I am pushing a pastel, blue-tinted 1956 Chevy Plymouth through the streets of Havana. To my right I am flanked by one of my best friends, Dakota, to my left is a benevolent Cuban who was summoned off the sidewalk to help us in our efforts as we maneuver the elder vessel through Havana’s historic city center.
The engine rattles as our driver attempts to gun the 60 year-old automobile into gear. A plume of arid dust kicks up around us. The young Cubano to my left looks back with wide eyes and a toothy smile.
“Bienvenido a Cuba”
Two weeks before we jet-setted to the island, Dakota and I were in the throes of discussion about where to meet up. The last time we were together in a foreign country was back in May of last year, where we fjord-ed our way through Stavanger, Norway.
I detailed our experience here, one of my very first blog posts. In it I wrote “where we go next is anyone’s guess, what I do know is that going anywhere with him is guaranteed to be an epic adventure.”
This was a lot to live up to. After a few days of talking we almost pulled the trigger on Peru, before finally arriving at Cuba. Our reasoning was simple: The doors have been opened and we don’t know what our current president will do with regards to Cuban relations. Conversely, we can’t be sure when relations will thaw to the point that the island is saturated with western tourism.
So that is how we ended up in Havana that morning, throwing our weight behind a 1956 Chevy Plymouth.
That microcosmic, seemingly quintessential Cuban experience served as a welcome to the island. It was the beginning of our great challenge. The challenge, as it turned out, was not to traverse a country still lacking in normative tourist infrastructure. This actually proved to be the least of our concerns. No, the great challenge of Cuba is not to navigate the island but to understand it.
How can I begin to tell you, sir or madam reader, about this place? How can I put it all into words when so much still eludes me, even after spending two weeks there?
As Americans, the first in our respective families to go to Cuba, Dakota and I arrived in Havana wide-eyed and eager to soak everything in. We walked, we talked, we saw, we read, we listened, and we engaged the Cuban people whenever possible. We lived with local families every night. We learned of their plights, of their successes, and of their future ambitions. Still, as I sit here typing this to you, there is as yet so much I am unsure of about this fascinating and endlessly complicated place. The only thing of which I am surefire regarding this great challenge is that, in attempting it, I will inevitably fail.
Indeed, show me a man who says he can succinctly describe Cuba to you and I will show you a liar.
But I have to try, right? I’ve got to give it all my gusto, to try and channel everything that lingers in my mind into something tangible and actionable. In 1934, Ernest Hemingway wrote his famed “A Letter from Cuba” for the world to see. I too feel compelled to write something of a letter, for those in my little corner of the world to read.
Okay…enough dramatic prose. I will start this story from where all great stories start, at the beginning.
The year is 1492.
La Pinta,La Niña and the Santa María, having completed their transatlantic voyage, land on the northeastern coast of what would centuries later become known as the Republic of Cuba. A young Spanish captain by the name of Columbus claims the island for the new Kingdom of Spain and names it Isla Juana.
Four centuries of Spanish dominion would follow, ending in the 1898 Spanish-American war. During their reign the Spaniards slowly but surely built a dynamic colony, largely on the backs of the slave trade and forced labor of the native Taíno people via the encomienda system. Cities were erected across the island and a thriving agricultural society emerged.
Today perhaps the most lasting and impressive Spanish establishment is the Fortaleza de San Carlos de la Cabaña (Fort of Saint Charles), colloquially known as just “La Cabaña”. Dakota and I made a trip there and walked all over, admiring the well-preserved walled enclave overlooking the Malecón, Havana’s sprawling seaside esplanade.
Several attempts at Cuban independence from Spain unfolded in the 18th and 19th centuries, fueled by the first successful slave revolution in the Caribbean, that of Haiti from France. In 1892 an exiled, vocal dissenter named Jose Martí formed the Cuban Revolutionary Party in New York. He later returned to Cuba in 1895 to help lead guerrilla forces against the much more powerful Spanish army. Martí died in battle that year, immortalizing him in Cuban history. Walk through Havana and you’ll see his statue everywhere, plus one of the city’s main roads is named for him.
Galvanized by Martí’s death, the guerrilla forces began to mount a potent opposition in the following years. On February 15th 1898, the USS Maine was sent to protect American interests, but exploded in Havana’s harbor, killing two thirds of the crew members. Suspecting the Spaniards were responsible, the US declared war on April 21st, 1898, beginning the Spanish-American War.
The war lasted less than four months, ending with the Treaty of Paris by which Spain ceded Puerto Rico, the Philippines, and Guam, plus temporary control of Cuba, to the United States for the sum of $20 million.
Cuba gained formal independence from the U.S. on May 20th, 1902, forming the Republic of Cuba. However, the US retained peripheral control of Cuba’s finances and foreign relations, and it leased the infamous Guantanamo naval base, still operational today.
Over the next 60 years Cuba would see a massive influx of tourism. Havana became a place of lavish luxury catering to celebrities, socialites, business magnates, and mobsters the world over. It was largely this infusion of cash flow that built downtown Havana’s colorful, fascinating, though now crumbling, architecture.
The bedrock of this early 20th century Cuban development was sugar production and the aforementioned tourism.
A huge draw for tourists to Cuba was (and still is) its world class rum and cigars. That day in the fort and castle, Dakota and I dabbled in our first tastes of these Cuban classics.
Bolstered by the cigar and rum industries, the tropical weather, and hedonistic appeal, Havana became a haven for bohemians and vagabonds alike in the 1920’s – 1950’s. If Miami is vice city, Cuba was vice island. Gambling, prostitution, drugs, and the filming of pornography, all became mainstays in Havana and elsewhere.
Some of the most iconic images of this time are of celebrities enjoying the Havana high life. Frank Sinatra, Marlon Brando, Ava Gardner, and a host of others, made Cuba one of their choice destinations. Stop by one of Havana’s historic bars to see pictures plastered on the walls of beloved celebrities, rum in hand, cigars hanging from their mouths. La Floridita is perhaps the nexus of historic Havana bars. Of course, Dakota and I had to stop by for an overpriced cocktail.
Though Hemingway and Brando may have sought out Cuba for creative reasons (and for the booze, let’s be real), others took to the island for more notorious affairs.
In the 1940’s, Mafia moguls such as Lucky Luciano and Meyer Lansky invested heavily in Cuban casinos and made Havana one of their prime meeting destinations. In December 1946, Luciano hosted a momentous Mafia gathering attended by a who’s who of powerful gangsters based in the US. The heads of the most influential racketeering families descended on Havana and gathered at the Hotel Nacional.
Dakota and I walked along the Malecón for about an hour to reach the infamous hotel situated on a hilltop in the Vedado district.
“Havana is a mistress of pleasure, the lush and opulent goddess of delights”
– Cabaret Quarterly, 1956
After touring through some of Havana’s fabled, luxurious spots of the 1920’s-1950’s, this quote starts to make a lot of sense.
Upon perusing the Nacional, Dakota and I walked a few blocks to a restaurant, Los Amigos, which has been endorsed by eclectic bad boy chef and world traveler, Anthony Bourdain.
Los Amigos is one of many “paladares” located throughout Cuba. These are essentially restaurants run out of Cuban homes, giving tourists an alternative to state-run eateries and providing for a more intimate interaction with the Cuban cuisine.
The food and venue were wonderful. Bourdain did not disappoint.
Ah, look where we are. We’ve taken a giant leap forward in the timeline. What did I leave out? How do we bridge the gap from Hemingway’s daiquiris to Bourdain’s Ropa Vieja? What happened between the 1946 Mafia summit at The Nacional and Barack Obama’s historic pilgrimage to the island 70 years later in 2016?