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A Recap Of My First Trip To Cuba: Did I Miss Something?

Yes, I definitely need to return.

Pretty Cuban girl
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ASTORIA, NYC- I went to Cuba with the plan of going back there again. I would fly in, look around a little, get the lay of the land, maybe even make some friends, find some stories, and then go back and pursue something a little more interesting.

This is all to say that I went in with no plan other than to just walk around and see what happens.

And that’s pretty much what I did.

To be honest, I’m not sure if I’ve ever been in a country that I’ve had so many reservations about — that I was so confused about. It was the polar extremes that got me: an extremely unique, one of a kind culture with a way of doing things that’s truly different (not many of these in the world) that is at the same time overtly underwhelming, heavily polluted, impoverished, desperate, stunted. They had a revolution but then what?

While the rest of Latin America is certainly interesting, I wouldn’t necessarily call it fascinating. You get a feel for the patterns of the culture and they are very similar from Mexico to Chile. The term fascinating only really comes into play in travel when you are unable to completely discern what is happening right in front of you. India is fascinating. Azerbaijan is fascinating. China is fascinating. Kazakhstan is fascinating. Cuba is fascinating.

Cuban artist

For many years I traveled all through Latin America listening to leisure travelers raving about Cuba. I’m not sure if this was because they thought it made them look cool, if they were enamored with socialism, or if they just liked the cheap, attractive, and readily available women (probably). It definitely wasn’t because they found the place fascinating.

But this left the thought in the back of my mind that maybe I missed something.

However, this all goes without saying — of course I missed something. It was my first trip there and your first trip to a country is basically a preliminary jaunt to let you know everything that you don’t know.

I know that I need a more holistic view of Cuba. Maybe I need to go back and venture to the tourist beach areas that are supposed to be nice, randomly bounce from little town to little town, go into the hills, and dive deep and find out a little more of what this place is really about …


Before leaving Cuba I did make a local friend that I feel could help me dive a little deeper into the place. While this is helpful everywhere, it seems more or less needed in Cuba.

Some places you can just show up and get down to work — China is like that (if you have the language skills), as is Central Asia, the Caucasus, Eastern Europe, Mexico, Malaysia, etc. Outside of isolated tourist sites, the confidence tricksters and scammers are few and nobody is coming up to you in the streets pretending to be your friend to get money out of you. And when someone invites you to come and visit their home and meet their family, you go. Even when mitigating for all the language, cultural, and administrative barriers, this makes it fairly easy to operate in these countries.

Cuban pot cleaner

Operating in places like Cuba, Central America, India, etc is vastly more challenging because there is often an issue of trust — or lack thereof — when meeting people. And you only learn that the stove is hot by touching it. Over and over again.

This is all to say that I’m planning to return to Cuba soon. I’m just watching the flight prices, and once things hit down around $200 for a round trip ticket from NYC, I’m there.


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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

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