Why Would You Sneak Into Cuba

In 2014 I sneaked (some would say snuck) into Cuba. That statement sounds more provocative and reckless than it was. The Cubans knew I was there, but the American State Department didn’t. Why would I do that? As an American citizen my government had decided (for me) that I wouldn’t be allowed to visit Cuba. On October 19, 1960 the U.S. government initiated an embargo on the island of Cuba, and though relations are normalising (after 56 years)  thanks to President Obama, the embargo still stands.

I thoroughly researched my adventure ahead of time, and quickly learned that I wouldn’t be the first (or the last) to pull it off. Cuba had been on my bucket-list since I was 12 years old, and watched Fidel and Raul Castro and Che Guevara march into Havana to reclaim the government for the people. Most of the Cuban aristocracy had already fled to Miami to establish an influential diaspora. They remain influential in American politics to this day (think Ted Cruz).

We had a chance early on to bring Cuba into our sphere of influence, but instead let the opportunity pass by and the Soviets filled the void. I clearly remember the Bay of Pigs fiasco in 1961, and the Cuban Missile Crisis in October (16th – 28th) 1962. We almost blew up the world and ended mankind. The CIA was clearly responsible for the first, and only JFK’s diplomacy saved us from the second. I will make some allowance for the context of the times, but our government still makes stupid-ass blunders (the invasion of Iraq has turned out to be a blunder of epic proportions).

I wasn’t getting any younger, and I wanted to see Cuba firsthand before I croaked. I was living in Yucatan, Mexico at the time so the trip was just a short hop-skip-and-a-jump. The Cubans welcome American visitors (it’s our government they find contentious), and won’t stamp your passport on entry. Instead they simply stamp your temporary tourist visa so there is no record of your visit in your passport. Entry into Cuba was easier than my exit from Mexico.

Cuba is not what you think it is. Ninety percent of what you know about Cuba is American propaganda. I was there for almost a month, and in that time I travelled and photographed the entire island. The Cuban people truly like the American people, I was welcomed with open arms everywhere I went. Cuba is a long way from perfect, but they have an exceptionally high literacy rate. Their medical system is first-rate and is one of their key exports (they barter medical expertise for goods and services throughout the world).

The average Cuban is very proud of their country and its accomplishments (despite our embargo). There  is a fair share of the old wink-and-a-nod when the discussion turns to politics, but it is mostly done in a jocular way (much like we do in the States). The typical citizen of any country I’ve visited holds their government in contempt, that is certainly how I feel about the buffoons that run my country (especially in this election year).

I fear the American developers will eventually get into Cuba to rape and pillage in the name of capitalism, and I wanted to see Cuba before that happened (or before I died). The cigars are good (but don’t live up to the hype in my opinion), the rum is excellent, and the everyday food runs from simple and bland to excellent. The beer isn’t half bad. I’m glad I took the risk (after all it’s not like visiting North Korea, Syria, or Libya). If you get the chance I would recommend a visit, but you better do it soon.

Some think I was a fool for undertaking such an adventure, some think I committed a traitorous act (defying the embargo and travel prohibition of my government), some think it was a political statement and a defiant act, some think it was brave, some continue to think that I’m a leftist, socialist, communist, anarchist (you better pick one, because I can’t be all of them). Think what you will. For me it was the right decision and the right time. Checkout my book Cuba at Fine Art Photography Books.


 Stephen F. Dennstedt


Photographer, Writer, and World Traveller

Lima, Peru


8 responses to “Why Would You Sneak Into Cuba

    • Hi Deborah. I’m glad you liked the photos. From Merida it’s an easy trip (short flight). I think it was $300 to $350 USD roundtrip if memory serves. I think you would LOVE it. 🙂

  1. I’ve wanted to photograph in Cuba for years. Now that we’re in Mexico I thought it might be possible but had no idea it could be so easy to get there. Thanks for the article and the lovely photographs.

    • It’s still technically illegal (for Americans) unless you travel with a USA certified educational group which can take months to arrange, and you would be very restricted in your travels. Going in under the radar eliminates all of that, but you could be held accountable by the State Department if they found out and chose to prosecute (unlikely). I think there is a daily flight to Havana from Cancun, and in 2014 the flight from Merida was a weekly flight. You won’t have any trouble with the Cubans, but you have to take cash because none of your USA credit cards or ATM cards will work. American banks still consider Cuba a restricted country. There is a lot of information about travelling to Cuba on the internet.

  2. I was like you Stephen and had a great desire to go to Cuba while at least one of the Castro’s was still in power . I am an Australian and flew in and out with the Canadians from Toronto. They mostly went to a resort type area for some well deserved sun and sand …
    It was everything that I thought/ wanted it to be. The people were very friendly with a resigned attitude to life- as if waiting for a chance to ” move up ” the socio-economic ladder a little.
    My big unanswered curiosity was why , in a tropical world that can grow giant avocados, was the food so bland. The only “spices” were sugar and salt, where is the chilli, lemongrass, basil , garlic etc
    Aside from the dreadful variety of food, the people are so inventive with their recycling of all sorts and improvisation- place is amazing and are yore photographs.
    Paul Close

  3. Excellent and timely post. Thanks for sharing this. It’s going to be interesting to see how this plays out in the future. Do you think a Trump Presidency (just threw up in my mouth a little) will reverse the progress made or has the course been set?

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