Ozymandias: A Reflection on Kayaking the Florida Straits

It was more like ink than water. Blackness was everywhere, we were breathing it. The moonless night took hold of the Atlantic and its guests. The surging and crashing of the support ships flanking the five kayaks overpowered the hypnotic rhythm of my paddling and I came to.

Cotopaxi has launched an annual international expedition called Challenge 113. For the inaugural adventure, a small team of entrepreneurs, philanthropists, and adventurers sailed from Key West to Cuba and then kayaked back to Florida – a distance of 113 miles. While in Cuba, the team met with local entrepreneurs, learning their stories, and volunteering as mentors and thought partners to help them advance their goals. 

Below is an essay about traversing the Florida Straits from participant, McKay Thomas, founder of CEO of First Opinion. Now it’s your turn. Challenge yourself to complete 113 miles of any human-powered activity by 11/3. Our partners will donate 10 cents for every mile you bike, 25 cents for every mile you walk/run. Sign up here!


It was more like ink than water. Blackness was everywhere, we were breathing it. The moonless night took hold of the Atlantic and its guests. The surging and crashing of the support ships flanking the five kayaks overpowered the hypnotic rhythm of my paddling and I came to. The blackness was in my lungs and in my mind. Control slipped precipitously. I needed to stay away from the darkness, but it was creeping into me. I talked to my paddling partner behind. He responded occasionally, but he was distracted and fighting his own war. I was grasping. The night would consume me without a proper defense, but nothing was coming. “My name is Ozymandias,” I mouthed the iconic line from the apocalyptic poem and it infected the creeping darkness in my mind. “Ozymandias.” I whispered it again and waited. Strength swelled, the crashing ships on either side of me, falling victim themselves to the six foot swells, faded in my mind. I started from the beginning.

“I met a traveler,” I said and waited for the next line to come to me, “I met a traveler from an antique land who said two vast and trunkless legs of stone stand in the desert. Near them, on the sand, half sunk, a shattered visage lies, whose frown and wrinkled lip and sneer of cold command tell that its sculptor well those passions read which yet survived.”

I paused. My head down, each paddle stroke gaining intention. I breathed. “Stamped on these lifeless things,” I continued whispering, “the hand that mocked them and the heart that fed, and on the pedestal, these words appear: ‘My name is Ozymandias, king of kings.’” I felt my breath warming my cheeks around the neoprene of my vest and the splashing paddles and crashing ships and the blackness of the night and the occasional shout from a kayaker or captain suddenly fit into an understandable, welcomed moment. I saw what was around me and felt at peace with the 20 or so hours that lay ahead.

“Nothing beside remains.” I said to myself, inside my vest, “Round the decay of that colossal wreck, boundless and bare, the lone and level sands stretch far away.”

Clarity. Left blade in, push, lean. Right blade in, push, lean. The darkness left nothing to paddle for, but the motion and the rhythm itself. Left blade in, push, lean. Right blade in, push, lean.  The rhythm my passenger and confidant against the blackness that I was being freed from. I noticed the other kayaks had begun to band together around us. The blackness and swells attacking everyone created an unconscious desire to band together. Ten feet away another team, paddling and fighting, suddenly disappeared into a valley of a swell, returning moments later only to disappear once more, the other side of us rocked and crashed the support ship. “My name is Ozymandias.” I muttered to myself, feeling the blackness continue its war on my mind. Right blade in, push, lean.

Kayaks weren’t discernible, even within close proximity, save a single light mounted to each hull, all else the blackness consumed. The four other lights bobbing in the inky ocean drew closer, the swells a magnetic field shepherding the kayaks closer and closer to the safety of the support ship. Our kayak’s hull constantly fought our rudder, like a muzzled dog. The front tip fighting for freedom from my paddling partner who controlled the rudder. Kayaks huddled. Right blade in, push, lean. I looked behind me just before it happened. The support ship, a 44 foot catamaran, rose up high on a swell, now directly above me. Clarity fled. The tip of our kayak broke free and swung hard right and I yelled. A loud crunch of buckling fiberglass sounded, then plunging silence. I hung beneath the kayak, consumed now, by the inky blackness I’d been fighting. The ocean now hiding the world from me.

Frantic under the water and still secured within the capsized kayak, I couldn’t breath, my spray skirt tight against the rim of the cockpit. I pulled, but it wouldn’t release. My loose fitting spray skirt at home suddenly had an appeal I hadn’t fully appreciated before. I pulled again. Nothing. Regret surged through me. Why was I here? How had I let this happen? Would we find a way through this? I suddenly jerked free. I swam out from beneath my kayak and breathed. And breathed.

“…Overboard!” I heard someone yelling. “Cut the engines!” I bobbed in the waves for a moment before I started grabbing my gear which was quickly escaping me. Davis. Where’s Davis? I swung my head around to find him gripping his own gear and clinging to the shining white belly of our kayak.

My life vest, triangular, nylon and neoprene, fit front and back and secured with straps, had been loosened to make for a less restrictive crossing. It was rising up to my face now, the neoprene covering my mouth. I pulled it down over and over only to have it shoot back up to float around my face. The kayak needed to be flipped over. I dropped below the waterline and, placing my hands against the side, kicked my legs. The kayak rocked. I kicked harder, and 30% became 40%. Harder. Progress slowed. I needed air. I came back up and opened my mouth and breathed in. Shock struck my system when all that came was the suffocating neoprene that stretched to fill my mouth. Holding my breath was one thing, but being denied the air I expected and that had always come when asked, was another. I frantically gasped for breath. None came.

I then whispered to myself, either in my mind or audibly I don’t recall, “Ozymandias.” I kicked fiercely, the neoprene mask my constant companion. My torso slowly gained leverage above the water, and the vest slid down just enough. Oxygen rushed in. My fingers found the buckle straps under the water and I pulled. And pulled. I felt the vest tighten around me. Davis and I, with our gear on one arm and the capsized kayak on the other, slowly swam through the waves to the second support ship, The Mirage.

It rose up four feet and then, as if suddenly released from a crane high above, crashed back into the ocean, sending shock waves around the two hulls. The kayak, a now half-ton ocean hammer, rammed The Mirage in a thunderous display of power. Each swell threw it around like a feather, returning every few seconds for another thunderous CRACK and SHATTER. A hand reached down to me, but I didn’t take it at first. I had left Havana in this kayak and I wasn’t going to leave the water until the beach at Key West. I hesitated and the hand stretched further and came commanding. “Out of the water now!” It was Captain Keith, he was yelling over the crashing waves and the stinging thunder of the half-ton kayak crashing into The Mirage. Davis was even more resistant. He swam to the opposing end of the kayak to help displace the flooding water. But he, too, eventually kicked his leg up.

Although completely filled with water, each wave found new crevasses to fill. Through the swells, we eventually got the bow onto The Mirage and tipped. Gallons and hundreds of pounds of water poured out. The kayak, no longer full of water, but still heavy and in need, clanged against the ship with each wave. Davis took position, squatted down parallel to the kayak and kicked out his right leg and placed it on the seat of his cockpit. He inched his body closer, the waves continuing to bang the kayak against The Mirage. CRASH. He slid his second foot in and positioned his arm on the opposing rim of the cockpit and lowered himself in. The kayak swung away instantly, placing stress against the bowline, lashed to The Mirage. Davis was pumping water out of his cockpit frantically. I stood looking at him, almost puzzled at our predicament, when a swell caught him. He flipped.

Clarity, which had left me cold and stranded in the ocean earlier, raced back to me. My senses grabbed hold and I yelled. The mind, in its moments, considers absurd scenarios. Death. Harm. What would I feel? Am I ready? These questions, a distraction at best, answer themselves when your closest friend loses his lifeline and begins to drift away into the blackness of the Atlantic.

  • • •

They were all wearing spandex, speaking to each other like classmates, or, perhaps more appropriately, like teammates. Their chests emblazoned with the Cuban flag. Three… two… one… Water instantly filled the air around the team as their kayaks rocketed forward, their giant torsos like a staccato metronome above their tiny lower bodies. At the dock, I got in first, our giant, yellow tandem kayak a brute ship compared to the Cuban national team’s K1s and K2s. My food and water tucked neatly between my legs while my mind raced to all the supplies I may have forgotten or had forgotten. I felt the kayak rock abruptly left and I heard Davis enter his cockpit behind me. We hadn’t pushed off yet, but my own timer was already ticking. How many hours would I be sitting here?

Challenge 113-Press conference in Cuba prior to kayaking the Florida Straits

Press conference in Cuba prior to kayaking the Florida Straits 

Joe and Amy slipped into theirs and joined the growing line of US and Cuban kayakers in the marina. The Commodore, the stout, half-stern, half-soft, but decidedly communist captain of the Marina Hemingway shouted the beginning of the voyage and we began paddling. Left blade in, push, lean. Right blade in, push, lean. Each stroke felt more conscious than I anticipated or wanted. The many, many hours that lay ahead needed to be more automatic than this. Left blade in, push, lean. Right blade in, push, lean. Rhythm found me soon enough and the warm sun, which first rose in the sky, blanketing Havana behind us, slowly lowered to the horizon and vivid oranges paddled away the blue of the day, and quickly yielded to the ever increasing blackness that overcame the ocean and sky.

  • • •

“Grab ahold!” A second kayak emerged, miraculously, and pulled next to Davis, who was drifting away, bobbing in the waves. He got to the stern and swung his leg over. Through my own fear, I looked to find meaning in Davis’s face and eyes, but it wouldn’t come. He was steady, his eyes affixed to The Mirage. A strange maneuver ensued, eventually transferring Davis from the sea tossed rescue kayak to the ship. Davis stumbled and then collapsed. He was panting. A loud BANG sounded and I shot my head back to our kayak which was fighting the bowline and the ocean in a two front war it had little help of conquering. My clarity slipped. Fear slithered into my mind and I saw the crossing fade and the feat of it all go with it. Confidence sunk. I leaned back against the ship next to Davis and battled my mind for control. “I met a traveler…” I whispered, “from an antique land…” I breathed in and out. The ship again was released from above and crashed to the valley of the swell. “My name is Ozymandias.” The support crew of The Mirage were all laying sideways on the boat, knees tucked into their chests. Their eyes squeezed closed as each battled the inevitable motion sickness. I wondered why I wasn’t feeling sick. Was I? I began to pace the ship, searching for the clarity that I let slip. “The hand that mocked them and the heart that fed,” I muttered under my breath, as I reached the front of the ship and turned around, continuing my search towards the back of the ship. “Look on my works, ye mighty, and despair!” Am I feeling sick? I thought it and became sure I wasn’t. I continued pacing. I walked to find something that I was avoiding. My mind raced to that morning and I saw myself get in. How simple the crossing seemed back then. I lapped the ship again and leaned against the rear pole, and that’s when I buckled. My head threw itself over the edge and I vomited. Again. Again. It wouldn’t leave me alone. “My name is Ozymandias.” I gripped my clarity and wouldn’t let go. We’re finishing the crossing.

Hours passed. We watched as our little vessel, tied with a single bowline, crashed and buckled and broke with each progressing swell. The ocean throwing it against The Mirage as if it wasn’t there. BANG. CRUNCH. The rope, the innocent dutiful bowline, would eventually break and we would watch our kayak slip beneath the surly waves to it’s ultimate destiny. If we were returning to the US, it would not be aboard the kayak we embarked in.“Current pace forty minutes, sixteen seconds.” Davis’s phone’s GPS tracker sounded every thirty minutes while we waited aboard The Mirage, praying the swells down so we could return to the ocean which had little taste for us. Hours passed and the sun peaked. Davis came and sat next to me. “It’s safe now.” I looked at him in the way you look in a mirror. Was all lost? Robin, a fellow paddler-turned-rescuer, relayed the news that progress had dramatically slowed during the night, merely half way, we heard. Impossible, we thought. But going through the GPS confirmed it.

Left blade in, push, lean. Right blade in, push, lean. The waves were rolling, but kind. We paddled over to the one remaining kayak team and congratulated them; Frank in the bow, Brian in the stern. They paddled like they had nothing to prove and time on their side. Stephan joined us in his kayak with the first of what would be many paddling partners who would look for their own rhythm in the eternal crossing.


Kayakers in the morning light

The morning completed into afternoon without warning. The audiobooks we frantically downloaded over hours in Havana, sat new and unlistened to on our phones along with our music and our movies. We paddled with ourselves, for ourselves. It wasn’t mindless, but it wasn’t mindful either. There was a perfectly consistent passage of time that enveloped the voyage. I was numb yet alive. My paddle, which stroked the ocean and kicked up mist and spray was, in many ways, beside me, not with me. I could look at it and touch it. I could wonder about it and take a break from it, all without ever leaving the second to second rhythm that was protecting us and the crossing. Left blade in, push, lean. Right blade in, push, lean. The ocean and the swell that had united us the night before, drifted the kayak team apart. We would paddle to a team only to be hundreds of feet away moments later. There is a driving force to the ocean, a force we had come to revere the night before. There was meaning in our driven loneliness. The voyage, no matter who would cross, would be done individually. Every stroke had to be completed by the arms bracing the paddle. No one could push or dig vicariously. It was an individual’s journey. Left blade in, push, lean. Right blade in, push, lean.

“If you had one wish…” I asked Frank.

“To see Key West,” he said, flashing his large cheshire grin. I looked off in the distance and paused.

“There it is,” I said, looking back at Frank. “Do you see it?” He looked out and then back at me, not sure what to say. “I see it, Frank. It’s straight ahead of you,” I said, pointing at the blank horizon. He looked back, continuing his own rhythm.

“I see it now.” We paddled near each other for a while until the ocean drove us apart, because it always drives you apart. We sang songs and chanted to each other and gave ourselves nicknames. We drank liters and liters of water and sweat it all out. “I see it!” we kept shouting to each other, as we imagined the feeling that would come when Key West would truly come to view.

We paddled under the perfect passage of time until the sun, whose early morning peak had welcomed us back to the voyage, slowly left us once again to the darkness. The Key West skyline emerged. Left blade in, push, lean. Right blade in, push, lean. Come on. Come on. Left blade in, push, lean. Right blade in, push, lean. The horizon slowly grew a continent. Structures became buildings, became antennas and lights became homes and traffic. Cars moved across the small segments we could see as Key West, U.S.A. slowly surrounded us. Left blade in, push, lean. The beach was in view and all at once the sound of slick fiberglass combing sand chimed in our ears. The rhythm, my eternal passenger, suddenly stopped. I threw the paddle on to the beach above the nose of our kayak and I pulled my knees up to my chest and stood. I nearly fell over and my fellow paddlers, including Frank and Brian who became the first kayakers ever to complete the crossing, fell over completely.

Challenge 113

Group after the crossing

We slowly learned how to stand again. And how to walk. We embraced each other and found ways to stand still for pictures. The slow pulse of the ocean, however, didn’t leave me immediately. I felt it under my feet and in my arms, the rhythm calling to me. As we walked away together, I looked back at my kayak and a part of me ached. I brought my arms up in front of me and motioned as if my left blade were entering the water and I pushed. Nothing happened. “My name is Ozy…” I whispered, cutting myself short. The world I returned to was my home, but the crossing… my arms came up again, right blade in, push.

See more photos from the experience and sign up to complete 113 miles of any human-powered activity by 11/3. Our partners will donate 10 cents for every mile you bike, 25 cents for every mile you walk/run.