We waited outside the small bed and breakfast where we were staying in La Boca, Cuba, groggy from a sleepless night. Down the street, we heard a car start up with a bang and watched as it came our way, its arrival preceded by a loud, rumbling engine. The rusty death-trap-on-wheels stopped in front of our house, and a man got out and waved. This must be a mistake, I thought. Surely this wasn’t our taxi?

My boyfriend and I were starting our fourth day in Cuba. We’d booked our casa particular through Airbnb, wanting to stay somewhere close to Trinidad but also within walking distance of the beach.

We’d arrived the evening before after a cramped four-hour drive from Havana. There were no seatbelts, and the 1980s sedan was a bit small for the four of us splitting the ride, but at least it had AC. On arriving at our casa, we’d eagerly set out for a sunset walk along the beach. This turned out to be less romantic than we’d hoped, as the beach was a stretch of rocky shore littered with cigarette butts and beer cans.

The La Boca beach

The La Boca beach


Our spirits somewhat dampened, we’d bought a couple of beers at a kiosk and continued walking around La Boca until the houses petered out, avoiding the crabs that scuttled across the pavement into the bushes. As it started to get dark, we made our way back to the bed and breakfast, cheered by the simple dinner prepared by our friendly hostess: fresh-caught fish with lemons, rice, and a luscious pumpkin soup.

We asked our hostess to help get us a driver to pick us up the next morning and take us down the road to Playa Ancón, which we’d heard was a white-sand paradise. Then we went to bed, anticipating a relaxing day ahead. I was a little concerned that the rooster crowing next door would wake us up early.

I shouldn’t have worried about that.

Instead, we spent the night tossing and turning on a hard mattress with even harder pillows while an an old air conditioner blasted us with the decibel level of a jet engine. At some point, after hours of turning the AC off, getting too hot, and turning it back on, I turned to my boyfriend in despair and wailed, “This is awful! What a horrible vacation!”

I was sleep-deprived and frustrated, so keep in mind that this statement was definitely an exaggeration. But in that 3 am moment, I’d had my fill of faded charm and local flavor. I wanted nothing more than to check into one of those charmless, cookie-cutter beach resorts.

To give you a little more context, I should probably describe our first few days in Cuba.

We landed in Havana on a flight from Cancun, Mexico, and waited for an hour on the runway before there was a gate free for us. After another hour in a dismally-lit hall dealing with immigration and getting our luggage, we finally escaped the airport and grabbed a taxi. The sky was overcast as we drove past grim, Soviet-era buildings plastered with pictures of Fidel Castro. Interesting, if not exactly what I’d pictured.


The view was more charming when we arrived at the pretty Hotel Florida, a 4-star accommodation with mediocre reviews (typical of Havana hotels). We checked in and asked about Internet, finding out that we could purchase wifi cards for $2 per hour, but not until 10 am the next day, when the hotel shop opened.

Ok, I thought, No problem. Some digital detox will be good for me.

The lobby of the Hotel Florida

The lobby of the Hotel Florida


We’d booked a place for us to eat on the first night so we didn’t need to do any internet research anyway. We left the hotel for a walk around town before dinner, but not before I’d managed to take a cold shower, swearing like a sailor the entire time (I later realized that I had mixed up the taps, but in the end it didn’t make much of a difference; the best I got was lukewarm).

As soon as we left, the clouds above us opened up, and we dashed into the nearest bar to escape the rain. The bar had a live band playing "Chan Chan" (of course), and we figured it was the perfect time to have our first Cuban mojitos.

“Dos mojitos, por favor,” I said to the waiter.

He shook his head. “No mint,” he told us.

We shrugged and ordered something else to drink, then pointed to some of the small food items on the menu, our stomachs rumbling and dinner still a few hours away. Tostones? The waiter shook his head. Ceviche? Again, he shook his head. “No food,” he said, even though we could see people eating in the restaurant. He left to make our mint-less cocktails.

We brushed off this small setback, determined to enjoy the music and shelter. After finishing our drinks, we pulled on our raincoats and set off for the restaurant. We navigated around potholes, piles of broken bricks, and trash.


The closer we got to the restaurant, the more rough and abandoned the buildings began to look. By this time the sun had set, and many of the streets were dark—no streetlights or even radiance from shop windows. Even though I had someone with me, and we’d heard how safe Cuba is, I felt nervous.

This was the point where it really began to sink in that I was traveling in a communist country that had been cut off from much of the developed world.

Sure, I’d read a few blog posts saying not to expect the same level of comfort in Cuba that you would have at home. But just five months ago, I was squatting over Asian toilets in Thailand, seeing rats on a daily basis, and sleeping on a thin mattress in the mountains of Vietnam. I can deal with a little bit of discomfort.

And yet, when I’d thought of Cuba, I’d only pictured sunshine, colorful buildings, and salsa dancers. I’d imagined beautiful smiling women and old men in hats driving shiny classic cars. I’d looked forward to the “faded charm”. I was determined to embrace Cuba, but none of the blogs I’d read had mentioned the trash in the streets, dark alleys, or the smell of car exhaust everywhere.

We reached the address I had for our restaurant, which looked abandoned. Several men stood around an empty foyer with graffiti on the walls.

“Um, La Guarida?” I said hesitatingly to one of the men. “Si, si,” he pointed inside and to the spiral staircase. We nodded and walked up, peeking into an apartment on the ground floor blasting music through an open door. 

The lobby of Paladar La Guarida

The lobby of Paladar La Guarida


After a few flights of stairs, we entered a completely different world: a pristine, elegant room with smiling staff. We waited for our table at the posh rooftop bar, where we finally had a mojito. A really good one.

Our first meal in Cuba was delicious, creative, and would have fit into any European city. While I absolutely loved the food and atmosphere, when it was over, we were once again walking along dark streets next to crumbling buildings. I couldn’t help but feel uncomfortable with the contrast of such relative opulence against so much disrepair.

A few lines from a book I’d read just a few days before came to my mind:

“It seems we may best be able to inhabit a place when we are not faced with the additional challenge of having to be there”
—Alain de Botton, from “On Anticipation”, The Art of Travel

My feeling of being out of place continued the next day as we walked around town, waiting out another downpour in another hidden gentrified cocktail bar.

My boyfriend could feel my unease, and he didn’t push me too much out of my comfort zone those first few days. We had coffee in a café that wouldn’t have felt out of place in Portland or San Francisco, waving the flies away from our sugary cakes while we watched schoolchildren, rickshaws, classic cars, and horse-drawn carts pass by the open door. 

View from El Dandy cafe

View from El Dandy cafe


We had a delicious Italian meal at the touristy Plaza Vieja, feeling as though we’d suddenly been transported to Spain. I sipped an expensive daiquiri at Hemmingway’s old haunt, El Floridita. Ok, maybe this wasn’t authentic Havana, but it was fun.

We also took a tour in a classic car, a 1940s Chevrolet Mercury kept in great shape by its owner, Enrique. Serious and in his early 20s, Enrique told us the car was originally owned by mobsters but he had inherited it from his grandfather. Whether the story was true, it was easy to imagine as we rode down the Malacón, the wind in my hair and my hand covering my mouth to avoid the fumes from the dozens of other classic cars taking tourists for rides.

Riding in a classic Chevy Mercury

Riding in a classic Chevy Mercury


I asked Enrique if he had ever traveled outside of Cuba. He told me no. Although he wanted to, the government wouldn’t allow him out, because they were afraid that he might not come back. He said that this was probably true.

So we return back to day four in La Boca.

Luckily for us, our sleepless night was the lowest point of our trip. The morning after was picture-perfect—literally not a cloud in the sky. We were tired but happy after a strong cup of coffee and a tasty breakfast of tropical fruit. One of the other guests had left, so our hostess kindly offered to move us into their room with a quieter air conditioner. Things were looking up.

Our spirits lifted even more after spending a day on the gorgeous white-sand Playa Ancon, which was everything we’d hoped for. We took neighbor's car back to the bed and breakfast and then into Trinidad, trying to ignore the fact that we could see the road through the holes in the floor. At this point we found it more funny than uncomfortable.

Our taxi in La Boca. Trust me, it looked bad up close.

Our taxi in La Boca. Trust me, it looked bad up close.

The beautiful beach at Playa Ancón

The beautiful beach at Playa Ancón


We spent a few more days lounging around on the beach and evenings in the beautiful yet touristy town of Trinidad. We spent a night in a very comfortable room at another casa particular, which we were sad to leave. We ate some incredible Cuban food, including ropa vieja at the Paladar San Jose, and our favorite meal of the trip at the incredibly lovely Paladar Son y Sol. And then we ended our trip in old-world comfort back in Havana at the classic Hotel Nacional de Cuba.

As I lay by the pool at the Nacional, I mused about our experiences. It had been an intense week. My initial sense of apprehension and the minor discomforts, though important at the time, faded in my mind when I thought of the beautiful sights, lovely music, and delicious food. But I kept asking myself some questions that have become a recurring theme for me: What does it mean to be authentic? And: Do you have to be uncomfortable in order to consider yourself a real traveler?

In Trinidad, we’d spent an hour chatting with our second host, who’d told us frankly about his (relatively good) life in Cuba. Despite being smart and motivated, he wasn’t allowed to open a business other than a bed and breakfast or a restaurant. I could only imagine how restrictive it would feel to be dependent on government-controlled internet and have to buy and sell items on the black market to boost a fixed salary of of $20 USD per month.

Before going to Cuba, I’d heard (and read) over and over to “go now before it changes.” But at the risk of wild oversimplification, after talking with Enrique and our hosts, and seeing Cuba myself, I’m not sure that we should want it to stay the same. Perhaps all of those photos of faded charm are filtering the way we view Cuba. It’s not just here: we romanticize many places that are broken down, or in development (Detroit ruin porn, I’m looking at you). We see the world through Instagram filters; we look at life through a rose-tinted camera lens.

Ruin porn? Or just reality?

Ruin porn? Or just reality?


In the end, this brings me back to the reason I travel: to learn a little about a destination, and in my reactions, to learn a lot about myself. Traveling is often uncomfortable, and I don’t always deal well with it. But in a way, isn’t that the point? To find out who you truly are when you have to deal with something challenging, whether it’s having your luggage stolen from a car in Malaga, or riding a mountain bike downhill for the first time, or being completely overwhelmed in a huge foreign city? Experiences like this make me accept that sometimes my true self is uncomfortable and childish and scared. And sometimes (thankfully) I am also patient and mature and brave. Traveling is helping me come to terms with many sides of myself.

So while I appreciate comfort, I will continue to intentionally choose situations that aren’t always easy. Not just because I like having new experiences, but also because it is only by being in a place so unlike my home that I can get to know myself and appreciate this unbelievably wonderful life I have. I don’t know whether that makes the experience itself more authentic, but I do hope it will lead me closer to the person I would like to be.

And if nothing else, it makes for much better stories.


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