Cuba: A Dry Run

North of Havana is a fantasy world of mangrove-lined cays and green water flashing with tropical fish—perfect sea-kayaking country. But the line between what's permissible and what's not in Castro's kingdom falls in a gray area, and comings and goings by water always mean trouble.

Peter Heller

Heading out the door? Read this article on the new Outside+ app available now on iOS devices for members! Download the app.

The Greek professor is getting to be a pain in the ass. He says he’s in Havana lecturing on the predominance of the female figure in excavated Minoan art. The archaeological record, he says, suggests that Minoan society was a matriarchy, an idea that appeals to his feminist Cuban colleagues. He smiles through his beard and looks around the hotel coffee shop. We don’t trust him. The night we arrived, he checked into the room next door, and he’s been monitoring our every move. Now he doesn’t want to talk about art, he wants to talk about our plans. Sea kayaking? How interesting. Where, exactly? The north coast. Show me the map. I don’t want to show him the map. I want him to bug off. I want him to quit calling our room day and night, an uncanny five minutes after we return to it. It’s starting to feel like a setup.

“So, my adventurous American friends,” the professor says, “what have you discovered?”
I want to say: That a ’55 Chevy Bel Air can run beautifully with a Russian Lada motor and a Toyota transmission. That the women of Cuba, unbombarded by media images of skinny blondes, don’t hate their bodies. (The reigning fashion among females of all ages and shapes is a Lycra catsuit, preferably with vertical stripes.) That a box of Montecristo No. 4s costs $25 on the street.

Instead I say, “We’ve discovered that we’re nuts.”

My old friend and paddling partner Adam Duerk and I have come here to do what we believe no one else has done: kayak a long stretch of the Cuban coast. We also want to see what Communism in the Americas looks like at the beginning of the third millennium. For the kayaking, we’ve chosen an archipelago of pristine mangrove-and-sand cays along the north shore. It’s a coastline Hemingway wrote about in Islands in the Stream. We’ve brought two exquisitely built collapsible Klepper kayaks and 20 boxes of Kraft Macaroni & Cheese. The dinners are backup; we’ve heard that in the ultraclear water on the Gulf Stream side of the island you can free-dive and pick out lobsters like deli sandwiches.

What we don’t have yet is permission. After months of faxing various agencies of the Cuban government and receiving no reply, and talking on the phone with officials who were enthusiastic, voluble, and completely unable to give an answer, I called the Cuban embassy in Toronto. The woman at the tourism desk was succinct. “If you row past the boundary of the resort you will be detained.”

“I’m not going to any resort,” I said.

“If you don’t go to a resort you will be detained.”

“You mean I have to go to a resort or I will be detained?”

“You misunderstand. If you take your boats outside a resort—”

“Don’t say it!” I pleaded. I thanked her and hung up.

We bought plane tickets. I figured nothing takes the place of face-to-face personal charm, especially when the face belongs to George Washington or Andrew Jackson. There are some 3,100 nautical miles of Cuban coastline. There are hundreds of fishing villages, scores of port towns, thousands of reasonable officials. If all else failed, we’d sneak. Both Adam and I had years of experience slipping our kayaks onto tightly regulated rivers in the American Southwest. How tough could Cuba be?

The commadore of the yacth club at the Marina Hemingway, just west of Havana, leans across his mahogany desk. Senor José Miguel Diaz Escrich is a big, affable, all-business socialist who clearly enjoys being at the helm of a conspicuously capitalist enterprise. Above him, lovingly framed, are two pictures of famously bearded men. Castro is shaking hands with a couple of Australian athletes who, in a delightful reversal of the usual direction, had swum to Cuba from somewhere else. Hemingway, in the other photo, is just being himself, which looks like such an effort it puts me in the mood for a double rum.

We’ve come to see Escrich because he is the man most responsible for the rising popularity of Cuba as a yachting destination. In a country with one of the most tightly regulated coastlines in the world, he’s convinced the government that cruising boats are not a big threat. Even Cuban fishermen in skiffs need daily permits from the military to throw a net in the bay, but because of Escrich the red tape for foreign yachters has been made manageable. We want to paddle about 120 miles from the sugar port of Caibarién, on the central north coast, westward to a tourist resort called Varadero. We have little drift sails, and we figure that if we can convince the Cubans that our kayaks are simply very small yachts, we’ll get permission.
“And what about your boats?” Escrich asks. “What happens in the waves?”

I understand his question. As poor as Cuba is, sports are a big deal, and the Cuban flatwater kayak team trains at the marina. The commodore is probably imagining us in sleek, tippy competition shells.

“These are expedition kayaks,” I say. “Built by Germans. A German paddled one across the Atlantic in 1956. Completemente loco, huh?”

Escrich smiles. “Yes,” he replies, executing the signature Cuban Ironic Eyebrow Raise, which can be made to speak volumes. “Loco. But to tell you the truth, what you are trying to do is even more loco.”

“It’s perfect for kayaking,” I argue. “It’s practically an inside passage.”

He does the eyebrow thing again. “Nobody has ever done this. Submit a detailed written proposal. We will submit it to the Ministry of Tourism. This will take time to analyze. And let’s be clear with each other.” He leans forward and gives us the same I-know-boys-will-be-boys look my hardass Uncle Wilson used to give me and my cousins. “If you go out to Caibarién and construct your kayaks you will be—”

I chime in: “—detained.”

Havana has no patience for nightfall. Dusk sweeps over it like the shadow of a wing and it’s dark. We tell the Greek professor we’re going to our room to have another look at our nautical charts and head straight out the front door. There are few streetlights in Havana. People stream in the close darkness of the narrow streets, lit occasionally by the passing of a rumbling Studebaker or a finned and sharklike Pontiac. We walk past block after block of colonial stone buildings with 12-foot doorways and elaborate lintels, grillwork balconies, and shuttered, glassless windows. Even at night you can see the weathered lack of paint, the laundry ghosting the ironwork. But it doesn’t feel like squalor; it feels like the unresigned and dignified demise of an antebellum manor house. Maybe that’s because, unlike Mexico, where we’ve just been, we haven’t yet seen a child who looks malnourished or unhealthy.

We turn down Obispo Street, restored to its colonial-era splendor. Throngs of Germans and Canadians stroll the swept cobbles beneath replica gas lamps. Policemen stand on every corner. We head toward the thrum and trumpet call of a loud bolero and enter the Lluvia de Oro bar just as the six-man combo breaks into a loud rendition of “Chan Chan,” the song made famous by the Buena Vista Social Club album.
We drink tall mojitos, juleps made with lime juice, rum, and crushed mint. Through the iron bars of a big window we can see well-dressed Cubans dancing on the sidewalk. Adam nods to the music. He isn’t good at being stalled out. He’s tall, athletic, an instructor at the Colorado Outward Bound School, and a director of Outward Bound’s sea-kayaking base in Baja. He’s always on the move. When I ask him why he didn’t bring a journal on the trip, he says, “The unexamined life is the only life worth living.”

Adam, who’s 30, sports a flattop, goatee, and earring. He looks like a Generation X version of Dirk Pitt, U.S. Commando. Given the current anti-Yankee climate in the wake of the Elián Gonzáles mess, I suppose it’s to be expected that the Cuban government would give us the full bureaucratic treatment.

“So, what do you want to do?” I say, stirring the ice in my mojito.


“Me too.”

“I don’t relish spending time in a Cuban jail.”

“Why not?”

“Food probably sucks.”

Back at the hotel, we commandeer the computer at the front desk and bang out a detailed proposal for a sea-kayak expedition along the north coast, complete with photocopied charts with circles and arrows. The next morning we deliver it to a surprised Commodore Escrich, who promises he will send it directly to the Minister of Tourism. We think we know what that means: weeks, maybe months, of “analysis.” So we buy a box of cigars and take the night train east to Santa Clara, a large town in the center of the country that will put us within an hour’s drive of our takeoff point at Caibarién.

Adam and I heave the kayaks into the dark baggage car and are waved inside by a thin old man in a striped shirt holding a flashlight. He makes his way past piles of luggage to a crate desk in the corner, where he sits stiffly and pulls several ledgers out of a stack. He opens one to a tattered table of figures but with the rocking of the car has trouble keeping it in the circle of light. I hold the flashlight, and he shakily reads down the columns with the point of his pencil and makes mysterious calculations on the back of a receipt. Then he pulls out another ledger. He multiplies and adds. After ten minutes he looks up and tells us that we owe 13 pesos—about 70 cents—in overweight baggage. I pull out a 20-peso note, and he says he doesn’t have change, we can pay him in Santa Clara. I say, “Keep the change.” He waves his hand: No, no. Adam and I walk unsteadily to our seats. The coach clatters and sways, lights dimmed, most of the passengers asleep. When I press my face against the glass I can see Orion hanging sideways in the sky, shooting his arrow upward to heaven, and the cut-out shadow of royal palms. The man in the seat across the aisle leans over and asks me where we’re headed. He says he’s from Australia, name’s Heath, and pulls a footlong Corona Double A cigar out of his satchel. He offers me one.

I tell him we’re trying to get permission to go paddling, and he twitches his mouth into a pained smile and jerks his head toward the beautiful green-eyed mulatto woman curled against him.
“I’ve been trying to get permission from the government to marry her for nine months. Full-time job. Best of luck.”

We smoke and talk and I think how lovely it is to be enjoying these fine cigars as we jostle through some of the world’s richest tobacco country. Soon there’s murmuring in the seats up front. Heath’s fiancée sits up and clucks loudly. She says that the Cubans are complaining about us: They wish the obnoxious tourists would pipe down. She says this in Spanish, and loud enough that the whole car can hear. Busted.

The people up front start to laugh. Cubans are nothing if not good humored. I think it’s funny, too, and I laugh a little like Tom Hulce’s Mozart in Amadeus. The car erupts. The woman conductor seated up front shakes her head and abruptly leaves for the next carriage. Then the door bangs open and she’s back, hurrying down the aisle, followed by two policemen who ask some of the Cubans for their papers. There’s no sound now but for train wheels and couplers. Palpable fear. The cops examine the documents and begin to write out citations. The offense: telling foreigners to shut up.

Nobody else, it seems is interested in going to Santa Clara; the station’s deserted. A cold front is moving down from the States, and a shank-of-the-night fog haloes the few lights. Beyond the station is a little plaza where a teal, late-fifties Cadillac is parked next to a horse and carriage. I have a momentary fantasy of my grandmother Barbara as a pretty brunette waving from the car.

A man with a thick mustache hurries down the platform, hands in jacket pockets.
“You need a room,” he says. “In a private house.”

I nod.

“Follow me.” He goes for one of the kayak bags and staggers under its weight. He leads us toward an idling yellow Lada. A thin man in a red baseball cap turns to us from the driver’s seat. He has a long, flattened nose like a boxer’s, shaved head, sad black eyes. “Fernando,” he says by way of introduction.

The car sputters through the misty streets of Santa Clara. Adam shoots me a look. He thinks we’re being handled, passed from one intelligence agent to another. Could this be true? Probably not. We’re probably paranoid. Navigating Cuba is like steering a deeply keeled ship through a sea of icebergs; just a fraction of the territory is explicit. The rest is below the surface, inscrutable to the stranger.

We arrive at Fernando’s house, with a comfortable front parlor and a long, narrow courtyard open to the hazy sky. In the kitchen we sit at a heavy antique table, and Fernando serves us espresso in china demitasse cups. I like Fernando right away. He has the loose-jointed movements of an athlete, and a brisk heedlessness as he crushes raw sugar into a splash of coffee. He smokes cheap Cuban cigarettes and listens with great attention to our plan. It’s evident that he loves the sea, and he seems fascinated by the idea of a long kayak trip. He says he’ll help us get to Caibarién. A friend of his knows the entire Cuban coastline, he adds; Fernando will invite him to dinner tomorrow night. As Fernando talks, I notice that his key ring is a miniature red-and-white fishing buoy.

The deiwns ia known simply as Guajiro, which means “farmer” or “peasant.” He was a field commander in the Angolan war, to which Cuba sent thousands of troops. He moves two glasses of rum and two demitasse cups to the edge of Fernando’s wrought-iron table and spreads the map. Above the little courtyard the sky is mauve with dusk. Fernando’s wife, Diana, is in the kitchen making dinner; his two small children, Laura and Fernandito, are at our feet, building parking garages with our dominoes.

Guajiro wears a camo bush hat, left over from his days in Nicaragua, where he also served, fighting against the contras with the Sandinistas. He’s my age, 40, but he looks older. It’s in the creases around his eyes and the stiffness of his shoulders. In Angola he and two Cuban comrades got lost in the jungle for 70 days, after a firefight with rebels who torched a church full of terrified villagers. The three men lived on insects and rodents. Later, Guajiro returned to the village and asked the priest, who survived, where God had been that morning, why he had let the church burn. “He was busy with other things,” the priest said.
Guajiro laughs and downs his glass of rum. “After that,” he says, “I didn’t have much to do with God. We were both very busy.”

He traces the route we will paddle and marks the islands. “Here, this is called Cayo Alto. On the outside is a sand beach, very clear, many, many lobsters. In the center of the biggest island you will see tall cedars that mark a spring of sweet water. Here is the Río Chica la Sagua. You can paddle up it through the mangrove some kilometers to a small village.”

Guajiro says that at night the cays are dangerous because cigarette boats come across from Florida—torpedo-fast with twin 500-horse Mercuries—to pick up fleeing Cubans from the estuaries. The Guarda Frontera, the border patrol, is helpless to stop them because the speedboats easily outrun their military frigates.

“At night, if the smugglers were to see you, and there was some confusion…” He shrugs. I ask him where, exactly, are the Guarda posts. It’s not a state secret; the Cubans are proud of their defense system. Guajiro makes a series of small X’s along the coast. Adam shakes his head. The stations are ten to 15 miles apart, almost within sight of each other. It’s like the Great Wall.

The old soldier sits back and smiles. He knows what we’re thinking.

“If you paddle out there, every Guarda station, every patrol, will know the length and weight and color of your boats, your passport numbers.” He leans forward. “They will know your mothers’ names.”
Adam and I stroll up to Santa Clara’s central plaza. We buy penny cups of espresso at the open-air coffee stand and watch the bustle. Dangling earrings and high heels are out in full force. A young man sipping from his cup beside us says, “Where you from? Alemán? Italiano?”

I love this part. “Estados Unidos.”

His head pulls back, eyebrows lift. We get this response everywhere. Often it’s followed by a question about the boy Elián. But not this guy. He begins to vent. “There are two Cubas,” he says. “There are the people and the government. Everybody knows this, that the government is for itself. The people are suffering.”

Adam and I look uncomfortably around us. This is the first time anyone has spoken openly and critically about the government within earshot of other people, and we’ve heard wild allegations that every fifth or tenth person in Cuba is a government informant. I wonder if the man is crazy. He tells us that a few years ago a tugboat called the 13 de Marzo, loaded with 71 illegal emigrants, was heading for Florida. The Guarda Frontera let it pass into international waters before turning the fire hoses from one of its frigates on the open boat. Mothers held babies up over their heads so the soldiers on the frigate could see who they were attacking. The 13 de Marzo sank, with 31 survivors to tell the story.

On our way back to Fernando’s, Adam was quiet.

“Do you think it’s true?” I say. “About the boat?”

“It’s fucking grim if it is,” he says. We later find out that it was.

There’s a kayaking culture in Cuba that surprises us. We knew there was a national kayak team, a remnant of the Soviet-era quest for Olympic medals, but we couldn’t have imagined that many of the provinces and municipalities have flatwater kayak and canoe teams. Sea kayaking, on the other hand, has been forbidden. Kayaks are difficult to pick up on radar, and a good paddler could make the crossing to Florida in 24 hours. In the interest of solidarity, Fernando takes us to visit the team outside Santa Clara. A dozen young men and women between the ages of 16 and 23 live in two small bungalows by the Río Manajanabo and train three times a day. Most go to the nearby Sport College during the week, where they study to be coaches and trainers. Cuba sends trainers all over the Third World to spread the gospel of athletic prowess and to earn money for the government back home.

The Santa Clara team is proud to have been national provincial champs for the last five years. Their dedication is remarkable, and their equipment is old and crude: battered and oft-repaired flatwater boats from the early eighties. A typical morning workout consists of a 12-kilometer paddle, a 10k run, and weight training. The rusting set of free weights is scattered under a ceiba tree. When I ask if I can take a team picture they disperse immediately and come out from around the buildings carrying their paddles. Most of the paddles are homemade, with aluminum shafts and fiberglass blades. One boy has a battered wood-strip canoe paddle. They hold them like spears or swords, personal Excaliburs. Before we leave, I try to describe whitewater paddling to the kids. When I tell them that the motion of paddling is lindo, beautiful, like a bird flying, they nod uncertainly. “Isn’t it beautiful? To paddle so fast?” They hesitate. I think that perhaps to them it’s a job.

We are tearing through sugar country. The mountains of the Escambray, where Che Guevara trained his guerrillas, rise ahead, forested and rugged. Randy Travis blasts on the tape deck. All the windows are open and cigar smoke billows.

“My love is deeper than the holler, stronger than the river, higher than the pine trees growing tall upon the hill…”

Fernando is bananas over Adam’s Randy Travis tape. Inside the Lada, the mood swings vertiginously between country-lovesick and Elvis Crespo’s power salsa.

We’ve given ourselves up to Fernando’s care. He’s savvy and well connected in the province; he’ll work the system for us as best he can. In Caibarién he’ll take us to a government Fishing Authority, where we’ll buy fishing permits that should justify our boats and, we hope, allow us to paddle around the cays. The little car is heavy with the weight of our kayaks and water containers, our dry bags and tent and drift sails.

We pass a mock village built of concrete, totally deserted. There’s a church, houses, and a square, all surrounded by barbed wire. It’s one of many such sites in Cuba where civilians meet for national-defense drills. Hundreds of thousands of men, women, and children big enough to hold rifles are organized into militias, which train regularly. They can be armed and deployed within hours. Underground bunkers honeycomb the countryside. It’s mind-boggling: This island the size of Louisiana is prepared for an invasion by the States at any moment.

The Revolution is still very much alive in Cuba, galvanized by the U.S. embargo and repeated attempts at insurrection and assassination. Adam and I believe that one reason wily Fidel remains so potent is that he has taken the country’s deep (though discouraged) Catholic beliefs and used them to his own advantage: He has co-opted the Trinity. Castro is God. You don’t see or talk about him much. Che is Jesus. He is everywhere, on posters and billboards, eternally young and handsome. “CHE—SER COMO ÉL” (“Che—To Be Like Him”) is scrawled across a thousand concrete walls. The Holy Ghost is José Martí, Cuba’s greatest poet and the leader of the 1895 uprising that nearly shook off the colonial yoke of Spain. And there’s a host of Revolutionary saints, all of whom live in the daily conversation of farmers as well as city folk. I think, Why can’t the U.S. be like this? When was the last time a bunch of American schoolkids went out to play and one yelled, “Hey, I’ll be George Washington, total badass, and you be Paul Revere, and Jason—quit sniveling, dude!—you be wicked Lord Dunmore”?

Cairbarién at last. It’s a quaint port town with pink and aqua houses and an ancient Spanish church. The cross streets end at smooth water, the dark cays laying along it like sleeping seals.

But the officers at the Guarda say we can’t paddle the coast, not even with our fishing permits. We can, however, head inland to Lake Hanabanilla, a ten-mile-long reservoir surrounded by steep jungly hills. Why don’t we take our boats there?
In Cuba, even on a lake, you don’t just shove your kayaks off the shore and paddle. You get permission from a state-run resort hotel. You pull up the circular drive and a bunch of uniformed porters carry your boats through a green marble lobby and down to the dock.

We paddle hard for a few kilometers, glad to stretch our muscles. Then we drift, weightless at last, and the quixotic nature of our expedition dawns on us. I look at Adam. We start to laugh.

“And then we went lake paddling in Cuba,” Adam says. “Cómo se dice ‘idiotic’?”

But it is beautiful here. The water is silk-smooth, and the mountains are lush and cradle the lake. Egrets perch in the trees along the shore. We hear salsa drifting across the cove from a shack covered in bougainvillea. We hop out of the boats into the cool water. We splash around and dive for the bottom. The kayaks drift away on the warm breeze and we have to swim after them. A few miles farther on we meet a decrepit ferry crowded with Cuban tourists. They hang off the rails and wave. It looks like a refugee boat, and the irony doesn’t escape me: Three oceangoing vessels passing each other on a tiny, bounded inland sea.

That night before I sleep I imagine we are paddling out from a sandy beach. The boats are red and the water is clear and green. Inches below us, we can see purple sea fans, black anemones, the translucent green shadows of schooled fish flashing to silver as they turn. The sun is hot, the trade wind is rising. I can feel it on the back of my neck. I think about the vacuum cleaner salesman Wormold in Graham Greene’s Our Man in Havana. He is recruited by the British Secret Service, and he proceeds to make up all of his Cuban intelligence reports. He invents a host of paid informants. It’s a lot easier that way. Soon his reports are given terrible credence by the police and spy agencies of several nations, and people are murdered as a result.

I wonder about the meaning of our expedition. I wonder if, at this point, imagining it might be just as fruitful as the real thing. The story seems to have become the act of trying to get on the water. What if we never actually get there? I can make it up: “Adam flips the heavy tuna into his cockpit and pries out the hook. The cay just to the west must be Cayo Nansanillo, for I remember the clump of cedars and the sweet spring marked on the map by the old soldier…”

As I drift to sleep I conjure the vast country just 90 miles across the strait to the north. The United States has lost so much that Cuba still has. I see it everywhere on the faces of Cuban children: a kind of secure sense of self, an innocence. Yet from this small room in Fernando’s house the freedom of the United States seems wild, intoxicating. Nobody writes me a ticket for laughing on the train. A few years ago I rode a horse from my doorstep in southern Colorado all the way to Wyoming, and nobody asked for my papers. There will be a time, soon, when Cuba is like that, when its mountains and thousands of miles of wild coastline will be open to adventure. Castro will be dead then, the embargo lifted, and, I fear, much of the country’s strange charm washed away in a tide of commercialism from the north.

Before we leave Cuba, Fernando takes us fishing. He drives us to his father’s cabin in a muddy hamlet carved out of the mangrove called Playa Francisco. He stops at the whitewashed Guarda station and buys our permits. The three of us wade out into the warm water, up to our waists. We bait weighted hand lines with shrimp and whip them over our heads. The sun is straight in our faces. The sand fleas are terrible. Across the slick-calm water a few fishing skiffs move slowly. Beyond them are the dark shapes of the cays.

I get a tug on my line, and then another, and I’m hauling in, hand over hand. The fish is fighting hard. I pull him in and lift out an eight-inch triggerfish.

“Hey, Pedro!” Fernando whoops. He’s smoking a Montecristo and he looks happy, in his element. “El Viejo y el Mar!” The Old Man and the Sea.
Three weeks after we return to the States, I get a startling e-mail. It’s from Commodore Escrich: “Congratulations. The government has approved your project…” I laugh. Perfect timing. I think about what many Cubans told me: that Castro is the ultimate micro-manager and that a proposal for an expedition of this nature, so novel in Cuba and so off the beaten tourist track, would end up on his desk for approval. He’s an avid free-diver and I think how this trip might appeal to the old athlete. We’re going back in October.