school uniforms, e.g.). One peso in M.N. equates, roughly, to about US$.04. This is the currency that will no longer exist in the near future, which, for some Cuba-watchers, shows the regime walking further back on the vestigial remnants of state socialist care for the poor. 

Then there’s the “unit of convertible Cuban currency”—called the CUC for short. This is supposed to be pegged to the U.S. dollar and served, initially, for purchasing imported goods at “dollar stores.” (A dollar store in Cuba has the opposite connotation as in the U.S.). The CUC has now, for many Cubans, completely eclipsed the moneda nacional because of the skyrocketing expense of all goods and services and the monumental role that imports play in daily Cuban lives (if you want to eat chicken, for example, you’re going to have to buy an imported bird).

Navigating between the two currencies requires some patience (or at least it did on my last trip to Santiago in 2012) because for many transactions, you need the one but can’t use the other. You can buy fruit on the street in pesos, but to pay for a fruit plate in a hotel you need CUC. You can buy low-priced rum in a store with pesos, but pricey drinks at a bar only in CUC (unless you’re in a special peso-only establishment). If you want books, you need pesos. If you want newspapers, pesos. But if you want to log on to your email or Facebook in a telecom depot, you need CUC. And so on.

You might think that paying with the more valuable currency everywhere you’d be fine. Nonetheless, for very poor Cubans who never buy anything in CUC, the CUC is nothing but trouble: it requires a buyer to make it liquid and useful in the economy of moneda nacional, or it requires a wait in a potentially long line at a special change shop (called a “Cadeca”) set up for swapping the two currencies.

Behind the two official currencies lurks a shadow currency: the U.S. dollar. But not because Cubans do business in U.S. dollars. They largely don’t, unless they have plans to travel outside of Cuba, or want someone to purchase them something outside of Cuba. But with more than 10 percent of Cubans living overseas virtually all Cubans have some interest in dollars. So, if they can afford to keep small stashes of cash, they might do so in U.S. dollars. And thus you can do some private exchanging to meet your needs. 

But your dollars will bring you unhappiness if you change them at a bank (or in the promised future, use your credit card to change them in the electronic ether behind the scenes). That is because even though the CUC is supposed to trade with the U.S. dollar at 1:1, it doesn’t (or at least it has not in my experience). And because the Cuban government taxes U.S. dollars at 10 percent. So the effective exchange rate for U.S. dollars can be as low as $.70. Your already not-so-cheap Cuban study tour just got 30 percent pricier.

You can partially preserve the value of your American greenbacks by converting them, first, to Canadian dollars, which you can exchange into CUC at whatever that rate is, and not suffer the 10 percent Gringo tax. I am pretty sure that I’ve economized this way, but oh the spreadsheets! Because, let’s not forget, I’m traveling under license and have to account for my expenses in order to make clear that the trip (are you listening Marco Rubio?) is licensed research and not unlicensed pleasure. 
 

3. Once You Get There, You Will Wonder Why Canadians Go All the Time and You Can’t.

“Nobody represents America's values better than the American people, and I believe this contact will ultimately do more to empower the Cuban people.”

You might consider avoiding the whole Miami-charter craziness by flying to Cuba via a third country. For me, that is out of Toronto, where several international airlines fly daily service to a number of Cuban cities. Canada? Canada, you say? Who knew that Canadians did so much travel to Cuba?

Indeed they do. In fact, more than a million of them a year pack planes all winter long, like airborne party busses, keeping seaside resorts flush with sunburnt business and helping make (according to a guest on the Diane Rehm Show) the Cuban military into the largest hotelier in Latin America (the army technically owns all the hotels in the country). 

So while the U.S. embargo keeps Cuba beyond the reach of Americans (but for those with a license), it provides no obstacle to Canadians, Europeans (who number another half million visits a year to the island), or other Latin Americans, Chinese, and so on. In fact, when you go to Cuba, be prepared to feel a bit had: I did. On my first visit in 2008, I found myself gaping at my ignorance: Cuba belongs to the world, though not to us.
 

4. The One Thing that Makes Travel to Cuba Easy Right Now—the Absence of Violent Crime Against Foreigners—Might Also Evaporate.

“This is fundamentally about freedom and openness…”

I find travel to Cuba really challenging. It stresses me out, well in advance of booking tickets until the moment I cross the border back into Michigan, after my four-hour drive (often in the wee hours) from Toronto. A few years ago something in my electronic immigration record about my Cuban travel made these trips particularly unpredictable (resulting on one occasion with my being handcuffed to a chair at the Port of Entry in El Paso Texas, while I waited for my secondary screening). 

I fret the entire trip about money: running out of it, having the right kind and about its fairy-dust effects of making some Cubans richer and others poorer. I worry about hurricanes and earthquakes: the former of which has not happened in my travels, the other which has (in Santiago). I bring my own toilet paper, medical supplies, and peanut butter. I hate it when Cuban officials paw through my notebooks and poke around on my computer.

But the one thing I do not find hard in Cuba, the one thing that doesn’t feel challenging, is that I feel safe there. That is not to say that I don’t worry about getting robbed (I do, for sure, as do all the Cubans I know). But I do not, however, worry about violent crime. 

Let’s be blunt: the upside of a police state that welcomes and embraces tourism is that tourists can move about pretty freely, day and night, with little fear of sexual or other physical assault. I don’t know any other place in the world where I feel comfortable walking alone, into the wee hours of the morning. But I do in Santiago de Cuba. And have done so plenty. 

Some day, of course, the embargo will end. And when it does, its mirror image—Cuba’s authoritarian state —may also evaporate. At least that’s what the Miami Old Guard say they want (though if China and Russia provide any examples, authoritarian states can stay very much alive overseeing free market economies). Many imagine that a trip to Cuba will yield a visit to a present frozen in the past, a charmed and unchanged movie set of the 1950s. 

But what you encounter in fact (if you pay attention), is the unpleasant present, dominated by deprivation and no real love for the things that Americans, long denied access, find so intoxicating: old cars, old homes, old ways.

Consider what populates American dreams of pre-Revolutionary Cuba: the glitzy world of bars, casinos, gambling, cabarets, and the indulgences of reckless spending wrought by mob investments in illicit entertainments. 

Left unchecked, that economic infrastructure surely would have made Cuba the ideal transshipment point for the international narcotics trade that blew up in the late 1970s. Recall Miami of the 1980s—with violent shootouts between city police and armed commandos of the Colombian cartels. And think Mexico – anywhere in Mexico—today. Cuba would have seen all that, and maybe more. 

The moment the Cuba of the present, isolated from that feature of the contemporary global free market economy, fully vanishes, that OTHER past (the one that didn’t happen) may well shape Cuba’s future.

I think Cubans know this for sure, and however much they dislike the existing regime, they worry about what happens when the state loses its monopoly on the use of force. On my last visit to Santiago a friend who hates, just hates her life there, cast a worried glance to a time not too far off from now. “You think it’s bad today,” she said to me, “just wait until Cubans have guns.”