Travel Guide: Cuban Christmas


If you don’t ask, you won’t receive. Photo by

If you don’t ask, you won’t receive. Photo by

Cuba is a dictatorship so this was not a decision I made lightly. The U.S. placed an embargo on almost all exports to Cuba in 1962. Since then Cuba has become a land locked in time. So even though Havana is only a 40 minute flight from Miami and 90 miles from Key West it is decades away in time. The U.S. is a natural trade partner and the impacts of the embargo and the fall of the Soviet Union are very visible. Corruption and limited resources plague the beautiful island nation. When I moved to Florida for work last year I was determined to make the most of the experience. So that coupled with the thought of flying cross-country to go home for Christmas during peak travel for just a few days did not appeal to me. I opted to do something that would scratch my adventure itch.*

*Once I had confirmed my parents and grandmother would survive the holidays without me.

What to Know Before You Go

It’s easy to be #1, when you're the only one. #Communism

It’s easy to be #1, when you're the only one. #Communism

You are probably vaguely aware of an embargo that meant Americans could not go to Cuba, then President Obama said they could, then President Trump revoked the option: That is sort of correct. What the embargo means for us Americans is that it is illegal for an American to go be a normal tourist in Cuba. You may have heard of some of the special exemptions you can travel under. I have heard often, even from Americans in Cuba, they were under the impression the Cuban government had imposed those rules (That is not true). The U.S. does not allow Americans to spend money that goes directly to the government. This means you will get to explore a side of Cuba you might not have sought out under other circumstances

Communist Dictatorship

Make no mistake Cuba is a beautiful, fun place, but it is also a brutal regime. Cuba’s government quashes internal dissent and props up regimes in places like Venezuela. Cuba is by no means a dictatorship on par with places like North Korea, but it is no communist utopia. You may have heard of their wonderful medical care, but you may not know about the exploitation of those same doctors. Many doctors were pimped out to Brazil for thousands of dollars a month while only taking home $40 USD a month. Many of Cuba’s problems are exasperated by U.S. policies. But those problems root causes lie squarely at the foot of the Cuban government. Cubans do not live in a free market so most resources are state run and held. People live on meager monthly salaries and rations. For the same reasons life is hard for locals, it is very safe for tourists. There is virtually no drug trafficking or mass violence in Cuba. Petty theft is the biggest threat to your safety. Enjoy Cuba, but do not forget their is a dark side to everything you see and do. AirBnB tour guides that operate outside of the control of the government will be more frank about life in Cuba than those working for state operated tours. Think carefully about the tacit support you provide to a government like Cuba’s before deciding to visit. I weighed the options and made the decision I wanted to visit to see underground art and academia. I was not disappointed.

. Here is my guide to what you need to know before going to Cuba:

  • Flights to Cuba are fairly easy to come by if you live in the right city. I happen to live in South Florida very near the Fort Lauderdale-Hollywood International Airport so I had a ton of options. I opted for Southwest because I have a bunch of miles with them which meant my flight was free (minus Cuban insurance included in airline ticket cost, the cost of the visa, and the 9/11 fee).

  • Where to Stay: Most Americans cannot stay in Cuban hotels. Cuba is communist so all businesses are owned by the government. The U.S. embargo is against the Cuban government. What this means is you can’t spend money that goes directly to the government, like at their hotels. You can stay in private Cuban homes called casas particulares and you can pay cash when you get there. I opted to stay in an AirBnB because it meant I could carry less cash by paying in advance.

    • On that note you should keep in mind whatever cash you take is all you will have access to. There is no access to money via credit cards or ATMs for Americans because of the embargo. We also pay a higher exchange rate. So if you have extra Euros or Mexican Pesos laying around use them now. I found it was worth the money to exchange from dollar to Euro to Cuban money. There are two different currencies in Cuba that use different exchange rates.

  • Tourism: Here is where the embargo matters to normal people. Americans cannot go and be normal tourists. We can travel on special exemptions. I went under the category of ‘Support for the Cuban People’.

    • You will need and should follow an itinerary of activities showing you are interacting with and supporting Cubans (think guided tours and not government owned beach resorts). I again opted to mainly utilize AirBnB experiences because I did not want to carry a ton of cash since I was traveling alone.

    • You can buy a limited amount of rum and cigars.

My Trip

La Marca

La Marca

A big part of the reason I wanted to go to Cuba was to get a tattoo from a particular artist so I planned my trip around it. Shoutout to for being the reason I pulled the trigger on going to Cuba. He is at a great studio in central Havana:

That said I had a list of things I knew I wanted to do while I was there: See a baseball game, smoke a real Cuban cigar, and most importantly for me was to see propaganda. I did a number of things I would rather not highlight, because a number of very good people went out of their way to help me explore an underground world of art and culture.

Cuba is a really cool place because of the people. It’s easy enough to get to and a place you should definitely visit if it’s on your list.

Do you want to go to Cuba? What’s on your list of things to do and see in Cuba?