Traveling to Cuba from the U.S. | Havana, Delays and First Impressions

Traveling to Cuba had lived in my mind for a long time. It was not just another island trip or a quick getaway close to home. Cuba carried history, tension, culture, music, architecture, and a kind of pull that made finally setting foot there feel bigger than a normal trip. Even before arriving, I knew this was going to be one of those places where the journey itself would become part of the story.

Getting there was anything but simple. Between the long-standing U.S.-Cuba barriers of the time, financial setbacks back home, and a route that felt far more complicated than it should have been for a country so close to the United States, this trip quickly became one defined by obstacles. But in a strange way, that only made Cuba feel more meaningful once it finally happened.

Coming to Cuba was not just another ordinary trip for me. A car wreck earlier that year had already set me back mentally and financially, forcing me to use travel funds for a replacement vehicle while I was also trying to save paycheck to paycheck for a much bigger gap year ahead. So by the time this trip came together, it carried more weight than most. It felt earned.

Why Cuba Had Such a Pull

Part of Cuba’s appeal was the fact that it felt close, yet somehow distant at the same time. It was geographically near, but culturally and politically it had long existed as somewhere many Americans thought about more than they actually experienced. That alone made the island feel different in my mind.

But beyond politics and distance, I was drawn to Cuba for what seemed to live within it: the street life, the old architecture, the music, the character of Havana, the movement of people through public spaces, and the feeling that everyday life there carried its own rhythm. Cuba felt like a place with soul, and I wanted to experience that firsthand.

Fortunately, my mom tagged along not only to help split costs and stretch out the budget, but to create some life long memories on this historic voyage, especially if I plan to be gone for so long around the globe in the next few years. While the planning was seemingly impossible despite the proximity of Cuba to the US mainland, we made a far-fetch itinerary with awkward plane layovers, work.

The Journey to Cuba

Fortunately, my mom joined me for part of the journey, which helped both with costs and with creating memories together. With the way flights worked out at the time, the route was awkward and far from ideal, stretching from the Carolinas to Cancún and then onward to Havana. Even when we thought we had everything in order, the problems did not stop once we left home.

The biggest test came with Cubana de Aviación, which quickly lived up to its reputation for delays and complications. After already being delayed, we were taken by bus to the aircraft, sat there for what felt like forever, then got sent back to the airport because the plane was not working. It turned into a full day of waiting, uncertainty, and wondering whether we would even make it to Havana that night. Thankfully, after all of that, we eventually did get back on and fly straight through.

By the time we landed at José Martí Airport, dealt with immigration, and pushed through the long currency exchange lines in a smoky airport, the frustration started giving way to something else: relief. We had made it. After all the obstacles, we were finally in Cuba.

Travel Snapshot

At the time, my route looked like this:

• Drive from Greenville to Charlotte
• Fly Charlotte to Cancún
• Long layover in Cancún
• Fly Cancún to Havana
• Two weeks in Cuba
• Return via Havana and Cancún

Approximate flight/transit cost at the time:
Around $780 total in air travel.

First Impressions of Havana

Even arriving late into Havana, the city made an instant impression on me. The first vintage American cars rolling through the streets, the music in the taxi, the fading Art Deco buildings sliding by in the night, and the life happening outside all felt worlds apart from what I was used to back home. It was the kind of arrival where exhaustion almost disappears because your mind is too busy taking everything in.

When we finally reached our casa, several hours later than expected, I assumed our hosts would already be asleep. Instead, they were awake and waiting for us with open arms, ready to welcome us in, hear about the long day, and settle us into our room. That first gesture said a lot. Even after the chaos of getting there, Cuba opened with warmth.

The next morning was the real icebreaker. We woke up to a home-cooked breakfast of eggs, cheese, bread, butter, fruit, and coffee, and the whole experience grounded me in the feeling of being there. Then came one of those small but powerful moments I had imagined for years: opening the balcony doors and looking down onto the streets of Havana as everyday life unfolded below. Vendors, balconies, voices, movement, and the layered architecture of the city all stretching into one living scene. That was the moment it really clicked for me. I had finally made it to Havana.

Havana Street Life, Landmarks, and Atmosphere

Like any major capital, Havana has more than enough to fill your time, but with the limited days my mom and I had together, we tried to take in as much as we reasonably could in one full day. That meant walking the Malecón, passing the U.S. Embassy, chatting with locals over cold Bucaneros, and taking in places like Plaza de la Revolución and El Capitolio while admiring the colors of the city and the character of its vintage American cars.

What stood out to me most was not just the landmarks, but the way life moved around them. Havana felt lived in out in the open. People gathered, talked, played dominoes, sold things from the street, leaned over balconies, and occupied public space in a way that felt different from home. That atmosphere gave the city its pulse.

From there, we watched salseros do their thing along the Paseo del Prado, wandered through the streets, and eventually ended the day watching the sunset over Havana from Castillo de los Tres Reyes del Morro. By that point, every frustration from getting there had already faded into the background. All that mattered was that I was finally in Cuba, taking in a place I had wanted to see for most of my life.

Staying in a Casa Particular

One of the most grounding parts of the experience was staying in a casa particular. It made the trip feel more personal from the start. Instead of disappearing into a generic stay, we were welcomed into a home, fed breakfast, and introduced to the day through local rhythm rather than distance.

That kind of hospitality helped shape my first experience of Cuba. It made the trip feel less like checking into a destination and more like stepping into a space that was lived in and shared. Those details matter. Sometimes they end up telling you more about a place than any landmark ever could.

What Made Cuba Feel Different

Cuba did not feel memorable to me just because it was difficult to reach. It felt memorable because once I was there, it gave back something deeper than the struggle it took to arrive. The city, the people, the casa, the street life, the music, the architecture, the old cars, and the human rhythm of Havana all made the place feel distinct.

That difference is what stayed with me. Cuba did not feel polished or over-explained. It felt layered, alive, complicated, and full of character. It was a place where the atmosphere itself became part of the experience.

Why the Journey Was Worth It

The obstacles were real. The delays were frustrating. The route was far more complicated than it should have been. But once I was there, none of that mattered in the same way anymore. The effort it took to get to Cuba became part of why the arrival felt so meaningful.

Cuba was not just another destination. It was one of those places where the journey in, the first impressions, and the life of the place all fused together into something I knew I would carry with me. And for that reason alone, every obstacle was worth it.