This was my first trip to Cuba and Janet’s second — she visited in 2016, essentially on the same itinerary, and it was instructive to have her perspective on what had changed in the intervening years. One caveat before I go further: anything I present as factual comes from our tour guides. They were, to a person, highly educated, and I have no reason to doubt what they told us — everything I saw tracked with their commentary. But I have no independent basis for verification. This review is necessarily long. Cuba has been a forbidden country for most Americans for most of their lifetimes, and I want to share enough of what we encountered to make your visit — if you choose to make one — as rewarding and as clear-eyed as possible. I had plenty of misconceptions going in. Most of them were shattered within the first day.

The Legal Situation — Then and Now

The legal framework for American travel to Cuba has always been complicated, and it continues to shift. The short version as of our sailing: American “tourism” to Cuba was technically still prohibited under the trade and financial embargo enacted after the Castro revolution, because the Cuban government controls the tourism industry — meaning tourist dollars flow to the government — which the embargo prohibits. President Obama’s executive orders opened a significant loophole through the people-to-people program, which allowed Americans to visit Cuba as part of organized educational and cultural tours operated by OFAC-compliant US entities. You couldn’t go independently; you had to book through a compliant operator. We did, and the tour structure that resulted — focused on history, culture, and direct interaction with Cubans — turned out to be a better way to experience the country than unstructured wandering would have been anyway.

Getting There

Clearing immigration at the port of Havana was a breeze. We got through the checkpoint with barely a flip of the passport. The security staff on our own ship paid more attention to our identification than the Cuban immigration officials did. My first impression upon arriving in Havana was one of mild surprise: the female immigration officers wore black fishnet stockings. Quite stylish. I wasn’t expecting that.

Cuba requires a visa, which our tour operator handled. It arrives as a loose paper document that doesn’t get stamped into your passport — you must surrender it when you leave the country, so keep it safe. You also pass through metal detectors both entering and exiting the immigration checkpoint. Neither process was difficult.

Cuban currency is another matter. Credit and debit cards are generally not accepted — the US banking embargo makes most American cards useless — and you can’t acquire Cuban currency outside of Cuba. Currency exchange kiosks at the port of entry are the standard approach. The system we encountered used two currencies: Cuban Pesos for residents, and Cuban Convertible Pesos (CUCs, pronounced “kooks”) for tourists. The CUC was indexed at an artificially inflated rate relative to the dollar, amounting to roughly a 17% tax on American currency exchanges. Our guides said there was talk of eliminating the CUC — that has since happened, though the currency situation in Cuba remains complicated by the country’s ongoing economic difficulties. Bring cash. Tip in CUCs or local currency rather than US dollars, which forces your guides and vendors to pay the same exchange penalty you did.

The Good — Cuba’s People and Culture

Perhaps the thing that surprised me most was the openness of the Cuban people we met when it came to talking about their country. Our guides were all clear that they were permitted — and in fact encouraged — to answer any question we had about their government, economy, and history. They didn’t pull punches. They shared the good, the bad, and the ugly with equal candor. Janet had encountered the same openness in 2016, and it was reassuring to see it was still there. Cubans are fiercely proud of their country and their history. They celebrate what works and are patient about what doesn’t. I found that combination harder to maintain in theory than they made it look in practice.

The people-to-people tour structure focuses heavily on Cuba’s history, culture, and arts — which I found far more engaging than I anticipated, partly because I arrived knowing almost nothing. The only Cuba history I could have recited before the trip was the Castro revolution, the Bay of Pigs, and the Missile Crisis. I am certain I was not alone in that, and as an American it is somewhat embarrassing that the average Cuban knows considerably more about our history and culture than we know about theirs. Our guides on the longer bus excursions used the transit time to educate us, and the history they laid out — particularly the depth of African and Spanish colonial influence — was genuinely fascinating.

Cuba’s culture bears two primary imprints: the Spanish colonial legacy — evident in the architecture, the language, the Catholic Church’s presence — and the profound influence of the African slave trade, known as Afro-Cuban culture. In many ways it reminded me of New Orleans, which should come as no surprise since New Orleans was also a Spanish colonial city with a deep Caribbean-African cultural substrate. The Afro-Cuban influence runs through music, religion, and art. The hybrid religion known as Santería blends Spanish Catholicism with African folk tradition in a way our guides described without embarrassment or apology. The music — several genres where the distinctions blur willingly — was a constant presence throughout our visit. Every bar and club we entered seemed to have a house band, and they were all good. Timba, a blend of Afro-Cuban folk, salsa, and American R&B, became my personal favorite. You cannot listen to Timba and stay seated. You will try. You will fail.

The visual arts scene was one of the unexpected highlights. Callejón de Hamel in Havana — a narrow alley in what was once a troubled neighborhood, given over to local artists to display their work — offered paintings and sculptures made from reclaimed everyday objects, including bathtubs and plumbing. Vivid, imaginative, and entirely different from anything in a conventional gallery. In Trinidad we visited the studio of Yudit Vidal Faife, an award-winning artist who incorporates needle work purchased from local artisans into her paintings — a play of color, texture, and shading that even someone as artistically uncultivated as me could appreciate. Yudit owns her studio outright and sells directly to the US market via the internet. She is a specific example of where Cuba’s emerging privatization culture is heading.

The Bad — Cuba’s Dependency Problem

Tourism accounts for the overwhelming majority of Cuba’s GDP — our guides put the figure at 93%, which tracks with what I’ve read elsewhere. As one Cuban told me with some despair, “we don’t make anything anymore.” The dependency on Soviet and then Venezuelan economic support left the country without productive infrastructure when those support structures collapsed. The government recognizes the problem and has been actively encouraging private business development and an expanded tourism sector. They were building a second cruise terminal in Havana when we visited, with berths for additional ships and a goal of multiple ships in port every day. That investment reflects where they believe the economy needs to go.

Thirty percent of the Cuban population was self-employed or working in the private sector at the time of our visit — a figure that would have been essentially zero a generation earlier. In the cities, private enterprise mostly takes the form of restaurants, shops, and bed-and-breakfast-style accommodations catering to tourists. The government had also begun expanding privatization into farming and ranching, and the evidence on the drive through the countryside to Trinidad was encouraging: healthy livestock, roadside produce stands, private butcher shops with well-stocked counters.

The most interesting observation on this topic came from a comparison our tour guides made repeatedly. A guide whose mother was a dean at Havana’s medical school told us her mother’s government salary barely covered basic living expenses. The guide herself — in tourism, where tips supplement a government base — made more in tips in a single day than her mother earned in a month. This pattern repeated across guides: we had a former lawyer, a former engineer, a former university history professor. All had abandoned professional careers where education was free but compensation was nominal, for tourism work where the economic gap between their skills and their government salary created the space for private income. It’s one of the more instructive illustrations of how a socialist wage structure operates in practice.

The Ugly — The Economic Reality

Anyone who advocates socialism should visit Cuba. That is not a political statement — it is an observation about evidence. From the moment you step into Havana, you see what sixty years of socialist economic policy has produced in physical terms. Building facades that were once painted bright with color are crumbling and neglected. The contrast between exterior and interior is striking and deliberate: the government owns all property, but individuals own the businesses and residences that occupy it. The government-maintained exteriors are in terrible condition. The interiors controlled by private individuals — particularly where the owner has private income — are often well-kept. Property maintenance follows the money, which follows whoever actually has a stake in the outcome.

The vintage cars deserve a note because they’re the image most associated with Cuba in American popular culture. They are not preserved out of nostalgia or as a tourist attraction. They are preserved out of necessity. Cuba doesn’t import new cars. Cubans couldn’t afford them if they did. The cars in pristine condition — the photographed 1957 Chevrolets and 1950s Plymouths — are the private taxis operated by drivers whose income from tourists allows them access to parts and paint. The others just keep running because there is no alternative. The romance of the vintage car culture is largely a story about a country that was cut off from automobile manufacturing decades ago and made do.

Cuba has also developed an efficient tourist economy in the street-level sense. Panhandlers were prevalent everywhere we went — less aggressive than what you encounter in most major American cities, but consistent and inventive. Human statues positioned for photographs, musicians playing for tips, women in traditional Afro-Cuban dress with fruit baskets or oversized cigars offering photo opportunities. In Trinidad, a man assessed me from across a square, produced a chalk sketch that bore only the most charitable resemblance to me, and presented it with a request for pesos. I turned him down without guilt — paper is cheap, I didn’t commission the work, and the likeness was not persuasive. He moved on without apparent offense to find a more receptive tourist. I was a more willing participant when I encountered a distinguished elderly Cuban gentleman in his finest clothes sitting quietly in a chair in Trinidad — he didn’t approach me, didn’t hustle me, didn’t have a hat out. When I asked if I could photograph him, he motioned Janet over to join the picture. I left him a few pesos he gratefully accepted. The transaction was entirely on his terms, which I respected.

Havana

Havana is a vibrant city with an even more vibrant nightlife, and it rewards wandering — at least within the structured context of the people-to-people tour. The Cathedral Plaza and Plaza de Armas are the photographed landmarks. La Bodeguita del Medio, where the mojito was supposedly born, and La Floridita, where the daiquiri has a similar origin story, are tourist institutions that the people-to-people program wisely treats as legitimate cultural experiences. We sampled the signature cocktails at both. Ernest Hemingway’s supposed regular patronage of each is folklore, according to every Cuban we asked — he may have dropped in, but he was not the fixture the marketing suggests. His actual residence, the Finca Vigía estate, is a legitimate site: tourists aren’t permitted inside the buildings, but the curators offer to take your camera or phone and photograph the interiors from inside for a small tip. The result is worth having.

Cigars and rum are inevitable topics. The cigar factories around Havana shut down for most of January — if visiting a factory is on your list, plan accordingly. Street vendors offering cigars at remarkable prices are offering counterfeits; state-run cigar stores, which all carry the same prices, are the only reliable source. Our Havana guide steered us to Legendario, one of the better-stocked shops, and I contributed to the Cuban economy without regret.

The rum experience was better than another distillery tour. We visited the Havana Rum Museum and learned the history of Cuban rum-making — including the Bacardi family’s Cuban origins and eventual departure during the revolution to reestablish in Puerto Rico. The highlight of the museum was El Maridaje, a curated experience pairing the flavors of a Cuban cigar, a cup of Cuban coffee, and a shot of rum in alternating sequence. The idea is that each element enhances the others rather than competing with them. I can report that this is not marketing language. It works.

Cienfuegos and Trinidad

Cienfuegos bore the most visible marks of Soviet-era influence of any city we visited. High-rise apartment blocks built in the classic Soviet aesthetic — rapid production, quantity over quality, adherence to the plan — dotted the landscape in various states of deterioration. People still lived in them. Our guide noted, without apparent bitterness, that this was simply the reality.

The excursion to Trinidad required an 80-kilometer bus ride through the agricultural heart of Cuba, which was instructive in its own right. Our guide in Havana had told us that nearly all meat consumed in Cuba is imported, and that staples including rice, beans, flour, cooking oil, and eggs are tightly rationed. Every Cuban receives a government ration of six eggs per month. I spent some time thinking about what American birthday cakes would look like under that constraint. The drive to Trinidad, however, showed encouraging signs of what the government’s privatization push in agriculture was producing: healthy livestock, roadside produce stands, well-stocked private butcher shops operating in the open air without refrigeration — which, as someone who once lived in Turkey, I recognized as entirely normal for a climate where meat doesn’t sit long.

In Trinidad we visited the studio of Daniel “Chichi” Santander, whose great-grandfather founded the pottery workshop the Castro government eventually nationalized — though the family remained and are now well regarded by the government. Chichi demonstrated his work with obvious enjoyment while three young apprentices worked behind a curtain producing the pieces sold to tourists. The speed and dexterity with which he worked belied his age. The craggy-toothed smile suggested someone who has made his peace with whatever life provided and found something to enjoy in it regardless.

Santiago de Cuba

Our final stop was Santiago de Cuba, home to Cuba’s best rum — the Santiago de Cuba label, produced in the old Bacardi factory the Castro government nationalized after the revolution. The rum is considerably more refined than the Havana Club we sampled at the rum museum in Havana. The day included Castillo del Morro, the harbor fortress that still has a working drawbridge raised nightly by a caretaker who stays inside, and San Juan Hill — where the significance of the Cuban-Spanish-American War (Cubans consider it their war, and not unreasonably, since they fought alongside Americans to expel the Spanish) was laid out in some detail by our guide. There is a monument at San Juan Hill honoring American soldiers killed in the battle. The Cubans erected it. I found that worth sitting with for a moment.

A Few Practical Notes

Since our sailing, Cuba’s cellular and internet infrastructure has continued to develop. When Janet visited in 2016, wifi hotspots were scarce and Cubans accessed them only in town centers or plazas. By the time of our visit, cellular service was spreading and a major fiber infrastructure project was underway. The pace of change in this area has only accelerated since. The Cuba you visit today has more connectivity than the Cuba we saw, which has implications for how information flows and how the younger generation engages with the world outside.

On the question of whether Cubans want to leave: our guides were consistent that the government permits Cubans to leave, and that many who do eventually return. Whether that reflects genuine contentment or the limited options available elsewhere was the one area where I felt the guided framing was doing some work. The millennial generation — roughly 40% of Cuba’s population at the time of our visit — was described as more interested in improving Cuba from within than leaving it. I don’t disbelieve the proportion. I’m somewhat more skeptical of the sentiment, at least as a uniform generalization.