Just weeks after writing about the legendary Cuban Revolutionary hero Ché’s travels across South America, I surprisingly found myself wandering the streets of Cuba’s most famous city, Havana. It may have been my second time on the island only 90 miles from the United States, but somehow it felt like the first.
Cuban contradictions. What I’ve always appreciated about Cuba is the contradictory romance and ironic truth of the place. Its romance is found in the legend and optimism of the place while its irony is that in reclaiming the country for the people, they wound up creating another kind of prison for themselves. Limits on travel, business and political freedoms became Cuba’s claim to infamy, overshadowing their heroic struggle for independence.
My first trip to Havana in the early 2000s was specifically to explore these uniquely Cuban contradictions. Working on a photo-journalism project and attending lectures, meetings with officials and museums, I learned an incredible amount about the people and history of the place.
But fast forward all this time and I don’t know if I ever really just experienced the place, took in what it looked like, smelled, sounded and tasted like without the requirement of it making sense. See, the thing about traveling with an explicit goal, especially a professional or intellectual one, is that you often stay busy making progress toward your project but might leave the place never having actually felt it.
If my first visit had been for academics, this second one would be for enjoyment.
Havana or Bust ’17. Spontaneously planned on a Monday, by Friday afternoon I was sitting in a cafe off the busy Calle Obispo with my friend Denver. You know things have changed in Cuba when you can Airbnb a flat one block from the Plaza de la Catedral for 40 Cuban dollars a night. Hosts Leticia and Alexsandra spoke fast Spanish and took great care to show us the ropes. Aside from a slightly sour bathroom smell, the place was kinda perfect.
Humble and comfortable and situated right in the heart of Old Havana. The balcony overlooking the Hotel Tejadillo let in the sweetest breeze as the street’s wind tunnel ushered cooler air across the vintage cobble stones.
Tip 1. Consider combining outbound and return flights on different airlines for more schedule flexibility. Remember the incremental tourist visa fee is en route to Cuba only, so opt for the carrier with the lowest fee on that leg of your trip.
Tip 2. If you’re only in town a couple of days, definitely stay in Havana Vieja. Other neighborhoods have attractions and lodging, but are far from the city’s best known activities. The majority of must-see stuff will be easily walk-able if you post up in Old Havana.
Friday, the first evening was spent just wandering the local streets and people watching. Eating cinnamon churros standing up, the first of many mojitos and sightings of El Capitolio, the spitting image of D.C.s own Capitol building.
I found awesome posters of Fidel and Ché in a San Francisco beatnik feeling bookstore that I would later regret not buying and drank daiquiris with a New Yorker and a Cuban transvestite at one of Hemingway’s favorite watering holes, the Floridian. Finally, the evening wrapped up at the popular Hotel Ambos Mundos bar, another notable Hemingway hideout.
Tip 3. When you see a souvenir that you really want, get it then. One major change since my first trip to Havana is the level of commercialization. Most shops sell similar versions of the same set of wood crafts, artwork and jewelry. To avoid the let down of not coming home with something you totally wanted, just snag it when you see it.
When in Havana, just go with it. The next day there wasn’t much of a plan – more like an outline. At some point that Saturday we needed to see the beach, experience a vintage car, smoke a cigar at the Nacional and go where hip Havana hung out after night fall. And maybe take a nap and snag a Cuban sandwich in between. Spoiler alert: a pretty damn perfect day can grow from just following your nose.
Tip 4. As awesome as a purely sensory Havana trip will be, take a little time to learn about the local history and culture. El Museo de la Revolución is the best place to understand what makes modern Cuba modern Cuba.
After breakfast across from the Plaza de Armas on the outdoor patio of the Hotel Santa Isabel we walked to where drivers woo tourists into city rides in classic cars and began the selection and negotiation process. On my first time to Havana, I must have taken more than 100 photos of vintage American rides, but I don’t think I ever actually rode in one.
Denver’s travel policy was do the one thing you couldn’t live without doing in that specific place and everything else would be gravy after that. The vintage ride was his one thing and although it would never have occurred to me to do on my own, it turned out awesome. Sounds silly perhaps, but I learned something: not every happiness comes from achieving a checklist of well-planned plans. Sometimes it pays to pick one thing that can make you happy right then and enjoy the hell out of it.
Among a row of American beauties we settled on Luis and his 1952 cherry red Chevy convertible. For 70 Cuban dollars, he would chauffeur us around town and then drop us at the Playa de Santa Maria del Mar, about 20 kilometers from Havana. We’d end up paying him 80 after all was said and done, his original ask.
Tip 5: To wrangle a vintage car tour, first decide what attractions matter most to you. Drivers will explain where the standard tour route will take you, make sure you know what you’ll be seeing and if there’s something else more important to you. Then, go to one of the plazas where the drivers stack up. More drivers mean better negotiating leverage, plus you can pick the car of your dreams. Align on a price and time and then have fun.
Over the course of 3 hours, Luis, Denver and I tooled around the fascinating city and, like all things in Cuba, the relaxing sight-seeing ride would offer some surprising twists and turns. We saw the Plaza de le Revolución, José Martí’s impressive monument and the famous Ché building commemoration.
We took in the decidedly suburban homes of Miramar and Playa and coasted down the Prado, separating Old and Central Havana. We rumbled down the Malecón oozing gas fumes and trying to have Spanish conversation over the dual roar of engine and wind. And then we got hustled.
Tip 6: Havana is better in Spanish, but you don’t need to be fluent. Learn a few key phrases in advance and then download Google Translate English -> Spanish version to your phone for real time help on the ground.
Don’t worry, it wasn’t rap lyric level hustling, in fact, it was just about a sandwich. After agreeing to get lunch to go en route to the beach, we ended up getting “guided” into a sit-down lunch at Restaurante Doña Carmela, a paladar on a tiny, crowded street over on the fortaleza side. We immediately knew our agreed upon plan wasn’t happening. On principle, we were American-style angry.
But once the food came out, we had to concede – that was the best damn meal of the whole trip. Oh, and did I mention that Beyoncé and Jay Z had eaten there on their Havana trip? I knew because blown up versions of their photos at the place were hung in high traffic areas. Ok, if it’s good enough for the original hustler Jov, then I was ok getting hustled into going there to follow in his footsteps.
Tip 7: All food is not created equal. In a place like Cuba that is becoming more and more commercial by the day, increasingly you will get what you pay for. Food isn’t cheap for them to prepare, so be ready for many menu items to be unavailable and for quality to be low if the price seems too good to be true. When in doubt, spring for a more expensive place or one recommended by a guidebook or friend. Having a pork chop at the wrong spot will not be pleasant. Ironically, curb-side pizza is pretty tasty.
On the final leg of our journey to the beach, it seemed Luis himself got hustled, by local police who pulled us over on the highway under a mile from our destination. It was hard to tell exactly what was happening as they talked in fast, local Spanish in our rear view. But as I sat in the back of the classic ride both trying to watch and listen in the rear view, it seemed that the Policía wanted Luis to let us out and not drive any further – something about his permit zone. I think Luis paid them, but it was hard to tell.
He got back in the car and we continued on until we got out at the beach, drama averted. I’m not gonna lie, that was more than a little nerve wracking. All the movies have that kind of situation ending differently, know what I mean?
Tip 8: Despite the tale end of this story, don’t be scared. A little hustle should be expected in Cuba and in many poverty-stricken countries reliant upon foreign tourists for income. Just by steering us to that restaurant instead of us choosing something different, Luis made a few Cuban bucks. It’s part of the service economy and going with the flow can help you discover cool local treats, just be ready to change course if you feel uncomfortable.
After that incredible meal, a gorgeous afternoon at the beach, we walked the mile or so along the Malecón at dusk, winding up at the most luxurious Havana hotel, the Nacional. It reminded me of the Waldorf Astoria, Cuba style. That night I had my first cigar, a small Montecristo and the biggest Cuban sandwich I’ve ever seen.
One of our very bearded friends had said the hottest spot in Havana was the Fábrica de Arte Cubano, so we taxi’d there and proceeded to drink rum, check out art and dance until 3 in the morning. A 3-story experience, FAC was part gallery, part bar and part club and based on the line to get in that wrapped around the sidewalk, it was indeed THE place to be and a great spot for truly unique souvenirs made by real Cubans.
Tip 9: Get to FAC before 10pm to avoid long lines and get a peek at the art without the crowds. You’ll need 2 Cuban bucks to get in and be prepared for an interesting – and calculating – way for paying for your drinks. You’ll get issued a punch card that each bartender will code as you get drinks. You pay at the exit door and lest you think you can outsmart the system and wind up drinking for free, there’s a plan for that. You’ll pay at least 30 Cuban dollars no matter what. Drink up!
Sunday, slightly less fun day. Well, it was my fault, really. A bunch of rum and a cigar were kind of destined to create a vacation sized hangover. But I wouldn’t change a thing. Dancing to DJs and live Cuban music, talk of life dreams, taxi drivers who will never forget me, “lo siento”, and a peaceful, near solitary nighttime walk from the Capitolio – all well worth the next day sluggishness.
Traveling back to the U.S. that afternoon it seemed nuts that only two days before I had left Fort Lauderdale. In such a short time I had seen a glimpse of a city and a culture that felt centuries and worlds away despite being just 45 minutes from home. Somehow I was worlds away from myself, too.
More spontaneous, more trusting, more curious, more relaxed and carefree, more embracing of the flow of things. Thanks to some combination of the place, the people and my own core spirit, I quite liked the version of me that I was in Havana.
Tip 10: Make your visit soon. New construction is going up all around the city. For a people whose primary living is tourism, this isn’t necessarily a bad thing. But the essence, the spirit of modern Cuba is about to change.
I doubt this will be my last time in Cuba, but mostly I hope it’s not the last bit of Cuba in me, so I’m learning how to preserve that Havana spirit in the every day. Cheers to you finding your own Havana adventure sometime soon!