¡Cuba Libre!

This post is a work-in-progress. Photos to come…

In February 2017, four members of our family boarded a Southwest Airlines flight and traveled back in time about 60 years. We were headed to Havana, Cuba for four days and three nights.

Because of the current political climate in America, who knows when this window might get slammed shut. So now was the time to go. And believe me, we checked the news every day leading up to our departure for any hint that Raúl Castro had dared mention our so-called President’s tiny hands. And without any access to the fake news while in Cuba, each day started with jokes about about whether we would be allowed to return home until groundbreaking at the inevitable Hotel de Trump.


I had booked a very nice “casa particular” called Casa Miramar on Airbnb for $487 and was able to pay with a U.S. credit card in advance. I had looked into rooms at the famous Hotel Nacional de Cuba but they go for over $500 per night for double occupancy. And worse, the few Cuban hotels tend to overbook and they don’t take American credit cards. Most of them are run-down and get sketchy reviews. So it’s best to arrange a private house in advance, pay for it, and get multiple confirmations up front—especially right before you leave the States. The last thing you want is to arrive in a third-world country without a safe place to stay. While some may like to tempt fate, we do not.

Travel Restrictions

Despite the recent death of Fidel Castro and President Obama’s subsequent easing of relations with Cuba, it is still technically illegal for American citizens to spend money in Cuba without a Specific License. But for now, the U.S. Treasury Department’s Office of Foreign Assets Control (OFAC) allows for travel under a General License as long as you qualify for one of twelve categories.

Basically, that means you must choose a category and check a box on a form when you buy your plane ticket. Then you just stick to your story whenever asked, according to Rick Steves.

In our case, my daughter was traveling to Cuba as part of a Study Abroad program at her university. So my wife and I qualified under the Family Visit category. Therefore, we merely had to time our trip to align with my daughter’s itinerary and accompany her. We then documented our activities in case we ever get audited in the future, which we assume is highly unlikely. In fact, there has only been one prosecution for such a violation, and that was a company who broke the embargo rules.

Meanwhile, my in-laws chose the People-to-People category for their general license, which implies that they were going to interact with Cubans to exchange ideas, learn about the culture, and so on—which we all did.

The rules are pretty clear that you’re not supposed to travel to Cuba just to hang out at the beach. But then again, who’s looking besides some retired Cold War spies? Remember that since the collapse of the Soviet Union, the Cubans desperately want our money and any gifts of American goods, so we never felt unwelcome.


Before you can get anywhere near a plane to Cuba, you must have a valid Cuban Tourist Visa in-hand. The best way for Americans to do this is via CubaTravelServices.com. The cost is $50 per person. (More if you screw up the form.) In our case, we picked up our cards at the Cuba Desk at Tampa International Airport, where they check and copy your passport a couple hours before boarding your flight. You are required to maintain health insurance while in Cuba, but fortunately a policy is built into your airplane ticket. So you must keep your boarding pass with you at all times, along with your passport and visa.


Because of the embargo imposed by President Kennedy in 1962, the Cuban government still imposes a 10% tariff on the exchange of U.S. dollars. So, you’ll want to take another currency with you to maximize your money. We chose Euros, and made that exchange at our American bank a few weeks prior. While that exchange rate included the bank’s hidden fee of around 5%, there is only a 3% additional exchange fee in Cuba when you change Euros to CUCs. So you wind up saving around 2% overall. Possibly more, while the Euro is stronger than the dollar.

Our first introduction to “Cuban Time” was at the currency exchange cage at the airport. Not only was it very difficult to find in our terminal, the staff didn’t seem very interested in doing their jobs. We were first in line but stood there for more than a half hour while two young women counted stacks of cash. They were frequently interrupted by friends who stopped by to chat at length, and then some other local rudely barged in front of my brother-in-law for another lengthy delay. We felt like we couldn’t complain to anyone, being the new kids in town. 

The Cuban Convertible Peso is what tourists will use for most transactions in Cuba, and no bank outside of Cuba sells them. Be sure to change whatever you have leftover back to Euros or Dollars at the airport on the way out of Cuba, or you’ll be stuck with what amounts to souvenir Monopoly money.

Getting Around

Here’s where the fun starts. First of all, we got taken outside Terminal 2 at the Havana’s José Martí International Airport despite reading up on it. The yellow taxis are state-run, and they’re fairly modern and clean. After trying to negotiate, we had to pay 30 CUC per stop to get into central Havana. That is, it cost us 30 CUC to drop our bags off at our casa in Miramar and then another 30 CUC to drop us off in town. The problem is, you are forced to take the first taxi in line at the airport so you don’t really have any leverage. That, and the drivers know you’re a rich, dumb American. This ride should have cost 20 CUC to Miramar and then only 10 to get into Havana. So Gustavo, the Future Capitalist, earned a 100% tip simply by exploiting a language barrier. Lesson learned.

The trick is to avoid the yellow state taxis and stick with the fleet of independent classic American cars, which are much cheaper and have a lot more character. Some of them looked like demolition derby cars, but some made you think “how can I buy this heap and get it home?” Because of the embargo, these cars are held together with incredible ingenuity. I could swear I saw some chrome trim that looked like it came off a retro icebox.

The original V6 or V8 gasoline engines have all been replaced with four-cylinder diesel engines, since diesel sells for 1 CUC per liter and gasoline is not an option. And since these old cars predated the catalytic convertor by decades, the air on the main roads can get heavily polluted with diesel exhaust, especially in the narrow streets of Old Havana.

To get from Miramar to anywhere in central Havana, 10 CUC was the norm. Getting back to the airport is equally cheap, once you know the ropes.


It’s all about the music. There was plenty of street music, and plenty of hole-in-the-wall bars along Obispo street. But our best night was spent at a candlelit table at the Hotel Nacional de Cuba where some surviving members of the Buena Vista Social Club were performing with a large ensemble. Much drinking and dancing ensued…


We were somewhat surprised by the lack of firearms at the airport and on the corner cops. Our first taste of communism came at the Museo de la Revolución, where a grand total of four toilets had to be flushed by a female bucket brigade.

Around the corner we found a mural depicting Ronald Reagan as a cowboy, George H. W. Bush as a Roman emperor, and “W Bush” as an illiterate Nazi. The work’s title (Rincon de los Cretinos) translates to “Corner of the Cretins.” So this is how Fidel Castro saw America, blaming us for a crippling naval blockade.

Inside, the museum displays artifacts from the Cuban Revolution with the presentation quality of a high school civics project. Outside, you can touch some cool guerilla warfare implements and see actual debris from the U-2 spy plane shot down by a Russian missile. Meanwhile, the Cuban Army’s best-looking soldiers guard the Granma, the yacht that Fidel Castro and Che Guevara’s men used to invade Cuba from Mexico.


After interacting with merchants, we got the sense that Cubans are “taxed” at the rate of 90%. That would include taxi drivers, tobacco farmers, artists and so on.

One day, three of us walked past a local school and got watched like a hawk before arriving at a local market, which seemed to have only flip-flops on the shelves. Locals were lined up to get in, but suddenly an armored vehicle pulled up and several soldiers jumped out carrying machine guns. They motioned for everyone to leave and then exited the store carrying a bag of cash. No one got hurt, we assume, but apparently this is how taxes are collected under a dictatorship. I later saw the same squad marching past our casa and was afraid to use my camera.


I can’t possibly write enough words to describe the Cuban culture, and especially not after such a short visit. But here are some take-aways:

Most Cubans are polite. Sure, they’re oppressed and careful not to make waves, but it was something more. They seem to eschew drinking, smoking and profanity without being overtly religious about it. I figure most of them simply can’t afford to drink or smoke, and probably just do their swearing in Spanish.

Everyone is “on the con,” as my brother-in-law put it. Everyone you meet in a tourist area wants to introduce you to their “friend” but when you press them on their name or where they live, suddenly they have a CD to sell you. And whenever they tell you something is “free,” that just means the hard-sell is deferred to the end of the tour. Remember, the average Cuban lives on $20 a month. So they go to great lengths to charm you out of a few bucks on the sly.

Many Cubans have no civic pride. I know that may sound harsh, even in the absence of social classes, but here are some examples:

A dog turd lies in state at the entrance of a busy shop. No one cleans it up. Not the shop owner, who sees it. Not the street cleaner, who also sees it. Not the landlord next door, who sees it. The turd’s destiny is simply to be stepped on by some barefooted child. No one cares, even though the street is crawling with tourists. Or perhaps because the street is crawling with tourists?

A woman directs her grandchild to throw his food wrapper and cup on the ground at a large festival, rather than find a garbage can a few feet away. This was at one of Havana’s most famous landmarks, the Morro Castle built by the Spanish in the 1589 to protect Havana’s harbor. There were thousands of locals there to celebrate some event, and the grounds of this sprawling structure looked like a landfill. There was garbage everywhere.

This leads me to believe that without any pride of ownership, there is very little room for civic pride of a voluntary or genuine nature. In most parts of America, the shopkeeper would bring out the pooper-scooper and the grandmother would scold any brat that dared to litter such a monument.


Few people outside the big hotels speak English in Cuba, so it helps if you know the basics. The free Google Translate app rescued us many times. You can speak or type a phrase and then show it to the driver or waiter as a flash card. It also helps to anticipate essential communications (especially addresses) up front, and the app will save them for quick access. Generally speaking, everyone we met was very patient with us. Because again, Cubans are very curious about America and they do want our money.