Cuba Libre:
An Exploration of America’s Little Brother
In 2019, I set out to leave the U.S. for the first time—solo, camera in hand—for a documentary project. I didn’t want to go far, but I craved something unfamiliar. Cuba stood out: close, complex, and cloaked in mystery, shaped by decades of U.S. embargo.
I’d heard stories of old Chevys, vibrant Colonial facades, sweeping tobacco fields, and forbidden rum. But I also read about the risks—no American embassy, no access to wire transfers, limited internet, and strict travel regulations for U.S. citizens. Still, I was drawn in.
I wanted to understand how Cubans live under socialism, how they view the U.S., and whether the Obama-era thaw in relations had made a difference—especially after Trump reversed course. So I packed my gear and went looking for answers.
Cuba Libre: An Exploration of America’s Littler Brother. Written by Stephanie Spence. Images by Stephanie Spence. Copyright Stephanie Spence 2025. I’m available for assignments. Fine art prints are available for purchase. Contact me for inquiries.
Havana, Cuba Skyline, shot from Cristo de la Habana, 2019.
To understand life in Cuba today, I first needed to grasp the complex and intricate history between the U.S. and Cuba.
Following the 1959 Cuban Revolution led by Fidel Castro, the new government began nationalizing U.S.-owned businesses and private property—actions that prompted the Eisenhower administration to impose partial sanctions. In 1960, the U.S. enacted a trade embargo, later expanded under President Kennedy in 1962, aiming to isolate Cuba economically and politically. The embargo, intended to pressure the regime toward democratic reforms, remains in place today and is widely debated for its effectiveness and humanitarian impact.
Tensions peaked with the failed CIA-backed Bay of Pigs invasion in 1961 and escalated further during the 1962 Cuban Missile Crisis, when the Soviet Union deployed nuclear weapons to Cuba. The standoff brought the world to the brink of nuclear war and cemented Cuba's role as a Cold War flashpoint. Ultimately, the crisis was resolved diplomatically, with the Soviets withdrawing their missiles in exchange for a U.S. pledge not to invade Cuba and the secret removal of U.S. missiles from Turkey.
As Cuba aligned with the Soviet Union, it received extensive military and economic aid. But when the USSR collapsed in 1991, Cuba plunged into a deep financial crisis known as the Special Period. With foreign aid having been cut off and the U.S. embargo still in place, the island faced severe shortages of food, fuel, and basic necessities. The government responded by cautiously introducing limited economic reforms, including self-employment and private enterprise, but recovery was slow and uneven.
Meanwhile, thousands of Cubans fled the island under the Cuban Adjustment Act of 1966, which allowed Cuban nationals to seek permanent residency in the U.S. after one year. Many settled in Miami, transforming it into a cultural hub known as “Little Havana.” For those who remained, daily life in Cuba has long been shaped by resilience, scarcity, and a complex relationship with both socialism and the United States.
A woman peaking through bars in her Centro Havana home, 2020.
Growing up in the 1990s, I remember news reports of desperate Cubans building makeshift rafts to cross the 90-mile stretch of ocean to Florida. Many died trying. But under the U.S. “Wet Foot, Dry Foot” policy, those who reached American soil were allowed to stay and pursue residency, while those intercepted at sea were returned to Cuba—unless they could prove a credible fear of persecution. The policy, part of the 1995 revision to the Cuban Adjustment Act, was repealed in January 2017 by President Obama, just days before leaving office, as part of a broader effort to normalize relations with Cuba.
Obama had already made historic moves: In December 2014, he announced the restoration of diplomatic ties with Cuba after more than 50 years of estrangement. In March 2016, he became the first sitting U.S. president to visit the island in nearly nine decades, meeting with President Raúl Castro, attending a baseball game, and promoting cultural and economic exchange.
With commercial flights between the U.S. and Cuba resuming, tourism—Cuba’s most vital industry—was poised for a boom. For the first time in decades, American travelers could fly directly to Havana, bringing money and opportunity to Cuban entrepreneurs. Before this shift, U.S. citizens had to route their travel through third countries like Mexico, risking fines or scrutiny upon return.
At the time, there was a buzz: “Go now—before it changes.” So I did. Alone, with a camera and curiosity, I went to see the island the world said was frozen in time.
1950s Opel Rekord, Chinatown, Havana, Cuba, 2019.
I traveled to Cuba in 2019 and again in 2020 under the U.S. visa category “Support for the Cuban People.” This license, issued by the U.S. Treasury Department, allows Americans to visit Cuba legally, provided they maintain an itinerary that supports privately owned Cuban businesses rather than the Cuban government. Travelers are required to participate in at least six hours of qualifying activities per day and retain records for five years, in case of an audit.
Under the terms, I avoided government-run hotels—many of which are owned by military-affiliated groups—and instead stayed in casa particulares, rooms rented from Cuban families through platforms like Airbnb. I dined at private restaurants (paladares), hired independent drivers, and booked Cuban photographers as local guides in Havana, Trinidad, and Viñales. They acted as translators and cultural interpreters, and in many cases, became lasting friends.
Cuban hospitality stood out. Despite language barriers, the people I met were warm and open, welcoming conversations, posing for photos, and often expressing fondness for Americans. “We love the people, not the politics,” one guide, David Martínez, told me. “Obama was good for Cuba. Trump made things harder.”
Indeed, while the Obama administration reopened diplomatic ties and relaxed travel and trade restrictions beginning in 2014, much of that progress was rolled back under President Trump. Starting in 2017, the administration tightened rules around travel and business with entities linked to the Cuban government. In June 2019—days before my second visit—Trump banned U.S. cruise ships from docking in Cuba. That fall, new restrictions capped remittances from Cuban Americans to relatives on the island. Then, in January 2021, the U.S. reinstated Cuba's designation as a “State Sponsor of Terrorism,” reversing its removal under Obama in 2015.
For Cubans, these shifts had real economic consequences—shrinking tourism, limiting financial support from abroad, and further isolating the island. But despite the tension, many Cubans continued to draw a clear distinction between the American people and American policy.
A woman makes breakfast and smokes outside her building, Centro Havana, Cuba, 2019.
During my two weeks in Cuba, I heard firsthand accounts of the Special Period—a period of profound economic crisis that followed the collapse of the Soviet Union in the early 1990s. “We barely had food or fuel,” said David Martínez, a Havana local and one of my photography guides. “We rode in trailers with whatever gas was available. My mother raised me alone after my father died. She encouraged me to learn English so I could earn money from tourists.”
David completed his mandatory military service—required of all Cuban citizens under the constitution—before pursuing a degree in IT at the University of Havana. He now splits his time between freelance tech work and guiding tourists. He taught himself English using a pirated copy of Rosetta Stone.
Despite economic hardship, Cuba has made significant strides in education and healthcare. The country has a strong university system and produces a high number of doctors per capita. Medical care is free and universally accessible, and during the COVID-19 pandemic, Cuba even developed its vaccines. Still, systemic challenges remain: salaries are low, and professionals are often underpaid. The average monthly income is around USD 50.
Many educated Cubans turn to tourism for supplemental income. “I’m a physician,” one taxi driver told me. “But this is how I support my family.” I learned it’s common for doctors to moonlight as bartenders, professors to rent out rooms to tourists, and engineers to guide walking tours—all for the opportunity to earn in cash and collect tips.
Cuba’s economy remains largely state-controlled, with subsidized healthcare, housing, and education. Basic goods are rationed, but shortages are a routine occurrence. “It’s never enough,” David said. “People are hungry. There’s not enough cooking oil, meat, or toilet paper.”
In Havana, I saw long lines outside government stores and banks. Though I couldn’t shop there due to U.S. travel restrictions, I noticed the stark imbalance: shelves stocked with one item, empty of others, and no certainty of what would be available tomorrow. It was a visible reminder of life under economic strain.
A relaxing man overlooks those waiting in the queue, Centro Havana, Cuba, 2019.
Beyond government-run stores, I found a range of privately owned markets in Cuba, selling fresh produce, meat, flowers, and other goods. These small businesses emerged from economic reforms introduced during the Special Period, when Cuba legalized certain forms of self-employment and allowed farmers to sell directly to consumers. The move was part of a broader effort to adapt the economy while preserving the country’s socialist foundations.
Today, Cuba’s economy operates as a hybrid of state-owned enterprises, cooperatives, and independent businesses. Ration cards aren’t accepted at private markets, so any extra income allows Cubans to supplement their state-provided goods with additional food and supplies.
Many storefronts double as homes, with families selling coffee, street food, rum, cigarettes, and other essentials from their front windows. But opportunities for extra income are limited, and economic mobility varies. “Some people are just lazy,” David remarked, reflecting a sentiment often echoed in debates about socialism’s effect on motivation and productivity.
A woman sells coffee and sandwiches in front of her building, Centro Havana, Cuba, 2019.
A street market, Old Havana, Cuba, 2019.
A street side meat market, Centro Havana, Cuba, 2019.
When I asked David how he acquired a Nikon DSLR in a country struggling to stock grocery shelves, he smiled. “An American friend,” he said. I recalled the plastic crates I saw being loaded onto flights in Fort Lauderdale—goods transported by Cuban Americans with proper visas, bringing supplies to family back home. For the average Cuban without overseas connections, a high-end camera like David’s is out of reach.
Cuba’s economy, though active in imports and exports, is limited by geography, scale, and decades of U.S. trade restrictions. Without access to U.S. ports, technology and machinery often come from farther afield, driving up costs. New cars and consumer electronics are available in Cuba, but they’re scarce and expensive, further restricted by government regulations and low average wages.
I asked David if he had ever considered leaving. “For work, once,” he said. He’d traveled to China on assignment through Cuba’s state-run IT sector. The country’s telecommunications company, ETECSA, sometimes contracts workers abroad. “I thought about staying. People do that. They’re sent for work and don’t return, especially doctors. But I couldn’t leave my mother.”
Passports, he explained, are another obstacle. “They’re expensive and hard to get. Mine was canceled. Some people pay bribes. I want to move to Spain, but most Cubans will never leave.”
His words landed heavily: They don’t want you leaving. Travel restrictions, high costs, and bureaucratic hurdles create invisible borders. For many Cubans, the island isn’t just home—it’s a place they may never be able to leave. As an old Chevy rumbled past, the charm of a “nation frozen in time” took on a more sobering meaning.
Bus stop, Vedado District, Havana, Cuba, 2019.
A woman simultaneously uses a cell phone and landline, Centro Havana, Cuba, 2019.
As I learned more about Cuba’s labor, agricultural, and communications systems, I began to examine its human rights landscape, particularly freedoms of expression, the press, and political participation. Compared to democratic societies, Cuban citizens face significant restrictions.
Freedom of the press is minimal. Nearly all media outlets are state-owned and operate under the control of the Cuban government, which censors content that contradicts official narratives. Independent journalism exists but is small in scale and often subject to harassment, surveillance, or other forms of pressure. International human rights organizations have consistently flagged Cuba’s lack of press freedom as a concern.
Freedom of assembly is also tightly controlled. Public protests critical of the government are rarely tolerated, and political dissent is often met with suppression. Cuba is a one-party state, and the Communist Party of Cuba (PCC) is the only legally recognized political organization. Political pluralism is not permitted, and meaningful electoral competition does not exist in the way it does in multiparty democracies.
While Cuba guarantees access to education and healthcare, its system remains highly centralized, and civil liberties—especially those related to political expression and independent media—are severely constrained.
A man reads a nationalist newspaper, Centro Havana, Cuba, 2019.
Despite economic hardships and restricted freedoms, the Cuban people remain remarkably resilient and take pride in their homeland. Many described their island as "muy tranquila"—very peaceful—and it was. Cuba is wonderful: vibrant, musical, and unlike anywhere else.
Classic American cars in bold colors cruise past crumbling yet majestic colonial architecture—reggaeton and salsa spill from alleyways, mingling with the scent of incense drifting from Santería shops. The atmosphere is both worn and enchanted—a place shaped by history, spirit, and unmistakable charm.
Basketball court, Centro Havana, Cuba, 2020
Santeria shop, Vedado Disctrict, Havana, Cuba, 2020
Stairs to La Guarida Restaurant, Old Havana, Cuba, 2019
The vintage cars and weathered buildings that give Cuba its iconic aesthetic take on a different tone when viewed through the lens of economic hardship. Much of this charm is a byproduct of the U.S. embargo, which has severely limited Cuba’s ability to trade freely, access modern goods, and import construction materials. As a result, many Cubans rely on decades-old vehicles and live in deteriorating buildings that lack essential repairs.
In parts of Havana, living conditions are harsh. Families are packed into small, often unsafe apartments. Streets are littered, infrastructure is aging, and basic services, such as running water, are unreliable. One morning, I discovered there was no water to shower or flush the toilet at my casa particular.
Lifting or easing the embargo could improve access to goods, modernize Cuba's infrastructure, and create jobs. The country has valuable exports, including tobacco, sugar, rum, coffee, nickel, pharmaceuticals, and medical services, that could support mutual economic benefits if trade relations with the U.S. were normalized.
A factory turned apartment building, Centro Havana, Cuba, 2020.
A mechanic's shop. Havana Centro, Cuba, 2020.
During my time in Cuba, David introduced me to people and places I never would have found on my own. “See? You’re becoming Cuban,” he joked, tying a Santería bracelet around my wrist. Between moments of documentation, I immersed myself in the cultural richness around me.
In Viñales, I learned about cigar and rum production, visited a UNESCO World Heritage site, sipped canchánchara, and rode bareback through the countryside with a local named Poncho—despite the language barrier and the tick I unknowingly brought home. In Havana, I learned to make a proper mojito, scribbled my name on the wall of La Bodeguita del Medio, and ate everything from ropa vieja to the best lobster of my life—plus some regrettable attempts at pizza and burgers. I discovered café bombón, rode in colectivos, bicitaxis, and antique cars, and toured El Malecón at sunset.
I played dominoes with strangers, met travelers from Colombia, Ireland, and Belgium, visited art studios and historic nightclubs, and sat where Obama, Anthony Bourdain, and Hemingway once did. I got scammed a few times, wandered a little too freely, and was reminded by a worried host to be more cautious.
In Trinidad, I danced salsa, swam at untouched beaches, navigated cobblestone streets, and survived the worst food poisoning of my life—only to be locked in by my hosts who feared I had COVID-19. I was scammed again by a woman asking for milk money. Still, it was an adventure I wouldn’t trade—and one I’d repeat in a heartbeat.
Tobacco country, Vinales, Cuba, 2019.
Despite Cuba’s vibrant culture, decaying beauty, and the unforgettable adventure I experienced, the hardship of everyday life is impossible to ignore. “Can you imagine?” David often asked, describing the daily challenges faced by Cubans: scarcity, inflation, and unreliable access to basic goods. Was this the future Fidel Castro envisioned?
Images of Fidel and Che Guevara—symbols of the Cuban Revolution—remain ubiquitous, appearing in murals, shop windows, and street slogans like “Soy Fidel” (“I am Fidel”). Whether these are expressions of lingering pride or simply remnants of outdated propaganda is unclear. More than six decades after the Revolution, its promise of prosperity remains largely unfulfilled.
Cuba was particularly hard hit during the COVID-19 pandemic. Border closures halted tourism—the country’s primary source of income—deepening economic strain reminiscent of the Special Period. Public frustration grew, and rare anti-government protests erupted in 2021, signaling a rising tide of discontent.
After taking office in January 2021, President Joe Biden expressed a willingness to revisit U.S.-Cuba policy and reconsider some of the restrictions reimposed under the Trump administration. But progress has been slow, and the Cuban people continue to bear the weight of a complex, deeply entrenched system.
A little boy smiles from a shop window. Che Guevara overlooks. Centro Havana, Cuba, 2019.
In 2023, David fled Cuba, crossed into the U.S. through Arizona after passing through Mexico, was briefly detained, and eventually released. He now lives in Miami with his wife and son, working in IT under a legal work visa. He has an apartment, a car, and a new life—an outcome still out of reach for most Cubans.
David never obtained a passport and had to leave his mother behind. He continues to work toward reuniting with her in the U.S. His story is one of rare opportunity, determination, and sacrifice.
For now, the island remains as I left it—decaying yet beautiful, filled with resilience, color, and the unshakable spirit of its people.
The images in this gallery were created in June 2019 and March 2020.
I’m available for assignments. Fine art prints are available for purchase. Contact me for inquiries.
