The Cuba Hustle

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The work grind between bouts of travel can be grueling, especially when you're slinging tacos and tequila or serving twelve-top bachelorette parties with phallic straws, sashes, and hats all day. I've worked in the service industry for a hot minute, and while I love the fluidity to perform backflips of scheduling acrobatics, and the constant flow of new faces, cocktails, and creative dishes, expelling that much social energy all day every day is exhausting. No matter the sector in which you're slaving away, it's important, nay, sanity preserving, to leave the grind behind and, in the immortal words of my favorite Pawneeans, Tom and Donna: "Treat yo'self!" This escape-and-unwind mentality spurred a travel chat between myself and a coworker-turned-bestie, Bobbilyn, which led us to the expedient realization that a little adventure was long overdue. It probably seemed a bit impulsive, and was definitely influenced by the ritualistic post-shift Espolon Blanco, but within a week of the first late night whispers of “Cuba” we took the plunge and booked our round trip flights to Havana.

Getting to Cuba involved a bit of maneuvering and some pre-departure jitters, but was ultimately manageable. As of June 2017, getting a visa and being granted entrance to the country was as simple as handing over $50 for a travel visa at the gate in Ft. Lauderdale or Tampa before boarding, and casually saying to the ticket agent that you fit one of twelve government approved categories for travel. Having my own low-key personal blog felt like enough backstory to claim journalism as my reason for travel, and we were never prodded for the deeper nature of our 'work' in the island country. 

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Now—real talk—my circumstances may be completely different than yours if you're thinking about planning a trip. The work the Obama administration did to facilitate the reinstatement of travel and trade relations after fifty-plus years of embargo is being attacked by our Cheeto in Chief—a polarizing topic on which I won't expand too much here. The week before our scheduled departure I woke up to an NPR notification that an address would be made about increasing restrictions between the US and Cuba. That address, delivered in Little Havana the Friday before our Sunday departure started, (among strings of pandering shout-outs and Seussian jibberish) "...effective immediately, I am canceling the last administration’s completely one-sided deal with Cuba." We were totally unsure where that left us, flights and accommodations booked, and the leader of the free world trying to ruin our vacation. The immediate political result was moot and we made it through the boarding process just fine...fingers crossed the door stays open for you.


The time warp we were about to engage in was immediately evident as we moved from the Ft. Lauderdale airport, fully equipped with the latest comforts an existence within the world's superpower provides, to the tarmac of the Havana airport, where corrugated sheet metal roofs lent shelter to what looked like decades worth of lost luggage, saran wrapped in large bales. The entire experience, from beginning to end, was like walking through a 1950s American dreamscape, left over pre-embargo cultural overlap everywhere. Or maybe it was more like a real life Groundhog Day—one in which everyone involved was aware of the arrested development and started slowly deteriorating, the whole dream becoming more of a rollercoaster nightmare, everyone teetering on the edge of a silver lining, somewhere between the thrill of a constant island party, and the terror of the results of seclusion from a global reality that marched ever onward without them. Deep. But that's how it was the whole time we were roaming the streets of Cuba—our heads spun every day from hyper stimulation, language hurdles, and I guess maybe a little dash of rum. 

Our AirBnB was right in the heart of central Havana, two blocks off the Malecon—an enormous ocean walk and must see—so we were surrounded by the crumbling modern affairs of old palatial haciendas. Once explosively colorful stone and plaster facades now lay in heaps around us. The roads were dirt, lined with ditches containing god knows what. The summer heat whipped up a thousand smells, most of them hideous, and amongst the rubble lived the people doing their best to keep the walls up, the electricity on, and their babies fed. It was hard, as was evidenced by the continuous hustle in the streets. 


A word of caution: everyone will try to be your friend, but few are. You'll get a feel for what's a genuine versus contrived interaction after a day or two, but at first the constant bombardment of friendly helpers offering advice, goods, restaurant recommendations, taxis, is overwhelming, and almost always comes with a catch (read: financial proposition). The first night out, Bobbi and I got taken for a hell of a ride. We started with a little rum tasting at El Presidente, a second floor restaurant along the Malecon with good views. When we got back down to the street, two locals, a man and woman, each about forty, came swooping in with huge smiles on their faces asking us all sorts of questions about where we were from and what we were looking to do for the night, building a profile. A restaurant recommendation turned into a game of follow the leader to a small spot serving up simple local fare. We all sat together, had some beers and a meal, which I paid for. Dinner chats led to planning the rest of the night, and these two beaming strangers led us through a menagerie of small clubs and neighborhoods, which our eyes may never have seen otherwise, ultimately leading back to the Malecon where things took an uncomfortable turn. Bobbi and I were separated from one another, somehow a block of distance ended up between us, and on both ends we started receiving a lot of unwanted attention.

Swatting away totally out-of-place physical appeals, we hurried back to each other's side to reclaim the direction of the night on our way to what would decidedly be the last bar. En route we were asked to help support our tour guides' family, given options for sending cash back into the country, and eventually had to break the fourth wall of this little play we were participating in, shutting down the prospect of future engagement. They insisted on walking us home, we insisted otherwise, not wanting to give a couple of kind-of-socially-aggressive characters a location pin to drop, and also out of respect for our AirBnB host and future guests. With an established sense of guard and boundaries, we entered the rest of the week prepared to firmly state confidence in our ability to find our own path, and let our type A adventurous spirits soak in all the sights.


Once you get past being hustled it's easy to find evidence supporting the Cuba hype. Our stay in Havana was a whirlwind of rum, salsa dancing, sweat, and sun. It was sexy, vibrant, and alluring. Around every corner lie remnants of strong American influence through the prohibition era, most visually supported by gorgeous old vehicles. With Caribbean rays beating hard upon our backs, we drank, ate, and danced our way up and down countless streets, pounding pavement every day until our legs refused to carry us any farther.

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Obispo Street in the afternoon sang with the velvety alto of vocalists accompanied by bands comprised of typically older gentlemen. The plazas of Old Havana lit up at night with the same nonstop buzz of restaurant- or hotel-sponsored performers. There were two bars in particular that stuck out. Gato Tuerto next to the Hotel Nacional de Cuba offered a lovely balcony dinner with a view of the Malecon and nearby colossal hotel. What really made it come alive was the transformation into an upbeat salsa bar with live music around 9 p.m. After dinner and dancing there, we may or may not have infiltrated the Hotel Nacional, winding our way through a maze of hallways and elevators to see just how high up we could get before hitting the anticipated firewall (eighteen floors or so).


El Dandy makes the list as well—a totally unassuming bar and bistro in Old Havana that reminded us of the hip vibes we thrive in back home in Lawrenceville. El Dandy was the jumping off point for our last night of debauchery, as we met a couple of gorgeous artist-student-club promoters who tipped us off to the invite only rooftop club to which they offer their patronage. Beautiful conversation with beautiful men and an opportunity to extend the party into the wee hours of the morning. Yes, please. In the spirit of conservation, I'm not going to call the club by name... I'll leave some of the mystery and adventure up to you. You never know where buying a boy a shot or a nod in the right direction can take you.


Two social creatures of the American hospitality industry released into the wild, smoggy dreamscape of Havana turned out to be exactly the invigorating escape it was intended to be. We engaged and were burned, re-engaged with context and flourished, and almost ended up engaged. Cuba forced us to deeply consider complex histories of conquest, dominance, and exploitation, all while keeping us down to earth as we hunted for our next mojito. The intrigue, risk, and passion of the Key of the Antilles is alive, intensified by decades of revolutionary history and recent political exclusion. This trip to Havana was only the beginning of a much longer love affair with Cuba, one we hope to keep burning with future visits, hopefully with a humanitarian aid slant. While it was fun, sexy, and enlightening, large swaths of the population are hurting for clean water, sex-positive resources, maternity equipment, and other basic human resources that we take for granted. With hearts and minds open and awake, we returned to the states, and deeply hope the door stays open so we can go back and extend the enormous surplus we experience in the continental US to our neighbors to the south.


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CJ Bonge

CJ Bonge is a twenty-something traveler, currently filtering experiences through the lens of agriculture and agri-tourism. Between gigs and side hustles he's rubber tramping the entire nation, WWOOFing, and studying with community leaders who work to enrich the human experience by replacing unreliable or flawed systems with sustainable, empowering alternatives.