Impressions of Cuba

Cuba Car

I don’t know what I expected, but it wasn’t this.

Maybe I thought I’d run into Hemmingway scribbling away while sipping a daiquiri. I’d see gentlemen puffing cigars on their verandas as they discussed the imminent horrors of the Cuban Missile Crisis, except probably just referring to it as “our missile stash, and what to do with it.” I’d ride in a red Chevy convertible and fawn over my chauffer, dressed in a three-piece suit and grey Fedora.

Which means I booked a trip to Cuba assuming it was 1950’s America, minus the democracy but plus the tropical fruit. Problem with embargos, Exhibit A: they don’t just cut off sugarcane and oil imports, but common sense.

You can sort of see where I was coming from, though. When people speak of Cuba, they go on and on about it being a time capsule, untouched by modern-day Capitalism and American fast food joints. (So why I thought it would be 1950’s America is beyond me, but hey.) We’re told we better get to the island soon before the floodgates are opened and it’s completely transformed.

But instead, I found Cuba to be not all that dissimilar from places I’d been in Latin America – at least at the onset. It felt like a developing country with few Smartphones and an annoying reliance on diesel. Sure, there are certainly markers of its colonial heritage, and old cars and communist propaganda posters abound. But spoiler alert: Ernest Hemmingway’s dead. You won’t find him deep in thought, and La Floridita, which serves his favorite daiquiri, is as overpriced as a wine bar on Paris’s Champs-Elysées.

Sometimes the motivations for a trip, and what we actually take away from the experience, are completely different. I ended up loving Cuba – just not in the ways I was expecting.

I’ve got your back

More than any other country I’ve traveled to, Cuba oozed a feeling of solidarity. It makes perfect sense – there are the Marxist beliefs that have pervaded the country for over half a century, preaching (if not always practicing) equality. And then there are the extreme difficulties of an impoverished nation beheld to conquerers and dictators, through which Cubans have banded together and struggled to survive.

There is a “look out for your neighbor” mentality that struck me as so unique, so foreign from my usual existence. One day we were negotiating a price for an excursion on horseback to a waterfall, and agreed with the guide on 17 CUC a person. A few moments later, feeling like we had perhaps been ripped off and could find a better deal, we asked another guide what he charged. He refused to even consider our business, saying that if we’d already given our word to someone else, there’s no way he would tread on that man’s territory.

It was the opposite of Capitalism. The poster child for what would be considered “bad sales strategy” in the U.S. And incredibly refreshing, at the heart of it – one man protecting another. Let’s just say returning to my San Francisco tech job has been kind of a shock.

Havana Alley

Streets of Havana

Bargaining gets you (almost) nowhere

It’s common practice in most “developing” nations to barter. I once lowered a teapot in Morocco from the “real bargain” of $120 down to $7. A delta like that throws off your gauge of what things should cost, and as a result, it can be hard to trust vendors – or anyone, for that matter. In Cuba, prices were refreshingly fixed, more or less. This is also due to Communism – by law, most prices, even in the tourism industry, are regulated. (Even more refreshingly, all currency exchange bureaus list the exact same rates, so you don’t have to scour the whole city looking for the best deal.)

Ever the barterer (and skeptic), I asked ten taxi drivers their price to the beach, and all quoted me 8 CUC. A small painting of a red Chevy (what else?) that I picked up as a souvenir cost the same in four different shops in Havana and Trinidad. It was jarring at first, hardly being able to knock a dollar off the stated prices, but I soon found great comfort in knowing that I wasn’t getting scammed or cheated – this is the price point, and if you don’t want it for that, don’t buy it. It seems like a small detail, but this was a distinguishing factor for Cuba, and a major point in its favor. After all, when you come from a non-bargaining culture, haggling can be incredibly exhausting.

Openness in a closed country

I pictured Cuba as a lips sealed kind of place – aren’t Americans taught that Communism strips away all liberties? While it’s true that the Castro regime censors much of the information, and speech, in the country, I found locals to be incredibly forthcoming when I expressed curiosity about the lifestyle, history, and policies of the country. Cubans had a wealth of information – more than the little propaganda pamphlets I pictured Fidel dishing out – and their willingness and enthusiasm to paint a realistic picture for me (an American! the enemy!) is something I appreciated to no end.

There was the man selling books in an open air market who explained to me the significance of poet, revolutionary and national hero Jose Martí. There was our horseback guide Luis who recalled his family’s near-starvation during the Special Period, right after the collapse of the Soviet Union. There was our taxi driver expressing his skepticism over the recent regime change, and wondering out loud – a risky thing to do – if things would actually be different. And then there was our AirBnB host Pedro, who patiently answered my many – borderline prodding – questions about health care, education, even how much he paid for electricity (he brought that one up – not me!). He also told me how his oldest son now lives in Florida to support the family, and how he hopes to do right by the guests who come to stay because they have transformed his circumstances, and his family’s prospects.

They’ve got rhythm

A Cuban band could be playing for a crowd of one or a crowd of 5,000 – it didn’t matter. The pure joy that emanated from the musicians was palpable, every time we saw live music. And that’s the great thing about Cuba – you’ll see it everywhere, without even trying. Most tourist restaurants (which, admittedly, is likely where you’ll be eating, as Cuba doesn’t have a great food scene) host a live band around dinner time.

One of the best memories from our trip was when we were the only patrons at an outdoor restaurant, and the band took up playing just for us, our own private serenade. They then insisted we join them with maracas and drums – and quickly learned that white girls from the San Francisco suburbs just don’t have that island rhythm. Who knew maracas were so hard to play. . . .

Playing with band Trinidad

Killin’ it.

Safety first

Safety is often top of mind for travelers to Latin America and the Caribbean. Cuba, I’m happy to report, is one of the safest countries in the Western Hemisphere, and truly felt like it. It makes sense, when you think about the strict level of social control and the strong police presence of the dictatorship. Violent crime is negligible, especially compared to many U.S. cities and Latin American countries. Some petty theft does occur, but even when you pin it against the likes of Barcelona or Rome, it’s not even worth mentioning. I felt safer walking around dark alleyways at night in Havana than I do leaving my office in San Francisco’s SoMA district at 5 p.m.


Traveling to Cuba didn’t provide me with my time-traveling fantasies. Instead it gave me insight into an enigmatic country (for Americans, at least) run by an entirely different system of government, with a nearly unfathomable history of occupation and rebellion. And I’m glad I got this perspective. Old cars and cigars are cool, but coming away with a better grasp of the culture, traditions and mindset of the present is even cooler.

  • Kitat Desdenu

    Jenny te felicito por la visión que nos has dado de Cuba sin los estereotipos que están tan extendidos fuera del país y al margen de ideologías, colocando en el centro de atención a lo que de verdad importa, las personas.

  • Jade Dsa

    Those old streets look so charming! And I love that solidarity you spoke about – its nice that people aren’t under-cutting each other for a change! Great read xoxo

  • Definitely sounds like you always have a great time! I’d love to do a trip like this someday!

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