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 and resilient. There is a genuine sense of timelessness in Cuba, a country untouched by heavy industrialization. It is a place where classic cars still roam the streets, ancient Soviet tractors and trucks are still in use, and farmers in straw hats puff on giant Cuban cigars. Visiting Cuba has never been easy for Americans, and it is only recently that such visits have been legally allowed. My first trip to Cuba, two decades ago under Fidel Castro’s regime-Communist Cuba Under Fidel Castro-Homestay with Cuban Family, Visiting the Bay of Pigs Invasion Site, and Exploring the Wild Caves of Vinales | Venture The Planet, 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 under certain restrictions, provided we avoid government-run hotels and prioritize supporting the Cuban people. Supporting locals is something I always strive to do when I travel, so this seemed like the perfect opportunity to return.
Knowing the U.S. presidential elections were only a few months away, I realized there was a strong possibility of Trump being re-elected. Given his historically anti-Cuba government stance, American tourism to Cuba might either 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.
Initially, I had wanted to visit the Isla de la Juventud, a rarely visited island in Cuba. My plan was to see the ruins of the prison where Castro had been held as a young revolutionary and to do some scuba diving in the island’s pristine coral reefs. However, the logistics proved too challenging with a young baby. The ferry ride had inconvenient hours, and the lengthy procedure of waiting in line to obtain tickets seemed overwhelming. Instead, I opted for the colonial-era UNESCO World Heritage town of Trinidad, located on Cuba’s southeastern coast, as our base of operations. Other than one night in Havana, we stayed in Trinidad for the entirety of the trip.
Cuba did not disappoint. Like before, it left me wanting to return and see more. Trinidad was a perfect choice, with its cobblestone streets, colorful colonial buildings, and warm, welcoming atmosphere. While I missed exploring Isla de la Juventud, the decision to stay in Trinidad made traveling with my family much more manageable. I’m already thinking about when I might return to see the parts of Cuba I missed this time around.
Cuba remains a communist country where human rights are heavily restricted. While it is not as extreme as North Korea, internet access is limited, and the press is heavily censored. Only recently did the government begin allowing cell phone ownership and internet access, though initially, the internet was slow and restricted. People circumvent this by using VPNs. The economy is in shambles, forcing the government to permit more private industry compared to what I saw during my first visit. There are now far more casas particulares (private homestays) than before. Since few people can afford a vehicle, there are few cars, meaning the roads are wide open, especially on the highways. Commercial advertising is non-existent, replaced by billboards portraying socialist slogans or giant murals of Castro or Che. Since vehicles are so expensive, Cubans have mastered the ability to maintain the ones they already have, even if it means keeping cars from the 1950s, before the revolution. This is why so many classic cars remain.
Cuba’s economy has long suffered due to the inefficiencies of communism and widespread corruption. On top of that, U.S.-led economic sanctions, compounded by pressure on other countries to comply, have further devastated the country. The COVID-19 pandemic made the situation even worse. The desperation peaked when blackouts became a regular occurrence, with entire cities losing electricity for weeks. This led thousands of Cubans to take to the streets in protest against the communist government.
Before my trip, I researched Cuba’s current issues and joined a Facebook travel group dedicated to Cuba. Many members strongly discouraged tourism, emphasizing how tough the situation is for regular Cubans. One poster stated, “Cuba is not a vacation destination; it is for adventure travelers.” Another warned about frequent blackouts affecting food refrigeration, which resulted in their whole family getting food poisoning. These concerns made me apprehensive, especially since I was traveling with my 16-month-old daughter. However, we prepared thoroughly by packing portable fans and plenty of food for her in case of blackouts, ensuring we were ready for any challenges.
When I mentioned to people that we were going to spend New Year’s in Cuba, many asked, “Can you even go there?” The answer is yes, provided you select “supporting the Cuban people” as your motivation for visiting when purchasing your airfare. We had to check a box swearing that we would not spend our money at government hotels or contribute in any other way that directly funded the government. Of course, there is no way for the U.S. government to verify how we spent our money in Cuba, and they do not have the resources to do so unless you really give them a reason to investigate, such as bringing back a box of Cuban cigars in your luggage.
There are numerous airlines flying into Cuba now, and we flew into Havana via Houston on United Airlines. United Airlines even helped us arrange our Cuban tourist visa, required by Americans for Cuban entry, at the check-in counter in Houston. Thank goodness they did because we never would have been able to navigate the complicated electronic visa form by ourselves.
Once we arrived in Cuba, the arrivals hall was drab and disorganized. The lines were long and slow, and after we passed immigration, the line to have our luggage scanned in the single working scanner was even longer. Luckily, an official saw that we had a baby and moved us to the front of the line.
Waiting for us in the arrivals hall was our taxi driver holding a sign with my name. I had pre-arranged the pick-up with the owner of the casa particular in Havana where we would be staying the night. During my last trip to Cuba, casa particulares were secretive, and we had to find them by word of mouth since many were illegal. This time, I booked all my casa particulares reservations via Airbnb and even paid for them in advance. They were cheap, and despite what many other tourists said on the Facebook travel forum, we thought Cuba, in general, was very affordable.
However, due to U.S. sanctions, credit cards and ATMs do not work in Cuba. It’s essential to bring enough U.S. dollars to last your entire trip because you can’t get more if you run out. We brought extra cash, and it turned out that small U.S. bills were just as handy as large ones. The exchange rate varied widely from day to day and place to place. There was the government rate and the black market rate, which was much more favorable. We exchanged money with the owners of our casa particulares at the black market rate. Given that most large purchases in Cuba can be paid for in U.S. dollars and even small items can be bought this way (though often at an unfavorable exchange rate), we only exchanged a fraction of our dollars into Cuban pesos. This allowed us to purchase small items while avoiding getting ripped off when paying in U.S. dollars.
Initially, I had wanted to visit the Isla de la Juventud, a rarely visited island in Cuba. I planned to see the ruins of the prison where Castro had been held as a young revolutionary and do some scuba diving in the island’s pristine coral reefs. However, the logistics proved too challenging with a young baby. The ferry ride had ridiculous hours, and the lengthy procedure of waiting in line to obtain tickets seemed even more ridiculous. Instead, I opted for the colonial-era UNESCO World Heritage sites in Havana and Trinidad.
On this return trip to Cuba, I wanted to explore a different part of the country from my previous visit to Viñales, Havana, and the Bay of Pigs. Initially, I considered visiting La Isla de la Juventud for its unique history, pristine reefs, natural beauty, and the prison ruins where Castro was held as a young revolutionary. However, the ferry hours were inconvenient, and the process to purchase tickets and board was unnecessarily complicated—especially with a toddler. I decided to save this adventure for another trip and opted instead for a much more manageable journey to the UNESCO colonial town of Trinidad, dating back to the 1400s, located approximately 4-5 hours southeast of Havana.
Our plan was to spend the first night in Havana and then dedicate the next four nights to Trinidad, making it our base for exploration. We arranged our taxis through the casa particular owners, and the trip was surprisingly easy to organize, even with the constant blackouts.
Our taxi was prearranged by the apartment owner, and the caretaker met us at the door to help carry our luggage up the stairs. The apartment was in a building that was at least 100 years old, built in a Baroque style. The narrow streets below were bustling with Cubans and tourists alike—classic cars, tricycle drivers, and old men selling bread.
We loved the apartment and opened the wooden window shutters to reveal the balcony overlooking the lively street from two stories up. The apartment had air conditioning in the bedrooms, a living room, kitchen, and a dining room with an open roof. It was a very quaint and comfortable space, full of nostalgia for the past.
In the evening, I managed to get away for a while and hired a tricycle driver on the street for a few dollars. Ten minutes later, I was at the Floridita, sipping a rum drink at the old wooden bar while watching a live band play lively salsa music.
I had heard that Cuba was no longer cheap, but so far, it was proving to be very affordable.
As we drove, I was struck by how little traffic there was in Havana and even on the main highway across the country. Most Cubans can’t afford cars, so owning one is a rare luxury. While there were more modern cars on the road than during my previous visit, the highway was still dominated by classic vehicles and Soviet-era Ladas and trucks. The buses seemed more modern, too, reflecting some progress since my last trip.
The drive was fairly relaxed until we left the highway and started navigating narrow roads that wound through sugarcane plantations. Massive Soviet-style trucks with mechanical claws and bins would lurch unexpectedly into the road, and other vehicles frequently darted around them, leaving our driver—who was behind schedule and heavy on the gas—swerving dangerously. There were a few close calls that made the last stretch of the journey nerve-wracking.
When we finally arrived in Trinidad, a 15th-century town that was once one of the world’s richest sugar-producing centers, I admit I was underwhelmed at first. While the town has undeniable historical significance, I didn’t find it to be the most beautiful colonial Spanish city I’d visited. Our homestay also didn’t make the best first impression—it looked modest and unassuming from the outside.
The owner of the homestay greeted us warmly, speaking mostly in Spanish. She was incredibly kind, but unfortunately, there was a blackout when we arrived. Our rooms were hot, stagnant, and full of mosquitoes. It wasn’t her fault—she didn’t own a generator like many government-run businesses and hotels, as the cost of generators and fuel put them far out of reach for most locals. Despite the uncomfortable conditions, she did her best to make us feel welcome.
Once we ventured inside and saw the beautiful garden in the homestay’s courtyard, my spirits lifted. This was the local experience we’d come to Cuba for, after all. We were here to support the Cuban people, and there’s no better way to do that than to share in some of the challenges they endure daily.
After exchanging some Cuban pesos, we set out to find dinner. The streets were pitch black due to the ongoing blackout, with only occasional headlights from passing cars or faint glows from generator-powered buildings. I was unfamiliar with the area, and walking the dark streets with a baby made me uneasy. Still, we needed to eat.
We stumbled upon a government grocery store, but it only accepted USD or euros from foreigners. My wallet was full of Cuban pesos, and my dollars were locked back 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.
Thankfully, we found an ice cream shop powered by a generator. It was cool inside and bustling with locals. The shop made its own ice cream, which was not only delicious but also incredibly affordable. They also sold water and beer, which made the place our go-to spot throughout our stay. Every night, we returned for a scoop of flavorful ice cream and some cold drinks.
That night, we still needed a proper meal but didn’t want to venture further into the darkness. The only open restaurant nearby was part of a fancy government-run hotel powered by a generator. Though I wasn’t thrilled about dining in a government establishment, there weren’t any other options. Inside, it was cool and nearly empty, with a staggering six servers attending to just a few tables.
To my frustration, the restaurant also only accepted USD, not Cuban pesos. Luckily, my wife’s mother found some USD in her purse, so we were able to order. The hotel manager mentioned that blackouts had been unpredictable and frequent, often lasting all day. Outside, the city square and surrounding homes were still dark, and I began to worry about sleeping without electricity at our guesthouse. While we had portable fans, I was concerned our infant daughter might overheat or be overwhelmed by mosquitoes.
I even inquired about staying at the government hotel for the night, but the price was a staggering $400 USD per night, compared to the $50 USD per night we were paying for two rooms at our homestay. We ultimately decided to stick it out at the guesthouse, and I’m glad we did. Despite daily blackouts, the electricity always returned by nighttime, allowing us to sleep comfortably with air conditioning and fans.
In the end, we grew to appreciate our homestay. The owner’s hospitality and the relaxing garden patio outside our rooms, where she served breakfast every morning, made our stay memorable. Though it wasn’t luxurious, it was authentic, and it gave us a glimpse into the resilience of the Cuban people.
Indie exploring our casa particular with my music playing in the background
Indie and Paula in a tricycle exploring Trinidad
The day was filled with highlights: meeting an old Cuban man who had a pet tarantula he had found in the forest, which he let us take turns holding; hiking down to the breathtaking Salto del Caburní waterfall, where I took a refreshing swim while my family relaxed at the top of the hill; and ending the day with fresh seafood and cocktails under a beach canopy at Playa Ancón, all while soaking up the white sand and stunning ocean views. To top it all off, we had dinner that evening at Trinidad’s most renowned restaurant, celebrated for its exceptional cuisine. It was truly a day to remember.
Paula’s mom and Indie relaxing in one of the plantation homes
