What Happened When I Traveled to Cuba Alone

I’d been talking about going to Cuba for years. So when my co-worker told me he’d booked a roundtrip plane ticket on Alaska Airlines for only $350, I made a reservation that same day. None of my friends or family could go, so I went by myself. I’d never traveled alone and was unsure about what to expect. Excited about the possibilities and the freedom, I was also worried about eating alone and filling my time.

Havana appealed to me because given its history it seemed inherently authentic. I’d seen the standard pictures of the colorful cars from the 50’s, but I knew there was more to the city. I wanted to get lost in its streets, to meet its people, to learn about its history, and to take photos from my perspective. I was also excited about the limited Internet access and couldn’t wait to put my phone on airplane mode and to keep it there for days.

I spent my days traversing the city streets, getting lost, and finding my way back. I walked over five miles a day and rewarded myself with fruity cocktails in the mid-afternoon. I fell in love with the decrypt abandoned buildings with flowers popping out the empty windows, with no ceilings overhead. I learned about the Bay of Pigs, the Russian influence, who Jose Marti was, that the country had free healthcare and that the literacy rate was 99.9 percent, that the people took a test when the graduated from high school, and the government decided what career they could pursue.  I saw the divide between rich and poor. I asked my tour guides question after question, but was disappointed I couldn’t ask some of the politically centric ones I wanted to. I learned there's a mix of pride, desperation, and sadness in the Cuban people. Proud of their ability to remain free, but aware they were in reality far from free. Desperate to get out, yearning to experience something else.

After a few days, there were things I came to expect. I could count on at multiple points of the day sweat would trickle from my bra down my spine to the top of my underwear. That someone would try to rip me off and I wouldn't care, that I’d gladly give them the extra money. I rationalized they needed it more than I did. That when I walked down the street men would hiss, make kissing sounds or some other indescribable noise, or would ask me to be their girlfriend. That the women I passed would look me up and down from toe to head. That I’d be asked a million times a day if I wanted a cab regardless of whether I even remotely looked like I needed one. That the cats living outside my apartment would wake me up at some point in the night with their fighting. That the sounds of the city coming to life would wake me in the morning instead of my phone’s alarm clock. That people would continue to speak to me in Spanish even after I told them I didn’t understand. That through open apartment doors, I’d observe Cubans eating dinner in their chairs in front of a TV, having intimate conversations, resting on beds, getting their ailments tended to. Moments in America that were private, but here there was no such thing. 

I had romanticized having no Internet or phone service, it actually changed decisions I made while I was there. The lack of access made me more cautious.  I didn’t want to get myself in a strange situation and not have the ability to get out of it. If something happened to me, not only did I not have anyone to call, but I couldn’t call anyone. If it had been feasible for me to make phone calls, I might have been more adventurous, but I choose to keep myself out of any potential trouble. For the majority of my eight days there, I relished in my respite from all forms of social media and the daily news. I plowed through chapters of books without ever having the urge to reach for my phone. But towards the end of the eight days, I began to miss the Internet and appreciate its existence. While I sometimes hate how much I need it, there’s no denying it makes life easier.

I’d assumed traveling alone would invite people to strike up conversations with me, but few did. Most Cubans obviously don’t speak English and I speak textbook high school Spanish, so it was difficult to communicate with most everyone besides the tourists. If anything, people questioned my decision to travel alone. They wanted to know why I was alone and if it was hard. I went to bars and restaurants, but met few people. Instead, I watched them.

Traveling alone allowed me to fine tune my already expert observation skills. I observed everyone and everything. To entertain myself, I made up stories about how people met, where they were from, who they are. I tried to guess how the people traveling together knew each other. Friends from high school? Recent college graduates?  I have an active imagination and put it to use. Since I didn't have the urge to check my phone every five minutes, I was present in the moment and attuned to my surroundings.

There was the young woman watching her famous much older pianist boyfriend perform at a small jazz club whose screensaver was a photo of herself on a beautiful beach in a skimpy bikini in front of I Heart Cuba written in the sand whose hair brushed my arm every time she flipped it from side-to-side. There was the young American couple, possibly on their honeymoon, who hated Havana and bickered about ever eliciting advice from a particular friend who advised them to come. Bitter because they felt they could only eat ham and cheese sandwiches for eight days. Yearning for their American way of life, unable to appreciate a break from it. They were determined to be more conscious and selective in the future. There was the Brazilian sun worshipper who was so dark she had to be destined for an eventual skin cancer diagnosis. There was the 40-year-old tour guide so desperate to leave Cuba for a better life he was convinced Guyana was his answer. There were the boys from Trinidad and Tobago who after staring at me all day at the pool finally worked up the courage to talk to me and were dismayed I only spoke English. There was the man holding hands with his girlfriend who winked at me and pursed his lips in a smooch as I passed, unbeknownst to her. There were the hordes of Americans taking photos to take photos at El Floridita, one of the two bars Hemingway frequented, many of whom have probably never read a single book by him. There was a Spanish family who sat on the communal hardwood chairs in thong bikinis. Unable to avoid mansplaining even in a foreign country, there was the Cuban waiter who lectured me on using sun tan lotion, min 30 SPF multiple times a day, he said. I nodded but refrained from pulling out the bottle I had in my purse and mentioning that I live in California and was accustomed to being exposed to the sun. There was the strikingly attractive professional Cuban volleyball player who I met at the airport who was terribly concerned about whether I was meeting someone in the city. I lied and told him I was. He was relieved. In my dreams, I’d instead told him the truth and he’d offered to give me a tour of the city. There was the 10-year-old girl from Miami obsessed with taking artistic photos, not selfies. There were 22-year-old American bros thrilled to be smoking cigars in the courtyard of a hotel formerly owned by the mafia. There was the Spanish girl who ignored her boyfriend’s kisses as she plowed through one of the Fifty Shades of Grey books. There was the pair of Spanish girls no more than 14, one a natural beauty the other with implants and bleached blonde hair who exhausted every position possible with their selfie stick. There was the American Jew who was so self-satisfied he was able to refrain from urinating in the pool even though he wanted to. There was the tour guide who revealed he was most excited to have Americans on his tour because tipping was a part of their culture. That he was least excited when he had the Germans because they wouldn't tip and would go so far as to ask for a refund if his German wasn't precise.

I came back to the States a little bit wiser to the country’s fight for freedom, armed with over 750 black and white, not color photos, of the city as I saw it, and newfound confidence in myself that I was capable of getting myself around a city with just a downloaded map, and a few words of high school Spanish. In the end, the worst part of traveling alone was not eating by myself, but having no one to put sun tan lotion on my back.