Hotel Nacional

The Thing About Havana

Havana. It’s a strange place. The entire city is a bustling, dirty, noisy contradiction.   The people live in complete poverty and relative fear of their government. There’s a guy named Che (not even a Cuban!) that is one of their minor Gods. Something like a saint. Or maybe just a martyr. I’m not sure, after much consideration, what is the true difference between the two.

The people. Some are surprisingly beautiful. Superficially, and some deeper too. Some give when they have nothing. But, sadly, the vast majority are looking for the nearest handout, which could be you – if you are traveling there. Even if you don’t dress flashy, and do speak decent Spanish, and don’t make eye contact. Anybody well-dressed is a walking dollar sign.

And since, after spending a couple of weeks there – I became too familiar with all of it’s history and it’s noise and it’s grime and it’s corruption and it’s contradiction – allow me to digress from the typical “we did this and that” post. If you want the highlights of Havana, Cuba – try the Moon’s Guide for Cuba. This is not that.

The Thing About Havana


The history of Cuba, and it’s bizarre relationship with the US, is … well… sordid. There were the glory days, when the mob had influence. When Tropicana ruled the nightlife of the rich and famous – and the dancing girls were still nude there. When Hemmingway fished and lived and wrote and drank here. When the casinos were among the best in the world and the cars were new and many of the people were oppressed and some were rich and the rest were standing on the outside looking in. When racism was rampant. That was Cuba’s peak.

Hemmingway's house

Hemmingway’s house

And then there was a revolution.

This revolution was a big deal. It changed the course of Cuba, completely. If you haven’t seen the effects of a revolution, you can travel around Central/South America for a bit. You’ll see the after-effects of revolutions, and, if you’re open minded and interested- you’ll see what the North Americans have done here, for better or worse. Often for worse.   It’s a strange thing to walk around a place that is (relatively) fresh from revolution. It makes you think differently about the word “revolution” and the concept.

But recent revolution is cake compared to active revolution.

It’s a dangerous thing to walk around a place that is actively in a revolution. But, to understand it, you really have to see it. Let me recommend Venezuela, it’s a short flight from the States.

That was sarcasm in case you didn’t catch it. Don’t go to Venezuela.

I went, a while back – even then it was a rough place.

Back to Havana…

The Hotel Nacional

The Hotel Nacional

If you’re curious, and not completely politically biased – that is to say if you hold politics at an arms length and seek understanding rather than follow a particular party with religious fervor (I’ve met very few people like this, but they do exist) – then communism (which they call socialism here) is mildly interesting. It is, if nothing else, a case study in how you can truly screw up a country’s long-term prospects, on the world’s stage. That’s true if you’re a country with remarkable natural resources (Russia) or a country with few natural resources (Cuba). It’s especially true of the latter.

It’s also a case study in how you can keep everyone at the same level. And, assuming this level includes basic health-care and a fair level of education – well… Maybe it’s not so bad. Right? Maybe. But not from what I’ve seen.

The thing is, by trying to create a common denominator – they’ve created the lowest common denominator. You can’t bring anyone up, without bringing everyone down.

So Havana, Cuba is a giant political/economic petri dish that sits only a few miles off of the coast of the United States of America.

The hypothesis was fair. The reasoning behind it sound and just. The attempt was valiant and brave and courageous in a way that other South and Central American countries have never been. It stands out in the Caribbean and Spanish speaking countries as – what could have been – a beacon of hope. It could have been the only country, or maybe just the first country, that defied American Imperialism and survived.

It could have been.

But it’s not. In reality, in every possible way, it’s a failure.

I don’t care what you read. I don’t care what they tell you about good healthcare here. I don’t care what they tell you about good education here. I don’t care how uninformed you are. It’s propaganda.

Cuba is a country that is stuck in 1959. Mired. Completely.

Taxi Ride

Taxi Ride

Since their revolution, which the citizens have been taught/forced/brainwashed to revere – they have been leeching off of the progress, the work, the movement, of the pre-revolution. There is nothing else. To say it’s like stepping into a time-capsule is far too simple. It’s like stepping into a time capsule where there are tourists from the future who destroy the fragile image of the people that live within the time-capsule, thereby destroying their concept of self.

Even that doesn’t capture the contradiction.

Classic cars from the 50’s and 60’s, but nothing original. Engines in classic Dodges that are small Korean diesels. Interiors imported from China, installed by Cubans – in colors that would make your grandmother blush. Everything a shade of gaudy.

Cuba is a bum wearing a poorly made imitation Armani suit. Trying. Trying so hard, but with the lack of mercy inherent in nature, failing. Failing publicly and openly. But still worth seeing. A trainwreck you can’t look away from.

Instead of being a beacon of hope and anti-American Imperialism, they’ve willfully turned themselves into an socio-economic freak-show.

But it’s a freak-show that’s worth seeing.

To be fair – they have figured vice. Vice is completely and beautifully understood in Cuba. It’s handcrafted here. That’s something you can’t get in the “civilized” world; you can’t get handcrafted vice. But in Cuba, it’s something that’s designed just for you. Custom vice. Bespoke. Fine. Elegant. Vice done right. Handrolled cigars that are the best in the world – or at least among the best. Handcrafted rum, steeped in tradition. The aged of which is widely known as a world contender for the finest of rums.

Vice in Havana

Vice in Havana

If you walk around on the streets, as a man, without a woman – you will be approached, again and again, by a remarkable variety of women seeking… well… You can guess. I was warned about this, and on the few times I ventured out alone – the propositions were endless. Anything for the almighty dollar. However you want it. Bespoke vice.

It’s far worse to be a woman walking around without a man, though.

Other things in Havana

There are other interesting effects of communism in Cuba. One being how often things “fall off the truck.” Another being the amount of counterfeits. And meeting in the middle is how often you find counterfeits being presented as the real thing that fell off the truck. Since there is no profit motive – ie workers get paid the same (low wage) whether they produce 8 widgets or 300 widgets – there is immense temptation to sell some of their widgets on the street, some personal income that can prove to be many multiples of their gov’t wage.

To give you an example of the level of poverty – when we made our last provisioning stop we purchased olives. The cashier (a lady in her mid-fifties) asked us if we had ever eaten black olives, or if this was our first time. She had never tried black-olives before – they are too expensive and not part of their gov’t allowance. The black olives cost $2.25.

Then there is the potato, cheese, and lime thing. You see – they are always running out of potatoes and cheese and lime. I’m not sure how much, if any, is allowed in their gov’t ration – but the point is, the locals usually don’t have it, can’t afford it, and therefore it exists only on the black market. As you walk down the street, people whisper to you – “Papas? Queso? Limon?” It’s the same whisper, the same secret, and the same tone they use in Colombia to sell cocaine.

Another, related, thing is the level of corruption that quickly takes hold as the populace (consciously or not) rejects communism and turns (semi) capitalist. In that, I mean the Cubans rip you off any chance they get. What they weigh as 1 pound of produce at the grocery store hardly makes ½ pound. When they exchange money on the street they regularly short-change you. In restaurants they overcharge religiously. All with a straight face. And when you catch them and call them on it – they just shrug their shoulders.

Recently we’ve encountered a specific breed of corruption that is especially frustrating, over and above the standard rip-you-off-every-chance-we-get. Recently we’ve been hassled by “park rangers” posing as actual government officials. They are employed by a company called Fly Fish Cuba (or something like that). The company in question brings tourist around in a luxury yacht, from which they launch small bay boats to fly fish the South Cuban coast. When they are in your area, they bring by these impostors and the impostors tell you that you can’t fish in this area. The entire thing is a ruse, designed to keep the fly fisherman (who pay copious amounts of money to fish in an “untouched” area) from seeing you fish said “untouched” area. When challenged, some of these fools produce a sketchy, worn document with a single line that reads “you may not fish in protected zones.” Of course, there is no map outlining protected zones, the impostors regularly get confused when attempting to recite the boundaries – and to top it all off – at every marina we have asked: you are allowed to fish and spearfish everywhere except the immediate area surrounding Cayo Largo. You could argue that it’s capitalism that is corrupting the communism, but the larger issue at hand is that this political system has entirely failed to recognize the profit motive of the individual – and in doing so, it has entirely failed.

But, well, what are you going to do?

Then there is the begging.

I was asked the other day, after nearly two months in Cuba, if I had any Cuban friends. I had to answer, after thinking, negatively. I do have one Cuban who I believe is honest enough that I could call him a friend. But every other Cuban interacts with you for the chance to get money.

The other night, in an attempt to get to know a few local Cubans – I brought a bottle of rum out onto the street with some ice and a glass. I drank it there and gave rum to anyone who stopped and chatted with me on the street.   It was a great experience, and it even gave me the illusion of having made friends. Of course, the night ended in most of my new friends asking for handouts. And the next day on the street, one of my friends from that night greeted us with “And you didn’t bring me anything? At least give me a dollar…You’re not my friend!”

Cuba, in a picture

Cuba, in a picture

The truth is, that’s not my responsibility. If it’s really that bad – they better damn well do something about it.


In the picture above, notice how long the scaffolding has been there, and note that this is on the same street as the CAPITOL BUILDING (you can see the building on the right).  Think about that.

Prison Camp

There was a boat in Cienfuegos named Harvey Gamage. It had a crew of young people. Good young people. Happy and positive young people. Idealistic young people. And one of these young people brought up the argument for communism, and it was apparent he strongly believed it. He believed that Cubans were better off in this system. I disagreed, having spent more time and more money and more energy here – but it’s a debate I was willing to entertain. And so we talked.

His belief was that the country was in good shape. It had education for all, healthcare for all. And for a Caribe country with few natural resources – they were doing alright.

I asked him, why then, were Cubans not allowed to leave this paradise? Why then do they continue to flee this paradise, despite the seriousness of the consequences? Why then is there no one trying to immigrate to this paradise? If you didn’t know this already – Cuba is a giant prison camp. And though they are making strides to open it up (and have, already) – it continues to be a prison.

Even if the healthcare and education were good and free, if this ideal is carried out successfully – you are still a prisoner. That, to me, is hardly acceptable.


It is challenging. It’s full of contradictions. It can be expensive and time-consuming. Nothing is done correctly. Waiting in line is a pastime here. The food is atrocious. Personal connection is rare. Corruption is rampant.

But, I’m not here to change the world. Merely to observe.

So I spent a couple of weeks in Havana. I went to Buena Vista Social Club (twice). I stayed at more than a few different places. I drank in famous hotels. I followed in Hemmingway’s footsteps. I danced and drank and ate and talked and sweated and cursed. I visited the tobacco factory and the rum factory and several museums. I argued with taxi drivers and told people “no, gracias” more times that I can count. I spent way too much money. I saw the underbelly, which isn’t all that well-hidden. I ate local and dined out with politicos and lived in the ghetto and saw the lavish houses of those in government.

THE Buena Vista Social Club

THE Buena Vista Social Club

Hemmingway and I

Hemmingway and I (and Castro)

The infamous PIlar

The infamous Pilar


And to that end – despite the many, many frustrating things about Havana, Cuba – I do love Cuba (outside of Havana, Cuba). From my vantage point (NOMAD) where I smoke the fine cigars and drink the great rum and have access to some of the best fishing in the world – Cuba is a fine place.

That’s Cuba. It’s changing already.

And when that change is complete, it just won’t be Cuba.








Opt In Image
Like what you read?

Subscribe to get notified when there's new content!

16 replies
  1. Jaime' Mas
    Jaime' Mas says:

    Great piece, Nate, and the kind of thing that Americans need to read as the island begins to open up. I trust you’ve read about Che, even his Motorcycle Diaries, and understand his revolutionary soul. Castro would not have happened if Fulgencio Bautista hadn’t paid every tobacco grower and casino worker and cane farmer in pennies. That’s an important part of the story you didn’t have time to cover. He had more political prisoners than Castro, and, as an American-backed dictator, killed anyone he could who opposed him. He skimmed all of the casinos in deals with the mob. Cuba could’ve balanced its budget on rum, cigars, and sugar. But America doesn’t do business with communist countries, at least not officially, and they’d opened up the island to Russian missiles. But we are culpable for where Cuba is now. It’s not all communism and Castro’s fault.

    • Nate
      Nate says:

      That’s one of the things I really didn’t get a grasp of. There’s too much misinformation out there (and here it’s all propaganda). And I agree about our role in much of this, I’ve seen enough to get that. But – the truth is – the responsibility of how one runs a country is always the responsibility of the people

  2. Todd Edger
    Todd Edger says:

    Nate are you there legally? Do you worry about running into the USCG? Where do you plan to go next Haiti, or Jamaica ? The fishing won’t be that good either place, but I bet you will enjoy the contrast in people.

    • Nate
      Nate says:

      Legality is a moving target, and here – it just doesn’t matter. I’ve had many a friend visit, no bad experiences. Really – nobody cares. I’m heading to Cayman, then to the Hobbies (Honduras), then back to Panama for hurricane season

  3. Dan Brown
    Dan Brown says:

    Nice account of your Cuban visit. It is a broken country! I recently visited several countries from the Czech Republic, Hungary, Serbia, Croatia, Bulgaria and Romania … the struggle of daily life in these countries which have been spoiled at one time or the other by socialist/communist rule is so disheartening and inhumane in many ways.

    Anyway enjoy the Cuban fishing, cigars and rum. And then sail on!

    • Nate
      Nate says:

      I didn’t dock in Havana – I anchored in Cienfuegos and went via taxi to Havana. Hemmingway Marina is in the area, but it didn’t seem to be much…

  4. CDB
    CDB says:

    We have been to Cuba many times, but never to Havana. A lot of what you say rings true, but not sure the “anything for a dollar” issue was much different than in the Dominican.

    I have to admire Cuba’s great (not just good) medical care, and education. Many other communist countries did far less for their people. I’d also point out, to give Cuba a fair shake, the US embargo has had a huge negative impact. If it weren’t for that embargo I’d likely try to hire software developers there.

    Would Cuba be prosperous without the embargo? There is a strong argument that well educated people, and a good medical system bring a country our of poverty. It seems to me that the US embargo is a direct cause of much of the Cuban weirdness you see.

    Maybe not all, but to throw all the weirdness into the lap of their socialist system is a bit of a reach too.

    BTW – Love that you are doing something you so enjoy …. and sharing. Thank you.

    • Nate
      Nate says:

      Anything for a dollar is the same anywhere, even in the US. But it was especially prevalent in Havana. Not so much in Trinidad, Cienfuegos, etc. Of course the embargo had an impact, that’s why the US did it. Great medical care? This I did not see. Decent? Sure. But “great” is a very strong word. The good news is that it doesn’t bankrupt the people.


Leave a Reply

Want to join the discussion?
Feel free to contribute!

Leave a Reply

Your email address will not be published. Required fields are marked *