Inside post-Castro Cuba: Can this complex country can ever be truly free?

Capitalism is making small inroads, yet many Cubans still feel prisoners of the old regime

Classic American cars are often used as taxis in Havana (Getty Images)

On the plane, something odd but also vaguely magical-seeming happened: namely, nobody knew what time it was. Right before we landed, the flight attendant made an announcement, in English and Spanish, that although daylight saving time recently went into effect in the States, the island didn't observe that custom.

As a result, we had caught up – our time had passed into sync with Cuban time. You will not need to change your watches. Then, moments later, she came on again and apologised. She had been wrong, she said. The time in Cuba was different. She didn't specify how many hours ahead.

At that point, people around us looked at one another. How could the airline not know what time it is where we're going? Another flight attendant, hurrying down the aisle, said loudly, "I just talked to some actual Cubans, in the back, and they say it'll be the same time". That settled it: we would be landing in ignorance. We knew our phones weren't going to work because they were tied to a US company that didn't operate on the island.

The six-year-old sat between us, looking back and forth at our faces. "Is something wrong?" she asked.

"No," my wife, Mariana, said, "just funny." But to me she did the eyebrows up and down.

"What?" I said.

"Nothing," she said, "just – into the zone."

Mi esposa travels to Cuba every so many years, to do movie-related research (she's a film-studies professor) and to visit her mother's family, a dwindling number of which, as death and emigration have surpassed the birthrate, still live in the same small inland town, a dusty, colonial-looking agricultural town, not a place anyone's heard of. To them, even after half a century, it's the querencia, an untranslatable Spanish word that means something like "the place where you are your most authentic self". They won't go on about Cuba around you in a magic-realist way. Nor do they dream of trying to reclaim their land when the Castros die. They tend to be fairly laid-back about politics. But their memories stitch helplessly back to and through that town over generations.

My wife's 91-year-old Cuban grandmother, who lives with us much of the time, once drew for me on top of a white cake box a map of their hometown. It started out like something you would make to give someone directions but ended up as detailed in places as a highway atlas. More so, really, because it was personally annotated. "Here is the corner where my father have the bodega. Here is the alley where the old man used to walk his grandson, in a white suit, and we always say, 'Let's go to watch it,' because he have his pocket full of stones, and when the boy runs, the old man throw and hit him in the legs." She was remembering back through Castro and Batista, back through all of that, into the time of Machado, even back through him into her parents' time, the years of mustachioed Gómez in his black frock coat.

The night I met her, 18 years ago, she cooked me Turkish delight-level black beans with Spanish olives, and flan in a coffee can. She said: "Mira, Yon, at this time" – she meant the early Forties – "they make a census, all the teacher go to have a census in Cuba. We see places nobody know the name. I ride a small horse. One night there is a storm – we pass the storm under a palma. In one house is un enano. You know what is? A dwarf. He say, 'I count half!'." Her stories are like that. You actually want them to go on longer. This is no small thing for me, as my life has evolved by unforeseen paths such that I see more of this abuelita than of any other human being. Neither of us ever leaves the house, and during the day it's the two of us.

Because my wife and her family have living relatives in Cuba, they can get a humanitarian exception that lets you fly direct from Miami. The legal loopholes combining to make that possible must fill hard drives. But you can in fact go that way, if you obtain one of these exceptions or are immediate family with someone who does. I first tagged along 12 years ago. It's hands down the strangest way to travel to Cuba, which you might not expect, because technically it's the simplest. But the airport bureaucracy in Miami was so heavy, at least back then, you had to show up the night before and stay in an airport hotel so you could wake up early and spend the day in a series of bewildering lines, getting things signed or stamped.

One line was for having your luggage wrapped in plastic. A couple of muscly Latin guys in shorts lifted each suitcase or bag on to a little spinning platform, turned it blazingly fast to seal it in industrial-strength shrink-wrap from a roll that looked like it held a landfill's worth and charged you for it. The reasons behind the plastic were not laid out. Later in the waiting area, a woman told us it was to discourage quick-fingered Cuban bag handlers on the other side. They took not gold and money, which few people were foolish enough to pack, but toothpaste and shampoo, necessities. This year, however, the plastic wrap was optional.

There were other post-Bush differences in the direct-to-Cuba zone. The lines had grown fewer and shorter. Most noticeable, the Cubans on our flight – a mixture of Cuban-Americans and returning f Cuban nationals who had been in Florida or DC on visas of their own (some people do move back and forth) – weren't carrying as much stuff. The crowd cast a fairly normal profile. Last time, people had multiple pairs of shoes tied around their necks by the laces. Thick gorgets of reading glasses. Men wearing 10 hats, several pairs of pants, everybody's pockets bulging. Everybody wearing fanny packs. The rule was, if you could get it on to your body, you could bring it aboard. At least five people carried giant stuffed animals and other large toys.

None of that, though, is what makes the Miami-to-Havana flights strange. It's that this most obvious route, more than any of the much longer workarounds by which American citizens can get to the island, lets you feel most fully the truth of Cuba's sheer proximity. It's one of those flights in which, almost as soon as you reach your maximum altitude, you begin your descent, and within minutes you're looking down on a diorama of palm trees growing incongruously in green fields, and within seconds you hit the ground and everyone bursts into applause. The country you land in is too unlike your own to have been reached that quickly, all but instantaneously, and is after all, you recall, on hostile terms with your own. As if you've passed through a warp.

"Why are they clapping?" the six-year-

old asked.

I explained that it was special, coming here. Some of these people, when they left Cuba, might have thought they would never see it again. Some had been hearing about it all their lives and were seeing it for the first time.

"Also, they like to clap and yell," my wife said.

The six-year-old did her philosopher face, gazing out the window. She gets a little dimple on her forehead when the big thoughts are brewing. "Now I'm here," she said.

"Yes, you are."

"And I'm Cuban," she said.

"You are part Cuban, that's true."

"You're not any Cuban," she said, not meanly, just sort of marvelling.

She looks like me, pale with blue eyes and light brown hair and freckles. Yet she has largely been raised day-to-day by intense, dark-eyed Cuban-American women, and their blood is in her, and the history of their family, with all of its drama and all of its issues, has exerted an incalculable influence on who and what she is. At some point in her life, she'll have to figure out what all of that means to her; the whole story and the way she looks will be part of its strangeness. For me it was all behind glass. I felt the sudden separation between us, between the relative depths of what this trip would mean to us, many years on. One of those moments of generational wooziness that come with having kids, like realising there's a part of their lives you won't see.

We landed under searingly vivid skies. The land right around the airport is farmed; we saw a man plowing with oxen. The fertility of Cuba is the thing you can't put into words. I've never stood on a piece of ground as throbbingly, even pornographically, generative. Throw a used battery into a divot, and it will put out shoots – that's how it feels. You could smell it, in the smoky, slightly putrid smell of turned fields. More and more, as we drove, that odour mingled with the smell of the sea.

This was the first time I was in post-Fidel Cuba. It was funny to think that not long ago, there were smart people who doubted that such a thing could exist, ie, who believed that with the fall of Fidel would come the fall of Communism on the island. But Fidel didn't fall. He did fall, physically – on the tape that gets shown over and over in Miami, of him coming down the ramp after giving that speech in 2004 and tumbling and breaking his knee – but his leadership didn't. He executed one of the most brilliantly engineered successions in history. First, he faked his own death in a way: serious intestinal operation, he might not make it. Raúl is brought in as "acting president". A year and a half later, Castro mostly recovered. But Raúl is officially named president, with Castro's approval. Amazing. So now they rule together, with Raúl out front, but everyone understanding that Fidel retains massive authority. What comes after is as much of a mystery as ever.

Our relationship with them seems just as uncertain. Barack Obama was going to open things up, and he did tinker with the rules regarding travel, but now they say that when you try to follow these rules, you get caught up in all kinds of forms and tape. He eased the restrictions on remittances, so more money is making it back to the island, and that may have made the biggest difference so far. Boats with medical and other relief supplies have recently left Miami, sailing straight to the island, which hasn't happened in decades. So, capitalism is making small inroads. And Raúl has taken baby steps toward us: Cubans can own their own cars, operate their own businesses, own property. That's all new. For obvious reasons it's not an immediate possibility for a vast majority of the people, and it could be taken away tomorrow morning by decree, but it matters.

Otherwise, our attitude toward Cuba feels very wait-and-see, as what we're waiting to see grows less and less clear. Earlier this year, Obama said to a Spanish newspaper: "No authoritarian regime will last forever. The day will come in which the Cuban people will be free". Not, notice, no dictator can live forever, but no "authoritarian regime". But how long can one last? Two hundred years?

My wife's people got out in the early 1960s, so they've been in the States for half a century. Lax regulations, strict regulations. It's all a oneness. They take, I suppose, a Cuban view, that matters on the island are perpetually and in some way inherently screwed up and have been forever.

There was a moment in the taxi, a little nothing exchange but so densely underlayered with meaning that if you could pass it through an extracting machine, you would understand a lot about how it is between Cubans and Cuban-Americans. The driver, a guy who said he grew up in Havana, told a tiny lie, or a half lie. The fact that you can't even say whether it was a lie or not is significant. My wife had asked him to explain for me the way it works with Cuba's two separate currencies, CUPs and CUCs, Cuban pesos and convertible pesos (also called "chavitos" or simply "dollars").

When I was last there, we paid for everything in actual, green US dollars. But in 2004, Castro decided – partly as a gesture of contempt for the US embargo – that he would abolish the use of US dollars on the island and enforce the use of CUCs, pegged to the US dollar but distinct from it. This coexisted alongside the original currency, which would remain pegged to the spirit of the revolution. For obvious reasons, the actual Cuban peso is worth much less than the other, dollar-equivalent Cuban peso, something on the order of 25 to one. But the driver said simply, "No, they are equal". "Really?" my wife said. "No… that can't be." He insisted that there was no difference between the relative values of the currencies.

He knew that this was wrong. But he also knew that it had a rightness in it. For official accounting purposes, the two currencies are considered equivalent. He also meant that if you're going to fly to Cuba from Miami and rub it in my face that our money is worth one-twenty-fifth of yours, I'm gonna feed you some hilarious Communist maths and see how you like it. Cubans call it la doble moral. Meaning, different situations call forth different ethical codes. He wasn't being deceptive. He was saying what my wife forced him to say. After it, he was totally friendly and dropped us at one of the Cuban-owned tourist hotels on the edge of Havana.

People walking by on the street didn't seem as skinny. That was the most instantly perceptible difference, if you were seeing Raúl's Cuba for the first time. The island's overall dietary level had apparently gone up a tick. (One possible factor was an increase in the amount of food coming over from the States. Unknown to most people, we do sell a lot of agricultural products to Cuba, second only in value to Brazil. Under a law that Bill Clinton squeaked through on his way out, Cuba purchases food and medicine from us on a cash basis, meaning, bizarrely, that a lot of the chicken in the arroz con pollo consumed on the island by Canadian tourists is raised in the Midwest.)

The idea was to spend some days travelling around, before going to see family. Once you see them, it gets emotional, and after that, sightseeing feels wrong somehow.

The ladies wanted to visit the Havana aquarium before it closed for the day – my wife went there when she was younger – so they took off. The hostility of the hotel workers was to be experienced. I started making up reasons to approach them, just to provoke it and make sure I hadn't imagined it. Loosely speaking, these men and women worked for the government and had zero motivation to be nice to tourists; for me, after years immersed in a may-I-pour-you-more-sweet-tea culture, the contrast held a fascination.

I kept seeing small groups of Asian men get on and off the elevators. That was new. Ten years ago, the only Asian faces you might have seen were in Chinatown. These guys – all men, I saw no women – seemed dressed as inconspicuously as possible, loose-fitting, light-blue jeans and generic polo shirts and sunglasses. The bartender told me that they were here to do business. China was doing "bastante de negocios" in Cuba these days, including in oil, he said. At that moment, a Chinese-made exploratory rig sat about 30 miles off the northern coast. We would be able to see it, he said, driving along the main highway. Cuba has lately been partnering with foreign petroleum companies to explore prospective undersea oil fields. A major discovery would be a mainline to economic independence, that most long-elusive goal of the revolution. So far, though, the wells have come up dry or disappointing.

We scanned for the Chinese-built oil platform the next day, and thought we saw something once, though it may have been a ship. To ride along the coastal road with the windows down was sublime. The gaps between houses kept giving you glimpses of the sea behind. We were driving down the spine of Cuba, into the vast green interior of the island.

I woke up the next day to the sounds of morning pool activity. It was about 8am in Varadero on a warm spring day, which I'm pretty sure is literally Utopia, in f some vague historico-linguistic way: the northern shore of Cuba, that supposedly moved Columbus to call this the most beautiful place human eyes had ever seen. My wife has a thing about going to Varadero when she goes to Cuba. I don't know if she even likes it. She does it for her family. To them it would seem insane to skip it – it was the place they most wanted to go when they lived there – not to go would be like taking a trip to Keystone, South Dakota, and not going to see Mount Rushmore.

Sitting up in my twin bed, I looked over at the queen bed – they were already gone. The massive cafeteria operation swung into motion for only a couple of hours each morning. You had to be there for the stampede, to navigate the omelette and cereal stations, in lines of mainly European tourists and also Brazilians, Argentines and Canadians. (You know when you're meeting a Canadian, because they always ask, in the same shocked tone, "How did you get into the country?". It's an opportunity to remind you that you can't go legally, and they can. And by extension, that they come from a more enlightened land.)

The cook at the omelette station, when he asked where I was from and I told him, put up his fists like a boxer, as if we were about to have it out, then started laughing. He told me that he had family in the United States, in Florida. That's what everyone says. You can't understand the transnationally- dysfunctional, mutually-implicated relationship between Cuba and Miami, that defies all embargoes and policies of "definitive abandonment", until you realise that the line often cuts through families, almost always, in fact. People make all sorts of inner adjustments. I told the man I hated the embargo (the blockade, as they call it) and thought it was stupid, which was both true and what he wanted to hear. He gave me a manly clap-grasp. I didn't go on and say, of course, that I disliked the embargo most because it, more than anything, has kept the Castros in power for half a century, given them a ready-made Goliath for their David.

Thanks to the embargo, when the Castros rail against us as an imperialist enemy, they aren't really lying. We have, in effect, declared ourselves the enemy of the Cuban people and done it under the banner of their freedom, hitting Cuba in a way that, after all, makes only the people suffer, and far from punishing those in power, rewards them and buttresses their story. All this because a relatively small but highly mobilised exile community holds sway in a state that has the power to elect presidents. There was no way to gauge how much of this the man would agree with. We left it at mutually thinking the embargo sucked.

Out by the pool, where my wife and daughter were swimming, I lay on a chaise in the shade. I had black sunglasses on, so after a while I propped myself at an angle at which I could seem to read my book but really be staring at everybody. God, the human body! It was Speedos and bikinis, no matter the age or body type. You would never see a poolside scene in the United States with people showing this much skin, except at a pool where people were there precisely to show off the perfection of their bodies.

The body not consciously sculptured through working out has become a secret shame and grotesquerie in America, but this upper-class Euro-Latin crowd had not received that news, to my distraction. I took in veins and cellulite, paunches and man-paps, the weird shingle-like sagging that starts to occur on the back of the thighs, cleavage that showed a spoiled-grape-like wrinkling, the ash-mottled skin of permanently sun-torched shoulders. All of it beautiful and tormenting. Everybody was stealing looks at one another, envying or disdaining or gazing, like me. We were all inside a matrix of lust and erotic sadness, all turning into versions of one another, or seeing our past selves.

My wife's people come from a small town with a strange name, a rare Spanish word that almost doesn't look Spanish when you see it. The first time I went, before we were married, they made a big thing of me. Yankees almost never appear in this town, unless they are lost. I walked into a stuccoed, leafy house on a quiet street, a house full of loud talking, hands grabbing my arms. Everyone kissed and cried over my wife, whom they hadn't seen since she was a teenager.

They nicknamed me 'Wao', because everything they would tell me, I would say, "Wow". It seemed the appropriate response. Wei-Wei, the abuelita, had come with us, or rather we had gone with her – it ended up being probably the last time she would ever go back – and she sent money ahead of our visit, for them to buy food with. She's always sending money, but this time she sent more, and they laid on pork and all the spices they needed. There was a long table. All of the men were named some version of Rafael, Rafaelito, Rafaelín.

The matriarch, a shy and tiny woman named Haydee (eye-day), presided with bird-like hands, making little apologies. You didn't even have to chew the pork, you could just sort of let it melt. They made chicharrones de viento, wind-crackers, the Cubans' witty name for a kind of poverty-inspired something, frisked up out of salt and flour and a little lard. There was a bottle of Havana Club on the table – the first time I ever saw or tasted it. Knowing only a little classroom Spanish, I struggled to follow their phrases, the swift and expressive but mud-mouthed Spanish spoken on the island.

After dinner, I made the mistake of saying something about a cigar. It wasn't as if I asked for one. I probably said something like, "I hear that your country is famous for its cigars". But they took this as an overpolite way of asking for one, so the hunt began. The shops were closed, but the Rafaels started working on the car. You've heard, no doubt, how in Cuba they still drive working American cars from the 1950s, but this was something else, a Frankenstein made from the parts of about four different cars from the Fifties and one Russian car apparently from the Seventies. They got this creature going, and we started moving through the streets. No headlights – one of them held an electric lantern out the window. It was wired to the cigarette lighter. We needed it badly. Within a mile of leaving the town, we were in the face-close darkness of unlighted rural roads. They took me to a kind of kiosk, an open bar in the middle of a field. Rafelito told me, "This is the puro puro".

Back at the house, half the neighbourhood gathered to watch me huff on this thing, many, I slowly realised, hoping to see me vomit. I stood outside on a back patio, amid chicken coops. The cigar went to my head like thunder. My knees became untrustworthy. But no throwing up. Rafaelito had too much to drink and danced like a crazy person. As a boy, he lost his only brother, drowned in the river. His father, Rafael, approached me with a wagging finger, asking me if I liked the country. Of course, I said, bonita, linda y la gente.

"Si." He looked a little bit like a Cuban Groucho Marx. "Si, te gusta el pais," he said. "Pero, te gusta el sistema?" He pulled the syllables of el sistema out of his mouth like draws of taffy.

Now they were all gone, all the Rafaels. The two older ones were dead from disease, and the youngest one had gone to Miami, I don't even know how. The house was completely different. The ground floor was empty and quiet. Haydee, the old woman f of the house, was still there, even more ancient but seemingly unchanged. I saw her do the same thing now to the six-year-old that she did to my wife those years ago, wrap her arms around the girl and sort of refuse to leave, the way a child would. "I'm keeping her here," she said. "You, go back."

Her husband and son were gone, her grandson gone to Miami. Her other grandson, Erik, half-brother of the boy who left, was still around. Erik's daughter, a young girl with glasses and reddish-brown hair, was as shy as her grandmother. She stayed on the edges of whatever room we were in. My daughter was at my feet, peeking through my legs at her. I could feel their intense awareness of each other, but neither would approach.

After lunch, while Erik was explaining different aspects of his furniture operation to me, my six-year-old came up and started tugging on my shirt. She was mouthing something at me. I kept saying, "Please don't interrupt, sweetheart." She said, "Give me your phone!" and ran off in a huff when I refused.

Barely 20 minutes later we went back upstairs and passed by the little girl's room. She and the six-year-old were sitting on the bed, playing on a phone. It was my wife's. The six-year-old had taught her cousin to play Angry Birds. They were smiling and leaning on each other. For the next two days they were inseparable. They communicated through my wife when they really needed to work something out. They will probably know each other for the rest of their lives, because of that game.

We went out walking the streets, making the rounds to see other family members – to the old church, with its brightly painted statue of St Julian, where Wei-Wei was married and where they remembered her, "la maestra," past the school where she taught and the corner store her father owned, where first she and then her children, my mother-in-law and her brother, grew up playing, before it was taken away – and as we strolled, I had a diminished, doubtless much-flawed version of the old woman's cake-box map in my head. I was hearing her voice-over, all the stories she told me over almost 20 years now, some of them repetitive, but with details emerging and receding.

Her memories of the revolution begin with the shortwave radio, kept in the back room by her husband. Wei-Wei and her husband would gather with friends to listen to the transmissions that the Castro brothers and Che and Camilo Cienfuegos were broadcasting from the mountains, giving assurance that they were about to ride down and liberate the island. For years I assumed that the family had been listening to these speeches in fear – as a couple, they were about as solidly middle-class as could be, a teacher and a tobacco salesman, and their later experience of the revolution involved only pain and regret – but the abuelita surprised me one night, at the table, by saying that, on the contrary, they heard those speeches with great excitement. No one liked Batista, no one who wasn't directly benefiting from his thuggery and favoritism. The powerful charisma of the freedom fighters had percolated down into even quiet, apolitical homes.

There was a night back home, after a long meal, when for the first time after knowing her for so long, I got a bit pushy with her – asked her follow-up questions instead of just mm-hmming – and she gave me a description of what it had actually been like to watch this optimism turn to fear, and something worse, what that had actually looked like. When the milicianos first came from the mountains, she said, "they come to say hello with this necklace made of pieces of wood and a gold cross". They mugged for the cameras with these crosses in their teeth. I asked why. "For you to look at. To pretend that they are Christian. That they believe in God."

"Everybody cooperate with Fidel," she said. "Everybody was happy that we had the opportunity to have all the freedom that he promise." She taught adult literacy classes at night.

Change came with the arrival of the comites, one house per block, appointed as the government representative for its households. The rapidity with which that degenerated into spying had been breathtaking. Within months, they were taking children aside at school and asking them about their parents. The parents started pulling the children out. The first non- political families started to flee. People betrayed their neighbours to the comites. A woman who lived in the neighbourhood, a woman named Solita, "somebody accuse her of having fried pork in her house. And they make – she was a teacher – they make a public, ¿Come se llama? Juicio?" Trial. "Exactly. Accusing her of having pork."

My wife's grandfather had let it be known that he was against the Castros – not because he had preferred Batista; in fact, the family had some obscure connection, that I've never been able to get anyone to be forthcoming about, to one of the other revolutionaries in the mountains, a rival who was executed not long after the uprising – in any case it was known that the family's sympathies did not lie with the Communists. "I remember one time we going to the farm," she said, "and when we was coming back, we stop in Mario's grandmother's house, and we saw my brother passing on the road very fast. We get scared. We say, 'What happened?'. He says, 'The police is going to ask for, getting into your house'. And at this time we was already saving some American money to come here. And you believe or not? The first thing that I do in the house was burning the dollars. To be sure that they don't find it out."

The party came and took away the family business. They took the store. They took the car, covered in tobacco advertisments. They took "a house of birds". Not yours anymore. They took a little dog, named Mocha. They took pictures off the wall. They came in and counted the number of pictures, and took a certain percentage of them. Absurd things. They took away the family's tiny beach house in Playa del Rosario, "gave it to some fishman". But this succession of losses came to seem indistinct against what was happening outside. The picture had darkened.

"So bad, so cruel all the things that they do it," she said. "The television was on all day long." She meant both that they were watching all day long, and that the revolutionaries were transmitting constantly. There was "a man that the name Blanco," she said. And his trial concerned "if he abuse the farmers, if he do all these things that accuse him to do it". They found him guilty. "Then the people go to the street, singing, 'Paredon, paredon, paredon!' Paredon means 'Kill in front of the wall'. And then they put this in television. And you see the brain of this man jumping out. It was getting gross and gross and gross." She resigned her job, and they essentially went into hiding.

She got her two children out first, my mother-in-law and her brother, on waivers made possible by the CIA-initiated, Catholic-sponsored airlift known as Pedro Pan. The story goes that the CIA started spreading rumours on the island that the government was about to take away the children, raise them in camps. People panicked, and f the planes were waiting to fly them away. The children wound up living with Catholic families all over the United States or, in this case, with an aunt in North Carolina. Eventually, Wei-Wei and her husband got out, through Mexico, and joined the children. But Pedro Pan tore apart many families.

We arrived at the house of some cousins, two twins, small men now in their fifties, one with a moustache and one without, who live with their mother, whom they hover about protectively. Their father died after having walked himself to hospital, after a heart attack. Nobody had a car, nobody's phone worked. The revolution is famous around the world for its health care, but for a Cuban, that care can be hard to access, if you live far from one of the major cities.

The six-year-old and her cousin were sitting on the sofa, ignoring everyone. They were holding up dolls to each other in different poses, sort of: "What do you think of this? Do you approve of this?" We unloaded the presents we brought for the twins. They handed my wife a book of socialist Cuban film reviews from before the revolution, actually a rare and useful book – one of them is a from-home bookseller, and he had come across it somewhere.

As we were standing around he said, "Did you know that my brother" – the one with no moustache – "was on a game show?" They brought forth a VHS tape and started reconfiguring the wires to make the VCR work. Soon a picture of the studio appeared, three contestants behind their buzzers. Felipe to the far left, smiling, looking confident in a short-sleeve shirt. The game had to do with rhyming. They would say, "Two words: one of them describes a fruit, one describes a family member". Answer: lima and prima. Felipe didn't win, but did well enough, as I understood it, to be invited back. He looked on screen like he was having a great time. The show had a carefree attitude, compared with something similar in the United States. The stakes were very low. You can't have games of chance or leisure games involving any amount of money, they said. It was outlawed by the revolution, as part of the purifying backlash against the mob-led casino power. So the prizes were things like a signed poster of a famous Spanish pop singer or a decorative mirror.

Before we left the country, we spent a last day and night in Havana. Heaven weather. There is a Havana – this was the second time I saw it, a confirmation – that cannot be captured on photographs, because it involves a totality of light from symphonic Caribbean clouds and the way they play on the whole city, and that appears often enough to represent one of the characteristic faces of the city. The diffused light turns all the buildings a range of pastels. Then as the sun reddens, it becomes rose-coloured.

It was 9.30pm by the time we got back to our hotel. Normally that would have been past the six-year-old's bedtime, but my wife had a telephone interview – meant to happen during the day, it got bumped – so she needed us out of the room for an hour.

Downstairs we sat and listened to the band do the inescapable (in Havana) "Hasta Siempre, Comandante" with its strange lyrics, "Here lies the clear/ The precious transparency/ Of your dear presence/ Comandante Che Guevara". Cats were slinking around. The people going by were of every shade, and many with striking faces.

On the sidewalk a young bicycle-taxi driver named Manuel approached us, a well-built kid in jean shorts and a tank-top, about 19. He said he knew an ice-cream place that was still open. We set out through the night. It was chilly already, and the six-year-old huddled against my side. It was one of those moments when you know that you are where you're supposed to be. If your destiny wavered, it has at least momentarily recovered its track. We ate our chocolate ice-cream at an outdoor bar, under a half moon.

On the way back to the hotel, Manuel asked what I did. When I told him I was a reporter, he said: "You'd hate it here. There is no freedom of expression here". He launched into a tirade against the regime. "It is basically a prison," he said. "Everyone is afraid."

The things he said, which I had heard many times before – that you can go to prison for nothing, that there's no opportunity, that people are terrified to speak out – are the reason I can never quite get with my leftie-most friends on Cuba, when they want to make excuses for the regime. It's simply a fact that nearly every Cuban I've ever come to know beyond a passing acquaintance, everyone not involved with the party, will turn to you at some point and say something along the lines of, "It is a prison here". I just heard it from one of the men who worked for Erik, back in the hometown. I remarked to him that storefronts on the streets looked a little bit better, more freshly painted. It was a shallow, small-talky observation.

"No," he said, turning his head and exhaling smoke.

"You mean things haven't improved?" I said.

"There is no future," he said. "We are lost."

The six-year-old kept asking me what Manuel was saying. I was doing my best to describe el sistema. Interesting trying to explain to a child educated in a Quaker Montessori school what could possibly be wrong with everyone sharing.

There was a time Mariana took me to Cuba, and we went to a town called Remedios, in the central part of the island. It is one of the most ancient Cuban cities. The church on the main square dates from the Renaissance. When it was restored in the 1950s, the workers discovered that under the white paint on the high ceiling was a layer of pure gold. The townspeople had safeguarded it from the pirates in that manner.

We stayed in the home of a man named Piloto. A friendly bicycle-taxi driver, who introduced himself as Max, told us that Piloto worked for the government and rented out his spare room only in order to spy on tourists, and that we should be careful what we said there. But all we ever got from Piloto and his wife was a nearly silent politeness and one night a superb lobster dinner. My most vivid memory of Remedios is of being taken to the house of an artist who lived there, a woodcarver. The bicycle-taxi driver told us that anyone who had "a great interest in culture" needed to visit the home of this particular artist. The next day he took us there, in the afternoon. We rode behind a row of houses that had strange paintings and animal figures hanging in their breezeways.

After what seemed a long time for a bicycle-taxi ride, we arrived at the woman's place. Taking out a cigarette, Max told us to walk ahead, he would wait. At the door of a small, salmon-coloured house, an old woman met us. Not the artist, it emerged. This was the artist's mother. We sat with her in a kind of narrow front parlour, where she made sweetly formal small talk for maybe 20 minutes, telling us every so often that the artist would be out soon.

At a certain moment, a woman appeared in the passageway that led from the front room into the main part of the house, a woman with rolls of fat on her limbs, like a baby, and skin covered in moles. She walked on crutches with braces on her knees. She had a beautiful natural Afro with a scarf tied around it. She was simply a visually magnificent human being. She told us the prices of her works, and we bought a little chicken carving. She said almost nothing otherwise – she had difficulty speaking – but when we stood up to leave, she lifted a hand and spoke, or rather delivered, this sentence. It was evidently the message among all others that she deemed most essential for US visitors. "I know that at present there are great differences between our peoples," she said, "but in the future all will be well, because we are all the sons and daughters of Abraham Lincoln."

Copyright © 2012, John Jeremiah Sullivan.

All rights reserved. A longer version of this article, 'Where is Cuba Going?', first ran in 'The New York Times Magazine'