The moment I thought I could actually die in Cuba came on the second to last day of my trip. For the previous two weeks, I’d been circumnavigating the island by motorcycle, visiting all 15 provinces and logging nearly 2,500 rocky miles. It had already been an eventful day: I started in the Viñales Valley, land of tobacco plantations and limestone hills, on the island’s western end, where I hit a bad hole and bent both my rims and had to visit a ponchera, a flat-tire repairman, who beat them back into shape with a hammer and a two-by-four. Since then I’d ridden about 200 miles — so far, so good — and was approaching Varadero, the glitzy resort zone east of Havana. But then it started to rain, and suddenly it got dark. Soon it was pitch-black and pouring. I was doing 60 on a curvy highway with no lights, and my visor was so wet that I was, for all intents and purposes, legally blind.

I never thought Cuba would be easy: bad roads, poor signage, minimal infrastructure, all that Spanish. I also had no business being there. I’m a novice rider and a worthless mechanic, and the longest motorcycle trip I’d undertaken until then was an hour . . . in Manhattan. But this journey felt like the last chance to see something important: Cuba as it is, before it becomes whatever it will become. I’d set out from Havana with few expectations and no plans, just a vague clockwise route and a list of private casas to stay in along the way.

When the magazine first proposed a Cuba trip, it seemed simple: Get out of the Havana rum-and-cigar rut and really see the country. The only hitch was that you couldn’t legally rent a motorcycle in Cuba (Communism) or ship one from the U.S. (embargo). We asked Triumph, a British company, to ship one. I recently went looking for our earliest emails about it, and I found one where a confident Triumph rep declares that the company could ship a bike from Panama “quickly and easily.”

That was in December 2012.

Things started heating up about a year ago, when U.S.-Cuba relations began to thaw. Last fall Triumph arranged to send a bike from Toronto to Havana’s José Martí airport. We weren’t quite sure how I would pick it up or what would happen to it when I left, but we stuck it on a plane and hoped for the best.

Steve McQueen took a similar trip in 1956. He was a young TV actor in New York who went to Cuba in search of a little adventure. He and a friend hopped a ferry from Key West to Havana and then rode off in search of McQueen’s neighbor and sometime marijuana connection, a journalist named Lionel Olay, who was in Havana writing a series of articles about Fidel Castro. At that point, Castro was still hiding out in the mountains, waging his revolutionary guerrilla campaign.

As McQueen later said: “We ran from Havana to Santiago, about 967 or so kilometers as I recall. Batista and Castro were shooting it out down there in the Sierra Maestra, and there were uniforms everywhere. I was still a little wild in those days, particularly when I was on the juice. So what happens? I get thrown in the calabozo.” According to the story, McQueen and his friends rode a little too close to a rebel outpost and got arrested as government spies. From his jungle prison, he sent a telegram to his then girlfriend, asking her to wire bail: “i love you honey send me money . . . in care of western union con amor esteban.”

“It wasn’t so bad,” McQueen recalled. “The guard was a friendly dude, and he’d let me out of the cell so we could have lunch together — cheese and onions and wine. . . . I suppose that’s the great romantic lure of the motorcycle. It’s a key to adventure.”

I arrived in Cuba on a Tuesday. The trip was weirdly easy — a JetBlue charter flight, direct from JFK, with a regular boarding pass just like one for Phoenix or Fort Lauderdale. I breezed through immigration and took a taxi to the Old City, where I had a daiquiri at Hemingway’s favorite daiquiri bar. The next morning I went back to the airport to pick up my bike from the freight shippers. A man named Gui­llermo told me that customs needed 24 hours’ notice to do anything, so I should come back tomorrow at 8 am.

That was day one.

The next morning I was back at 8 am sharp. While a small crowd gathered to watch, a kindly freight handler named Yoleidis and I spent a few hours reassembling the bike — hooking up the clutch and throttle cables, reaffixing the handlebars, connecting the battery — while the customs agents buzzed around, making carbon-copy rubbings of serial numbers and churning out forms to stamp on their dot-matrix printers. I had a minor freak-out when we got everything put together and the engine wouldn’t start — my journey finished before it had begun — but Yoleidis figured out how to pop-start it, and as it roared to life, the crowd cheered. “So do you need any mechanics in the U.S.?” Yoleidis asked.

On my way out, I stopped by the freight company (the cargo branch of Cubana, Cuba’s national airline) and talked to an immensely helpful clerk named Rosie, who arranged the return shipping. Now all I had to do was get the bike registered, but when I got to the registration office, the lady said they were closing, so I should come back tomorrow at 8 am.

That was day two.

The next morning it was raining in Havana, a driving downpour that bowed the palm trees and kept the old Chevys and Studebakers with their 60-year-old brakes off the road. Cold and soaked, I rode back to the registration office, where a stern inspector looked over my paperwork and told me I was missing a stamp, something that proved the bike would leave the country and that I wouldn’t be selling it or giving it to a Cuban. I pointed to the large X in the box that said temporary import. But the inspector was unmoved.

(I later learned that Cubans have a word for this phenomenon: peloteo, from pelota, or “ball.” It’s the same word they use for a warm-up kick-around in soccer or a long rally in tennis. Only in this case, I was the ball.)

So back I rode to the airport for a fourth time, still in the rain, and told my now-friends in customs what the inspector had said. They were confused. “Never in my life have I heard of such a thing!” scoffed one agent. She printed a new form with my departure date on it and had the chief of customs sign and stamp it personally. I rode back to the registration office — where the inspector nodded and said I should come back tomorrow at 8 am.

At this point I started to lose it. What could possibly be the problem this time?

“Las nubes,” he said, pointing to the clouds. “No hay conexión.” It turns out the Cuban internet runs on satellite, not cables. Since it was overcast, the connection was down all over the city. There was no way to register the bike. He smiled and said I should come back tomorrow at 8 am.

By now it was Friday. I knew that if I didn’t get my plate the next morning, I’d have to wait until Monday — too late to do my trip. I’d be fucked.

On Saturday, I woke to water in the streets. A norte had blown in overnight, and Havana’s famous seawall, the Malecón, was flooding. I stood on the porch of my casa and watched five men in wetsuits wade down the river that was my street, looking for people to rescue. Fortunately, my bike was parked on high ground a few blocks away. And despite the flooding, the sky was clear — so the internet at the registration office was working fine. The inspector examined the bike and stamped a few forms, and two hours and $45 later, I was the proud owner of Cuban license plate K60338.

But when I went back to my casa to get my things, the situation had worsened. The army had blockaded the streets; no one was allowed in or out. I went up to some Red Cross workers to plead my case. “We can’t guarantee your safety,” one said. “But you can try.” That was enough for me: I rolled up my jeans and waded in, trudging the three blocks to my house. The water was still rising when I left carrying my backpack and tank bag, so some soldiers insisted on escorting me out, holding me by the arm as news cameras snapped photos of these Cuban heroes saving the lucky, hapless foreigner. The indignity was a small price to pay to get out of Havana. At a nearby gas station I toweled off, bungeed down my gear, and got ready to hit the road.

You know all those clichés about motorcycles and freedom? They’re probably 80 percent bullshit, but when you’ve been trapped in bureaucratic hell for four days and just escaped town in the middle of a flood, riding a motorcycle along the Malecón as the wind whips and the waves crash is, if not the best feeling in the world, pretty up there.

I’d been riding about an hour when I encountered my first cop, a fat guy on a Suzuki on the side of the highway. Leather boots, dark shades: a real Ponch-looking motherfucker. The speed limit was 80 kilometers per hour, and I was doing maybe 85 so, I figured I was OK, but he started waving his arms and telling me to pull over. “Why were you going so fast?” he asked in Spanish. I told him I was going the same speed as everyone else. But it soon became clear that he really just wanted to talk about the bike. “What year is it?” he asked. “How fast does it go?” He walked around to the front. “Do you know your lights are on?”

This was my first exposure to a question I would go on to hear roughly 14,000 times. In Cuba, it’s apparently against the law to operate a motor vehicle with your lights on during the day. Unfortunately, as with almost all modern bikes, mine came on automatically. I couldn’t turn them off. People would honk or flash their lights or do that quacking-type hand signal and shout, “Tienes la luz encendida!” or sometimes just, “La luz!” I’m not exaggerating when I say this happened hundreds of times a day. Imagine if, for some reason, you couldn’t tie your shoelaces and everywhere you went, every couple of minutes, a stranger would scream at you, “Your shoes are untied!” It was like that.

For a long time I struggled with how to respond. I tried a thumbs-up, a thank-you wave, a weary nod. If I was riding slowly enough, I’d shout back, “It doesn’t turn off, thank you!” — but that was a lot to communicate at highway speeds. I didn’t want to be a jerk foreigner, ignoring people who were trying to help, but it got pretty aggravating being yelled at all the time. I couldn’t understand why everyone was so insistent, even angry. It was as if Castro himself had made it a national priority: No lights in the daytime.

Some other fun things happened that first day. In Máximo Gómez I took a wrong turn and dropped the bike in three inches of mud; some guys ran off a porch to help me faster than if I’d been their own abuela. I also killed a chicken. It was an accident. I was hurrying to get to Remedios before dark when a small black chicken pecking around in a ditch suddenly decided to dart into the road. That day, I’d passed dozens, maybe even hundreds, of similar chickens that had not done this, so I was wholly unprepared when this one did. I grabbed the clutch and squeezed the brakes, but when the bike started to fishtail, I knew it was me or the chicken. My front tire caught it square in the neck.

On the side of the road, a wrinkled old black man in a guayabera watched the whole episode unfold. I tried to convey to him that I was sorry, I didn’t mean to hit the chicken, in fact, I felt pretty badly about it, but I had no choice. What else could I have done? He stared back impassively, full of judgment. Then he quacked his hand and told me my lights were on.

In a way, modern Cuba was founded on a motorcycle. After all, it was an eight-month bike trip through South America that inspired a young Argentine medical student named Ernesto Guevara to leave behind medicine and take up arms — a journey that culminated in his becoming the public face and incomparable tactician of the Cuban Revolution. It was this trip that awakened him to poverty, racism, and injustice. No trip, no Che; no Che, maybe no Communist Cuba.

Guevara and his friend Alberto Granado set out in December 1951 on a 12-year-old Norton 500, which they jokingly nicknamed La Poderosa (“the Powerful One”). My Triumph was English, too, which I liked — less imperialist than a Harley-Davidson but still representative of the free world. The name in Spanish also had a nice connotation: Triunfo, as in Triunfo de la Revolución, the national holiday celebrated every January 1 to commemorate Castro’s victory over Batista, in 1959.

Back in the Sixties, Castro used to say that every Cuban family would one day own a home, a refrigerator, and either a car or a motorcycle. They’re not quite there, but motos do abound. Most of them, unsurprisingly, are from the Eastern bloc — Russian Urals with sidecars, East German MZs, Ukrainian Dneprs, Czech Jawas — and most are at least 30 years old. Everywhere I went, people marveled at the size and sleekness of the Triumph: How fast does it go? How many cc’s? What year is it? This year? How did you get it here? What will you do with it when you leave? (This last one always asked with a hint of hope.) People called it a truck, an airplane, a UFO. One woman teased, “No es una moto, es un terremoto!” punning on the Spanish word for earthquake.

Everyone wanted to know how much it cost. I usually said $9,000, which is basically right. I assumed Cubans would think that was a lot, and they did, but it was also less than they expected. Because cars and bikes are in such short supply, $9,000 in Cuba might buy you, say, a 1985 Suzuki with 40,000 miles. When I’d ask how much my Triumph would go for there (if such a thing were remotely possible), estimates ranged from $30,000 to “millions.” One guy kept asking how much my wheels cost, how much my seat cost, and when I told him I didn’t know, that I’d bought the whole thing together, he looked confused. He conceived of the world only in terms of parts.

I spent the next four days winding my way along the island’s north coast, through tobacco fields and Texas-style cattle country and past glittering blue bays. Outside Havana, Cuba is basically one giant farm, where sun-weathered guajiros carry machetes on their hips, and horse-drawn carts vastly outnumber cars. In Yaguajay I stopped to watch a pickup baseball game on a diamond cut in a sugarcane field, and outside Velasco I saw a man using a tractor tire like a sled, riding it as a pair of horses pulled him down the road. In Mayarí I stayed in a near-deserted pine forest villa that cost a tenth what it might in, say, Costa Rica, and in Gibara I swam in the bay where Columbus first landed in 1492. “The most beautiful human eyes ever beheld,” the explorer wrote. It was certainly the nicest place I’ve ever washed my jeans.

I spent a lot of time consulting my road atlas. I had no navigation, no GPS; it was muy analog. I usually had to ask directions a few dozen times a day. One guy told me to always ask at least three people, because no Cuban would ever say, “I don’t know.” The road quality ranged from good to nonexistent: The worst were dirt trails or boulder-strewn tracks, and even the decent ones had signs indicating the number of accidents, injuries, and deaths in the last two months, illustrated by little cartoons of colliding cars, wheelchairs, and cemeteries, respectively. The numbers were always higher than I would have liked.

I usually stayed at casas particulares, the privately owned guesthouses (really just spare bedrooms) that have proliferated since the rules were relaxed a few years ago. For $25 a night — less than an Airbnb cleaning fee — you get your own room, a bathroom with hot water, air-conditioning, a TV, and a fortifying breakfast of fried eggs, toast with jam, fresh fruit (pineapple, bananas, guava), fresh-squeezed orange juice, and all the café con leche you can drink.

Americans are still somewhat rare in Cuba, especially outside Havana, and when they learned my background they were always surprised. “Americano Americano?” (“American American?”) I never talked politics unless they brought it up first, and anyway there wasn’t a whole lot to say. We all agreed that the embargo was mutually unproductive, we were glad relations were improving, and we hoped Cuba would continue opening up to investment. The only time I felt even the slightest rancor or bitterness was at a casa where an endearingly grumpy old man lectured me about economic imperialism, then disappeared into his bedroom and came back wearing a guantánamo bay hat. But then we started talking about the upcoming American elections. When I told him that one of the leading candidates was a socialist, even he had to admit he was impressed.

On my sixth morning in Cuba, I got hit by a bus. Just grazed, to be honest — and only the bike. It was completely my fault: I was in Baracoa, a 500-year-old colonial town, the oldest in Cuba, going the wrong way on a one-way street, when a bus came around the corner and scraped my back fender. It would turn out to be only the second-worst accident of the day.

I was on my way to Maisí, the easternmost tip of the island. The road was scarily steep, full of switchbacks and blind curves, and I was ascending very slowly when I took one curve too wide and a chicken truck suddenly appeared in the other lane. I swerved back to my side but wasn’t quick enough on the throttle, and the extreme steepness of the road, coupled with the extreme slowness of me, caused the bike to stall. For a few gut-churning moments I found myself rolling backward toward a 100-foot cliff that disappeared into the ocean. What happened next is blurry, but it ended with the bike on its side and me next to it, both of us scraped up but, miraculously, more or less OK.

By now I’d ridden about 900 miles and had 1,500 to go. From Maisí I headed south on the Viaducto de la Farola, probably the most action-packed road on the island. Completed by Castro in the Sixties as a thank-you for the region’s early support for the revolution, it’s a steep, spectacular winding road that follows the path of an aqueduct through a mountain pass. At the coast I turned west and cruised through Guantánamo, the Cuban military town near the U.S. base of the same name. The town was full of soldiers ready to defend against the next American invasion. Then came Gran Piedra, in Baconao National Park, where Castro fled to after his first, ill-fated coup attempt, in 1953. In Santiago de Cuba, I met up with the photographer and his assistant, and together we caravanned along a stunning stretch of road, just barely clinging to the coast between the Sierra Maestra and the Caribbean.

This stretch of road was absurdly picturesque, and we stopped for photos often. As a result, we ran out of daylight about two hours shy of our destination and had to seek refuge at the nearest hotel, a third-rate resort full of Canadians in the middle of nowhere. The desk clerk apologized and said they had no rooms, but she offered to call some friends in the nearby town. When she had no luck, the other clerk tried, and then the bellman, and then a security guard. Eventually they found a friend of a friend half an hour down the road with a couple of extra bedrooms. The husband met us at a gas station and guided us in the dark, and the wife set about whipping up a head-spinningly good dinner of roast chicken, black beans and rice, and sweet-potato fries.

I experienced this kind of generosity all over the island. Granted, it was a win-win — we got shelter, they got some cash — but I got the feeling it would have happened even if we hadn’t been tourists with money. There’s a deeply ingrained sense of cooperation in Cuba, a default willingness, even eagerness, to help one another out. I could never figure out whether it was a cause of Communism or an effect — whether this collectivist, we’re-all-in-it-together spirit is what powers the Cuban experiment or whether it’s a coping strategy made necessary by the five decades of poverty and deprivation that the experiment has brought about.

During dinner, the couple brought out a ziplock bag filled with salt and pepper packets they’d gotten from a visiting Canadian. Each was adorned with a familiar-looking yellow M. “McDonald’s,” I said. They said they’d heard of the restaurant but didn’t realize this was its logo. In 40-something years, they had never seen an ad for McDonald’s.

By now I had four days left and a lot of ground to cover, so I split from the photographer and started booking it. I spent one epic day getting from Granma to Trinidad, logging 400 miles in eight hours. In Manzanillo, I got caught in a speed trap and got a speeding ticket from a gruff motorcycle cop — $60 and 12 points on my license. (Good luck cashing that check, Fidel.) Near Yara, I rode through an Old Testament–size swarm of locusts fleeing a fire in a sugarcane field, and outside Ciego de Ávila, I got pulled over by another motorcycle cop, who, it turned out, just wanted me to wear my jacket so my arms wouldn’t get sunburned. And in Playa Girón, a beach town on Bahía de Cochinos — a.k.a. the Bay of Pigs — I stayed with an out-of-work carpenter and his wife, who’d opened their casa just a few days earlier. I was their very first guest — capitalism in real-time.

Eventually I arrived at the Autopista Nacional, Cuba’s slightly incongruous superhighway — six lanes, no traffic. It was so deserted kids were playing soccer on it. After weeks of navigating spine-rattling potholes, the smooth ride was a relief, though I couldn’t help but have mixed feelings about its joyless efficiency, how very un-Cuban it felt. But I also realized how hypocritical that sentiment was: the same kind of neocolonialist attitude that causes Americans to lament that Cuba will be “ruined” by getting half-decent grocery stores and cars that weren’t built in the Eisenhower administration.

Finally I reached Varadero and the last stop on my trip, the fifth annual Encuentro de Harlistas Cubanos, or Cuban Harley rally. Experts suspect there are about a hundred Harley-Davidsons in Cuba. Before the revolution there was a Harley-Davidson dealership in Havana, but these days the only bikes on the island are from the Thirties, Forties, and Fifties. Just like those of their more famous four-wheeled counterparts, their owners have kept them alive with nothing but spit and spare parts — a crankpin from a Russian here, a chain welded together from two bicycles there. It’s the quintessential Cuban virtue called resolver: making do with what you have.

In a sunny, tree-lined park, I watched as tattooed bikers in leather vests and ripped jeans (it turns out that Cuban Harley riders look a lot like other Harley riders) drank cans of Bucanero beer and admired each other’s bikes. I met 65-year-old mechanic Sergio Morales, the godfather of Cuban Harlistas who is legendary for the magic he can work with a moto. Sergio once got hold of a perfectly preserved exhaust system — ultrarare — and rather than install it in a bike, he sliced it in half, sacrificing it so he could deconstruct it and build his own. He asked about my trip and what I thought of Cuba. I told him I’d loved it all. If I had one complaint, it was an extremely minor one — namely, the way people constantly told me my light was on.

Sergio smiled. Slowly, patiently, as if he were talking to a child, he explained that in Cuba, if a headlight burns out, you can’t get a replacement. Especially for a new bike like mine — they just don’t have them. That’s why everyone was so adamant about my turning mine off. They weren’t upset; they were worried for me. They were trying to save me from wasting it.

It was raining when I finally rode back into Havana. I parked the bike near my hotel and paid a couple of security guards $20 to watch it, then woke up around sunrise and rode to the massive Plaza de la Revolución to burn off some fuel before shipping it back. I snapped photos of the moto with the famous Che sculpture until a soldier chased me off. Five minutes later I was on my way to the airport, approaching a red light, when the bike let out a strange sound, coughed twice, and died.

The death was sudden and catastrophic. The electrical system was totally shot, the speedometer frozen in place like a rictus. I was later informed that it was most likely a battery issue, a lead — one that I had helped to install — that had gotten knocked loose from the terminal. But in the moment, all I could think was that I was 20 minutes from the airport and I just wanted to be done with it.

I found a cop on the street and asked if he could help me find a tow truck. “There are no tow trucks,” he said. “You have to call a friend.” I told him I didn’t have any friends. He shrugged and walked away.

Just when I was imagining calling Triumph to say their bike was on the corner of Avenida de la Independencia and they could come get it anytime, I heard a woman behind me. “Is something wrong with your moto?”

I turned around, not really in the mood to chat. “It won’t start,” I said curtly. “It died.” The woman smiled wide. “Don’t you recognize me? It’s Rosie — from Cubana.”

My mind exploded. Rosie from Cubana! The woman from the freight company, the very person I was on my way to see. Somehow, in my moment of crisis, a city of 2.1 million people had delivered to me the exact person I needed. I couldn’t believe it. I hugged her, maybe a bit too enthusiastically.

It turned out she lived around the corner and was waiting for a ride to work. I told her I was on my way to the airport to ship the moto when it shut down on me. “It doesn’t want to leave Cuba!” she said, laughing.

Rosie called a friend who could give me a tow. I’d been in Cuba long enough that I should have known better than to expect a tow truck, but I was still surprised when a beat-up yellow Russian Lada pulled up and Rosie’s friend got out holding a frayed green cargo strap. Together we tied my bike to his back bumper.

And that’s how I left Cuba — my non-functional $9,000 motorcycle getting towed behind a 30-year-old Soviet taxi. Cubans on buses laughed and waved as we passed. I smiled and gave them a thumbs-up. No one told me my lights were on.

Josh Eells is a contributing editor for Men’s Journal. Except to take a few select photos, Eells wore a helmet for the duration of his two-week ride.

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