Days and Nights in Havana

My journal notes, one week after I arrived in Havana:

Seven days have passed since my plane took off from Cancun and touched down here in Cuba at José Martí International Airport.

The view from Supercake, my apartment building in Centro Habana

We seek comfort and context through comparison; past experiences bring order to new, complex situations. This city shares so many physical, sociological, anthropological, and spiritual characteristics with New Orleans, my favorite city in the world. But Havana is truly singular, unlike any other place I’ve ever visited, and I find myself struggling to put pen to paper.

I’ll skip descriptions of colonial architecture, classic cars, salsa music, and beautiful women. They are all marvelous and described elsewhere more eloquently, often in great detail. The food is simple and good, and my portions usually too large, whether at restaurants or in the homes of friends.

Moving on then, briefly, here are the experiences that have made the greatest impression:

  • I’ve walked miles along El Malecon, Havana’s seawall protecting the city against the smashing waves crossing the strait of Florida.
Havana’s Malecon
  • I eat breakfast and sometimes lunch at a small restaurant near my apartment. After several meals and conversations, I sat with my 27 year old waitress as she shared her family photographs. She grew up in dozens of countries on several continents around the world with her father, a Cuban diplomat, and her mother, who now owns this restaurant. They work with joy, but don’t have an easy time of it; it is difficult to imagine an American family of such means transitioning to this dramatically different life.

In the elevator of my building (famously: Supercake, thanks to the pasteleria at ground level), I met Adrian and Eva. Adrian is 21 and the most talented artist I’ve ever encountered. He works across mediums: painting, drawing, sculpture, life. Art is everywhere here; in the street, in mixed drinks, in museums, in the way custodians push their brooms. Most Cubans take tremendous pride in their work regardless of the type, and it shows in the quality of their production.

  • I saw a 75 year old man fall to the street in the grips of a seizure. His head bounced off the concrete like a basketball. What happened next was amazing; strangers lay hands all over his body, supporting him as he convulsed. Until his jerky movements subsided, a teenage boy cradled the man’s head in his hands, gently blowing cool air onto his forehead. This is a scene I will not soon forget.
  • I’ve been having issues with my back — nothing too serious. Coincidentally, the man who owns the apartment where I’m staying is an orthopedic surgeon. He makes exponentially more money renting his flat than tending to patients, so he’s given up doctoring for the time being.

When I told him about my backpain, he suggested we visit a hospital. As we walked, he asked me for my wallet and cellphone. Confused, I asked why; he explained I would have to pass for a Cuban national — up to and including pretending to be a deaf-mute, so the administration wouldn’t be able to hear my foreign accent.

We entered the hospital, and I pantomimed not being able to speak or hear as he explained that his nephew needed medical attention. Once we entered the X-ray room and met his doctor friend, we dropped the ruse, and I left with the placard after leaving the technician a $5 bill.

I’ll be in Havana for another five days or so before I start my walk. I’d planned less time in Cuba’s capital, but, well, I could spend a lifetime exploring this fascinating city. The walk can wait a little longer.


This is part ii / iv of my walk across Cuba. Check out part i to learn more about why I started this journey.

I’m publishing these stories as we build the DNA of SlingShot, your personal concierge for free reward travel. Our mission is to help more people travel further by embracing smart personal finance.

Thanks to Sarah Judd Welch and Rob Pierson for editing this post.