April 2006: Cuba is one of the last remaining Marxist-communist countries in the world and the only one left in the Western Hemisphere. It is also an island that, at the time of my trip, I was forbidden to visit by my own government. These reasons alone made me want to experience it for myself. So, my friend and I traveled to Cuba for six days, entering through Mexico.
The communist system and decades of U.S. sanctions effectively trapped Cuba in the past, preserving it from modern mass tourism and commercialism. This made the experience feel more authentic. Cuba lacked advertisements, as well as American chain restaurants and shops, offering a stark contrast to what I was used to. I was also motivated to visit while Fidel Castro was still alive and in charge. At the time of my visit, he was 80 years old, and he would remain in power for another 10 years.
Fidel Castro, the world’s longest-reigning dictator, was a bull-headed leader who, as the head of a small Caribbean island nation, defied the most powerful country in world history for five decades. This defiance endured despite repeated attempts by the United States to overthrow him, assassinate him, and cripple Cuba’s economy through an embargo. While I didn’t support Castro’s ideology, I was curious to see what life in Cuba was like under his rule. I wanted to hear directly from the Cuban people about their experiences living under his version of communism.
Beyond that, the very fact that I was told I couldn’t visit made me want to go even more—especially because I didn’t agree with the embargo. This is the story of my trip to Cuba.
Yellow line marks my route in Cuba
Cuban and American Relationship
The relationship between communist Cuba and the United States has been strained for decades. Despite being a small island nation, Cuba has had an outsized influence on American foreign policy. When Fidel Castro and Che Guevara led a communist revolution to overthrow the dictator Batista, the world took notice. While I don’t support communism, I can understand the justification for removing Batista. Under his corrupt rule, American mafia bosses controlled Havana, most of the sugar industry was in American hands, and foreigners owned 70% of Cuba’s arable land.
After coming to power, Castro implemented sweeping communist reforms, including nationalizing land across the island. This caused Cuba’s upper class to flee, many settling in Florida, where they became a politically influential bloc advocating for tight sanctions on the Cuban economy. In the decades since, Cuba has relied on communist or socialist allies like the Soviet Union, Venezuela, and Nicaragua for survival. The most infamous chapter in this alliance came during the 1960s when Castro allowed the Soviet Union to station nuclear missiles on the island, bringing the world closer to nuclear war than ever before. The crisis was narrowly averted through last-minute negotiations by President Kennedy.
Efforts to overthrow or assassinate Castro became a hallmark of U.S. foreign policy, all of which ultimately failed. The most famous of these was the Bay of Pigs invasion. My own uncle, a Marine at the time, was waiting in a submarine for the green light to invade Cuba. However, the U.S. withdrew support, leaving the Cuban exiles leading the invasion to be slaughtered or captured.
Over time, America shifted its focus from removing Castro by force to isolating him economically, hoping his people would overthrow him. This strategy included a strict travel ban on Americans. Ironically, Cuba wasn’t opposed to American visitors—on the contrary, they welcomed them. It was the U.S. government that barred its citizens from going. At the time of my trip, there were no direct flights between the U.S. and Cuba, and American credit cards couldn’t be used to purchase tickets. Even traveling to Cuba from a third country could get me in trouble with the State Department.
To visit Cuba, I had to be resourceful. I purchased my flights in cash across the border in Tijuana and flew to Cuba from Cancun, Mexico. I also had to ensure I left no evidence of my visit—no Cuban cigars, no Cuban entry stamps, and no suspicious Mexican exit stamps pointing toward a Cuban trip. To avoid this, I slipped a $20 bill into my passport when leaving Mexico, subtly encouraging the immigration officer not to stamp it.
Arriving in Cuba felt surreal. The flight from Cancun was operated by a Mexican airline and was filled mostly with Mexican and Cuban passengers. The immigration hall in Havana had a distinctly Stalinist atmosphere—intimidating, with dark, oppressive colors. When called to the desk, I stepped into a small, prison-cell-like room where the officer asked a few questions about my visit. Despite the stern setting, the officer was polite, welcomed me to Cuba, and pressed a button. An automatic sliding door opened, and I stepped out into the country.
There was no US embassy in Cuba but the US did have an interests section which was sorrounded by black flags placed around it by the Cuban government. The “Mount of Flags” in “Anti-Imperialism Park” obscuring the US Interest Section’s (now US Embassy’s) electronic billboard
Although I never felt any hostility from the Cuban people during my stay, I did encounter some striking anti-American propaganda. Near the American Interests Section—the de facto U.S. Embassy in Havana—rows of black anti-imperialist flags were prominently displayed, symbolically obstructing the view of the building. Billboards throughout the city carried anti-American slogans, some more dramatic than others. One particularly memorable billboard depicted President George W. Bush as an evil vampire, complete with fangs.
While these displays served as stark reminders of the strained relationship between the two nations, they contrasted sharply with the warmth and friendliness I experienced from everyday Cubans. It was clear that whatever grievances existed between governments, they didn’t extend to the people I met.
Anti-American billboards
Giant Image of Che Guevera-one of the founding revolutionaries of the Cuban revolution
President Bush was not well liked by the Cuban government
One of the billboards depicted both President Bush and a Cuban exile, who had blown up a Cuban plane, killing all those on board. Both were portrayed as Hitler. The Cuban government had requested the exile’s extradition, but this request had been denied.
Havana Homestay
One of the main reasons I decided to visit Cuba was a chance encounter with a Cuban boat guide during a whale-watching trip in Mexico. He invited me to stay with his parents in Havana if I ever visited. I saw this as a unique opportunity to immerse myself in Cuban life and connect with locals, so I gladly accepted his offer.
At the time, Cuban law restricted foreigners to staying in government-sanctioned hotels or guesthouses, where the majority of the proceeds went to the state. My goal was to avoid this system whenever possible and instead provide support directly to the Cuban people. To ensure the family hosting us wouldn’t face repercussions, we had our airport taxi drop us off a few blocks from their apartment building—a stark, concrete communist-bloc high-rise. The elderly husband met us at the corner and led us to their apartment via a rickety, cramped elevator.
The contrast between the building’s exterior and the interior of their apartment was striking. While the Soviet-era complex was visibly decayed and crumbling, their home was spotless, well-maintained, and clearly cared for with pride. From their windows, we enjoyed a sweeping view of the ocean, a surprising luxury amidst such humble surroundings.
The couple couldn’t have been more gracious. They prepared delicious meals for us—despite our insistence that it wasn’t necessary—and welcomed us with warmth and generosity. Our conversations were equally memorable, offering an unfiltered look at life in Cuba. Like many others, they were opposed to communism but felt powerless to challenge it. One poignant observation was their refusal to say Fidel Castro’s name aloud. Instead, they would silently stroke an imaginary long beard whenever referring to him, a precaution borne of years of fear and surveillance.
Adding to the irony of our experience, just beyond their window stood a Spanish-era stone fort. It had reportedly been used by Che Guevara and the Cuban secret police to interrogate and torture political prisoners. The juxtaposition of this grim history with the kindness and resilience of our hosts was a reminder of the complexities of life in Cuba.
Apartments where most Cubans in Havana live and where we stayed with an elderly host couple
Us with our host couple
Dinner time
Spanish era fort in Havana where Che Guevera tortured political prisoners.
While in Havana, we explored the city by bus and occasionally hired private taxis—classic 1950s-era cars that have become an iconic symbol of Cuba. Due to the U.S. embargo and the difficulty of obtaining modern cars, these vintage vehicles remain in use, lovingly maintained and preserved by their owners. Seeing these classic cars everywhere, often in vibrant colors, added a unique charm to our experience and has become one of the highlights of travel in Cuba.
We spent much of our time wandering through the old colonial Spanish section of Havana. Though left in an unrestored state of picturesque decay, the area was undeniably beautiful. Strolling through its narrow streets, we had the chance to observe the daily rhythms of Cuban life—children playing, neighbors chatting, and musicians practicing in the doorways of crumbling yet elegant buildings.
One evening, I visited the Tropicana, a historic nightclub dating back to the American Prohibition era when the mafia ran much of Havana’s nightlife. Today, it’s famous for its vibrant cabaret shows featuring traditional Cuban music and elaborate flamingo dancing. I stayed just long enough to admire the energetic performances and unexpectedly found myself solicited by Cuban prostitutes—a moment that underscored the city’s raw and unfiltered character.
Another unforgettable experience was visiting a cigar factory. Watching skilled workers hand-roll cigars, renowned worldwide for their quality, was fascinating. The precision and craftsmanship involved were mesmerizing, and it was a privilege to witness the creation of such a quintessential Cuban product.
Old havana
Havana Traffic Jam
Classic cars
Classic cars
Classic cars
Daily scene in old Havana
May Day Celebration
By sheer coincidence, our visit to Cuba aligned with one of the biggest celebrations in communist countries—May Day, a day dedicated to honoring workers. The entire city seemed to come alive in celebration. The streets were packed with people dancing, singing, and engaging in various activities that continually surprised and delighted us.
One particularly memorable moment was stumbling upon a group of kids playing baseball near the Capitol building. Their equipment was improvised—sticks served as bats, and they played with a worn baseball coming apart at the threads. Despite the simplicity, their enthusiasm and energy were infectious. At one point, one of the kids hit the ball so hard that it soared straight through a Capitol window, shattering the glass. The children froze for a moment, wide-eyed, before bursting into laughter and running off. It was a small but unforgettable glimpse into Cuban life—full of resilience, resourcefulness, and a touch of mischief.
Giant people mover monster truck used for public transportation
Giant statue of one of the most respected early leaders of Cuba-Jose Marti who helped lead a revolution to overthrow the Spanish colonia masters.
May Day celebration
May Day celebration
May Day celebration
Caving in the Wild Caves of Vinales
In addition to staying with the parents of a Cuban whale-watching guide I had met in Mexico, he also connected me with his friend Humberto, a geology professor with a PhD who taught at a university in Havana. Humberto was also an avid explorer and had visited the caves in Viñales, a region known for its dramatic karst mountains, extensive cave networks, and sprawling tobacco fields. He generously offered to take us to one of the most renowned caves, Gran Caverna de Santo Tomás en Pinar del Río. What I didn’t realize was that his last visit had been over a decade ago.
We met Humberto at his home in an old Havana neighborhood filled with grand but decaying Spanish colonial houses. These homes, once owned by Cuba’s wealthiest, had been redistributed among the working class after the revolution. Despite his impressive credentials as a university professor, Humberto admitted he earned only about $20 USD per month from the government, supplemented by basic food rations and housing. Later, when we tipped him $50 for his time and effort, his eyes welled up with gratitude—it was humbling to witness how much it meant to him.
We took a public bus to the western end of the island, eventually arriving in Viñales. From there, we began our journey, hiking through lush tobacco fields and into the jungle, following Humberto as he searched for the overgrown entrance to the cave. When we finally found it, the entrance opened into the massive Gran Caverna de Santo Tomás, the largest cave system in Cuba and the second-largest in the Americas, still being actively explored by scientists.
Equipped with hard hats I had brought from home and flashlights, we ventured into the cave. Inside, we navigated an intricate labyrinth of dark, damp tunnels, crawling through mud and squeezing into tight passageways. The cave revealed its wonders in vast rooms adorned with sparkling crystals, towering stalactites, and stalagmites. In some areas, dolines—collapsed ceilings—allowed beams of light to filter in, creating surreal pockets of greenery within the cave.
We also encountered unique wildlife, including pigment-free insects, whip scorpions, and translucent white fish thriving in isolated cave ponds. Exploring the vast subterranean world consumed our entire day, and by the time we emerged, it was through a random exit that led directly into a tobacco field.
As we crossed the field, we met local farmers donning traditional straw hats, who warmly welcomed us. They were eager to share their craft, showing us the process of cultivating and curing tobacco leaves. It was a fascinating glimpse into one of Cuba’s most famous traditions.
Afterwards, we hitched a ride back to Viñales, grateful for the experience. It had been an unforgettable adventure through both Cuba’s natural wonders and its rich culture.
Bus stop on a small rural road to Vinales. Since the average person doesnt have a car, public transport is the common way to get around
Hiking to the cave through fields in Vinales
Vinales Mountains
Lake inside the cave
Tobacco field
Tobacco being dried
Tobacco farmer
Daughter of the tobacco farmer
We spent the night in Viñales at a government-approved homestay, a small, modest home in a typical Cuban neighborhood. The family who hosted us was kind and welcoming, offering a glimpse into daily life in this rural part of Cuba.
During our stay, we noticed a large gathering at one of the neighboring houses. Curious, I asked Humberto about it, and he explained that it was a neighborhood watch meeting. These gatherings, held monthly, brought residents together to discuss ways to improve their community. On the surface, the event appeared friendly and collaborative, but Humberto explained its deeper roots in Cuba’s communist system.
Neighborhood watch groups, known as Comités de Defensa de la Revolución (Committees for the Defense of the Revolution), were established to ensure that citizens kept an eye on one another, reporting any unusual behavior or activities to the authorities. While they served practical purposes, like fostering community improvements, they also acted as a mechanism for surveillance and the promotion of government propaganda.
It was fascinating—and a bit unsettling—to witness how deeply the state’s influence permeated even the most ordinary aspects of daily life in Cuba.
Vinales neighborhood street
Snorkeling in Cenotes in the Southern Coast
On our last full day in Cuba, we hired a classic car taxi to take us across the island to the southern mangrove forests, where we visited a nature reserve renowned for its pristine beaches, coral reefs, and freshwater cenotes hidden within the mangrove jungles. We snorkeled in the crystal-clear waters, swimming among vibrant marine life, and also explored the freshwater cenotes, where we encountered tropical fish, massive land crabs, and even a few iguanas. The area was a true natural paradise, a perfect way to end our trip.
Afterward, we headed to the Bay of Pigs, site of the infamous failed invasion in the 1960s. Cuban exiles, with CIA support, attempted to overthrow Castro but were defeated in what became a significant moment in Cold War history. Today, the area is home to a rundown hotel, popular with European tourists, which includes a restaurant offering basic food and notoriously poor service. We also visited a museum and monuments dedicated to the Cuban fighters who bravely resisted the invaders, preserving the legacy of the revolution in this quiet, historical spot.
Freshwater cenote
ocean at the nature reserve
Land crab
Iguana
Like many places in Cuba, the Bay of Pigs was undeveloped, shabby, and uncommercialized. The area still held onto its raw, untouched character, far removed from the mass tourism seen in other parts of the world. When we visited the museum and signed in at the visitor’s log, the curator was visibly surprised to see American tourists. She made a comment about it, clearly taken aback by our presence in a country where relations with the U.S. had been historically strained.
Bay of Pigs Propaganda
Bay of Pigs Beach now a hotel for European tourists
Museum honoring the Cubans who fought the Cuban exiles in the invasion
Post card for sale showing Revolutaniries Che and Castro
Returning to the USA
I made sure to eliminate any evidence of my trip to Cuba. I wish I could have brought back some cigars, especially since we visited a cigar factory, but I knew this would be a dead giveaway. On the last day, we departed Cuba without any issues at immigration and flew via Cancun to Tijuana, where we crossed back into the USA through a land border. Since we were crossing far from Cuba, there were no suspicions whatsoever, and we crossed uneventfully.