Cuba Pt. 2: The Ups & Downs of Traveling Alone

Solitude is nice, but not at night in dangerous back alleys

Time To Read: 6 mins | January 2, 2017

If I had an infinite supply of beer and a high-speed internet connection, you may never see me again.

I like my solitude. I mean, sure, I handle myself in social situations well enough, and enjoy a night out with friends as much as the next guy. But much more often than not, come the time of evening when girls are changing shoes for the fourth time and guys are trying to decide how much cologne is too much, I’m putting my phone in the other room, pouring double measures of whiskey, and watching The Dark Night Rises while playing X-Com. Ironman, obviously.

When you’re traveling solo full time, being a recluse has positives and negatives. On the one hand, if you end up with nothing interesting to do for a stretch, no worries. There’s books and movies and games a plenty. A day or two with minimal human interaction doesn’t depress.

Thing is though, at least in my case, sometimes I do want to go out and play. Sometimes I’d like to, with minimal effort, find a bar full of people with similar interests and have an evening. That’s more easily achieved when traveling with friends, or when you’re the type who’s constantly starting conversations with anyone and everyone.


Which I’m not, because if I don’t defeat the aliens on my laptop, who will?

As with everything, there are apps for this. A dozen different programs and websites designed for tracking down strangers with similar interests in your area. And if that sounded like the description of a dating site, that’s because it is – Tinder is widely used internationally not for making casual whoopy, but for simply finding friends. After a couple months of being above such new-age tools, I finally broke and downloaded a few. This is a story for another time, but suffice to say I’ve had mixed results.

Anyway, here’s the rub: you need an internet connection for those apps to work. And Cuba has about as much internet as Amy Schumer has original jokes. Meaning, in case you weren’t aware, very little.

All wifi in the country is managed by the government. It’s available in just a handful of public parks, most of which are in Havana. To access it, you have to purchase cards with personalized passcodes that expire after so many hours. And because I’ve spent my first 3 days here holed up in my apartment, drinking hot water with lemon and eating saltines, I haven’t once gotten online.

That’s not the worst thing for me. Again, I’ve got my books and my games and, while the grocery stores are seriously lacking in food, every shop sells very decent fifths of rum for just $3 US. So assuming this cold breaks, I’ll live.

But even a hermit like me gets an itch to explore, and illness or no, after forty-eight hours of nothing, I needed a night out. I put on my warmest clothes to fight the shivers, then began wandering aimlessly because, of course, no internet means no maps or recommendations.

I’m staying in Vedado. It’s supposed to be Havana’s more ‘hip’ scene, away from the tourist traps yet with a nightlife of it’s own. Of course, I knew nothing of where to find these places, especially in the dark, so I just walked for a while in, I’ll admit, not the most chipper of moods.

Twenty minutes later, I stopped outside a chain pizza restaurant. I had no interest in pizza, especially not from a knock-off Cuban Sbarro, but I was leaking snot from my face and losing momentum fast, so I resigned to taking a few pieces of pepperoni back to my crap room and calling it a night.

A guy walked up on my right. A local, by the looks of things – his shirt was appropriately neon, and he’d carved a swirl design into the side of his buzz cut. He started a conversation – “What’s up man?” – and I judged him for a street hustler that I’d usually ignore. But I’d barely spoken to anyone in three days, much less in English, so what the hell.

“Is this place any good?”

“Man, fuck this place. You’re on vacation right?”

Not wanting to explain fully, I responded, “Sure.”

“You want good Cuban food?”

Again, “Sure.”


To hell with it. I’m sick, lost in a city where I know no one and, per the lack of internet, have no better options. If I’m murdered and left in a dumpster, well, I won’t have to do all this again tomorrow.

We chatted on the walk. He was the height of politeness, mixing in some Spanish with his English, asking questions and joking about how dirty the city is. Everything was pleasant for the first 10 minutes.

It got sketchy in the eleventh. My guide turned down a back sidewalk, just three feet wide between two tall, ramshackle apartment buildings. Exactly the sort of place you’d avoid on your own. Which, technically, I was. Being led around like a sheep by a stranger with a fancy hair-do. He’d stopped talking too, I’d noticed, which didn’t ease my concerns.

I’ve seen this movie; I was about to be short a few organs.

My guide/potential murderer stopped in front of an unmarked metal door. No light, no sign; there was nothing to distinguish the outside of this place from, say, that bathroom in the first Saw movie. As he knocked three times, I involuntarily staggered my feet and flexed my hands. I haven’t been in a fight since college, but I can still land a punch when the occasion calls for it.

A waitress in full evening attire opened the door. White shirt, bow tie, black pleated pants. Behind her were about ten 4-tops, all full of diners, in what must be a converted apartment. Someone had tucked a small bar into the corner, where a bartender was making lines of mojitos at a furious pace.

The probably-not-murderer greeted the server like an old friend, then led me to a back room. Here were four small tables, a more romantic and intimate setting, lit by candles on the tables and Christmas lights hanging from the walls. Because I was now too busy giggling with joy, he took over and ordered my Caipirinha.

My meal wasn’t worth $10, even though I paid $20. The food was unbelievably bland, my pork overcooked, and I’m convinced the bartender forgot to put liquor in my cocktail. But I ate dinner in a Havana-hole-in-the-wall I’d never fathomed existing. I was about to go home with floppy soggy pizza; instead, a stranger with a goofy haircut showed me a hidden local gem.

The guide didn’t stay for dinner; after ordering my drink and glad-handing the owner, he quickly made to leave. But first, he leaned into my ear and said what I’d expected all along:

“OK buddy, if you need anything later – coke, girls – you let me know?”

I said yes, out of gratitude. But don’t worry Mom, I didn’t follow up.


photo: lifesize nativity scene, locked up in a gated church courtyard. antigua, guatemala

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Malcolm Freberg
Malcolm Freberg
American writer living permanently on the road. Believes rye whiskey is superior to bourbon, Belle is the best Disney princess, and that selfie sticks should be snapped in half on sight. Hosted a travel documentary for AOL & played Survivor a few times.

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