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  • Jenna Gleespen

An American in Cuba: Memories of my trip to "The Pearl of the Antilles"

Updated: Jan 16, 2021

In the turquoise seas and rose kissed skies of the Caribbean, just over 90 miles south of the neon bikini-clad beaches of Miami, lies Cuba, an island nation that sits bordered in mystery and allure. Its past, shrouded in revolution, change and oppression, and its future that is what stories like Les Miserables are made of, is what makes Cuba an intrigue to travelers of all walks of life.

Not quite knowing what I was in for after a week in Belize and a night in Mexico with a good friend, we boarded a plane from Cancun direct to Cuba one hot and hazy afternoon in late May. Arriving in Havana, I had my eyes held wide as my mind raced with questions one should never ask while there. The women working at the airport, as everything form security to baggage clerks, were dressed in fish net stockings and very military-esque style dresses, similar to a fashion a housewife might gawk at in a 1962 issue of vogue magazine. The contrast was mind boggling and I knew immediately I was in for more than ever expected. I grinned at my friend with hope and with certain nervousness. As we exited the airport terminal, we met our taxi driver which our Cuban host set up for us, and climbed into the leathery back seats of a 1951 black Chevrolet. We cruised past locals laughing, children playing soccer, and billboards with Fanta ads followed by others with pictures of Fidel Castro and the ominous words, in a startling yet silent reminder, "Socialismo O Muerte." The reality of it all was starting to settle in.

Upon arriving at our rented apartment, we were greeted at a quintessentially Cuban Cafe, affectionately called Cafe Bohemia, by our host, Diana. She owns both the apartments on the property as well as the cafe and bakery, which we were given a free breakfast at each day of our stay. She, like the other locals were friendly. In fact, they were more than friendly. Being an American in Cuba is almost like reaching a level of celebrity of some sort. To many Cubans, Americans are a thing of tales told by an older generation. What they know about those in the States is highly monitored by the government and what there is of the Cuban media. I couldn't count the times I had heard a local we met and spoke with say, "We are very excited that we might have more Americans here soon." I am not quite sure what I expected to hear upon telling people I was from the United States, but it surely was not that. For exactly this reason, I love travel. No matter what one thinks they may know, no matter the experiences one has had, it only takes a simple sentence like this to open your mind to broader cultures and tear down the social and media constructs which keep us so far apart.

At dusk we headed out of our apartment in Old Havana, the downtown and most populated of all the fifteen boroughs of Havana. We traversed Plaza Vieja, a lively square filled with delicious cafes, street performers and children running about. The Plaza Vieja Micobrewery on the southwest corner of the square serves authentic Cuban sandwiches, mouthwatering selections of braised meat and refreshing beers all brewed in-house. Walking though Old Havana one will find shops selling local wares, cathedrals looking atop rustic apartment buildings, and locals conversing outside bars and homes. We made our way to The Plaza De Armas, the main square in Havana were one of the only hotels (and places in general) that offers Internet (for a price) sits. We wanted to check in with our families, so we sat at the bar in the hotel and paid for 30 minutes of internet access, and sipped our Mojitos calmly. The Plaza De Armas is lined with red, flowering Red Stopper trees, which seem illuminated at dusk as the city's streetlights dance around them. In this square is where La Floridita still stands, one of Ernest Hemingway's old haunts and popular spot for the famous Hemingway daiquiri. The beauty and unsurpassed liveliness of the city make it easy to understand why some of the great writers of the early twentieth century fell in local with this place.

The street food and fruit stalls all around Havana are inviting, as are the local bars, where striking up conversation with anyone from the barkeep to another patron will result in a warm reception and chat and banter that easily lasts into the late hours of the night. On one street, just off the main promenade, we met Peter, a thirty-something public relations specialist who has resided in Havana his entire life. He took us to a family run, no named bar that sits high above the cobbled, narrow streets. We took a seat on the balcony with Peter as he told us of the wonderdul things all around the country, shared news of change that was finally starting to happen, and looked out with a true sense of pride as he proclaimed, endearingly, "this is my city."

One of our days in Havana was spent with Carlos, a local teacher who we also met wandering the streets in search of refreshing libations one humid night. He took us to his apartment, a one room flat that sat atop a set of very rickety and winding wooden stairs. His home had no running water, a tiny battery powered radio, and was sparsely decorated except for a framed photo of his mother on the bedside. "This is my home, welcome," he said, smiling with dignity and satisfaction. It all became a little much for me at that moment, and I had to turn to stop any flow of tears about to stream down my face. It is truly a life altering feeling when one realizes that happiness is not contingent on anything material or even tangible in this world. Carlos certainly opened my eyes even wider that day.

We went with Carlos to a nearby beach, Santa Maria, his favorite, and in his opinion, the most beautiful beach around. We caught a ride for a mere five pesos and jumped in the back of a 1950's sedan with some other passengers before the driver took us the twenty or some minutes away to the beach Carlos loved so much. We spent the afternoon sharing tamales sold by pedestrians on the beach and sipped on rum we bought at a nearby store. Theater was cold, but the feeling in the air was warm, glowing and effervescent.

Another of the days on our trip was spent meeting back up with Peter, who met us with one of the many old, classic American cars that consume the streets of the city. He took us on a tour to many places of notoriety in Havana, including the magnificent El Capitolio (national Capitol), The Havana Club rum distillery, where we were offered a free drink, and an old military fortress, perched seaside above the old town. The Fortress of San Carlos de Cabana is filled with missiles and canons which are ceremoniously set off nightly (the cannons, that is!) We ventured to new Havana as well, a stark difference from the romantically withering buildings and pathways of the old city. New condos, houses that looked like something out of Beverly Hills and well paved streets filled with new model Europen cars highlighted the blunt disparity between the civilians and those in power in Cuba. Arriving backing Old Havana, we stopped to have lunch with our new friend and tour guide at a quaint rooftop restaurant, just next to the Arco de Belen.

Each day and every night we were encompassed by the spirit of Havana, from tasting the local cuisines to dancing on the streets with musicians carrying their guitars and voices through the evening air. The people of Cuba will forever be in my heart, and Havana is a city which brings tears to my eyes as I revel in the memories I shared with so many there, as it is a place that is buzzing, vivacious, and tragically beautiful.

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