Luis does a quick, almost reflexive sweep of the street. His voice lowers again, his head bent, close enough to mine that his breath tickles my skin. He doesn’t smell like the expensive cologne I’m used to men wearing. There’s something intimate about the scent of soap and man, layers stripped away between us.

“We live in curious times here,” he says, speaking as though we share a secret. “Throughout history, we’ve always been dependent on an outside benefactor—Spain, the United States, the Soviet Union, Venezuela. When the Soviet Union fell and we entered the Special Period, a bad situation grew worse. Then Chavez came to ‘save’ us, sending Fidel tens of thousands of barrels of oil each day in an unholy alliance. They were friends, and in that friendship, we found ourselves beholden to yet another foreign power. Once Chavez died, we faced uncertainty again. And now we’re opening up dialogue with the United States after nearly sixty years of hatred on both sides—perceived hatred, at least,” he acknowledges. “Castro—Raúl, that is—began loosening restrictions on private enterprise in Cuba because otherwise who knows what would have become of us. And really that was merely a formality, acknowledging black market businesses as legitimate for the first time.”

I’m struck by his comments and even more so by the incontrovertible truth behind them. Signs of Cuban pragmatism are everywhere I look, both in their relations on the world stage and in the daily life most Cubans lead here. The legendary cars like the one we’re sitting in now are of course eye-catching with their bright colors and history, but perhaps more impressive is the amount of work that must go into making them run for over fifty years.

Luis laughs when I tell him so.

“Yes, we’ve learned to become inventors, repurposing everything we can. This car is a luxury. My grandfather was a well-known photographer before he died. The regime liked him, and life was easier. The car was his. For many Cubans, though, something as simple as owning a car is an exercise in all the ways the government can screw you over. Getting gas used to be nearly impossible. So yes, I work hard to preserve the one thing I have.”

“That must be exhausting.”

He shrugs. “It is what it is. In a way, things are better. Having access to the tourists in the paladar has made a huge difference. I have friends who are doctors and lawyers, but also work in the big hotels on their free time because they make a fortune in tips. We all live under the shadow of the almighty Cuban convertible peso.”

“Why is the Cuban convertible peso so important?” I ask, pen poised for his reply.

“Cubans are paid in Cuban pesos. Everyone makes a set level of pesos every month. But having a private business or working in the tourism industry gives you access to the Cuban convertible peso, which foreigners use here. The convertible peso is pegged to the dollar. The national currency is worth a fraction of it. It’s a different world when you’re paid in convertible pesos. Cubans make more serving those who come and go, treating the island as a vacation destination, than they do in careers building infrastructure or helping their fellow citizens. And ironically, there is a substantial difference developing in Cuba now between those who have access to the convertible peso and those who do not.”

I was prepared for the differences between Cuba and the United States, or at least I thought I was, but I truly feel as though I’ve stepped into another world. My sisters and I grew up with every opportunity available to us, never had to struggle financially, never knew the kind of pressures I see here. There’s a different level of poverty in Cuba that suggests that not only is the deck stacked against you, but someone keeps stealing all the cards.

“And yet you still teach,” I say.

“I do. The money is important, yes. And believe me, I have fought hard for us to have the restaurant in our family. At the same time, my students are the future of this country. Eventually, things will change. They have to.”

He says the words with a ferocity that catches me off guard, even as they’re muttered under his breath.

“And now that Fidel is dead?” I ask.

“I’d like to believe things will change, I hope they will, but who knows? Perhaps the infrastructure is too much, his brother too stubborn, the country too entrenched to really change after his death. He hadn’t been running the show for a very long time even before his death, but he still casts a long shadow. Older Cubans, the ones who lived through his particular brand of hell, are reluctant to refer to him by name for fear of the ramifications of speaking ill of him, for fear of the perception that they are criticizing the regime. That trend is changing little by little, but words have power here. Deadly consequences.”

I’m not sure if he delivers the last lines as a warning to me or a reminder to himself.

“From everything we saw on TV, it looked like people mourned him in Havana,” I comment.

“Some probably did. Others put on the show they’ve been participating in for decades now, because it’s expected, because it keeps them and their families safe,” he replies.

Luis gets out of the car and comes around to the side, opening the door for me. Does the chivalry come to him naturally or through his grandmother’s instruction? It’s certainly part of his charm.

Now that we’re out of the privacy of the car, the whispered conversations have ceased, and he’s all business, history professor and tour guide. We begin walking, Luis pointing out sites as we go, his shoulder occasionally brushing mine.

There’s the Capitol building that resembles our own Capitol in the United States. He explains that it’s being renovated, scaffolding dominating much of the dome’s exterior.

A bright red tour bus passes us, kicking up water lying near the curb. Without breaking stride, Luis puts his arm around my waist, guiding me away, his body between mine and the street. It lingers there for a beat before he lets me go.

The Hotel Nacional de Cuba is ahead, the design and entryway lined in palm trees, reminding me of the Breakers back home. We walk past a row of vintage cars and head inside.

Luis walks behind me, silent, as I explore. He seems uncomfortable here, his hands shoved into his pockets, his head bent, his eyes downcast and hiding whatever emotions linger in his gaze. The contrast between the bisected home he shares with his wife, mother, and grandmother, and the tourists’ domain is stark. Thirty minutes pass—we explore the lush gardens, the public rooms, the infamous café bar—and then we leave the hotel behind us, in search of the next landmark.

We walk by the Museum of the Revolution, the old Bacardi building. I’m more interested in my grandmother’s Havana, the sites that formed her love of the city, but I mark my impressions of the other places for the article, my grandmother’s ashes in my bag weighing heavily on my mind.

Havana is a beautiful city shrouded in sadness, yet the remarkable thing is that it’s almost as if the people didn’t get the memo. They laugh, and there’s a jubilant quality to the air. The frenetic pace I’m used to is replaced by an ebullient atmosphere that gives the impression that life is a big party. The Cubans probably have the least to laugh about compared to everyone around them, but they laugh the loudest.

We continue walking, Luis pointing out more sites and answering my questions with thoughtful precision. It’s impossible to walk these streets and not feel a measure of pride as a Cuban for the beauty that is our capital city. The Great Theatre of Havana is stunning architecturally; the Cathedral of Havana is equally so.

I hesitate at the church’s entrance, watching the tourists file in.

“Do you want to see inside?” Luis asks.

“Do you mind?”

He smiles indulgently, glancing over his shoulder and gently guiding me out of the path of a group of tourists. “Not at all.”

I grab a scarf from my bag, covering my shoulders as we enter the church.

Beautiful chandeliers punctuate the interior, the landscape peppered with elegant statues sculpted and carved to exquisite detail. My grandmother and her siblings were baptized here, my great-grandparents married at this very altar. I imagine my grandmother here as a young girl, sitting in the pews beside her sisters, Beatriz whispering and gossiping to Isabel as the priest says Mass.

The sensation of standing in the spot where she once stood, sitting in the wooden pews where she once sat, brings a tear to my eye. And another. This is a piece of my family’s history I didn’t expect to have returned to me.

I don’t realize I’m crying until Luis silently hands me an ivory square handkerchief, his expression somber. My breath hitches, and I stare down at the fabric in my hands, anything to distract myself from his searching gaze.

His initials are embroidered on one corner of the handkerchief, the fabric slightly yellowed with age. I rub my fingers over the letters there, a smile playing at my lips. It seems somehow fitting that a historian would carry a handkerchief, and I have no doubt his grandmother painstakingly embroidered his initials.

“Thank you,” I whisper.

Despite the Catholic Church’s difficult relationship with Castro—his attempts to wholly eradicate religion from the country—there are a few Cubans sitting in the pews praying, their heads bent, rosaries in hand. Tourists mill around us—I recognize two men who were at the Hotel Nacional earlier. Clearly these are the popular spots to see in Havana. I make a few notes about the church on my pad.

I turn away from Luis, lingering over the artwork, exploring the side chapels, attempting to soak in every inch of the beautiful building. I’ve never been particularly religious, but the ambiance adds an air of solemnity to our surroundings.

Luis trails behind me, leaving a few paces between us, and the few times I glance back at him, his gaze is fixed on me and not our surroundings.

“What’s it like to be Catholic in Cuba?” I whisper to Luis once he’s caught up to me, his earlier warning about curbing my words fresh in my mind.

His gaze sweeps across the church before returning back to me. “Nearly as difficult as it is to be Cuban in Cuba,” he replies, his tone dry.