The customs agent was a beautiful coffee-skinned woman in a prim khaki uniform with perfectly coiffed hair, not a ringlet out of place. In the giant humidifier that is the José Martí International Airport, I already had sweat dripping off my nose.

Given the complicated history between the United States and Cuba, I was anticipating a degree of rousting from the officials. It wasn't the nationality listed on my passport that concerned me so much as the 8-foot boardbag I dragged behind me, filled with jugs of epoxy resin and rolls of fiberglass cloth--enough grist to patch up a few of the locals' hand-me-down surfcraft, or make an old dinghy seaworthy again. Exactly the types of activities that the Cuban government, with their refugee crisis, is trying to preempt.

I'd done my homework. I contacted consulates, read canonical histories, and spent a year emailing back and forth with local Cuban surfers. They said they needed boards. They said they needed fiberglass. They said it's never been easier to get there.

It's in the news every week: Political tensions between the U.S. and Cuba are thawing like, well, a snowball in hell. We’d been locked in a geopolitical stalemate since the Cold War, when Cuba became the Western Hemisphere’s first communist country, housed Soviet warheads, piled up human-rights violations, and had over a million political refugees escape to U.S. shores. From their perspective we were an imperial power trying to undermine Fidel Castro's regime at every turn through covert CIA operations, an economic embargo, and an illegal military base on their land. Cuba was on the short list of states with which we'd completely cut off diplomatic relations, including North Korea, Iran, and Bhutan. Travel between our two countries was explicitly illegal, and a Hatfield-McCoy scenario had evolved: we'd opposed each other for so long that most people couldn't even remember why anymore.

And then there was the obvious surf potential: 3,000 miles of untapped coastline. Roughly three times more shore than California. A beguiling swath of ocean marked by a bevy of bays, reefs, points, sandbars, offshore isles, and fluvial outlets. Cuban surf has near-zero documentation,
but you don't need surf cams or complex forecasting models to see how real the prospects are.

Then, in December 2014, Obama made some surprising steps toward normalizing relations. The easing of travel restrictions and the embargo signaled an impending onslaught of tourism, investment, and change. By the time you read this, nonstop flights from LAX and New York to Havana likely will have begun their daily laps.

Selfishly, I wanted to go before the window to old Cuba closed and the forces that be transformed it from a Left Bank on the Caribbean into another glass-plated spring-break destination with a selfie stick in every hand and a W Hotel on every corner.

And then there was the obvious surf potential: 3,000 miles of untapped coastline. Roughly three times more shore than California. A beguiling swath of ocean marked by a bevy of bays, reefs, points, sandbars, offshore isles, and fluvial outlets. Cuban surf has near-zero documentation, but you don't need surf cams or complex forecasting models to see how real the prospects are. It's flanked by the Atlantic Ocean, the Gulf of Mexico, and the Caribbean Sea--three bodies with three unique fetches, all intersecting on this massive island ridge. An isobaric orgy. Mostly short-period swells, not unlike those that bring world-class waves to other Caribbean standouts like Bocas del Toro in Panama or Soup Bowls in Barbados.

While planning the trip, I got a message in my inbox with this subject line: "The season has begun!!!" Attached was an image of a reeling right, well overhead and slightly feathering as a surfer paddled into a clean pocket. The photo was a bit grainy, but you could see the lineup was empty. Even more surprising was how meaty, organized, and clean the swell looked. I immediately pulled up East Coast forecasting models. The animation showed purple blobs marching across the mid-Atlantic for weeks on end. A separate cell in the Gulf was broadsiding the island from the west.

But first I had to pass the customs counter. As I stood there nervously, pondering my jet-lagged reflection in the agent's blemish-less forehead, she took the $25 tourist visa I'd purchased during the layover in Mexico City, brought her passport stamp down in a sudden thump, and waved me through without even lifting her eyes from the desk in front of her.

That was it. I was in Cuba.

GALLERY:

The quality of light in Havana was otherworldly. The brilliant façades of decaying colonial buildings streamed past our taxi window; dappled sunlight poured from the thick clouds above.

The city was teeming with people, sweaty bodies weaving through traffic, clogging sidewalks, and sitting in folding chairs on roofs--everywhere but inside their houses. It was as if some kind of blackout had forced everyone outside.

Our cab driver was listening to a curious mix of Top 40 pop, reggaeton, classic rock, and rap from a USB drive plugged into his car's stereo--the latest Paquete Semanal, a bootlegged 1-terabyte flash drive of music, movies, news, and YouTube videos distributed weekly on the black market, the locals' workaround in lieu of broadband Internet. The Cuban government had only recently started allowing access to the Web, and only in a few big hotels and Wi-Fi-equipped parks.

It takes a coalition of the willing to throw in for a trip like this, but the prospect of exploring Cuba's surf potential was enough to lure an international crew of wave chasers, including Cyrus Sutton, Otto Flores, Jared Mell, and Lex Weinstein. Our meeting point was a casa particular--a family-run house that rents out rooms--a few blocks from Calle 70, Havana's most trafficked break. There were several large state-run hotels along the beach, filled with middle-aged Spanish, French, and Argentinian tourists, but just a few blocks back inland it was a hodgepodge of tenements, vine-covered bungalows, and deteriorating colonials.

Margot's casa was modest but impeccably kept. She was the white-haired matriarch of a three-generation family, all of whom lived under her roof along with a cage of 30 or so hamsters. And now us, too. Margot glided about the house in a flowing nightgown, her small body in a near-constant state of genuflection. But when it came time to talk room rates, she led us firmly by the arm to the kitchen table, where the family business was conducted.

Calle 70 breaks in front of the Russian Embassy, a probe-like high-rise that looks like a cross between an air traffic control tower and a federal penitentiary. It does not emanate feelings of benevolence--we took to calling the Embassy "Bad Vibes, Incorporated"--which made the freaky, deceptively punishing wave that broke in its shadows seem all the more appropriate. The break was essentially a shelf of sharp coral upon which short-interval waves would heave themselves. The crew took turns pulling into closeouts, and Flores found an especially wedgy section for airs, but no one left the reef unscathed. I walked away with several gouges in my back, boardshorts ripped open and blood-soaked, and my wedding ring ripped from my finger.

Calle 70 breaks in front of the Russian Embassy, a probe-like high-rise that looks like a cross between an air traffic control tower and a federal penitentiary. It does not emanate feelings of benevolence--we took to calling the Embassy "Bad Vibes, Incorporated"--which made the freaky, deceptively punishing wave that
broke in its shadows seem all the more appropriate.

The local surfers--not even remotely aware of the surfing cliché--told us that the waves were much better last week. This is the hermetic bubble within which Cuban surfing has grown. The head of the local surf club, Yuniel, told us they'd started out riding pieces of plywood, gradually adding resin and fins to their equipment. In the mid-'90s, a neighborhood guy who had traveled a bit in the Cuban Navy got his hands on a kneeboard. "Rocker like a plantano," Yuniel said, referencing its plantain-like curve. Soon they were collecting foam from old coolers that fishermen had discarded and using potato peelers to shape it.

Today, local surfers have a few modern boards--gifts from rare visiting surfers--but there are still no surf shops, places to acquire equipment, surf magazines, or surf movies. The government, Yuniel and his friends explained, has historically promoted team sports that emphasize ideals like cooperation and solidarity. Surfing is seen as a kind of zany fringe sport.

Havana is many things: It's sunsets on the Malecón, hipsters in Old Havana, and on-trend restaurants. It's warehouse raves and microbreweries where you can order huge towers of beer for a table. It's money changers, cigar pushers, aggressive prostitutes, government men, and cheap rum that you truly pay for in the morning. It's dazzling racial diversity, widespread higher education, free 24-hour health care, and an absence of drugs, poverty, and violent crime. But Havana is not--or at least it wasn't for us--surfing, so we decided to push on.

I didn't know much about Cuba's surf outside Havana, and neither did anyone else, it seemed. Few travelers venture beyond the immediate enclaves of Havana unless they're on a guided tour or a luxury bus to one of the government-run resorts. In terms of waves, however, all signs seemed to point farther east. The locals offered only hazy details about the setups. So, without the benefit of surf reports, forecasting sites, or guidebooks, we followed a hunch that would take us 800 miles across the island.

Caption

Making all use of a ’50s Chevy exterior before the crew moves out. Photo: Gordon

Yurie was thick-necked and cauliflower-eared. Mell said he looked like a heavyweight boxer from the '40s.
His blond-haired, blue-eyed Slavic features, and his vaguely Russian name, were an anomaly even among Cuba's racial rainbow.

I knew that a lot of ex-military men had immigrated to Cuba after the dissolution of the Soviet Union, but when I tried to ask Yurie about it, he wouldn't even humor the question.

His vehicle was the automotive embodiment of his persona: a blue behemoth that was part school bus, part military transport. It was made from a 1950s Chevy body jury-rigged to a Russian engine, resulting in an 11,000-pound chunk of steel. Yurie was the owner and sole mechanic, but because he didn't have a driver's license, he'd partnered with a pudgy kid in aviator glasses, who looked like a prepubescent Kenny Powers, to handle driving duties. The Chevy still had a trombone-sized air horn screwed to the hood and a Via Azul logo from when it was still part of the national bus fleet.

When it pulled up to the house early in the morning, Margot came out into the yard in her nightie and kept repeating in her small voice, "Esta comico eso." How comical this is.

John Steinbeck, who knew a thing or two about road trips, once cheekily credited the Model T with the disappearance of the "concept of private property" in America. He said those cars broke down so frequently that their basic operation necessitated a kind of highway communalism. To own a Model T was to be constantly sharing tools, mechanical knowledge, and, ultimately, the cars themselves. Well, I can't say if all cars in Cuba are that cumbersome, but I can say that our beast drew us deep into the familial space of an impressive cross section of Cuban society.

Just a few minutes into our trip, we sideswiped a sedan in an intersection and were instantaneously surrounded by a platoon's worth of Havana's notorious traffic police, with whom Yurie proceeded to argue for over an hour, even though our bus' cheap blue paint was clearly all over their car. They took Kenny Powers (KP) to the hospital to give him a Breathalyzer. Several hours later he was released. We paid an $8 fine, and started off again. We were only two blocks from Margot's house.

One of the consequences of this incident was that the unlicensed Yurie took over driving duties while KP seethed. Yurie tried to make it up to us by pinning the accelerator for the next seven hours, but now every time he saw a checkpoint approaching, he'd make KP take the wheel mid-drive and switch seats, performing these terrifying go-behinds as we hurtled down the road at 75 mph.

We traveled through lush farmland as we cut lengthwise across the country's interior. In a small town, I peered through the fence of an elementary school and saw an old man tending neat little rows of collards, lettuce, bok choy, arugula, rosemary, and sweet potatoes. "That's how the school make the lunch," Yurie pointed out.

The hours we spent barreling full-tilt through the country were lumbar crunching, sleep deprived, and bladder torturing. A faint diesel gas leak we'd sniffed earlier grew into a noxious cloud, constantly licking at our eyes, noses, and mouths. Sutton, sitting right over the gas tank, was ill for several days, having inhaled a toxic level of raw ether. In this manner we slowly, messily learned what it means to take a surf trip in Cuba.

And yet it was not so long ago that food shortages and extreme rationing had caused Cubans to lose, on average, 11 pounds each. They'd started eating cats. It was part of the reason tourists were confined to certain zones: The government didn't want them to see how skinny people in the most impacted areas had become.

We pulled into a dusty town called Las Tunas before dawn and a local family--relatives of a surfer in Havana who'd notified them we were coming--cleared out a bedroom and living room so we'd have a place to sleep. In the morning, they sent us off with egg sandwiches, happy to share what little they had.

The hours we spent barreling full-tilt through the country were lumbar crunching, sleep deprived, and bladder torturing. A faint diesel gas leak we'd sniffed earlier grew into a noxious cloud, constantly licking at our eyes, noses, and mouths. Sutton, sitting right over the gas tank, was ill for several days, having inhaled a toxic level of raw ether. In this manner we slowly, messily learned what it means to take a surf trip in Cuba.

We became connoisseurs of the various grades of fumes that permeate the highway system. We never gave the bus a name, perhaps not wanting to tie our fate any closer to its own. But the bus became our home, its roof our patio. At one point we spent a long night drive sprawled out on the roof. Up there we could get a little fresh air between us, kick our heads back to enjoy the thick ribbons of stars overhead, and even, very gingerly, stretch out a bit.

We eventually arrived at a cluster of wooden fishing shacks sitting on a blue 2-mile-wide bay. The swell we'd chased across the country materialized over the reef in the form of choppy knee-slappers, the dregs of a brutal, but not brutal enough, windswell. It didn't matter; we were just ready to submerge ourselves in the ocean and wash off the dirt accumulated, both physical and spiritual. Every so often, a proper wave would pop up among the withered swell and wink at us. But it was probably just a mirage.

We were starting to realize that surfing couldn't run the show. The show was too busy being hijacked by a series of misfires, misfortunes, and misinformation. If a leg of a trip was said to take three hours, you could count on nine. Words like timetable, map, schedule, calendar, and appointment don't mean the same thing in Cuba that they do back home.

In the fishing village, at a beachside restaurant made of driftwood, a man with a prodigious belly cooked us plates of diced octopus, rice, and beans, with fried sweet potatoes to scoop it into our mouths. After eating that for several consecutive meals and sleeping on his sand floor, we started calling him Papa.

There's a certain point on any wave-starved surf trip when you begin to wonder if it's just a unicorn hunt. Lying on Papa's restaurant floor was, in retrospect, that moment.

Photo: Gordon

A welcomed meal with locals after a steady diet of diesel fumes. Photo: Gordon

If you head far enough east, literally to the end of the road, the over-900-mile central highway that spans the length of Cuba turns around at a place called the Bay of Honey.

This is cacao, coconut, and banana country. It's cut off from the rest of Cuba by a ring of wet, jungle-carpeted mountains. Divers walk the coastal path here every morning with spear guns and dive masks that seem inspired by the 1870 novel 20,000 Leagues Under the Sea. There's a wave around here that's been likened to Lowers. The spot fronts a river mouth, which has deposited the smooth, melon-sized boulders that we often associate with point perfection. The local guy who lives on the point, Roberto, says the wave is a real peeler. Climb the anvil-shaped El Yunque Mountain, look north, and you might even be able to see the small gaps in the Lucayan Archipelago that a long-period Atlantic swell would have to sneak through to light this place up.

We gave Roberto's daughter a lift to school, and he showed me a scrapbook of glory shots collected from the point in front of his house over the years--images of big, clean, perfectly tapered walls. But when we surfed it, whatever pulses the break typically receives this time of year had flat-lined.

Was it really possible that our trip coincided with the only two-week flat spell of the winter? Information in Cuba is still largely an analog affair, traveling person to person, syllable by syllable, sincerely and susceptibly. At that moment, conditions may have been perfect elsewhere on the island, but after having undergone several weeks of a technological uncoupling, we resigned to the fact that we just couldn't know.

The locals didn't help much either. They greeted questions about the conditions with a kind of detachment, preferring to talk about the surf in symbolic terms rather than objective facts. When the waves were sub-par, one surfer told me it looked "honest." I noticed that kind of symbolism in other aspects of Cuban life as well, where imagination took on a kind of social currency, a substitute for what might be lacking in economic currency. It's one of the many ways they'd reverse engineered the social contract they'd been born into, just like they've reverse engineered old American cars out of tractor parts, the Internet with paquetes, and surfboards from old refrigerators.

Photo: Gordon

Jared Mell arranges a single fin in the sunset. Photo: Gordon

Cuba's first capital, the cobblestoned town of Baracoa, isn't far from Roberto's. Columbus parked his vermin-infested ships in its bay during the fall of 1492, taking special note of the gold earrings the local Indians were wearing. A legend from that time has survived, about an old Taíno warrior named Hatuey who bravely fought the Spanish out of Baracoa. Hatuey was later captured, and before burning him at the stake, a Spanish priest tried to convert him to Catholicism, offering salvation in heaven. "And the Spanish, where do they go?" Hatuey asked. The priest replied that they also went to heaven. "Well, then send me to hell" Hatuey said.

Hatuey was named Cuba's first national hero. It's his ponytailed image you'll find on Cohiba cigars. Given that rebel legacy, you might imagine how Cubans feel about housing America's most notorious military prison. It's right there, in Guantánamo Province, just over the mountain from where you can check the surf.

For over 50 years, everything in Cuba has been framed in terms of resistance, everything a shared battle. So what will happen when that battle is over?

It's already happening. People I met openly mocked the Castros. It's not like the old days anymore, when people spied on their neighbors for the comités. There is apathy today for that old ideological posturing, yet it lives simultaneously with a pride still felt about the defiance Cuba asserted for half a century against the world's biggest hegemon looming just 90 miles away. Perhaps they simply love their country beyond all proportion of what it represents. Who would blame them for that?

There was a moment on the beach when I asked Yurie about the changes over the last few years, and if he was hopeful for Cuba's future. "Del lobo un pelo," he said. "A single whisker on the wolf."

Regardless of this precious "window" Americans are tantalizing over, of all the ink spilled on the topic, Yurie seemed to be implying that, for Cubans, it's just more wait and see. Perhaps sweeping change will come to Havana; international companies will build towers into the sky and the first billboards will begin popping up on highways. But there, on the coastal fringes, watching windswell lap onto the shore, the gutless surf seemed incompatible with our insatiable desire for new surf destinations.

"Look at where we are," Yurie said with outstretched arms, gesturing to the enormity of the windswept bay where we were sitting. "Does this place look like it likes change?"

[This feature appeared in our July 2016 Issue]

Photo: Gordon

Voices of revolution are still near even in Cuba’s new era of national transition. Photo: Gordon