Back in the summer of 2017, I took a trip that has become infamous in my memory—the gold standard of difficult, troublesome travel.

Whenever I start to stress about packing or worry over inevitable travel foibles, I often comfort myself with the thought, “At least we’re not going to Cuba.” But looking back, I think those memories might be misleading.

In my mind, it was a long and grueling adventure—but photo evidence confirms we were only there a week. A single week! And yet, it felt like nothing but trouble from the get-go.

First of all, nothing from the United States works in Cuba. You can’t use U.S. currency (we brought Canadian dollars), U.S. credit cards are not accepted, and U.S. cell phones get zero service. That forces you to rely on Wi-Fi, which only exists in hotels and approximately three public squares in Havana.

Second, infrastructure outside Havana is limited, and trustworthy information is hard to come by. I’d read that toilet paper was scarce, so we traveled with a dozen jumbo rolls… all of which came back with us. But it is true that you can’t flush anything but bodily waste, meaning used toilet paper must go in a trash can. Which can lead to some very stinky situations.

And the most difficult part for me? The language. I’m moderately fluent in Spanish and have generally done well in Spanish-speaking countries. But Cuban Spanish is different. It’s fast, heavily accented, and filled with slang and dropped syllables. I could communicate—kind of—but not well. And since I was the only one in our group who spoke any Spanish at all, it was all on me.

WE RELY FAR TOO MUCH ON THE KNOWLEDGE OF OTHERS

We had joined the trip last minute, tagging along with a group of five women (two of whom we knew). One of the two didn’t make it onto the plane—her passport had some exterior damage, and the gate agent was in a mood. So, that was our first hurdle: trying to stick to the group’s itinerary while still meeting up with her later.

Because we joined late, we had different accommodations the first night. No biggie, we thought. (Spoiler alert: it was a very biggie.)

Apparently, the others were convinced by a taxi driver to leave early. We had no way to know. We waited at the bus stop for what felt like hours, then made our way to a posh hotel lobby with Wi-Fi. We emailed, messaged, tried everything. But they couldn’t get online to check.

Thank God I’d packed a guidebook.

WE RECOVER, RALLY, AND SET OFF TO FIND ADVENTURE

After that chaotic first 24 hours, things got markedly better.

When our missing friend finally arrived—passport replaced—we headed to Viñales, our group’s original destination. After a smooth 3-hour taxi ride, we found our lodging with a lovely señora who spoke no English but was very patient with my Spanish. And when one of us inevitably came down with the tummy troubles, she provided an excellent herbal remedy.

VIÑALES:  WHERE WE THRIVE

Viñales is a magical place—lush, tropical, timeless. The little village is nestled in a valley surrounded by the Sierra de los Órganos, dotted with dramatic karst mogotes. Colonized in the early 1800s, the town still reflects that era in its architecture, agricultural methods, and rhythms of life.

There wasn’t much to the town—we dined in both of its restaurants, and that was about it—but nature was abundant. We rode horses through the hills and visited a completely unmechanized tobacco farm. Later, we hiked to a nearby cave.

It was one of those beautifully imperfect days, the kind that lingers because it’s so real. Questionable cheese sandwich? Check. Overly flirtatious vaquero? Yep. And yet the landscape still shimmers in my memory: the undulating mountains, the waving grasses, the dense green thickets, the towering palms, and those strange, sculptural mogotes.

The Valle de Viñales, named a UNESCO World Heritage Site, was the pinnacle of our trip. A memory I’d happily recreate.

THE DARK FORREST: WHERE WE STRUGGLE TO SURVIVE

But of course, we weren’t done struggling.

We all battled massive intestinal distress—at different times. I got about 10,000 bug bites one night. And we had a travel day so stressful it still makes me clench. I had misunderstood what a comunale was: not a taxi, but a series of overcrowded vans that redistribute passengers along chaotic routes. A private taxi would have been cheaper and far more comfortable.

When we arrived at the Bay of Pigs—where I’d imagined a bustling beach town, full of vacationing locals—we found it deserted. Apparently it was off-season. My guidebook had said this was when Cubans vacationed, but it lied to me!  We struggled to find food, lodging, anything. The beach was nice but didn’t redeem the hassle.

Back in Havana, exhausted and without a reservation, we lugged our bags across the city looking for a place to stay. Eventually, we landed a great spot with air conditioning, but the heat and our collective mood dulled the joy.

And then—hours before our long day of flights home—I succumbed. After being smugly immune to the diarrhea bug, it hit me in the middle of the night.

There are few things more harrowing than facing a travel day in that condition. And during our layover in a U.S. airport, it happened: I pooped my pants.

It wasn’t catastrophic, thank God. My luggage wasn’t checked yet, so I was able to change and discreetly dispose of the evidence. But still. Humiliation of humiliations.  Even thinking of it now, some eight years later, my cheeks are burning with the shame of it.

THE STORY DOESN’T END IN THE DARK

And maybe that’s the crux of my whole life.  Adventures are awesome, and essential for growth.  Yes, you might stumble. But if you’re someone like me—restlessly curious, endlessly eager—the risk is worth it. Every time.

Because adventure is out there.