New Year’s in Cuba: A Journey Back in Time
December 2024: Cuba has long been one of my favorite countries in the Americas. Despite enduring over 60 years of communism and crushing sanctions, its people remain kind, resilient, and full of life. There’s a timeless quality to Cuba—a country untouched by heavy industrialization, where classic cars still roam the streets, Soviet-era tractors and trucks rumble through the countryside, and farmers in straw hats puff on giant Cuban cigars.
Visiting Cuba as an American has never been easy, and only in recent years has it become legally possible under specific restrictions. My first trip, two decades ago under Fidel Castro’s regime, was done without permission. Back then, I stayed with a Cuban family, visited the Bay of Pigs invasion site, and explored the wild caves of Viñales. Now, with Castro gone but a communist government still in power, Americans can visit as long as we support local businesses rather than government-run hotels. That was something I was happy to do.
Knowing the U.S. presidential elections were just months away, I couldn’t ignore the possibility of Trump being re-elected. Given his historically hardline stance on Cuba, American tourism could soon be halted or become far more restrictive. With this in mind, I decided to book a December trip with my family to celebrate New Year’s in Cuba while we still had the chance.
Originally, I had hoped to visit Isla de la Juventud, a rarely explored Cuban island. I wanted to see the ruins of the prison where Castro had been held as a young revolutionary and dive in the island’s pristine coral reefs. However, the logistics—long ferry rides, unpredictable ticketing procedures, and the challenge of traveling with a baby—made it too complicated. Instead, we based ourselves in Trinidad, a UNESCO World Heritage town on Cuba’s southeastern coast, with just one night in Havana.
Cuba did not disappoint. Like before, it left me wanting more. Trinidad was the perfect choice—its cobblestone streets, vibrant colonial architecture, and warm, welcoming atmosphere made the trip both relaxing and immersive. While I missed out on Isla de la Juventud, staying in Trinidad made traveling with my family far more manageable.
Cuba Today
Cuba’s Complex Reality: Between Resilience and Hardship
Cuba remains a communist country where human rights are heavily restricted—not as extreme as North Korea, but still a place where internet access is limited, the press is censored, and government control is ever-present. Only in recent years have Cubans been allowed to own cell phones and access the internet, though speeds are slow and restrictions remain. Many circumvent these barriers with VPNs.
The economy, in shambles for decades due to communism’s inefficiencies and corruption, has only worsened under U.S. sanctions, which pressure other countries to comply. The COVID-19 pandemic further devastated the country, leading to widespread blackouts, food shortages, and protests against the government—the largest in decades. In response to economic desperation, the government has reluctantly allowed more private enterprise, evident in the growing number of casas particulares (private homestays).
Driving through Cuba, the impact of these struggles is clear. Cars are rare, roads are eerily open, and commercial advertising is nonexistent—instead, socialist slogans and murals of Castro or Che dominate the billboards. Classic cars from the 1950s still roll through the streets, a testament to Cuban ingenuity and the inability to afford new vehicles.
Before my trip, I researched Cuba’s current hardships and joined a Facebook travel group dedicated to visiting the country. Many members strongly discouraged tourism, warning that blackouts were frequent, food shortages were severe, and traveling there wasn’t for the faint of heart. One traveler bluntly stated:
“Cuba is not a vacation destination; it’s for adventure travelers.”
Another warned that unreliable refrigeration had led to food poisoning for their entire family.
Given these concerns, I felt apprehensive—especially traveling with my 16-month-old daughter. To prepare, we packed portable fans and a stockpile of food for her, ensuring we could handle any disruptions. Cuba is not an easy place to visit, but for those willing to navigate its challenges, it offers an experience unlike anywhere else in the world.
Getting There
Navigating New Year’s in Cuba: Flights, Visas, and the Black Market Economy
When I told people we were spending New Year’s in Cuba, the most common response was, “Can you even go there?” The answer is yes—but only under specific conditions.
To visit legally as an American, we had to select “supporting the Cuban people” as our travel purpose when purchasing airfare. This meant avoiding government-run hotels and ensuring our spending directly benefited locals. Of course, the U.S. government has no real way to verify how tourists spend their money unless they give them a reason to investigate—say, by bringing back a box of Cuban cigars in their luggage.
Getting There: Flights and Visas
With numerous airlines now flying to Cuba, we booked a flight to Havana via Houston on United Airlines. Fortunately, United assisted with our Cuban tourist visa right at the check-in counter, saving us from the nightmare of navigating the electronic visa process ourselves.
Upon landing in Havana, we were greeted by an arrivals hall that was drab, disorganized, and slow-moving. Immigration took time, but the real bottleneck was the single working scanner where all baggage had to be screened. Thankfully, an official noticed we had a baby and moved us to the front of the line.
Outside, our pre-arranged taxi driver was waiting with a sign bearing my name. I had booked the ride through the owner of our casa particular in Havana, where we’d stay for the night. On my last trip, casa particulares were secretive and often illegal, found only through word of mouth. This time, I reserved all of ours through Airbnb, even paying in advance. Despite warnings from some travelers about rising costs, we found Cuba to be very affordable.
The Black Market Economy and Surviving Without Credit Cards
Due to U.S. sanctions, credit cards and ATMs do not work in Cuba. We had to bring enough U.S. dollars to last the entire trip—there would be no way to get more if we ran out.
We quickly learned that small bills were just as useful as large ones. The exchange rate fluctuated wildly, with the official government rate being far worse than the black market rate. Instead of going through banks, we exchanged money privately with our casa particular hosts, getting significantly better deals.
However, since most large purchases in Cuba can be made in U.S. dollars, we only exchanged a small portion into Cuban pesos—just enough for minor expenses. This strategy allowed us to avoid getting ripped off when paying in dollars while keeping our spending flexible.
From flights to finances, traveling in Cuba requires extra preparation and awareness, but for those willing to navigate the challenges, it remains a fascinating and rewarding destination.
Choosing Trinidad Over Isla de la Juventud
Originally, I had hoped to visit Isla de la Juventud, a rarely explored Cuban island with a fascinating history, untouched reefs, and the ruins of the prison where Castro was held as a young revolutionary. However, the logistics quickly became a nightmare—the ferry schedule was impractical, ticketing was a bureaucratic mess, and the thought of navigating it all with a toddler was simply unrealistic.
Instead, I opted for a more manageable and culturally rich experience by focusing on Cuba’s colonial UNESCO World Heritage sites—Havana and Trinidad. This return trip was an opportunity to explore a different side of Cuba from my first visit, when I had spent time in Viñales, Havana, and the Bay of Pigs.
Trinidad, a beautifully preserved colonial town dating back to the 1400s, became our base for exploration. Located about 4-5 hours southeast of Havana, it offered cobblestone streets, vibrant architecture, and a slower pace of life—a perfect contrast to the chaos of the capital.
Our plan was simple: one night in Havana, followed by four nights in Trinidad. We arranged our taxis through our casa particular hosts, making travel surprisingly easy, even with the ongoing blackouts. While I still hope to visit Isla de la Juventud one day, Trinidad proved to be the perfect choice for this trip.
Our path in Cuba during this trip
A Night in Old Havana: Nostalgia and New Perspectives
During my first visit to Havana, I stayed with a family in a Soviet-era apartment on the city’s outskirts, only getting a glimpse of Old Havana. I had loved what little I saw back then and wished I had more time to explore its historic streets. So this time, I made sure to stay right in the heart of Old Havana, booking an Airbnb for one night.
Our apartment was in a century-old Baroque-style building, perched above the narrow, bustling streets filled with classic cars, tricycle drivers, and old men selling bread. The caretaker met us at the door and helped carry our luggage up the worn stone staircase. Inside, we found a quaint and nostalgic space, complete with air-conditioned bedrooms, a cozy living room, a kitchen, and a dining area with an open roof.
At first, I was hesitant about staying in a place with a balcony now that Indie was more mobile, but we figured we could keep her safe for just one night. When we finally opened the wooden shutters, the view did not disappoint—Old Havana unfolded below us, vibrant and full of life.
A Drink with Hemingway: Visiting the Iconic Floridita
There was one thing I wasn’t going to miss in Old Havana—a visit to Floridita, the legendary bar once frequented by Ernest Hemingway. Having grown up reading Hemingway, I felt drawn to this historic spot, known for its rich history, elegant architecture, and, of course, its Cuban rum drinks.
That evening, I managed to slip away for a bit and flagged down a tricycle driver on the street. For a few dollars, he pedaled me through the bustling streets of Old Havana, and ten minutes later, I was stepping into Floridita.
Inside, the bar exuded old-world charm—dark wooden counters, classic bartenders in red jackets, and the hum of conversation mixing with the sound of clinking glasses. I ordered a rum drink and took a seat at the bar, soaking in the atmosphere as a live band played lively salsa music.
For a moment, it felt like stepping back in time—a place where Hemingway’s presence still lingered, and Havana’s soul was alive in every note of the music and every sip of the rum.
A Slow Morning in Old Havana
We slept in and spent the morning rocking in chairs on the balcony, taking in the sights and sounds of Old Havana. Below us, old men pushed their bread carts, calling out in a harsh, nasal accent, “¡Pan dulce!” as they made their morning rounds.
For just $30 USD total, including a tip, we had a huge, freshly prepared breakfast—eggs, coffee, fruit, and bread—delivered right to our table. The cook arrived, prepared everything in our kitchen, served us at the dining table, and cleaned up afterward.
I had heard that Cuba was no longer cheap, but so far, it was proving to be very affordable.
Arrival in Trinidad: A Journey Through Blackouts and Resilience
At noon, our taxi driver from the previous day picked us up—perfect timing, as our apartment’s ancient toilet had just clogged and overflowed. Given its state, there was no chance it would be fixed anytime soon. With that, we set off on a five-hour drive to Trinidad.
The Road to Trinidad: A Glimpse of Cuban Roads
Driving through Havana and onto the main highway, I was struck by how little traffic there was. Most Cubans still can’t afford cars, making car ownership a rare luxury. While I did notice more modern vehicles than on my previous visit, the roads were still dominated by classic American cars, Soviet-era Ladas, and massive trucks from the USSR. Even the buses seemed more modern—a small but noticeable sign of progress.
The drive was relaxed at first, but as we left the highway and entered narrow roads winding through sugarcane plantations, things got tense. Huge Soviet-style trucks with mechanical claws would lurch into the road unexpectedly, and drivers frequently darted around them at high speeds. Our own driver—running behind schedule and heavy on the gas—swerved dangerously, making the last stretch of the journey nerve-wracking.
First Impressions of Trinidad: Not Love at First Sight
When we finally arrived in Trinidad, I’ll admit—I was underwhelmed. As one of the world’s richest sugar-producing centers in the 15th century, the town holds undeniable historical significance. But compared to other Spanish colonial cities I’ve visited, it didn’t immediately strike me as the most beautiful.
Our homestay didn’t help with first impressions either. From the outside, it looked modest and unassuming. However, the owner greeted us warmly and with kindness, speaking mostly in Spanish. Unfortunately, a blackout had just hit the city when we arrived, and our rooms were hot, stagnant, and full of mosquitoes.
Unlike government-run businesses and hotels, most locals can’t afford generators, leaving them powerless during frequent outages. Though uncomfortable, this was part of the real Cuban experience—something we had come here to support.
A Challenging First Night in the Dark
As soon as we stepped into the homestay’s courtyard, our spirits lifted. A lush garden filled the open-air patio, creating a peaceful oasis amid the city’s chaos. After exchanging Cuban pesos, we set out in search of dinner.
The streets were pitch black, illuminated only by the occasional headlights of passing cars or the faint glow of buildings with generators. Walking through unfamiliar dark streets with a baby made me uneasy, but we needed to eat.
We stumbled upon a government grocery store—but there was a catch. It only accepted USD or euros from foreigners. My wallet was full of Cuban pesos, and my dollars were locked in our room. Even water couldn’t be purchased without foreign currency—a stark reminder of Cuba’s economic struggles and its desperate need for hard currency.
Luckily, we found an ice cream shop powered by a generator. The cool air was a relief, and the place was packed with locals escaping the heat. The shop made its own ice cream, which was both delicious and shockingly cheap. They also sold water and beer, making it our go-to spot for the rest of our stay. Every night, we returned for a scoop of refreshing ice cream and some cold drinks.
A Frustrating Lesson in Cuban Currency
That night, still needing a proper meal, we didn’t want to venture deeper into the darkness. The only open restaurant nearby was inside a fancy government-run hotel, powered by a generator. Though I wasn’t thrilled about supporting a state-owned business, we had no other choice.
Inside, the restaurant was nearly empty, yet six servers attended to just a few tables. To my frustration, they only accepted USD—not Cuban pesos. Thankfully, my wife’s mother found some dollars in her purse, so we were able to order.
The hotel manager mentioned that blackouts were frequent and unpredictable, sometimes lasting all day. Concerned about sleeping in a hot, mosquito-filled room with no electricity, I inquired about staying at the hotel. But at $400 USD per night—compared to $50 USD for two rooms at our homestay—it was out of the question.
Growing to Appreciate Our Homestay
In the end, we stuck it out at the homestay, and I’m glad we did. Despite the daily blackouts, the electricity always returned by nighttime, allowing us to sleep comfortably with air conditioning and fans.
Over the next few days, our appreciation for our homestay grew. The owner’s hospitality and warmth, combined with the peaceful garden courtyard, made our stay memorable.
It wasn’t luxurious, but it was real.
And in a place like Cuba, that’s exactly what we came for.
Discovering Trinidad: A City That Grows on You
The next day, we ventured deeper into Trinidad’s old town, weaving through its cobblestone streets, colorful buildings, and hidden alleyways. As we explored, we stumbled upon charming eateries, cozy cafés, and fascinating historic corners that gave the city more character than I had initially realized.
With each turn, Trinidad grew on me. What had seemed modest at first now felt rich with history and atmosphere. I began to appreciate the slow rhythm of life here, the mix of local energy and colonial charm.
Even with three nights in Trinidad, I quickly realized it wouldn’t be enough to fully explore the city and its surroundings. The more I saw, the more I wanted to stay longer, dive deeper, and uncover more of what made Trinidad special.
Indie exploring our casa particular with my music playing in the background
Indie and Paula in a tricycle exploring Trinidad
Falling for Trinidad
The next day, we ventured deeper into Trinidad’s old town, discovering hidden cafés, charming eateries, and intriguing historic corners that had escaped our notice before. The more we explored, the more the city revealed its charm.
At first, I hadn’t been sure about Trinidad, but it quickly grew on me. Its laid-back vibe, colonial beauty, and rich history made it a place I wanted to experience more of.
Even with three nights here, I soon realized it wouldn’t be enough to fully explore the city and its surroundings. Trinidad had far more layers than I had expected, and by the time we left, I knew I’d want to return someday to see the rest.
The Museo de la Revolución in Trinidad features a display of wreckage from an American plane that was shot down during the Bay of Pigs invasion.
Santería in Trinidad, Cuba: When Faith and Fear Cross Paths
A City Shaped by Sugar and Spirit
Trinidad, Cuba, is one of the best-preserved colonial towns in the Caribbean, a UNESCO World Heritage Site famous for its cobblestone streets and pastel-colored buildings. But beneath the charm lies a deep African heritage. Enslaved Africans were brought here in the 18th and 19th centuries to work the surrounding sugar plantations, and with them came Yoruba spiritual traditions from West Africa.
Over generations, these beliefs fused with Spanish Catholicism, creating Santería—a religion that honors African orishas (deities) through Catholic saints. While it shares roots with Haitian Vodou and the traditional religions of Benin, Cuban Santería has its own pantheon, ceremonies, and symbols.
A Chance Encounter on the Street
While exploring Trinidad’s bustling center, I noticed an elderly Afro-Cuban woman dressed in the flowing white garments often worn by Santería initiates. She was part street vendor, part beggar, selling small charms and trinkets.
As we passed, she reached out and gently took our infant daughter’s hand. The gesture appeared warm and grandmotherly, but my mind flashed back to my travels in Haiti and Benin, where I’d learned that, in certain traditions, even a single hair could be used in spiritual rituals—including harmful ones.
I remembered a disturbing conversation years ago with a voodoo priestess who admitted she had once been paid to cast a curse on a child. Whether or not I truly believed in such things, I wasn’t willing to tempt fate. I bought one of her trinkets, hoping to keep the exchange positive.
Inside a Santería Temple
Later, we visited a Santería temple in Trinidad. It was a small, dimly lit space with a palpable sense of reverence. Hand-carved wooden idols stood in corners, and certain spots showed signs of ritual sacrifice—dried chicken blood and scattered feathers.
Rows of simple chairs faced a small altar, but the room was empty except for a quiet custodian who warned us not to touch anything. Creepy dolls were everywhere, including one in a pure white dress with an unnervingly black-painted face.
I learned this figure represented a syncretized saint—sometimes identified with Obatalá, an orisha associated with purity and creation. Devotees bring gifts, light candles, and pray to such figures for blessings, protection, or help in solving life’s problems.
Respecting the Unseen
We left the temple without touching a thing, and I made sure our daughter hadn’t either. Whether it was superstition or spiritual respect, I treated the space as I would an unpredictable ocean—something powerful and best approached with caution.
Santeria Idol Doll
A Relic of Conflict: The Museo de la Revolución in Trinidad
At the Museo de la Revolución in Trinidad, one exhibit stood out—a display of wreckage from an American plane shot down during the Bay of Pigs invasion.
This battered relic serves as a stark reminder of the tense history between the United States and Cuba, particularly during the early years of the Cuban Revolution. Standing before it, I reflected on how this failed invasion shaped decades of hostility, economic sanctions, and Cold War tensions that still linger today.
View of Trinidad from a bell tower at the Museo de la Revolución
Hiking in the Rainforests of Topes de Collantes & Salta Caburni
A Perfect Day in Trinidad: Rainforest, Waterfalls, and White Sands
On what might have been the perfect day—and one of the best of 2024—we embarked on an adventure into the rainforest-covered mountains outside Trinidad, exploring Topes de Collantes National Park. We hired a taxi for the day, seamlessly combining Cuba’s wild landscapes and pristine beaches into one unforgettable journey.
The day was filled with incredible moments:
- Meeting an old Cuban man who introduced us to his pet tarantula, found in the rainforest. He let us take turns holding it—a surreal and unexpected encounter.
- Hiking to the breathtaking Salto del Caburní waterfall—a steep, three-hour round-trip trek through dense primary rainforest and deep into a canyon. The effort was worth it—the idyllic waterfall was absolute heaven to swim in. The challenging climb back up filtered out the crowds, leaving me mostly alone to enjoy the falls in peaceful solitude.
- Ending the afternoon at Playa Ancón, where we dined on fresh seafood and cocktails under a beach canopy, with soft white sand and the turquoise ocean stretching before us.
To cap off the day, we returned to Trinidad for dinner at its most renowned restaurant, indulging in exceptional Cuban cuisine to close out the night.
It was truly a day to remember—one of those rare perfect travel experiences where everything just falls into place.
Afternoon Relaxing at Playa Ancón
A Rare Beach Day—With a Twist
I’m not normally a beach person, but after a long and challenging rainforest hike, it felt incredible to kick back, sip a few cocktails, and savor fresh seafood while sinking my feet into the soft white sand of Playa Ancón.
But not everyone shared my enthusiasm. Indie, for reasons unknown, suddenly became terrified of the sand and water. No matter how much I tried to comfort her, she just screamed, completely overwhelmed.
I had imagined a perfect moment—watching her play in the waves, feeling the sand between her toes. Instead, I was left trying to console a distraught toddler who wanted nothing to do with the beach.
I wish she had appreciated it more, but not every travel moment can be perfect. And honestly, that’s what makes them real.
Day Trip to Valle de los Ingenios
New Year’s Eve in Trinidad: A Journey Through History
On New Year’s Eve, we embarked on another immersive journey into Trinidad’s past, exploring the valley where colonial-era sugar plantations once thrived, fueling the city’s immense wealth for centuries.
With a different taxi driver for the day, we explored the remnants of this bygone era—visiting grand plantation mansions that once symbolized the power and opulence of Cuba’s sugar barons. But what left the greatest impact was venturing into the towns where locals now live—many of whom are descendants of the very slaves who once labored on these plantations.
It was a stark reminder of Cuba’s complex history, where beauty and hardship remain deeply intertwined. As the final hours of 2024 approached, we weren’t just looking forward to a new year—we were looking back in time, reflecting on the past, and gaining a deeper appreciation for the people who shaped this land.
A Surreal Dinner in Trinidad’s Old City
After returning to Trinidad, we had dinner in the old city—at what was, surprisingly, a slavery-themed restaurant. The decor was unsettling by modern standards—walls adorned with shackles, whips, and other bondage devices—and the servers wore clothing resembling what enslaved people once wore. It was a surreal experience, the kind of establishment that would never exist in the U.S., where such themes would be condemned as racist. Yet in Cuba, history is often presented more openly, without the same cultural sensitivities or taboos.
This was also evident in the small, handmade Black dolls sold everywhere, featuring exaggerated African features—another reminder of how racial representations differ across cultures.
Despite the strange theme, the food and drinks were excellent, making for a memorable final meal of the year.
A Quiet New Year’s Eve and One Last Ice Cream Run
As the New Year’s Eve revelry began to ramp up, we decided to head back to our guesthouse early, knowing that a wild celebration wasn’t ideal with a baby in tow. But before calling it a night, we made one last stop at our favorite corner ice cream shop—a ritual that had become part of our stay in Trinidad.
With a few celebratory beers in hand, we returned to the safety and quiet of our guesthouse, ready to welcome 2025 in our own way—reflecting on an unforgettable journey through Cuba’s past and present.
Paula’s mom and Indie relaxing in one of the plantation homes
An old Cuban man I met selling some pieces of scrap metal on his porch
A Glimpse into Cuba’s Resourcefulness
While exploring, I met an old Cuban man sitting on his porch, selling scrap metal pieces—likely to be repurposed by the ever-resourceful Cuban people. In a country where scarcity breeds ingenuity, recycling and reusing materials isn’t just a habit—it’s a necessity.
For decades, Cuba’s economy has functioned on creativity and resilience, with people finding ways to make the most of whatever they have. Watching this man, I was reminded of how deeply ingrained this way of life is—turning scraps into something useful, a skill perfected through years of survival under tough economic conditions.
A Quiet Farewell: Leaving Trinidad on New Year’s Day
On New Year’s Day, we awoke to a sleepy, silent Trinidad. The entire city seemed at rest, with not a soul in sight—except, surprisingly, for our taxi driver, who was not only on time but also sober. Despite confessing that he hadn’t had his morning coffee, he was friendly and engaging, ready for the long four-hour drive back to Havana.
After saying our goodbyes to our gracious host and thanking her for her hospitality, we hit the road. The first order of business? Coffee. At the first opportunity, I made sure to stop so both my driver and I could get a much-needed caffeine boost.
The highway back to Havana was even more empty than when we first arrived. It was surreal—an eight-lane highway with no lane markers, stretching for miles with barely another vehicle in sight. It felt like we had the entire road to ourselves, making for an easy and eerily peaceful drive.
By the afternoon, we were back in Havana, checking in for our scheduled United flight home. A few hours later, we were safe and sound, back home, with memories of Cuba still fresh in our minds.