Havana was easily the most affable and unpredictable place I had ever been. As I walked around the city, it seemed I was constantly falling into conversations—chance encounters that inevitably altered my plans and led me in unexpected directions.

Case in point: I was walking along the Malecón, the photogenic seaside boulevard that gives Havana much of its visual identity, when a peanut vendor intercepted my path. He greeted me like an old friend, calling me compañero and asking about my activities for the day. Shortly into my Havana visit I had learned to welcome these encounters. No need for the usual tourist leeriness: Habaneros are innately curious and outgoing, an attitude worth emulating. So I stopped to chat with the peanut vendor.

I had just left my hotel, I told him, pointing to the Riviera a block away, and now I was on my way to the Cementerio Colón to see its famously ornate mausoleums and vaults. The peanut vendor approved of my intention to visit the cemetery (and advised me not to miss the firefighters’ memorial therein), but he did not approve of the hotel. The Riviera was, in his view, much too expensive and not sufficiently Cuban. Before he continued on his way, the vendor gave me a packet of peanuts—a gift, he insisted, when I tried to pay. He also gave me a handwritten card bearing the address of a house with rooms to let—his parents’ house. It was now legal, I had learned, for ordinary citizens to rent rooms to foreigners and to operate restaurants in their homes, an initiative the Cuban government had recently adopted to allow for modest private enterprise. The peanut vendor’s parents were trying to make a little money by renting out a spare room. I would find it hospitable and comfortable, he said, and much cheaper than the Riviera.

It seemed like a pretty good idea—forgoing the tourist hotel for a private home. The peanut vendor was right about the Riviera: it was expensive, on par in fact with hotels in Miami Beach. I had wanted to stay there primarily because of the hotel’s connection to pre-Revolutionary Havana—a period of glamor, intrigue, and vice, when mobsters ruled the city and Cuba advertised itself as “a tropical playground.” Reading about the period in a couple of novels—Graham Greene’s Our Man in Havana and Cabrera Infante’s Tres Triste Tigres—had piqued my curiosity. All around the city you could find vestiges of this louche era—hotels, casinos, and nightclubs—some now shabby, some nearly pristine—that imbued Havana with retro allure. The Riviera was one of these vestiges. The mobster Meyer Lansky had built the swanky hotel in the late 1950s, just before the Revolution brought an end to the party. It had not been updated since then, and the musty but gleaming tropical moderne interior looked like a stage set for the Havana scenes in The Godfather II. Cool as this was, staying at the Riviera had its drawbacks, and the peanut vendor had pegged them exactly. Besides being expensive, the Riviera was also cut off from the city around it. Ordinary Cubans could not enter the hotel, and I was aware that staying there meant that I was getting a distorted picture of Cuba. So I decided to leave the Riviera in favor of rooming with the peanut vendor’s parents. Better to stay with a family and learn more about daily life in Cuba.

The next morning, I gave the peanut vendor’s card to one of the many taxi drivers waiting at the cabstand outside the hotel. The driver frowned at the address and called a second driver over for a look. This compañero also frowned at the address. Soon, six or seven drivers got in on the discussion—a typical Havana confab with everyone talking at once. Eventually, the drivers agreed upon a solution, and I was on my to visit the peanut vendor’s parents at last. Or so I thought. Once we got underway, the driver asked me if I was already renting the room or just looking.

Just looking, I said. This revelation gave the driver his opening. He announced that he knew a better place—good family, nice house, great location, and (he added with an implied wink) a pretty daughter. Two daughters. By this point I had figured out that Havana was best experienced through a kind of acquiescence—just go along with whatever suggested itself and something unexpected and intriguing would soon manifest. In Cuba, it seemed, all my plans were fluid, changing moment to moment, such that I could not reliably predict where I would be in an hour’s time or what I would be doing or with whom. I started to insist on the original address then thought, why bother? After all, I owed no allegiance to the peanut vendor and had no reason to believe that his parents’ house would be any better than the one now on offer.

I agreed to check out the place that the driver recommended, and the old taxi lumbered toward this new destination. But the spirit of randomness that sometimes presides in Havana would not let things resolve so neatly. Although the place looked agreeable enough, no rooms were available. The landlady suggested another house—her cousin or somebody—and off we went, only to get lost. Meanwhile, along the way the driver stopped to pick up a few additional passengers, and the four people now in the back seat, strangers to one another only moments before, immediately and eagerly entered into an animated conversation about how best to arrive at the notional address. Sitting up front, I tried to follow along, my Spanish no match for a full-blown Cuban charrette.

The talk was fast-paced, but the denouement was slow in coming. Eventually, one of the passengers, a middle-aged woman clutching a live chicken, realized that the yanqui was looking for a room. She had a bedroom available in her house, she said, and the yanqui was welcome to stay there if he so desired. I gladly accepted the offer, and off we went to the señora’s house, the yanqui paying enough at the end to cover everybody’s fare (though it was never clear to me where the others in the car were headed; they seemed all too content just to ride around to find out what would happen).

I now found myself in Miramar, a formerly elegant section of Havana where the houses were larger and the streets more tranquil than elsewhere in the city. The señora lived in a spacious three-story house; but only the first story belonged to her family. After the Revolution, most of the larger houses (formerly belonging to families that had since fled to Miami) were divided into flats and assigned to multiple families. The señora’s family—five people in all—shared the flat, a tight squeeze. Even with so little space, they had partitioned the largest room in two, creating an extra room that they hoped to rent to foreigners. They had not yet filed the appropriate papers or paid for the license, which meant that I was technically an illegal guest. There were government spies on the block, the señora said, so if the matter came up, I was to say that I was visiting the family. Under no circumstances should I disclose that I was paying the family twenty dollars a night.

Because I was their first American boarder, I was treated as a great curiosity and received plenty of attention from the family, which consisted of the señora—her name was Esmeralda—her husband, two sons, and the wife of the eldest son. For two days, I was their chief entertainment, and our conversations went long into the night. During these conversations, my Spanish—competent in most situations—was put to the test. I generally had a hard time understanding Cuban Spanish (not at all like the Mexican and South American Spanish that I was accustomed to) unless people spoke slowly and deliberately—which almost never happens in Havana, for Cubans do not like to speak slowly. I was forced to concentrate, trying to catch a few key words that would allow me to guess at the gist of the conversation.

Our discussions ranged over a variety of topics, with money and baseball being the recurring themes. The family questioned me about life in the United States, about salaries for different occupations, about fashions, about the cost of various consumer items, and about the political opinions of Americans. Struggling to keep up, searching for the right Spanish words for my answers, I fielded their many questions (often asked simultaneously) and tried to feed their apparently genuine enthusiasm for learning about my daily life back home.

When they asked about my reasons for visiting Cuba, I told them about my interest in the pre-Revolutionary period—especially the famous nightclubs and casinos that had once made Havana a glamorous (and lurid) tourist destination. Hearing this, they all agreed that I should meet Lety and Orlando, the señora’s aunt and uncle. Before the Revolution, these two had worked at some of the biggest nightclubs, Lety as a cocktail waitress and Orlando as a musician. They could tell me all about it. So the next day, I went with Esmeralda on an excursion to another part of the city to visit with her relations.

To get there, we had to take a bus. I offered to pay for a taxi, but Esmeralda said that the bus was a true Havana experience, a good way for me to learn how Cubans live. She was right.

A group of people had clustered on the sidewalk at the bus stop. Upon reaching the cluster, Esmeralda called out, “Ultimo.” A young man answered, “Yo.” Moments later, a new arrival called out ultimo and Esmeralda responded by saying yo. This was how Cubans determined the order for boarding a bus, Esmeralda explained. Rather than actually queuing, the people waiting on the bus formed an imaginary line according to temporal precedence. Upon arriving at the bus stop, you have to ask who is last in line (ultimo). That person responds (yo) and you know that you are to board the bus after the respondent. The next person to arrive at the bus stop follows the same procedure, and it is incumbent upon you to respond yo to the newcomer, who will follow you aboard the bus. And so on.

We waited about ten minutes, during which time some ten or twelve people arrived to engage in this call-and-response exercise. Then the bus came, and the boarding went smoothly, although there were no available seats. Somehow, we squeezed in among the other passengers standing in the aisle. The buses in Havana were rather odd looking. Called camelos (camels) they were actually trailers attached to truck cabs. Despite the stuffy, crowded conditions and the heat inside the camel, the passengers seemed good-natured, even upbeat. They certainly kept up the chatter, which never really ceases in Havana. All around me, there were probably a good ten discussions—lively discussions—going on simultaneously. On a couple of occasions, participants in different conversations appealed to me, as if seeking my insight on some matter that remained inscrutable to me. Clueless, I offered my assent to whatever was said, much to the passengers’ gratification.

When we left the bus at last, we were in an outlying part of the city, a street of concrete-block houses reminiscent of a Florida bedroom community, circa 1950. There were small, fenced-in yards and carports—though few cars were in evidence. For the most part, hammocks and bicycles occupied the carports, with one exception: a mammoth rusted Chrysler from the 1950s. Its wheels missing, the car was propped on concrete blocks. It sat like a stalwart old gentleman in the shade ready to collar a passerby with stories of the good old days.

Esmeralda led me to a pink house, wherein we found precisely such a gentleman seated in a wicker rocking chair, a cane by his side. He was wearing a dapper guayabera shirt. An elderly woman sat on a couch whose cushions were protected with clear vinyl covers. Esmeralda introduced me to Orlando and Lety. In their late seventies now, they belonged to the last generation still alive that had grown to adulthood before the Revolution, a generation that dwindled by the day. They were a living connection to a bygone era.

Hard of hearing and apparently senile, Uncle Orlando sat grinning and disconnected throughout the ensuing conversation. In contrast, Aunt Lety was animated, energetic, and sharp. She was pleased that an American had come to her house. She had always liked Americans, she declared, and she didn’t believe that America was really an enemy. Lety had a very good memory, and when Esmeralda explained that I was interested in learning about Havana nightlife in the 1950s, Lety launched into an animated discourse about how wonderful Cuba had been in those days. I caught only a small portion of her exuberant monologue, but I readily understood Lety’s main point: In those days, Cuba was a paradise. Food was abundant, movie stars came to visit, and everyone was happy.

Lety waxed nostalgic while I sipped homemade lemonade and listened. A warm flower-scented breeze blew through the open windows and door. Now and then the old man coughed, shifted his weight, and kept on grinning bemusedly at the people in his parlor. My attention drifted toward a tabletop clock. Like the other furnishings in the room, it was old and well worn. It kept ticking, its pendulum swinging back and forth, but the hour and minute hands never moved. Our visit lasted hours, but the clock stayed stuck on two twenty-five.

At one point, Lety took out some old photographs to show me, photos of places where she and Orlando had worked—the Tropicana, with its lovely glass arches; the Montemarte with its streamlined art deco bar and stage; the Capri, where movie star George Raft had greeted patrons at the entrance to the casino; the Sans Souci with its exotic garden setting. Each photograph, Lety seemed to think, provided further evidence of a lost paradise. Studying a picture of herself in cocktail waitress attire, she fell silent, the first pause in her steady discourse. Tears came to her eyes. During the momentary silence, I heard a distant grumble of thunder. It was getting on toward late afternoon, when the heat of the day would generate the inevitable daily rain shower.

The tabletop clock still marked two twenty-five.

Collecting herself, Lety flipped through some photos of a young Orlando dressed in Desi Arnaz type outfits, posing with his band mates. He had been a trumpet player in various groups, including the big band of the Sans Souci stage show. He had played with all the great ones, Lety said. Beny Moré. Nat King Cole, Pérez Prado.

At that moment, the old man cackled something and then started singing. Lety laughed with pleasure. “Ah, he heard me say Beny Moré, pobrecito. He loves Beny Moré. All right, papi, we will listen to Beny Moré.”

“Do you know Beny Moré?” Esmeralda asked me.

“Yes, I know the name.”

“Ah, well, Beny Moré is the greatest Cuban of all,” Lety said. “Not only the greatest Cuban singer, I tell you, but the greatest of all Cubans.”

And with that declaration, she took out a record album and placed it on a creaky Soviet turntable. There was a crackle through the old speakers, then big band music and the silky romantic tenor of Beny Moré. It was one of the old songs, a bolero. The three Cubans in the room were instantly transported. They sang along, but softly, as though chary of competing with the greatest of singing voices. I watched and listened. This was soul music, I thought, the music of the Cuban soul.

Halfway through the third song, the thunder intensified. The day darkened considerably, and a strong wind picked up. Thunder boomed and lightning crackled. Then came the first splatter of rain on the tile roof, prelude to a hard tropical downpour. The room’s single low-watt bulb struggled against the gloom. Beny Moré sang on—the rain and thunder seemed to be nothing more than new backing instruments to the music.

At the height of the storm, the electricity failed. The room went dim. Beny Moré was silenced. But after the briefest of pauses, the senile old man—in a quaking, tremulous voice—picked up where the song had left off. And he sang the rest of the song straight through, a voice in the shadows, the words of the old song fixed in his mind no matter how much else had vanished. Lety and Esmeralda joined him. It was extraordinary to hear, sitting in twilight while lightning flashes illuminated the three ghostly Cubans singing a cappella over the grumbling thunder: Cómo fue, no sé decirte cómo fue...

More than anything else I experienced in Havana, this one tableau stands out as emblematic somehow: a nostalgic, bittersweet song of the old days interrupted by a power failure; an aging generation left to sing to themselves.

They sang and sang. Oh, how they sang—imperfectly, but with conviction, undeterred by whatever storms raged outside.