Our Cuba Trip Report & Photos

Cuba has been on our travel bucket list for years. Since first seeing post card-perfect photos of Old Havana’s vibrant Spanish colonial architecture and classic American cars from the 1950s, we yearned to visit. After extensive planning and postponing, we finally had the chance on a recent cruise, and thought we’d share thoughts from the experience here, along with a scattering of 20+ photos showcasing the beauty of Old Havana.

Following changes to both United States and Cuba laws, our desire to visit Old Havana took on a new immediacy. Our first fear was that Cuba would begin importing new automobiles, with its fleet of classic cars being put to pasture. Second, that foreign developers would see the pent-up demand for travel to Cuba, and begin developing hotels and other property inconsistent with the Spanish colonial architecture, some of which dated back to the 16th century.

While our fears were well-founded, policy rollbacks by the U.S. government led to increased confusion about the legality of visiting Cuba, which led to decreases in Cuba tourism the last couple of years. We were among those confused by travel restrictions, and also how the State Department might “react” to our original plan to cobble together our own itinerary with flights and an Airbnb rental. Hence going the more straightforward path of taking a cruise…

Before we dig into the substance of the report, it’s probably worth briefly addressing the ‘morality’ of traveling to Cuba as Americans.

We subscribe to the Rick Steves’ philosophy of travel as a political act, and with that saw a lot of pros in visiting Cuba, but also some cons. To be frank, most of those downsides were not in the act of visiting Cuba, but in the perception of it.

Personally, I don’t think travel to Cuba should have been prohibited in the first place.

While purportedly resulting from communism and Cuba’s oppressive government, the United States hasn’t had a similar embargo in place elsewhere for those rationales. The embargo seems to me more about politics, and the outsize influence wielded by Cuban-American groups in Florida.

Moreover, Americans have a constitutional right to travel, and laws comprising the embargo constitute a de facto ban on travel to Cuba that has only been upheld on specious grounds.

Suffice to say, we felt seeing the contemporary context of life in Cuba and connecting with its people outweighed any potential downsides.

Nevertheless, I realize this is a complex issue; one with compelling arguments and strong opinions in both directions. However, that’s about as deep as I want to wade into the politics of visiting Cuba.

The ultimate point here is that traveling to Cuba was not a decision we made lightly or irresponsibly. Even in retrospect, I’m entirely comfortable with having visited and would not hesitate to do so again.

Once we came to the realization that we’d have to visit Cuba via a cruise, we narrowed our choice to a 5-night itinerary from Royal Caribbean with an overnight in Havana. Cruises visiting Cienfuegos were also attractive, but we figured we could revisit Cuba at another time for that.

The 5-night cruise ended up not working out with our schedules, forcing us to choose between a single day in Cuba on the Majesty of the Seas, or postponing the trip another year.

Since you’re reading this Cuba trip report, the choice we made should be self evident. The cruise ended up being incredibly cheap, and stopped in Key West for a day before heading on to Havana.

This was also my first (but not last) visit to Key West, which was far more lovely than I expected. It has the touristy stretches of kitschy bars, but away from port, Key West is beautiful and charming. That’s another topic for another post, though.

On our Cuba morning, we left the ship as early as possible, wanting to make the most of every moment in port.

As soon as we cleared customs and headed out of the cruise terminal, we immediately saw the iconic scene of Havana with classic cars whizzing past historic architecture.

I’ve read and seen a lot about Cuba in the few years that we’ve been thinking about this trip, to the point I was worried the real thing might be a letdown as compared to the glamorized image I’d painted in my head.

So many destinations have that postcard-perfect quality in one direction, but when you look the other way, there’s a Starbucks, Hilton, or worse yet–nothing at all. They are, essentially, one dimensional scenes existing for photos, but that’s about it.

Old Havana was not that at all. As we strolled deeper down the cobblestone streets, we encountered a seemingly endless supply of public squares, engaging architecture, and a steady stream of classic cars.

With so many American automobiles, it felt a bit like stepping back in time, but to a place that never existed in the United States.

This scenery was surreal, and ‘classic cars with colorful Spanish colonial facades in the background’ is the indelible image of Cuba that remains in my head, and probably will forever.

We covered a ton of ground and did a lot of things during our day in Old Havana, but watching cars pass buildings, as simple as that might sound, was absolutely entrancing. I could’ve done that all day. (And judging by my vast collection of car photos from Havana, that is what I did all day.)

In reality, our day was a mix of looking at cars, walking through historic districts, and interacting with locals. One of the twelve authorized categories allowing Americans to travel to Cuba is known as the “People to People” provision.

This is how most, if not all, visitors aboard cruise ships qualify to visit.

And let me tell you, we certainly had a day full of activities enhancing contact with the Cuban people and that resulted in meaningful interactions with individuals in Cuba.

What we found is that Cubans are incredibly friendly and eager to chat, mostly about how the disputes between our respective governments are not held at an individual level.

Early in the morning, a woman suggested we follow her so she could show us where a particular festival would be occurring. We were a bit apprehensive at first, but felt completely safe, so we followed.

This turned into a multi-block tour of her neighborhood, as she showed us various buildings, introduced us to a few of her neighbors, and showed us where she lived.

Other interactions weren’t quite this involved, but they were a number of them. There were also a handful of interactions that started amiably at first, before slowly transitioning into a sales pitch.

This was almost always for cigars, and we simply put an end to these discussions by saying we don’t smoke.

That was usually met with an aghast, “how can you come to Cuba and not have a cigar?!” To which we responded simply, “we came to experience your rich culture and meet your incredible people.”

Hard to argue with that. In other attempts to sell us things, we firmly stated, “sorry, no cash.”

Talking to Cubans was fun and fascinating at first, but about halfway through the day it admittedly started to wear on me.

“Extroverted” is not a word I’d use to describe myself, and after a while the repetitive interactions took their toll, especially the ones that were roundabout pretexts to sell us stuff.

On the plus side, this category of authorized travel pretty much had the intended effect. Cubans we encountered learned a bit about life in America, and we did the same with Cuba. The interactions were always cheerful, which was interesting given some of the circumstances we encountered.

This is to say, our observations felt at odds with these firsthand accounts. While the photos here might create the impression of a country that’s retained its historical character, that’s only part of the story.

It should bear underscoring that poverty is rampant in Cuba. This is not an ‘old world’ European village that has deliberately preserved its historic charms. Cuba has this ‘oldness’ at least in part out of necessity.

Old Havana is also not as pristine or meticulously presented as what you’d encounter in parts of Europe. Rather, there’s dilapidation in plain view, and it’s much more rough around the edges. This has a way of making Old Havana feel much more “real.”

If anything, I feel more conflicted by my photos that romanticize scenes belied with poverty than I do about traveling to Cuba as an American.

This is a common moral dilemma of traveling to impoverished places, and one that has no easy answers. In this case, I want to think it was not exploitative, and a positive experience for both Cubans and us.

The Cubans we encountered were proud of their culture, cars, design, art, cigars, and their various personal interests or talents. They seldom brought up the struggle of life in Cuba. It’s possible to cynically think that this is governmental manipulation, but they didn’t seem afraid to cast aspersions on their leadership.

Most sincerely appeared more interested in demonstrating that the Cuban people are not monolithic, and there’s more to them than what their (and our) governments represent and reflect.

Obviously, this all only reflects our experience in Cuba, and our interactions in a single day could be radically different from others. We did notice that we attracted far more attention than other tourists.

It probably didn’t help that Sarah and I wore vibrant outfits and generally look fairly non-threatening, but it seemed like everyone wanted to talk to us. All in all, it was interesting and illuminating.

I know this only creates an impressionist sense of visiting Cuba, rather than covering the nitty-gritty of what we actually did during our day in Havana. The goal here was to establish some context and a backdrop for our visit, while also preemptively answering some of the questions we expect about traveling to Cuba.

Your Thoughts

Have you visited Cuba? If so, what did you think of experience? What did you think of Old Havana? Other places you liked (or didn’t)? If you haven’t been, is Cuba a place that’s on your travel bucket list? Would you feel comfortable visiting Cuba as an American? Any questions or things you’d like us to cover? Hearing feedback about your experiences is both interesting to us and helpful to other readers, so please share your thoughts below in the comments!