Cuba: Three Trips. Two Sons. One Extraordinary Country
- Aug 6
- 14 min read
Three visits over nearly a decade showed me three different versions of Cuba. The architecture drew me in, the people kept me coming back, and sharing it with my sons became one of the greatest gifts of all.
Recently, I read about two American journalists who had managed to obtain Visas to travel to Cuba during yet another difficult chapter—fuel shortages, rolling blackouts, and people quietly adapting. It immediately transported me back to my own three journeys there.
I realized I hadn’t simply visited Cuba. I’d watched it change.
In late 2014, when the United States and Cuba announced a diplomatic thaw after more than five decades of silence, Cuba suddenly became the place everyone was talking about again.
By the summer of 2015, the embassies had reopened, magazines were running “Go now before it changes” headlines, and commercial flights and cruise ships were lining up to return.
Naturally, two of my favorite travel buddies said, “Let’s go.”
We planned everything — private guides, hotel reservations, and a day-by-day itinerary — then Fidel Castro died in November 2016. Cuba entered an official mourning period. Entertainment stopped. Alcohol sales stopped.
So did our trip.
By the time we rebooked for the following spring, U.S. policy had shifted again. Americans were no longer allowed to stay in government-affiliated hotels, and the visa categories had tightened.
We were now traveling under “Support for the Cuban People,” which meant one thing:
Hello, Airbnb.
I thought I knew what I was heading into. I’d seen the magazine spreads, the documentaries, the iconic photos of candy-colored vintage cars and sun-faded facades.
But nothing prepares you for Havana when you’re actually standing in it — feet on the ground, head spinning, a guide pointing out centuries of history piled one on top of another. Havana’s architecture is basically a layered timeline shaped by every power that ever touched the island.
Spain gave the city its bones — three centuries of colonial baroque plazas, convents, and grand civic buildings.
In the early 20th century, sugar magnates and foreign investors poured money into Havana, building elegant mansions, private clubs, and modern commercial buildings that stretched westward across the city.
That momentum came to a halt with the 1959 Revolution, when many owners fled, and their homes were repurposed, subdivided, or left to weather in the Caribbean sun.
Beginning in the 1960s and expanding through the 1970s and 80s, another force had stamped itself onto the skyline: the Soviet Union. Soviet engineers arrived with their concrete housing blocks and government complexes, dropping cold, rectangular slabs right beside ornate Spanish façades and early‑century mansions. The contrast was surreal — like watching two different centuries argue across the same street.
From the balcony of my first Airbnb, I didn’t have to imagine it. Looking one direction, I saw an elegant Baroque facade. Looking the other, a hulking slab of gray Soviet concrete.
Soviet built building Havana Cuba
I was fascinated.
I've spent more than twenty years renovating and flipping houses, so maybe I was seeing Havana differently than most visitors.
While everyone else was photographing the classic cars...
I couldn't stop looking up.
Cornices.
Ironwork.
Balconies.
Grand staircases.
Ornate building Havana Cuba Ornate building Cienfuegos Cuba
Buildings that still hinted at extraordinary lives despite decades of neglect. The city’s eclecticism feels so singular, so unmistakably Havana. And it’s why, after that first trip with friends, I knew I wanted each of my boys to see it through my eyes — not as a place frozen in time, but as a place still very much alive.
Walking through Old Havana is like flipping through centuries.
The Havana Cathedral, all asymmetry and baroque drama, rises from its square like a weathered sculpture.
havana-cathedral
The Castillo de la Real Fuerza, a 16th‑century fortress built to guard the harbor, still stands with its thick stone walls and watchtower.
In Parque Central, I felt like I was walking through a time warp. Colonial baroque plazas from Spain’s 300‑year rule, the Grand Theatre of Havana, and Hotel Inglaterra — the oldest hotel in Cuba, from 1875 — all with José Martí standing center stage, watching over the city.
In Plaza de San Francisco, the old customs house and basilica open onto a sunlit square that feels more like Seville than the Caribbean. I became oddly attached to one specific statue in this square. Somehow I ended up photographing it more than once over the years.
Plaza-de-san-francisco-havana Plaza-de-san-francisco-havana
In Parque Cristo, everyday life was ambling along at its own pace: children in school uniforms dancing in the square, old men playing dominoes, men on bicycles with wagons attached carrying goods to restaurants and hotels, all against a backdrop of faded, pastel, crumbling buildings.
And laundry fluttering six stories above the street like colorful flags.
Palacio de los Capitanes Generales — once the seat of Spanish colonial power — anchors the city with its arcades, courtyards, creaking wooden floors, and street entertainers on every corner.
Once I stepped into Plaza Vieja, the vibe shifted completely — outdoor cafés, people lingering over coffee, a sunny afternoon that felt almost European.
For a moment I forgot we were the only nation shut out as tourists.
The food on my first trip was less than memorable. My travel friends like to chase restaurant trends, and I don’t know who was curating those for Americans, but we were misinformed. We had one memorable dinner at La Guarida. Thankfully, that would change dramatically on later trips.
Instead of memorable meals, this trip introduced me to Cuba’s underground art scene.
We visited artists in their apartments - not galleries built for tourists, but real homes. If you bought a painting, it wasn’t wrapped at a cash register. It was rolled in brown paper, delivered later to your Airbnb, and payment quietly found its way to relatives living in the United States.
It all felt wonderfully clandestine.
Fusterlandia was a complete surprise. As far as I knew, we were heading to the fishing village of Jaimanitas, just outside Havana, for lunch at a waterfront restaurant. I had no idea one of Cuba's most colorful surprises was waiting just around the corner.
We pulled into a fantasy village started by Cuban artist José Fuster. Beginning in the 1990s, he transformed not only his own home but eventually the surrounding neighborhood into a living mosaic.
fusterlandia-havana fusterlandia-havana
It’s a massive public art installation. It’s not polished. It’s not curated.
It’s alive and worth the stop.
I don’t know why we Americans insist on riding around Havana in a 1950s convertible…
… but we do. So, of course, I did.
Twice.
I’ll admit riding in a convertible while cruising down the Malecon with the sun setting on the Straits of Florida was thrilling. In the car next to us, a couple had just gotten married. They were perched on the back seat in full wedding attire, waving to everyone that passed.
That first trip wasn't about perfect meals or luxury hotels. It was about discovering a city unlike most I experience — a place where astonishing beauty stood right beside buildings literally crumbling in the street.
Somewhere between the architecture, the neighborhoods, the artists, and the people, Cuba got under my skin.
I left knowing one thing.
Someday, I wanted both of my boys to experience it through my eyes.
Cuba with Andrew
When I returned to Cuba a second time, I brought my younger son, Andrew. The plan was to spend a few days in Havana before driving along Cuba’s southern coast.
Andrew was studying Marine Science at the University of Miami and had always been fascinated with wildlife. If there was an opportunity to see an unusual animal, hike into the jungle, or dive beneath the surface, he was all in.
With the help of the same travel curators I had used on my first trip, I built an itinerary I knew he would love.
Before we even left the airport, we met Pablo, our driver for the next nine days. Calling him a driver hardly does him justice.
He was our navigator, translator, money changer, local fixer, unofficial bodyguard, storyteller, and by the end of the trip, our friend. He seemed to know everyone, everywhere. Whether it was finding fuel, introducing us to a local family, arranging a salsa lesson for Andrew, or pulling over because he wanted us to see something special, Pablo quietly opened doors we never could have found on our own.
Cuba is known for rum and cigars, so I arranged an afternoon devoted to both. We learned how cigars are properly rolled, cut, lit, and smoked. Our host explained that a fine Cuban cigar isn’t merely smoked—it is slowly savored, much like wine.
The rum? Yes, please.
The cigar? Once was enough.
We revisited many of the same neighborhoods and plazas from my first trip, but this time I wasn’t trying to take it all in at once. I found myself slowing down and noticing details I had missed before.
Thankfully, both of my boys inherited an appreciation for architecture. Andrew patiently indulged me every time I stopped to admire an ornate doorway, elaborate iron balcony, or weathered facade.
Fusterlandia looked completely different through Andrew's eyes. On my first trip, it had simply been another stop on the itinerary. This time, I slowed down enough to truly appreciate José Fuster's vision.
Murals at Fusterlandia Havana Andrew at Fusterlandia Havana Cuba Pool and Fusterlandia village Cuba
Maybe it was watching my son's reaction. Maybe I had simply returned with different eyes. Whatever the reason, it became one of the highlights of the trip.
What began with one artist decorating his own home has grown into an entire neighborhood transformed by mosaics, sculptures, and hand-painted tiles. Fuster was still actively working there, continuing to add to the sprawling creation that had become his life's work.
As we left Fusterlandia, we stumbled upon a mural covering the side of an abandoned building seemingly in the middle of nowhere. Neither of us expected it, and that was part of the fun.
Having lived amid Miami's thriving street-art scene, Andrew immediately appreciated Cuba's bold murals and unexpected public art. Before long, every walk became a scavenger hunt. We ducked down side streets searching for hidden murals, wondering who had painted them, why they had chosen that particular wall, and what story they were trying to tell.
On the Road with Pablo
As we prepared to leave Havana, Pablo quietly loaded several gasoline cans into the trunk. I knew fuel shortages existed, but I hadn't realized just how serious they were. He had waited hours in line to fill the car and, as a professional driver preparing for a long trip, had managed to secure enough extra fuel to carry with us
.
I was suddenly very grateful for those cans.
Every morning, before we had even buckled our seatbelts, Pablo would reach for the radio. Without fail, Camila Cabello's "Havana" filled the car as we pulled away. By the end of the trip, we were all laughing and singing along with him.
Even now, whenever that song comes on, I don't think of the radio charts.
I think of Cuba.
And Pablo.
Our route toward the Bay of Pigs took us through the Zapata Peninsula, a UNESCO Biosphere Reserve I had never heard of before planning this trip. Andrew’s love of wildlife dictated our first stop: a crocodile breeding center filled with tanks of baby crocodiles.
Baby crocodile tank Cuba Andrew with baby crocodile Cuba Andrew with baby crocodile Cuba
I spent the entire visit keeping one eye out for Mama Crocodile—and wondering what they did with all these babies once they grew up. As it turns out, many are part of an important conservation breeding program for the critically endangered Cuban crocodile.
Thankfully, they weren't all headed to become someone's boots.
Our destination for the day was Cienfuegos, but first we had plans to meet a local dive guide for something I had certainly never tried before.
Spearfishing for lionfish.
This trip was definitely taking a different turn.
Crocodiles.
Lionfish.
Okay.
The dive was a success, and the Caribbean couldn't have been more beautiful. Our guide carefully removed the lionfish’s venomous spines before filleting our catch on the beach. Andrew helped build a fire using sticks we had gathered while the guide's girlfriend spread enormous tropical leaves on the sand as our plates. She had brought rice and a homemade sauce to accompany the freshly caught fish.
It wasn't the best meal I ate in Cuba, but it was one of the most memorable. Freshly caught lionfish, cooked over an open fire on the beach and shared with new friends—I'd choose that experience over several restaurant dinners from my first trip any day.
Cienfuegos: The Graceful Sister
We spent the next few nights in Cienfuegos in what had once been a grand mansion. A Spaniard was lovingly restoring it as a boutique hotel and was still working on the property while we were there.
I was completely smitten.
The soaring ceilings.
The intricate moldings.
Lobby in Cienfuegos hotel Cuba Tall doors in Cienguegos hotel
The towering doors that nearly reached the ceiling.
Every room reminded me why I can’t resist old houses.
If Havana is Cuba's heartbeat, Cienfuegos felt like its graceful sister.
Founded in Spanish Cuba by settlers largely of French origin, the city later flourished through trade and the wealth generated by the surrounding agricultural region. Its elegant neoclassical buildings have been remarkably well preserved.
The city was almost eerily quiet. I kept expecting a film crew to appear around the next corner because the entire place felt like a perfectly preserved movie set waiting for the actors to arrive.
Even the 18th-century Castillo de Jagua looked as though it had barely aged.
One afternoon, we stopped at Palacio de Valle, an architectural fantasy overlooking the bay. While I admired its eclectic design, Andrew had something else on the schedule.
Pablo had arranged a salsa lesson.
I happily volunteered to sit this one out.
"Wine, please... and don't mind me."
I claimed a table on the rooftop terrace with my camera while a three-piece band played what felt like a private concert for us—or perhaps just for Andrew as he attempted to find his rhythm.
Palacio de Valle
Leaving Cienfuegos, we passed one magnificent abandoned home after another.
Ornate wrought-iron fences.
Wraparound verandas.
Plantation shutters.
Some overlooked the Caribbean, their bones every bit as beautiful as the day they were built.
I couldn't help myself. I mentally restored every single one.
I wanted them all.
Finally, Andrew looked over and laughed.
"Mom, I think the only way you're getting one of these is if you marry a Cuban."
“A Spaniard counts, right?” I joked.
Somewhere along the drive, Pablo turned off the main road without explanation. A few minutes later we were standing in a family's garden watching bee hummingbirds—the smallest birds in the world—dart between flowering bushes.
It wasn't on any itinerary.
It was simply something Pablo knew Andrew would love.
Into the Mountains
On the drive toward Trinidad, we detoured into the mountains of Topes de Collantes for a hike to a cave and a waterfall. We began in the middle of a working coffee plantation surrounded by dense jungle and dramatic mountain scenery.
Topes de Collantes Topes de Collantes
Coffee trees stretched in every direction while the day's pickers bundled freshly harvested beans into heavy plastic sacks and dropped them along the dirt road for collection.
I couldn't help thinking...
If only I knew a coffee roaster.
Surely they wouldn't miss just one bag.
Trinidad
Before our final leg of our trip, we spent one night in Trinidad. It felt small, quiet, and wonderfully artistic. We wandered through galleries where local artists displayed everything from traditional landscapes to provocative contemporary work. It reminded me that Cuba's creativity extends far beyond Havana.
We managed to buy a few small pieces — or at least the ones that would fit inside our suitcases.
Nothing clandestine this trip. Everything completely aboveboard.
A small local market lined the path leading toward Santa Ana Church and its bell tower. Andrew happily climbed all the way to the top, where I could make him out through the tiny uppermost window.
Santa Ana Church bell tower Santa Ana Church bell tower
I happily remained below and took his picture.
Santa Clara
Before arriving in Santa Clara, we stopped at Capiro Hill, overlooking the city, where monuments commemorate one of the decisive battles of the Cuban Revolution.
Our hotel in Santa Clara wasn't exactly memorable from the outside. Functional might be the kindest description. Dinner, however, completely surprised us. Thankfully.
Afterward, we wandered into the town square expecting it to be quiet.
Instead, it was packed.
Children rode bicycles in circles. Teenagers clustered together on benches. Parents and grandparents filled the plaza, nearly all of them holding phones.
Nobody seemed interested in going home.
Pablo smiled.
"The Wi-Fi just came on."
At the time, household internet was still beyond the reach of most Cubans. Getting online usually meant purchasing a prepaid Wi-Fi card and gathering at one of the country’s public hotspots. The cards weren’t inexpensive for local families, and the connections weren’t always reliable.
Suddenly, the scene around us made perfect sense.
The square wasn’t merely crowded.
It had become the community's living room.
Before leaving Cuba, I handed our unused Wi-Fi cards to Pablo. His gratitude surprised me.
They weren't souvenirs.
They were valuable.
It Was His Brother’s Turn
Several years later, when I decided it was finally Austen’s turn to experience Cuba, there was one person I contacted before making almost any other plans.
I opened WhatsApp.
"Hi Pablo... It's Tracey. Any chance you're available for a few days in Havana? I'd love for you to meet my older son."
Pablo said yes.
I knew from the moment he answered that Austen's trip was in good hands.
It was Austen's turn to see the Cuba I loved.
For Austen's visit, I once again chose an Airbnb. Like the apartment from my first trip, it had soaring ceilings, original tile floors, elegant furnishings, and all the architectural details that kept drawing me back to Havana. Both homes had been lovingly restored by owners who had found success abroad and invested in preserving a small piece of the city's architectural history.
Balcony of Airbnb Havana Interior Airbnb Havana Morning breakfast terrace
Each morning breakfast was prepared and served on the rooftop terrace by two local women.
Fresh tropical fruit.
Eggs.
Bread.
Butter.
Strong coffee.
By then I knew enough about life in Cuba to understand that the breakfasts we enjoyed each morning were luxuries the women preparing them rarely experienced themselves. Like most Cubans, they relied on government food rations to feed their own families.
One morning I complimented one of the women on her dress.
"Where do you shop?" I asked.
She smiled.
"You can't shop where we shop."
I never forgot that answer.
Havana looked different this time. Several luxury hotels had risen above the skyline, upscale boutiques catered to international visitors, and something else caught my eye.
Ford F-150 pickups.
Lots of them.
They looked strangely out of place.
Havana had always surprised me with its contrasts—grand colonial mansions beside Soviet apartment blocks, horse-drawn carts sharing the road with shiny new Ford F-150s.
Fuel had become even harder to find.
Pablo routinely waited as long as nine hours in line for gasoline before picking us up each morning.
Because he owned a taxi, he qualified to use the professional driver's line. He would drive us to a museum or neighborhood, return to the gas station to reclaim his place in line—carefully protected by the other taxi drivers—and then wait until I texted him to come back.
Austen's visit was only a long weekend, but we didn't need an itinerary packed with must-see attractions. We wandered Havana one neighborhood at a time, ducking into museums when they intrigued us, lingering over long lunches, and letting the city surprise us.
One afternoon Pablo drove us through Miramar, Havana's former mansion district. Before the Revolution, these were the homes of Cuba's wealthiest families. Today many serve as embassies, government buildings, or cultural institutions.
Even after years of traveling with me—and hearing me stop to admire old houses everywhere from Croatia to Vienna—Austen stopped in his tracks.
"Mom," he said, looking up at one particularly grand estate, "these look like the mansions from old Hollywood."
Exactly.
That was what I'd been hoping he would see.
Cuba wasn't simply a collection of crumbling buildings. It was a country that was once built with astonishing ambition, craftsmanship, and elegance. You just had to look past the peeling paint to imagine what had been.
The one restaurant I couldn't wait to return to was La Guarida. Tucked inside a faded mansion whose sweeping staircase—still marked with the faded “FIDEL” graffiti made famous by the film Fresa y Chocolate—is almost as memorable as the food itself. Bringing Austen there felt like introducing him to an old friend.
Austen at La Guarida stairway Ceiling at La Guarida Restaurant
Havana felt wonderfully alive that weekend. The plazas filled with local families, children rode bicycles through the squares, skateboarders claimed every open stretch of pavement, and people lingered over food from neighborhood vendors.
Cocktails one afternoon were in the famous El Floridita - a legendary bar from 1817 and a favorite haunt of Hemingway. Ok I said. Let’s try his drink - two daiquiris, please.
Floridita bar Havana
Cuba may be famous for daiquiris, but Austen and I found ourselves taking a mojito-making class at a small boutique hotel.
After muddling mint leaves and squeezing fresh lime, I asked the bartender if he knew how to make a frosé.
He looked at me blankly.
"Frozen rosé," I explained.
Since both tourists and Cubans seemed to love frozen drinks, I suggested it might make a fun addition to the menu.
"Show me," he said.
So I did.
He took a sip, smiled, and nodded his approval.
I want to think there's a tiny chance someone ordered a frosé in Havana after we left.
I surprised Austen with dinner and a show at the legendary Tropicana. With an open- air jungle-theatre setting, massive chorus lines and sequined costumes. It was a glamorous cabaret show straight out of old Cuba.
I spent half the show wondering how anyone balanced those towering feathered headpieces - let alone danced in them wearing heels.
The Cuba That Changed
Every time I returned to Cuba, something had changed.
The restaurants were better.
New luxury hotels had appeared.
Wi-Fi was easier to find.
Fuel was harder to get.
Yet the reason I kept coming back never changed.
Cuba still rewarded anyone willing to slow down.
To look up.
To notice the architecture.
To appreciate a meal prepared with limited ingredients.
To admire extraordinary craftsmanship beneath peeling paint.
Somewhere between Miramar's grand mansions, breakfast on that rooftop terrace, another unforgettable dinner at La Guarida, and one last evening beneath the lights of the Tropicana, Austen finally understood what I'd wanted to show him all along.
He wasn't simply seeing Cuba.
He was seeing it through my eyes.
And maybe that was the greatest gift Cuba had given me.
Not that I had the chance to visit three times.
.
But that I had the privilege of sharing it with the people I love most.