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Should You Travel To Cuba? Read This First

It was the best of travel destinations, it was the worst of travel destinations.

Cuban man on the Malecon
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HAVANA, Cuba- Cuba is a place that gives you mixed feelings as a traveler. It’s concurrently exactly what you’re looking for while also being exactly what you aim to avoid.

On the one hand, it’s a truly unique place with a different history, political and economic system, and culture than anywhere else in the world. It’s a place in a time capsule, with very little evidence of the progression of time beyond the 1990s.

It’s an anomaly — there’s nowhere else like it. The Post Soviet States in Central Asia, Eastern Europe, and the Caucasus don’t even flinch at being adequate comparisons. Equally poor at being a parallel are the other Latin American states — especially neighboring Dominican Republic and Puerto Rico.

Cuba is it’s own universe, it’s one of the rare countries in the world that you can say are truly something different, ranking up there with Turkmenistan and Bhutan. It’s the kind of place that you want to experience, dive into, and start to understand — the reasons to go to Cuba and the reasons you travel. On the other hand, it’s an extremely impoverished, heavily polluted, authoritarian backwater that can’t get out of its own way.

Old HavanaI walked into Old Havana for the first time and it was like something out of another world. The streets were lined with these beautiful, ornate colonial buildings. Street after street was nothing short of magnificent. However, most of these impressive arrays of architecture were in the active process of falling down — they’re covered in soot from automobile exhaust with pieces of stucco flaking off and roofs collapsing in on themselves.

I couldn’t help but to have been reminded of the movie Idiocracy, where skyscrapers in the future are held up with rope because nobody knows how to build or fix them anymore. Havana is a place where you can’t help but to exclaim “What happened here?” And marvel about how beautiful it must have been. At one time.

Old HavanaYou can almost see it everywhere. The vibrancy of a place that is booming, the men walking down the streets in their tweed sports coats and fedoras toking cigars, the women in their big ornate hats and white frilly dresses. You can imagine the bars (some of which still exist) being packed with expats and exiles.

It’s difficult to walk the streets of Old Havana and not feel nostalgia for a romanticized rendition of the Hemingway era. It’s easy to imagine how absolutely marvelous this city must have been.

Walking through Havana is like walking through the ruins of a once great city … only UNESCO is nowhere to be found and people are still living in the ruins. The things that still work seem to do so solely because they haven’t broke yet.

Cuba was once one of the wealthier places in Latin America. Prior to the 1959 revolution, the country was basically an economic lackey of the United States, with the neighbor to the north controlling 80% of the country’s trade over 60% of its food production. But this meant that Cuba was the fifth wealthiest nation in the western hemisphere, had the third highest life expectancy, and was actually number one in the per capita number of televisions — and indicator of wealth in those days.

However, this wealth severely unevenly distributed, with a quarter of the population being unemployed … There wasn’t a revolution for nothing.

Cuban man This place was so much different than I thought it would be, so much different from what I’ve read from travelers (racking up cool points talking about how incredible it is there). But I have to admit that it’s difficult to marvel over a place when people are walking up to you asking for your table scraps as you sit eating at a sidewalk restaurant.

“We don’t make anything here,” a local on the Malecon said to me one evening. He was well groomed, wearing a button down shirt and had nicely cropped, short curly hair.

He spent his days walking up and down this seaside strip, apparently looking for foreigners to sell his services too. These days, there aren’t too many of us, and the fact that he didn’t want to stop following me attested to a touch of desperation. But he was ingenuitive, offering to take me to a poor area of the city so I could take pictures of street kids.

Apparently, he has met tourists before.

Cuban man portraitI questioned him about his statement that Cuba doesn’t make anything and and he gave me an example:

“Even your water isn’t from here,” he said while pointing to the plastic bottle that was sticking out of the pocket of my jean shorts.

“What? You import water?”

“Yes, everything is imported. Look at it. That water came from Colombia or somewhere.”

I pulled it out of my pocket. He was right.

This sentiment was magnified when I met a German traveler who was around my age at a bar later that night. 

“When you go out to the countryside you will see, it’s all empty. They don’t grow anything. They have fertile soil but they don’t grow anything.”

He was right. I did not see a single agricultural field or even a garden along the entire 20 kilometers to Guanabo.

“Covid destroyed this place,” he continued. “It’s still not back to what it was. Nobody is coming here anymore.”

This fact was obvious. I was spending my days walking around the prime tourist areas, going into tourist establishments, and hardly ever sharing space with my own ilk. It was to the point that when saw another traveler in a bar you’d check in with and share notes rather than pretend they didn’t exist.

Cuban fisherman Cuba relies on tourism. Without it, the country doesn’t have much of an economy. When the Covid pandemic hit the entire country lost its economic lifeline. Before the pandemic, Cuba received over 4.7 million tourists per year and tourism amounted to 15% of its GDP, along with employing half a million people officially — and much more than that unofficially (sex tourism is big there and the providers are generally independent operators). This sector was absolutely decimated by Covid travel restrictions and hysteria, plummeting 56% from 2019 to 2020.

Cuban womanI have to acknowledge here that my experience of Cuba was probably very different than that of someone who visited pre-Covid and, likewise, that of someone who visits in the near future, as I imagine things will eventually get back on the previous trajectory.

I also don’t want to make it seem as if the travel experience in Havana is by any means unfavorable. To the contrary, once you accept the place for what it is, this city is incredibly easy to enjoy. Delicious food is cheap. Cocktails are dirt cheap. You can get an AirBnb that’s comfortable and well located for $20 a night. You can live to excess here on $50 a day. And all around you are things to pique your interest, things to question, things to learn about … The cost-to-experience ratio is off the charts — you pay a little and get a lot to chew on.

The German guy was beginning to fascinate me. He was thin with blond hair that hung down over his ears and curled up upon his shoulders. He was wearing a white undershirt and shorts.

He had been traveling for five years straight but seemed to have spent his entire adolescence and adult life on the road in some capacity. He went to high school in Tegucigalpa. He went to college in Boston. He told me that at one time he held a top position in a finance firm but quit just before he made it big. “I always quit a little too soon,” he said with a laugh.

He asked me what I thought of Cuba.

Some days I love it and some days I hate it.”

He knew what I meant. He had been here for five weeks and was done. He said he’s been spending his days sleeping a lot.

“It gets bad near the end of the month,” he said. “That’s when their rations run out and people are hungry. Their rations aren’t enough.”

Cuban people He then told me about how at the end of the previous month he had to walk for two hours to find a bottle of water. This was a topic that was being hotly debated on travel networks, with some travelers claiming that Cuba was out of bottled water while others claiming that they were nuts and bottled water was readily available.

I suppose it’s all a matter of when you come here.

Sometimes there’s stuff; sometimes there isn’t.

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Filed under: Cuba, Travel Diary

About the Author:

I am the founder and editor of Vagabond Journey. I’ve been traveling the world since 1999, through 91 countries. I am the author of the book, Ghost Cities of China and have written for The Guardian, Forbes, Bloomberg, The Diplomat, the South China Morning Post, and other publications. has written 3706 posts on Vagabond Journey. Contact the author.

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VBJ is currently in: New York City

2 comments… add one

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  • Rob March 15, 2024, 8:54 pm

    Thanks for the look at Cuba.

    Link Reply
    • VBJ March 15, 2024, 9:18 pm

      Thanks for reading!

      Link Reply