My First Bike Tour Was Not the Cuban Vacation I Anticipated

My First Bike Tour Was Not the Cuban Vacation I Anticipated

HAVANA, Jan. 23dt. I’d be lying if I said this was an easy trip. I was in tears within the first 24 hours of landing in Havana. The plan was to rebuild my bike out of the box,test drive it, and catch a bus out of the city to meet my travel partner, Mandi. She was already on the ground at the Bay of Pigs where we’d spend a couple of days seeing historical sites and snorkeling.

If I missed this bus, I’d miss our 65-mile ride to Cienfuegos, our next city. Preparing for this trip was a three-month process, so I was eager to meet her and finally get some miles in.

Because the transportation system in Cuba is erratic, this bus only runs every other day (if you’re lucky). I wasn’t able to contact Mandi either. because neither of us had cell service.

Her WiFi was spotty and mine was non-existent: accessing WiFi required buying prepaid internet cards, and the store was closed when I tried to go. I’d soon learn that, everywhere in Cuba, the listed hours of operation were erratic, too.

Maegan Gindi My fully-loaded bike with military devices outside the Parque Histórico Militar museum in Casablanca.

Having never ridden a fully loaded bike, I walked it through the broken sidewalks of Havana. I didn’t understand the mechanics of my rack, and the physics of balancing the weight was new to me.

This caused my rack and all the gear to fall off my bike—three times—within an hour. The bus was still there when I arrived but, naturally, boarding had just closed. I sobbed.

Feeling devastated, I tried to explain the situation through hand gestures and broken Spanish. “Un accidente con mi bici! Mis bolsos!” Because the staff thought I was in an actual bike accident, they extended pity to me and allowed me on! And then I cried from a sense of relief.

Maegan Gindi How you get your bike 115 miles from Cienfuegos to Varadero with a sprained ankle.

There’s a saying in Cuba that goes, “Nothing in Cuba is easy.” From twisting my ankle while walking, to eating abysmal food, and getting my phone stolen off my body, I found this to be painfully accurate.

It took time, but I realized that the actual cycling was the best part—all 15 days, all 225 miles through the country and along the coasts. I was finally in a place I dreamed about, experiencing it on a bike that I had sized and fit perfectly, like an extension of my body.

I reveled in the feeling of being completely at home, and yet having no idea where I was. It crossed wires in my brain. I liked it.

Maegan Gindi I met Luis, my new Cuban friend, through cycling. Here’s us at dinner, smoking cigars on the rooftop restaurant of Fábrica del Arte in Havana. My phone would be stolen two hours later.

The bike allowed me to meditate, so much so that hauling 70 pounds worth of food, clothes, tools, camera gear, toiletries, and shelter in direct sun was barely an inconvenience. With very few cars on the road, I was able to clear my mind—a novel treat when compared with weaving through Brooklyn’s traffic.

Traveling by bike gave me access to the deeper beauty of an otherwise sociopolitically and socioeconomically depressed place. I saw glimpses of life outside the tourist centers in those tiny, in-betweens towns—the kinds that are not travel destinations but rather acted as rest stops.

I’d often get a beer and a sandwich, but at one little roadside stand, I got introduced to Túrron de Maní—a delicious peanut butter bar that was the ideal cycling snack.

Maegan Gindi Cuba is hot, even in winter.


Maegan Gindi Road-side rest-stop for snacks on the way to Cienfuegos.

Staying in casas particulares—traditional bed-and-breakfasts—allowed me to spend intimate time with the locals. I ate with my hosts every morning, still speaking broken Spanish, and asked about their lives.

I learned about the complicated politics, the strong community ties, and the deep sense of pride that shaped the country. Genuine connections like these, where empathy transcends language, is why I travel.

Maegan Gindi Live music, dancing, and daiquiris at El Floradita in Havana, a favorite spot of Ernest Hemmingway.

Maegan Gindi The most perfect place in Cuba: Cueva de Saturno.

The bike stepped in for the lack of reliable transportation. On my schedule, I swam in the Cueva de Saturno, a tucked-away cenote cave, which felt like stumbling upon a secret. It was a pin-drop quiet sanctuary with crystal-clear water.

Because of my bike, I was able to stop and photograph for miles along the Malecón—an active strip of seawall where people fish, read, dance, kiss, and relax against an endless sky. These little vignettes of daily life were some of my favorite moments.

The bike solidified my conception of what it means to be fully present—to appreciate that I’m here (in Cuba, and on Earth) for a limited time and to focus on what’s in front of me, both literally and metaphorically.

The bike taught me that therapy works, and that cycling is, in fact, therapy.

Maegan Gindi Life on the Malecón, where I spent many hours watching the world go by

This experience wasn’t what I expected it to be. I expected more beaches, better food, funny stories to share, and that the old cars existed out of charm (and not necessity due to embargoes and sanctions).

For all the “vacation” elements this adventure lacked, other aspects made up for it in ways I couldn’t anticipate.

This trip tested my resolve as a person, showed me what genuine hospitality looks like, and took me to parts of a country I wouldn’t have otherwise seen.

My first bike tour was admittedly a mess, and I can’t wait to do it again.