Cuba Car driving havana

I’m drenched in my own sweat standing in an overheated room in obnoxiously thick jeans, tight boots, and a furry winter jacket that I've worn on my flight from New York. I’ve also started to perspire profusely in places I didn’t know existed and am chomping rigorously at my freshly-painted nails. This is what I do when I'm nervous.

After a short three hour flight, I’m standing in line at customs with two of my friends that I’ve dragged along with me on this trip to Cuba. Ah yes, Cuba — a country that has been restricted from me for so long. As an American citizen, it has always been this mysterious place; one I never thought I’d have a chance to visit in my lifetime. The inability to visit this alluring, inaccessible country only furthered my desire to venture here, however my dreams were consistently crushed by the realities of the severed relations between Cuba and U.S. I used to lay in my bed daydreaming of what life was like there. What were the people like? What did they think about? What did they know? This perpetual thought had always both intrigued and intimidated me.

So when the laws changed last year to allow U.S. citizens into Cuba, it was without hesitation that this country was next on my travel list. This is how I've found myself here, sweating and hurdled amongst hundreds of other tourists all waiting to pass through. Yet, for some odd reason, no one else here seems to share the same anxious symptoms as I do. Maybe it’s my type A personality and the fear of the unknown that’s terrifying me. I mean, of course I've done my research, but this whole American-now-allowed-into-Cuba-thing is all still quite new. Even with this new precedent allowing us to visit Cuba, there still hasn’t been a large influx of Americans rushing to these borders.

I'm quickly snapped out of my own bubbling thoughts as a customs agent aggressively waves her hands at me yelling, “Ven aqui!" I'm still chomping down on my nails as I approach the woman who tiredly gazes over my passport. Bored and unamused, I hear a ‘stamp stamp’ and a quick hand motion that shuffles me to move along.


We are spit out onto the curb with hundreds of other tourists as taxi drivers holler at us to hop in. We randomly appoint a guy as the chosen one and within moments, a 1956 Classic Chevy pulls up and we're on our way. My friends and I are busy discussing our plans for the next few days, filling the car with buzz and laughter, but as soon as Cuba’s colorful buildings, rich landscape, and street chatter start to present itself, we are quickly hushed and our conversations start to fade. Fidel’s face is plastered on the walls of decrepit buildings and red paint is splashed on walls reading, “Socialismo es Muerte.”Just as I suspected, I feel both intrigued and intimidated at the same time.

We start to enter Old Havana and the entire scene feels as if you are stepping back into the 1950s, with old classic cars and colonial style architecture in the surround. Dashing through the narrow streets in our taxi, I get a quick glimpse of people relaxing porch-side, kids playing soccer in the streets, old men playing board games on their terraces, and people whistling at us as we whiz by. It is as if time had stood still and it was the year 1961 when the U.S. cut all diplomatic ties with Cuba. Our taxi suddenly screeches outside of a deteriorating pastel-pink building and points straight ahead.


We drop off our bags in a hurry, grab some must-see suggestions from our Airbnb host, and embark into the streets to explore Havana Viejo’s nooks and crannies. The entire city represents this blend of old and new with the streets lined in cobblestone and plazas filled with an array of restaurants, stores, and parks — reminding me of my summer afternoons spent in Madrid.

We are quickly bombarded with men yelling, “Tours! Vintage car tours ! Lady over here! Taxi!” Along with some “I love you’s” and “Son bonitas !” and to be honest, we aren’t so annoyed by it either (it’s been a long winter in New York). After some time surveying the busy streets, we dodge out of the main area and dive into a more quiet street to see a group of Cuban men ahead. They're hanging outside of a particularly lively neighborhood with salsa music blaring through colorful, crumbling apartments. Without hesitation, I walk up and in my broken Spanish ask, “Where should we go? We want somewhere authentic!”


The boys start speaking all at once, each louder than the other and the entire conversation starts to resemble an argument-like state of debating. Hand motions mixed with laughter and loud banter fill the next few seconds until Eduardo, a young Cuban man sporting an eyebrow ring and tattoo under his lower right eye, jumps up and decides to take us. We are now running after him as he navigates these parts, giving us some rich context on the neighborhood he grew up in. Ten minutes into our adventure of zipping in and out of alley ways dodging people, dogs, and taxis, we arrive at old lavender apartment building. The place is mixed with chipped paint and wallowing empty echoes that fill it’s dark entrance. I turn to my friends only to see their eyes darting at me.

I flag them to follow and we all slowly start to walk up a flight of janky-looking stairs. Surprisingly, with each step the place gets livelier and the apartment building begins to transform. Without warning, we have managed to enter into a home-turned- restaurant surrounded by radiant decorations and pictures of Fidel pinned up against brightly sunflower-colored walls. Three ladies are standing nearby with warm eyes and enormous smiles signaling for us to come have a seat. And for the next two hours, we find ourselves feasting, drinking, and laughing over a traditional Cuban meal with Eduardo and our hosts. As the night goes on, locals are coming and going, stopping in to give us kisses on the cheek, and to say hello and good night.


Our night continues with overflowed shots of rum and deep conversations about history, life, and politics. Questions on both sides fill the room as we, curious of what life is like living in a world with such little access to the outside and they, curious what life is like to have so much access. As the hours go on and the locals start to shuffle home, we realize the night is winding down. I start to get up only to realize how buzzed I am off of the Cuban rum that has been generously poured throughout the night. I manage to get my belongings when Eduardo quietly turns to me in a private conversation and says, “I may not know what it is like to live in any other country, but I do know that here I feel free.” 

I pause for a moment, unsure where the comment came from and unable to gather my thoughts. I’m not sure if it’s all that Cuban rum or if it’s this entire experience, but I find myself stumbling out onto the streets trying to take a moment to take it all in. For some reason, Eduardo’s lasting comment is deep and profound and really got me thinking. I look up at the evening sky and wonder how to describe it all. It’s as if this entire place and the people in it are some sort of vintage beauty mixed amongst extreme poverty.


I was told Cuba would be a tricky place to get under the skin of. That it would be difficult to find people who would be willing to talk about their lives, their issues, and the deeper stories of their culture. I was told to expect “orchestrated tourism” and that I wouldn’t get the authentic Cuban experience that I was desperately seeking. I was told all of these things over and over, yet here I was standing in the middle of the streets of Havana surrounded by new Cuban friends, having the complete opposite experience.

So what is it really like to visit Cuba as an American? I think it’s the same for anyone visiting from any other country, be it Canada, Germany, Spain or any other place for that matter. Because as much as Cuba is a tourist haven, your experience won’t matter much depending on where you are from. What will be significant in your experiences is if you are willing to do the work. Because when you dig deep and ask questions and put yourself out there, you’ll find a country rich in history, culture, beautiful people, and uniqueness. Yes, you will find the classic cars, preserved colonial buildings, colorful slums, and everything you can think of from pre-modern times. Yes, you can bask in the sun at some of the most beautiful beaches in the world, wine and dine at Cuba’s fanciest restaurants, and be entertained at the famous Tropicana club —but it’s the people that beautifully make up the country of Cuba.

If that got your travel bug going, you'll love this cool video on Puerto Rico.