Visiting Cuba: First Impressions

Like most who return from a first-time trip to Cuba, I’ve struggled to write about it.

I’ve struggled even as the cultural visitor that I was, on a people-to-people tour. In essence, a tourist like everyone else.

The truth is that I had no plan to post anything on my blog at all, because this wasn’t for work for a change. It was for cultural and educational purposes–I’d always wanted to visit Cuba and understand it. It’s also a neighboring country to the Dominican Republic, and yes, I did need to know a little of it from that standpoint. But I wasn’t on assignment, and I wasn’t there as a travel journalist… although, it’s always hard to put that hat away.

I’ve received numerous messages asking me about my impressions or perspective of Cuba. The most recent question was: tell me in one word, did you love it?

After I answered, I began to wonder–how much can one judge anyway after 11 days in Cuba, across several regions? Anyone who knows me knows that I don’t favor writing about a place after a short stay. That’s why most of my writing sticks to my expert destinations.

But that’s the thing. There are times I traveled on press trips for a short time, and came back enchanted (the reverse is also true). I spent a week in Martinique and returned with plenty of positive impressions. Four days in Haiti, and I was mesmerized by the cultural wealth on display. A weekend in Barbados and I was not enthralled.

Cuba can’t be compared for obvious reasons. And in that same vein, as a tourist destination it felt… different. Old Havana charmed me on my first day and evening, despite the strange casa manager experience (and another incident which I haven’t shared). And then it turned into a rollercoaster for the following 10 days. In under two weeks, I felt a whole range of emotions that surprised me. Happy, annoyed, frustrated, compassionate, amused, happy again, disappointed, and then exhausted. It was all there, in just a few days!

It was tougher (even though locals often mistook me for a Cuban) to navigate solo during the short time I had to myself before or after my group arrived–mostly due to male harassment, and constantly warding off hustlers. But also, my quest to experience something real felt like a struggle. Perhaps I was looking too hard?

Calle Obispo, La Habana

It’s the first communist country I’ve ever visited. I didn’t fully absorb all the details that I did read about before visiting. In hindsight, I hadn’t read enough about the day-to-day challenges, or even the negative effects of tourism. I only remembered the romantic scenes told of the Hotel Nacional in novels, or the mystery of Old Havana mentioned in articles, and Cubans described as the friendliest people in the Caribbean. I began to think of how I portrayed my own destinations for work, and whether I had over-romanticized a population (but I don’t believe I have).


Once in Cuba, I sensed plenty of stories behind people’s facial expressions, and while most were polite when addressed, the majority were indifferent to having an exchange. I learned a ton from my young, dynamic, and smart local guide, who was forthcoming about all topics. He had worked in a sugar cane factory, making a pittance and feeling hopeless, before getting the opportunity to become a private tour guide.
Later, to my greatest shock, one Cuban housekeeper had opened up to me at breakfast, of her own will. When I left Cuba, her words (in Spanish) were what I remembered while seated on the plane: “I’m 60 years old, and I’ve never seen a copy of the Constitution. I’ve never read my country’s Constitution. The government makes it hard for us to get, they don’t make it widely available. But I’m trying again to get a copy, through a contact in Havana. I’m not giving up.”

She had continued to ask me about the places I’d visited around the world, and what they were like. She’d shared her dreams of wanting to see “not the United States like everyone else,” but Hawaii (I smiled), or Dominicana (the Dominican Republic), which must be beautiful. “But I know I’ll never get to see them,” she’d said. “The Government doesn’t allow us to travel. I just hope that one day, our grandchildren will get to see the world like you do. Americans are so privileged… the most privileged… in everything.”

By this point she was seated at the adjacent breakfast table. It was the first real talk conversation I was having with a Cuban. And she had chosen me to share her sentiments; the prior Spanish guests had left long ago for the day. I agreed with her, and told her that despite this incredible privilege, many still didn’t take full advantage of it. Perhaps that was indeed the inherent result of privilege – taking opportunities for granted.

I felt her disappointment in my core–I couldn’t fathom a life where one is never allowed the freedom to travel even if they had the means. Or what it must be like to wonder how beautiful magazines must be to read, or to wonder how different your life might have been if you were given opportunities. This was true of so many countries (including my own birthplace, Ethiopia), but here it’s as if that truth hit me harder. When I left her a tip before my departure, she politely refused, as if hinting that she had simply told me the truth.

La Habana

My biggest surprise about Cuba? How developed its tourism is, and all the good and bad that comes with it. Yes, I know Canadians and Europeans have visited for decades. Still, the level of modern infrastructure development and the number of tourist attractions surprised me. In every corner of every region I visited, from Havana to Cienfuegos, Trinidad, Viñales, and Santa Clara, tourism was full on–in some spots, almost every private home was turned into a casa particular. It wasn’t cheap either; museums ranged at $8 per person, a two-minute cave boat ride at $5, while taxis often said (even to my Cuban host) they wouldn’t budge for less than $10, among other examples.

In the Valley of Vinales, where we biked for an hour.

Every activity, sight, or bar was filled with foreigners. At one live music venue on the main road in Viñales one evening, I glanced around the room and there wasn’t one Cuban to be seen except for our guide. Cubans can’t afford the drinks here so this isn’t where they hang out, he had answered. That’s true of other destinations in the Caribbean with respect to high end venues, but it also didn’t seem like the kind of music they’d listen to … and again, it made sense.

The continued struggle to find or experience something real and authentic led me to start questioning: what’s real anyway, and what’s authentic? And how do we find it when tourism is all over a destination, and not just in some areas? The more I thought about it and about Cuba’s history, about what my guide told us about the hard times under the embargo and the government’s cut in pretty much every incoming funds, the more I understood the why behind the need to hustle hard core, and extract as much plata as possible from visitors. Whether it’s the costumed characters in the plaza who will take a photo only if you pay 2 CUCs (US$2)–which was fun to do once at least–or the taxis who charge $5 instead of $1 or $2 (or an “American privilege tax,” as one of my friends calls it), or the endless tales from fellow travelers about hustles and tricks encountered during their road trips across the country (hitchhikers who want to take you to a restaurant for kickbacks)–it’s all about survival.

And let’s be clear: the hustle and struggle isn’t just in Cuba. It’s a reality in the Caribbean. One that is more evident as you live in the region and see the injustice around you. It may be more evident and worse when you visit Cuba because of its history and government, but in the end, a form of this struggle is present in every developing Caribbean destination you visit. The abysmal low income (in Cuba the average monthly salary is $40; in the DR, it’s $100), the lack of jobs for the youth, among other issues, and on the flip side a giant tourism industry where one population is forced into service to another with more buying power, or to ruthless foreign corporations.

Floats parading down the Malecon on the way to Carnival celebrations.

In 11 days of touring, I learned a ton about Cuba’s history and people, and I have a greater appreciation for it as a country. Sure, I enjoyed the Malecon, rode in a classic car, and had a salsa lesson, even if I didn’t get to dance after it. But there’s a lot more beyond the surface, and I understand now why people say it make take you decades to begin to understand this country.

One thing is for sure: Cuba made me think. About travel. About life. About a whole lot of things.

To view more of my Cuba images, visit my Instagram page.

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