The shortest distance from Cuba to the United States is about 90 miles across the Florida Strait. By the standards of human-powered sea travel, it’s extremely doable, and it has been done for decades by refugees aboard the most makeshift of watercraft, driven by desperation. In the peak years, tens of thousand of Cuban balseros staked their lives on the journey, in hopes of finding something better at the end.




The very shortness of the trip testified to the artificiality of the separation between the neighboring countries. The bodies lost in the waters of the strait testified to how real it was. Last year, as the Obama administration set about restoring diplomatic ties with Cuba after more than half a century of mutual antagonism, the outdoor-gear company Cotopaxi decided to mark the new era with a kayak expedition across the strait, a gesture of international outreach.

A friend who does PR asked me if I’d be interested in documenting the trip. In addition to writing about it, I’d have the chance to paddle along if I wanted. It felt strange to consider the voyage as a form of recreation or as a stunt, after all those who had braved the crossing before. No matter how hard the kayak crossing might be, it wouldn’t be anywhere near as hard as it had been for the men and women on boards lashed to inner tubes. But what did normalization mean, if not the taming of the strait?

I agreed to go. I’d done a little sea kayaking when I was 12, but my kayak experience since then consisted of maybe 10 short sit-on-top paddles in whitewater. I figured I had a month to train up, and then, two days after I’d said yes to the trip, I broke a rib in a mountain-bike crash. I’d be going in cold.

Cotopaxi’s core kayak teams had been training for six to eight months. The company had also enlisted Olympic gold medalist Joe Jacobi to be one of the paddlers, and the teams were being coached by Carter Johnson, the current world record holder in distance kayaking. Still, I figured I was in decent shape. I could go along to observe them, and I’d get a look at Cuba before the inevitable post-embargo Disneyfication.




The plan was for the group to sail from Florida to Cuba aboard a pair of support boats named the Sunluver and the Mirage, then make the return trip by tandem kayak. The paddling route would be roughly 113 miles, from Marina Hemingway, just outside of Havana, to the Stock Island Marina in Key West.

First, though, we had to get to Cuba. Days before the group was scheduled to arrive in Florida, Cotopaxi ran into paperwork problems with the United States Coast Guard. It was unclear whether the support boats would be allowed to leave for Havana. We decided to go to Key West anyway and wait it out at the marina.

For three days, we slept on the support boats and tried to prepare. Cotopaxi had four paddlers who intended to make the full crossing without stopping. They had already partnered up: the company’s CEO Davis Smith was in one kayak with his cousin, the entrepreneur McKay Thomas, while the company’s other co-founders, Stephan Jacob and Jordan Allred, shared the other one.

Photo by Cassandra Allred

That left the rest of us to choose up teams, like playground kickball on the first day of school. Jacobi, the Olympian, partnered with Amy Kassem, a former Peace Corps volunteer who’d won an essay contest to join the expedition. There was another guy who seemed promising: 25 years old, six-foot-six, and a former rower for the University of Michigan. He seemed pretty chill to talk to, and he looked like Thor. I asked if he wanted to partner up, and he said sure. His name was Frank Sedlar.




Frank, like me, was a journalist. After we were committed to our cross-ocean journey together, he told me he had spent maybe half an hour in a kayak in his entire life. We promptly dubbed ourselves Team Underdog.

Cotopaxi had secured about eight tandem kayaks for the journey, but they ranged widely in quality. Everyone agreed that the top teams should take the nicer, newer composite boats, to have the best chance of success. Frank and I went for what we were told would be the next-best thing, one of the older composite boats.

We took it out for a practice paddle and it was terrible. Within five minutes, both of us were cramping in our shoulders. The pedals that controlled the rudder required about 60 pounds of pressure to get it to budge. I had no idea whether that was normal. I’d never once been in a kayak with a rudder before. But I was in back, so I was in charge of steering. We returned to the dock with our heads down. We weren’t going to make it 13 miles, let alone 113.

On the morning of September 5, the Saturday before Labor Day, the Coast Guard paid us a surprise visit. We’d assumed we were stranded through the holiday, but they had brought the paperwork clearing us to depart. We scrambled to get some last-minute supplies and headed south into the ocean.




When I awoke the next morning, tall buildings were visible in the distance. We were already almost there. We sailed into Marina Hemingway, along waterways where small houses and larger, newer buildings pressed close. On closer view, the newer construction was vacant and dilapidated inside. The facilities we’d left Key West felt posh by comparison. Cuban officials boarded our boats and we filled out visa forms. The officials stamped our passports, drank the American Coca-Cola we offered them, and welcomed us to Cuba.

We spent five days in Cuba, with the entire group staying in a single casa particular, a private home, similar to a B&B (you can book one through Airbnb now). We were doubling up in beds with people we’d just met, or sleeping on couches and air mattresses. After two days, most of the group planned to head to Trinidad for a day and a half and to scuba in the Bay of Pigs. Amy convinced Joe to break off from the main group to explore tobacco country, and Frank and I went with them. It was maybe the smartest thing we would do on the whole trip. In two quiet days in the small town of Viñales, our kayak teams figured out how to read each other—how to make one another laugh, and how best to communicate. We would need it.

Photo by Cassandra Allred

Our other breakthrough happened right before we headed to Viñales. Out of curiosity, Frank and I decided to try one of the other kayaks. It was a cheap, bright blue plastic one from Wilderness Systems. It was heavy and looked funny, but as soon as we got in it, we were 20 times more comfortable than we’d been in our previous vessel. We only had time for a quick one-mile paddle, but that was enough. We had an Instagram contest to name it, offering a bottle of Cuban rum as a prize, and a friend of mine christened it Fidel Fastro. Team Underdog had its boat.

We made it back to Havana just in time for a press conference with the commodore of Marina Hemingway and the head of the Cuban Kayak Federation. An agreement of friendship and cooperation was signed between the Cubans and the Americans, with both pledging to try to bring the two countries closer through sport. The next morning, Frank and I scrambled to get ourselves and our new kayak ready, taping garbage bags to the seats, stuffing the boat with food and meds, putting tape on nipples and covering ourselves with diaper rash cream to prevent chafe.




At quarter past noon on September 11, with the final all-clear from the Cuban authorities, we headed out to sea: four all-the-way tandem kayaks, accompanied by one relay kayak that would have different paddlers subbing in and out, and one lightweight single-man kayak, a surf ski (also a relay boat). One support boat, a 44-foot catamaran called the Sunluver, led the way, while the other, a 60-foot single-outrigger vessel called the Mirage, brought up the rear.

The goal for the top kayak teams was to make it across without ever touching the boats, for a clean, unassisted crossing. It was a cool day for late summer in the Caribbean, and the sky was pleasantly overcast. The Cuban national kayak team paddled out with us for the first mile, then waved goodbye, and we were on our own.

I had a GoPro camera that I’d stuck under some bungees on the deck of the kayak, to use as a sort of journal as everything unfolded. In one of my first updates, Frank and I are laughing about being “novice kayakers” and being “dumb enough and inexperienced enough not to be so afraid of this.”


Photo by Cassandra Allred

By 4:30 in the afternoon our backs and shoulders were feeling it. Still, we were averaging about 3.8 knots, or 4.4 mph, which was damn good. I was wearing a gigantic hat and a Buff around my neck for sun protection, but all day we were blessed with nice cloud cover. By 7:10 the sun was setting and I could take the hat off, which was sweet relief.



Behind us in the distance, we could still see the lights of Havana. After seven hours of paddling, it was depressing that we remained in sight of where we’d left. All in all, though, everything was going incredibly smoothly. I should have recognized that this meant everything was probably about to go horribly wrong.

A little more than two hours later, it did.


It was after 9 p.m. and we were going in near total dark. The night was moonless, and while the stars above were stunning, they didn’t give off much light. Each paddler had tied a glow stick to their life vest and each kayak had an LED light stuck to its tail. We were ordered by Captain Bob, the Sunluver’s captain, to stay close to each other and to the boat.



The waves were starting to come up. They were only two or three feet, but they were coming directly from the east, our starboard side, and they kept pushing at our rudders.

Around 9:30, Davis and McKay got a second wind and surged ahead of the group. Their speed carried them ahead of the Sunluver, and then they mistakenly crossed in front of its bow. It was the shortest lapse of focus, by our strongest team, but it was enough. As they tried to correct course, the boat’s port pontoon collided with the starboard side of their kayak with a noise like a Taiko drum. They tried to grab the boat to stabilize but couldn’t recover their balance. I heard McKay shout “We’re going in!” and they plunged into the darkness.

I shouted “CUT THE ENGINE!” because in the moment I couldn’t remember if the Sunluver had inboard or outboard motors. The latter would have shredded them. Someone else shouted “MAN OVERBOARD!” and the expedition swung into rescue mode.

We were told to sit tight by the Sunluver. The Mirage, trailing a couple hundred yards behind us, would pick up Davis and McKay. At that point, Kassem decided she’d had enough. From the beginning, she’d only given herself a 50-50 chance of trying to make it the whole way, and seeing the dramatic wreck in rising seas clinched it. So she and Jacobi also paddled for the Mirage.


It was a good thing they did. Davis had managed to right his kayak and got back in. McKay, having climbed onto the Mirage, was trying to reach into the kayak with a bilge pump to get the water out. Davis was still trying not to touch the Mirage at all, to keep his crossing clean.



The ocean had different ideas. Larger and larger waves hit the Mirage from starboard, till the outrigger lifted from the water and came crashing down on the deck of the kayak, flinging Davis back into the water.

Davis had only the dim light-stick on his vest, and it was mostly submerged. He began drifting away from the Mirage, just as Kassem and Jacobi were making their retreat toward it. Kassem spotted him in the water, and the two were able to grab him and tow him back to safety.

The kayak that Davis and McKay had been using, however, was a loss. The crash with the Mirage had essentially split it in two. When they tried to use the boat’s winch to bring it on board, the cable broke from the weight of the water. The Coast Guard was alerted, and the remains of the kayak were jettisoned at sea.


Davis and McKay had planned to hop into one of the backup kayaks the Mirage was carrying, but that plan proved impossible. The same wave action that was tossing the kayaks up and down was tipping the catamarans around so violently that everyone who set foot on them was instantly seasick. This was compounded by the fact that about half the people aboard the support boats had contracted food poisoning that morning. People were puking everywhere, and there was no way to relaunch a kayak till the waves eased up, but they were continuing to grow.

At the time, off in our own kayak, we had no idea that any of this was going on. Our remaining two kayaks and the Sunluver were now about a half-mile from the Mirage, and the Mirage’s captain had turned the radio to the wrong channel. For more than half an hour, our requests for updates were met with troubling silence. And then:

“Our rudder just broke! We can’t steer!”

It was Allred’s voice in the other kayak, calling out from the dark about 30 feet away. One of the cables from the foot pedal to the rudder seemed to have snapped or come disconnected. It took him and Jacob a few moments to remember that they knew how to steer a kayak the ordinary way, without using a rudder, and then they were able to get to the Sunluver. The waves somehow calmed enough for them to get themselves and the kayak up onto the deck of the support boat.

Frank and I were alone in the water. We realized this meant that things had gone very wrong.


Aboard the Sunluver, by the time the rudder was working again, Allred was too seasick to go on. They decided Jacob could relaunch the kayak alone, make his way to the Mirage, and pick up a replacement partner there. But the seas had gotten rougher. As Jacob tried to get the kayak back into the water, he was thrown overboard. The Sunluver’s crew grabbed him before he could drift away. The kayak was pulled back on deck.

Frank and I had been bobbing on the current, waiting to see what came next, for something like two hours. Finally George Pardillo, the Sunluver’s second captain, yelled out. “Hey, guys, they’re calling it,” he told us. “Everybody is out of the water, so the expedition is over.”

Photo by Michael Boren

“We want to keep going!” I shouted back.



I wasn’t just speaking for myself. Frank and I had already talked about this. We were feeling good. We weren’t seasick, we’d gotten comfortable in the waves, and the two plus hours of rest had left our shoulders and backs refreshed.


With the misplaced confidence of the ignorant, we wanted to try—and not just for ourselves. We thought about all the pomp and circumstance that had launched us in Cuba, and we thought about the charity Cotopaxi had built around it, Challenge 113, and Davis’s emphasis that this was all about the team’s goal. If we had a chance to keep the expedition going, we wanted to do it.

We relayed this to George, who sounded doubtful, but he said he’d talk with the others and radio to the other ship. Ten minutes, then 15, slowly ticked by as we waited. It would have been understandable for them to pull us out. We were a couple of yahoos from the press in a plastic kayak. This was their trip.

George reemerged on the deck and called out to us.

“OK, follow us! Next stop, Key West!”

We couldn’t believe it.


For the next few hours, Frank and I put our heads down and white-knuckled it. We should have been taking more breaks to eat, but we wanted to focus. The waves had gotten bigger and were frequently breaking over our bow, filling our boat with water despite our spray skirts. Every 15 minutes one of us would stop paddling and bilge-pump the water out, while the other kept us moving forward. The wall between our compartments was broken, so water moved freely between the two. This was handy for pumping, but not so great for other things: Specifically, the bathroom.



We were both carrying wide-mouthed Gatorade bottles in our kayak compartments. The system was, whoever had to pee would open up their spray skirt, gingerly pee into the bottle, and then dump it overboard. It was neat and tidy. It was also now completely impractical because of the waves. If one crested over our deck while we had a spray skirt open, we would have flooded and capsized in an instant, no question.

Between the paddling and the bilge-pumping, moreover, we didn’t have time for other breaks. We’d been going that way for an hour, and I hadn’t peed in at least two, while drinking lots of water to stay hydrated. The situation was getting uncomfortable.

Finally, I couldn’t take it anymore. “Hey man, I’ve really got to take a leak and it’s too risky to open my spray skirt.” I began, apologetically. “We’re getting a lot of water flushing into the compartments anyway and we’re already pumping it out. I know it’s nasty, but is it OK I just let it rip?”


“Oh man,” Frank said, gravely. “You’re nice to ask. I’ve been pissing on you for the last 90 minutes.”

“You’re nice to ask,” Frank said. “I’ve been pissing on you for the last 90 minutes.” In that moment I determined that we were going to be friends for life.

In that moment I determined that we were going to be friends for life.

It’s still not 100 percent clear to me how we made it through the night. Both of us were night owls, which helped. And while I had zero oceanic kayaking experience, I’ve been surfing for a decade, so I’m used to the feel of waves. Compared to pounding breakers, the three-to-five foot ocean swells were gentle. Also, in my tiny bit of whitewater kayaking, I’d been taught, counterintuitively, to lean into waves, rather than away from them—to dig into them with the paddle, almost as a brace. I told Frank this, and he mastered it almost immediately.

Above all, Frank and I kept talking, no matter what. We’d spot waves and call them out as they approached from the darkness, and we’d remind each other of proper technique: to breathe, to relax, to paddle easy. We had to move and think as one if we were going to make it.


When there was nothing else to talk about, we ran through every dirty joke we could remember, and sang every song we could recall the lyrics to. A lot of it was ’90s hip-hop. Our Snoop, Digital Underground, and Wu-Tang impressions kept us alert and cheerful. And we needed that, because it was creepy out there.

There was still no moon at all. Beyond our feeble lights was blackness as far as the eye could see, with two exceptions. One was an absolutely breathtaking array of stars. The nearest light pollution would have been Havana, now some 50 miles behind us. We took turns watching out for waves so one of us could just stare up into it.

Photo by Cassandra Allred

The other illumination was lightning, directly ahead. It looked like three separate storm cells, at our 10:30, 12 o’clock, and 1:30, but in reality I think it was one gigantic one. Huge bolts would light up the entire sky in front of us, dramatically showing the Sunluver’s silhouette bouncing in the waves. We seemed to be heading into it, which made my stomach churn, but it was far enough off that we couldn’t even hear the thunder, and we never ended up reaching it.



Of course we worried about sharks, but the only things we were ever attacked by were flying fish—dozens of them, throughout the night. They look cool in the daytime, but it turns out that they’re drawn to lights, such as the one we had on our stern. They’re about 10 inches long, and they travel fast, so when they hit you—which they did, repeatedly—it would make a hard smack against the side of your face, your shoulder, your paddle. They’re oily bastards and they absolutely reeked. Soon our boat did, too.


The other force that got us through the night was a guy named Robert Cary. He had come on the trip to accompany a friend, who’d ended up dropping out at the last minute. Now he sat vigil on the deck of the Sunluver, watching us and blasting Bob Marley, Bob Dylan, the Stones, and some classic disco hits to keep our spirits up. When we needed food or water, he’d grab it and toss it to us. Aboard the Sunluver, others tried to persuade him to get some sleep, but he refused to go in until we’d made it safely through the night.



Somewhere in the middle of the night, the wind and the waves, which had been hitting us in the side for hours, began to change direction. Gradually they shifted to be almost perfectly at our backs. Not only did the wind help us along, but if we saw a good wave coming, we could give a few good hard strokes, and swoosh, we were surfing. It helped us save energy, and the fun took our minds off the steady ache that was now permeating every major muscle group in our bodies.

The sky grew brighter and the stars began to fade. We decided to pick up the pace and go hard till the sun rose, then take a proper break to eat breakfast and stretch. For the last half-hour, we were going more than 4 knots, or 4.6 mph. About an hour before the sun was up, we were told we’d passed the halfway point.

As we paddled over to the Mirage for breakfast, in the cool new morning, the first face we saw belonged to Davis. He sat cross-legged on the deck, looking stoic. We hadn’t seen him since the crash.




“You guys are awesome,” he said, but the words sounded flat, and his face seemed to disagree. It felt more like he was telling us we were assholes. Frank picked up on it too. Our hearts went out to him, and to his dream crushed along with his kayak, but we didn’t know what to say.

We slurped cups of stew that were handed down from the Mirage, grabbed a few bags of snacks, and pushed off again. We never got out of our kayak. We weren’t finicky about putting a hand on the boat since its engine was in neutral. As long as we weren’t being dragged forward, we didn’t care.

Bellies full, we started pushing along again. At 7:15, we were informed that we had 51 miles still ahead of us. We put our heads down.

Day two was worse. This shouldn’t have been a surprise, but up to this point, we had been figuring that if we could make it through the long, crazy night, we would be all right. Of course, that was not the case at all. Frank and I had been awake for more than 24 hours, and we’d been paddling for more than 18. Neither of us was an ultramarathoner, so we had no idea what we were in for.

Photo by Michael Boren


So we started off more or less the way we’d left off, paddling and cracking jokes. In the video, though, you can see my form definitely beginning to suffer. Throughout the first day and night, I’d tried to keep switching between major muscle groups: When my upper back got tired, I’d focus on twisting with my abs; when my abs got tired; I’d push through my feet to get my legs to do some of the work. By morning, though, every set of muscles was sore. I was having trouble keeping my wrists straight. During breakfast, when I took off my gloves, I discovered the hands of a corpse—stark white, grotesquely wrinkled, and starting to blister.



Around 9 a.m., more kayaks joined us in the water. Davis and McKay relaunched in one of the backup kayaks. Jacob did too, but Allred was still too sick, so another Cotopaxi guy, Rawley Nielsen, subbed in. Jacobi was in a surf ski, an ultrafast single kayak designed for riding big swells. Coach Carter and another beast of a kayaker from the support crew, Robin Graham, would sub in and out for the rest of the day.

The only thing Frank and I insisted on was that with everyone else paddling again, he and I would still dictate the pace. Everyone agreed that was only fair. By 9:30, we were told we’d gone 75 miles.

I hope Frank will not begrudge my saying this, but on day one, I was the stronger paddler. He was certainly the stronger human, but I started out with slightly more kayaking technique than he did. That meant that when he dropped out to rest, I would keep us on pace with the Sunluver, but when I rested, we’d start falling behind. In my darker moments I wondered, “Am I going to be able to drag his big ass all this way?”


On day two, I was the one who needed to be dragged. Things started getting bad for me around midday. We’d been paddling for a full 24 hours, and I’d begun to have indigestion. Despite a steady onslaught of Tums and Pepto, my guts continued to feel sour. The result was having to cop a squat on the deck of my kayak, just behind my seat, while Carter helped stabilize our boat from the surf ski. It was awkward, and frankly, humiliating. It also resulted in me accidentally breaking my back rest, which would really hurt my form from there out.

As awful as that was, what was really killing me was the sun. The lovely cloud cover of the day before was gone, and the Caribbean summer heat was coming down. No matter how much I drank or how much water I splashed on myself, it kept getting worse.

After the last two hours of backbreaking paddling, we were four miles behind where we thought we’d been.

At 3 p.m., we received a mental blow to go with the physical misery. We’d been told around noon that we had just 20 miles left. Elated, we picked up the pace and went hard for more than two hours. Then we checked in again. How much further? The answer came back: 24 miles.

Someone had misread the GPS, hours earlier. After the last two hours of backbreaking paddling, we were four miles behind where we thought we’d been. It was a simple but crushing error. We were struggling to maintain a 3.5 mph pace. If we were lucky and held steady, we were still staring down another eight hours of pain.


Right about then was when the heat overwhelmed me. My heart was racing, I could barely lift my arms, and I couldn’t catch my breath. I asked Frank for a break, but the bad news had made him want to push on. Later, he would admit to me that he’d had some mild hallucinations on our first night, and he was hoping not to repeat that experience. For the first time since we started, he and I weren’t talking much. There was a disconnection between us.

He’d had some mild hallucinations on our first night, and he was hoping not to repeat that experience.

Things started to get blurry, and then the corners of my vision began to turn black. I’d never fainted or experienced heat stroke before, but I knew that I had to make a change or a bad thing was going to happen. I stopped paddling, leaned forward, and tried to take deep breaths. The crew of the Mirage dumped ice down my shirt and into my hat, but nothing helped. As soon as I’d start paddling again, I’d start blacking out.

Suddenly, Frank snapped out of his own dark haze. “All right—can you give it ten hard strokes?” he asked. “It’s called Power Tens. We used to do it in rowing. You go hard for 10 strokes, then you can drop out and I’ll keep us going with the boat for a little bit. When we fall back again, we’ll give it another ten. We’ll count out loud, together.”

I didn’t think I had it in me, but I agreed to try a set. It worked. Something about changing up the rhythm allowed my system to reboot. I was still exhausted, but I was able to go hard for ten and get us surfing on a wave. Then I’d drop out, breathe, and come back in a little bit later. Gradually, we upgraded to power 15s and then power 20s, and after a while I didn’t even have to drop out in between. I’d just paddle more gently.


That was the point where Frank earned hero status in my eyes. He had basically carried me for an hour before I fully came back to life. He and I got back to joking and singing terrible power ballads, though we’d still be hit with long periods of despondent silence in between. Our companions in the other kayaks kept cajoling us out dark places.

Around 4:30 we started seeing our first glimpses of land ahead of us. Just the merest of shadows that might be buildings, or might be wishful thinking. It seemed very, very far away.

Around the 20-mile mark—the real 20-mile mark—Davis and McKay paddled by us.

“Well, congratulations,” said Davis. “You guys are the first.”




We were perplexed. “The first what?” I asked.

Davis looked exasperated. “Nobody’s ever done this in a kayak before,” he said.

Suddenly, things seemed both clearer and more confusing. For the first time, we understood why Davis had seemed so devastated. He wasn’t just trying to make the crossing, he was trying to be the first on record to do it. That was why he didn’t want to touch the support boats. Being first was part of the dream, and part of the campaign to boost his company’s name, to get word out not only about its products but its charitable endeavors.

And here Frank and I were, screwing it up. If we’d gotten out when we were told to, the Florida Strait would still be virgin territory for kayaks. The expedition could have made an understandable retreat: unlucky weather, big seas, a treacherous night. A month or two later, with the record still unclaimed, they could have tried again.

Instead, two jackass writers—who didn’t train, who were drinking rum the nights before departure, who’d named their boat Fidel Fastro as a stupid gag—had blundered within sight of Key West. We were supposed to bear witness to their project, and without even knowing what we were doing, we’d trampled on it.


Photo by Cassandra Allred

But this brought us to a rather important question: Why the hell hadn’t anybody told Frank and me that nobody had done this before? You’d think that that would be a critical bit of information to impart to the journalists you’d invited along to chronicle your undertaking. That’s the kind of tidbit that gets stories sold.



Ultimately, our bafflement had worked to our advantage. Frank and I had assumed that people had made the crossing by kayak with some regularity. We hadn’t known that we weren’t supposed to be able to do it. If we had, that knowledge would have stuck in our heads while our bodies were falling apart. The Cotopaxi crew was burdened by knowing the stakes. Frank and I weren’t.

Still, too, it’s crucial to acknowledge the narrowness of the phrase “first official kayak crossing from Cuba to Florida.” It’s extremely unlikely that we were really the first people to cross the strait by kayak. Refugees had gone before us in every sort of floating craft they could get, cobbled-together hydrodynamic nightmares that could make the journey a week-long endeavor (or worse) and made our “low-end” plastic kayak look like a cigarette boat. Someone in the thousands and thousands of them must have gotten their hands on a kayak before. They just weren’t in any position to tell the world about it.

Yet there we were, officially leading the way. We didn’t know what to say, so we just kept paddling.


Around 7:20, the sun set, and we finally got relief from the heat. I’ll never forget the glorious sensation of simply taking off my hat. Just off the bow we saw what we guessed was the bloated corpse of a manatee. Suddenly a head popped up from the water. It was the largest sea turtle I’d ever seen. It gave us a curious look, then put its head down and kept going. We stopped and stared at it, grinning from ear to ear. This was our dove, returning to Noah’s ark with an olive branch. We were told that you typically only see sea turtles close to land.

It just wasn’t our land. A point jutted out toward us, but one of our minders on the Sunluver told us we weren’t going there. We were supposed to turn right and head all the way back to the Stock Island Marina, where our journey had begun. This effectively added three or four miles. On the highway, the four miles is nothing, one song on the radio. On the ocean, Frank and I were now struggling to maintain a two-mile-per-hour pace. Four miles meant an additional two hours of torture.

By this point, Frank and I had spent everything we had. In my stupor, I’d never stopped to fix the strap that held the back of my seat upright, and now that was coming back to haunt me. Leaning back, clutching my paddle by my chest with wrists bent nearly 90 degrees, I looked like a shrimp tickling my way through the water. “Keep shrimping!” Graham shouted.

Frank wasn’t doing much better than I was. Our 2 mph pace felt like we were barely crawling. The nearby point of land beckoned us, singing siren songs of solid ground and rest. I inadvertently kept steering us toward it, and Carter had to come along in the surf ski to subtly corral us back on course. We didn’t realize what he was doing; we were too far gone.


All the other starters were back in the water now, keeping us talking and laughing. Davis and McKay pulled up to tell us that they wanted us to be the ones to hit the sand first, a magnanimous gesture, I thought. Cary again blasted Bob Marley from the Sunluver. All of it barely registered.

For the last two miles, all we could manage were light tapping strokes. Save for my near blackout, it was the hardest stretch. It was well past nightfall and completely dark. The lights of the marina didn’t seem to be getting any closer. We tried to think of what it would feel like to be back on land. We tried to think of what it would have been like on a makeshift raft, coming under cloak of night into an uncertain world. Mostly, we couldn’t think at all. Frank admitted he couldn’t remember what my face looked like, and I only knew the back of his head.

At 10:11 p.m., we rounded the corner of a dock and made our final approach. The Sunluver turned left toward its berth, pointed us in the right direction, warned us about rocks ahead, and shouted congratulations. I asked Frank if he had one last burn in him. We picked up the pace. Floating by Davis and McKay, we thanked them for everything.

And then we came within inches of crashing into the submerged rocks we’d just been warned about. We laughed, backed up, and took a hard left and then a right around them. The bow touched sand.


Almost exactly 34 hours after we’d paddled out of the Cuban marina, we were touching Florida. All told, with eight miles of drifting off course, we’d gone 118 miles. Frank and I whooped, ripped off our spray skirts, stood up, and instantly fell into the American water. Our legs were too weak to hold us. Laughing some more, we crawled toward each other in the shallows and threw our arms around one another, mumbling unintelligible words of glee.

There was no media waiting for us. We would have been the media. Nor was there a ceremony, or speeches. I did try to thank everyone and to say something about it being a team effort. We were still the wrong guys, and things felt awkward.

Frank and I were still staggering and stumbling. We tried lying flat on our backs, and Carter ordered us to get up, so we wouldn’t go into shock. We had the hands of zombies, and I could feel some sort of nerve pain that began in my hips and extended all the way down into my toes.

We’d planned to sleep on the boats in the harbor as we had before we sailed to Havana, but someone told us we couldn’t. This was a surprise. The Cotopaxi crew booked their own hotel rooms and scattered. I’d wandered off to try and find a shower and found myself lost, disoriented, and and more alone than I’d ever felt. I went to the Mirage, where my stuff was—down a steep ladder in my cabin, irretrievable in my condition—and dragged myself into the shower. I’d never needed one more in my life. The water was cold and barely dribbling, and I kept lurching and propping myself against the walls to keep my feet.


After I’d toweled off, as I was about to retreat to my cabin to try to figure out what to do, Jacobi swooped in. He had got us set to stay at Captain Bob’s for a couple days. I nearly burst into tears. I’d have to share a bed with Frank. “Is that OK?” he asked.

“We just spent the last day and a half pissing on each other,” I said. “Sharing a bed is nothing.”

For the next two days, whenever we weren’t eating, Frank and I were sleeping. I spiked a fever and broke out in a rash from the chest down, probably due to too much time in the unsanitary conditions under the spray skirt. Blood blisters swelled up under five of my fingernails. I shivered despite the Florida heat. Jacob had packed up my stuff and brought it back from the Mirage, a day after he’d paddled 90 miles himself.

While Frank and I slept, the day after we got back, I had an incredibly vivid dream. We were paddling through the ocean, about 80 miles in, and my body quit on me. I keeled over and we capsized. Upside down in the water, my arms were too weak to unhook my spray skirt. I went limp and I felt salt water fill my nose and mouth, then my throat, then my lungs. I couldn’t move, but I could still see. “Oh, thank God, there he is,” someone said as my lifeless body floated to the surface. “WAIT, HE’S NOT BREATHING!” Hands began pulling at me, trying to raise me onto the deck of another kayak.


I woke up in bed, with Frank still passed out next to me. The dream wouldn’t leave me. It seemed more real than my exhausted, broken state did—and more plausible. Which was more likely? “Untrained Idiot Paddles 120 Miles in the First Cuba-to-Florida Kayak Crossing”? Or “Untrained Idiot Underestimates the Power of the Ocean and Drowns”? Days later, I still wondered if, on some other timeline, I hadn’t actually been lost. I may always wonder.

Three days after we landed was my birthday, which I spent flying from Florida to Portland, Ore. to see friends and resume my year in a van. In 36 years I could honestly say I’d never been happier to see another birthday.

It took weeks for my back, shoulders, and legs to recover. One of my blackened fingernails fell off entirely. There’s a scar on my left thumb where the paddle wore away at me, and it’s probably there for the rest of my life.

I could never shake the feeling I wasn’t supposed to have done this. In the few news stories about the trip, Frank and I were generally barely mentioned. One TV piece heralded the Cotopaxi teams without even mentioning Team Underdog; one report repeatedly called me “Brian.” Part of me was angry that no one was giving our account of what happened.

But then, that’s why Cotopaxi had brought us along, wasn’t it? We were the writers. So this is my crossing story. You can (and should) read Frank’s at Caryology. Read Joe Jacobi’s two pieces at Morning Joe. Read McKay Thomas’ at the Cotopaxi blog.


Frank is currently in Indonesia on a Fullbright scholarship, trying to find better ways to prevent flooding. I’m driving around the U.S. in a van, writing about my travels. We haven’t seen each other since we left Key West, but we’re already trying to figure out when we can go on another adventure. I’m thinking something on land.

Photo by Michael Boren

Brent Rose is a freelance writer, actor, and filmmaker. You can follow his adventures on Instagram, Twitter, and Facebook, at brentrose.com and connectedstates.com. Top photo by Cassandra Allred.

