We were a month at sea, sailing from Ecuador to Chile, when our jib’s furling line snapped. Our engine wasn’t working, our food was low, and we were in the middle of a southwestern gale. The winds were coming up from Antarctica—the swells had been building since Cape Horn, a thousand miles to the south—and they brought the bitter bite of a desolate cold. Winter had begun her siege on the southern coast, and we were still far from shore. So when the line fastening our rolling-furler gave, and the entire forward sail unfurled and filled with wind—yanking our mast into the water—that southwestern gale turned into a survival storm.

            It happened at midnight, as these things always do. The clouds were thick in the sky. It was so dark I couldn’t see my hand in front of my face. In conditions like that, you steer by feeling. You feel the ocean beneath you, the swells lifting you up and rolling you down their back. You feel the strength of the wind in your hands, through the resistance of the helm, the heel (e.g. lean) of the boat. And you listen.

            When the furling line snapped, all I heard was a gunshot crack in my ear. A stillness followed as the forward sail unfurled. And during that moment, the entire boat hung in the air as if suspended above the water.

            It took no more than half a second for the sail to unroll, but on a pitch-black night—in the middle of a storm—that half-second was enough for my stomach to drop; for my fingers to tighten around the helm; for the terror to set in.

            We’d been cruising at about four knots with a quarter of the jib out. When the whole thing unfurled and caught wind, it grabbed our mast and slammed us sideways. By then it was too late. The seas were too big. A wave caught our edge and the cockpit filled with water. We were going under.


It’s about 2,000 nautical miles from Ecuador to Valparaiso, Chile. However, there were a number of things keeping us from sailing in a straight line to Chile. For one, we’d be fighting a headwind all of the way down. The systems that circle Antarctica break to the north at Patagonia, tracing the coastline of Chile and generating—along with upwelling and other underwater systems—the Humboldt Current. We’d already fought the Humboldt in Colombia, then again in Ecuador. We didn’t want to fight it off of Peru and Chile.

            Peru as a country, meanwhile, is notorious for their extortionate clearance fees and check-in procedures. It costs a whopping $2,500 to clear into their country by sailboat. Then you have to pay additional fees for every harbour you enter, afterwards. But (the Humbolt current notwithstanding) just avoiding Peru is a hurdle. International Maritime law dictates that a country can only “own” waters up to 12 nautical miles off their coastline. Peru claims everything within 200 nautical miles. So, in accordance with their clearance procedures, as soon as we came within 200 miles of their coast, we’d have to sail straight to the nearest port of entry. Cruisers who violate these procedures have had their boats confiscated. Boats they can’t sell or salvage have been used for target practice.

            Circumventing Peru, then, was not really a choice – it was a necessity. We just couldn’t figure out how to pull it off. For one, Taylor and I still didn’t have any kind of autopilot or self-steering system. Sailing down the Colombian coast alone, with the odd anchorage or dock to raft alongside, we still arrived in Ecuador delirious and fatigued. Trying to sail for several weeks straight, without anchoring or docking to rest, was incomprehensible. Holding the helm and fighting the winds made for a taxing shift at the helm, and we were talking about 6-hour shifts, 12 hrs a day, for three weeks straight. A wind- or hydro-vane would make it more feasible, but the cheapest we could find at that point would’ve cost us upwards of $5,000 (with a “sponsorship” discount).

            The only other option, then, was to bring on a third crewmember. One that we could trust with our lives (and that wouldn’t drive us insane after three weeks of confinement to a single 36ft monohull). But who, fitting that description, would want to join us? We couldn’t pay them, we couldn’t feed them—hell, we hardly had enough money to feed ourselves—and we were asking them to sail into some of the harshest waters on the planet. 

            Who on earth would willingly sign up for that?

            Enter: John Rose.


The short version of John’s story is that he was a rescue swimmer with Taylor. He’d been following our journey ever since we cast off from Florida, and he happened to be out-processing while we were stuck in Ecuador.

            John left the Navy, like most veterans, in a daze. They worked him up to his final hour, and then they kicked him to the curb. He was technically on terminal leave, but when he asked for counseling a few weeks later—freefalling into depression, openly admitting that he was suicidal—the base psychiatrist wouldn’t see him. To quote a commander at their hospital: “He’s the VA’s problem, now.”

            John was directionless, without a prospect for work, and lacking that sense of purpose the military so effectively instills in its members. He also wouldn’t have access to the VA for months, and he could no longer afford his rent and lifestyle in Southern California. But despite everything that was happening to him, his thoughts turned to us. He finally understood why we were battling the high seas; why we were risking our lives to change the way veterans are out-processed and received back into the civilian world. So, despite his own struggles—or perhaps because of them—he volunteered to join us.

            When Taylor got the call from John, checking to see if we needed another hand on deck, it seemed surreal. He was, quite literally, the answer to our prayers. But I also had the impression that he didn’t entirely understand what he was signing up for. We were about to sail the longest stretch of open-ocean in our entire trip. This wasn’t going to be a scenic, explorative leg. Instead, it was going to be the same scenery for days on end. “We’re going to be hundreds of miles offshore,” Taylor said to John over the phone. “It’s going to be one of the most physically and mentally demanding experiences of your life. You’re probably going to hate us by the end of it, and,” he said, summoning his flair for the dramatic: “… you might die.”

            Taylor might as well have been selling it to him.

            “I’m in,” said John. Two days later he sent us a screenshot of his flight itinerary. He’d purchased tickets.


We ran a few offshore prediction programs that put us in Valparaiso after three weeks at sea. The projected distance was 2,500nm, with a maximum length of over 500 miles offshore to circumvent the Humboldt Current. 

            In the end, it us over five weeks, with a total of 3,700 nautical miles. At our farthest, we were almost 1,000 miles offshore.

            Our sail to Chile, then, became a test of endurance.

            Our motto had always been hope for the best, and prepare for the worst. But we had never provisioned for three people, and—despite working tireless for a financial cushion—we spent our last penny on canned foods before leaving Bahia. We did everything in our power to provision. 

            Our transmission fell to pieces a dozen miles past Isla de las Platas. We were a hundred miles from the coast, and still thousands of miles from Chile.

            We gathered in the cockpit that evening. Hours had passed without a breath of wind, the water like glass, our boat lolling in the calm. Taylor started. 

            “Without an engine,” he said, “our timeline is going to double. We’ll have to begin rationing food and water now – today. And we’ll be at the mercy of the winds.”

            I looked at John. His teeth were gritted, face set.

            “But if we turn around,” I said, “we can’t afford to have the transmission rebuilt. We’ll have to haul out the boat.”

            “Correct,” said Taylor. “We’ll have to work through the summer, save up money, and fly back next winter.”

            But for John, that meant flying home for good. He’d come out here for a life-affirming experience, and so far all we’d given him was a month of waiting. He’d been with us in Bahia de Caraquez while we waited for our starter to clear customs. He’d been with us in Salinas when we had to turn tail and fix a faulty spring in our choke. He’d been just as frustrated and eager to get underway as we had, and now – to have wasted his time, completely – would’ve been cruel.

            “What do you guys think?” said Taylor.

            But there was no need for a discussion. Taylor didn’t want to fly home with our mission undone. John didn’t want to return to the same home that he’d flown here to escape. And I’d put my whole life into this trip. We were all in, and we were past the point of no return. For better or worse, we were going to see this thing through to the end. And if that meant sailing 3,000 miles without an engine, so be it.


Spend over a month at sea, and you’ll experience a good variety of weather. As it happened, we caught a good stretch of steady winds just south of the equator. We were able to lash down the helm on multiple occasions, and at sundown, like clockwork, the fishing lines would start to sing. A week went by where, about every-other-night, we’d pull in a Bluefin tuna as the sun fell.

            Then the weather turned.

            Spring in the north is autumn in the southern hemisphere, and the further south we sailed, the harsher the seasons became. We reached a thousand miles offshore before we turned inland, battling our way against the current and headwinds. The bounty of fish brought on by upwelling along the coast of South America lurked well below the stormy waterline. Weeks passed without a bite.

            We had been a month at sea, and were still a good four hundred miles offshore, when we finally caught a break. We were in a window between low-pressure systems, and the skies cleared. The Ole Lady hit her stride, and we started cruising at six-knots, on course. The sun hit our skin for the first time in days, and our fishing line whirred like a siren in the night.

            “FISH ON!!!” said Taylor. John and I flew up the companionway to Taylor abandoning the helm. I grabbed the wheel to keep us from stalling out, while John jumped over me to help with the fishing line. Even with a low resistance, the pole was bent half into the surf. And so began our long and brutal struggle with the largest fish I’ve ever seen.

            We were sailing too fast, so I let out the sheets and furled the foresail in half. Even then, the guys were struggling.  “Dammit, Stephen!” Taylor called, “Let out the mainsheet!” I looked up at the sails, the sheet slack in my hand. There was no more rope to let out. We were drifting at less than a knot, and going on thirty minutes of reeling this fish in. We still couldn’t see it on the horizon, and the fishing line dipped down into the water behind us.

            We began trading shifts at the reel. Taylor was panting, his arms quivering. John’s face was beat red and sweating. When my turn came, I barely broke even. Sometimes, it felt like the fish was winning.

            Our catch began to fatigue after an hour or so. We felt ourselves reeling in more line than we were letting out. Then we saw its fin on the horizon. Straight and sharp, like a dinosaur tooth. It weaved through the water in a serpentine pattern. It was massive. Bigger than any fish I’d ever seen in my life. If not for the yellow glow of it’s fin, I would’ve called it a shark and cut our losses. But it wasn’t. It was a yellowfin tuna, and we had just reeled it to the side of our boat.

            We’d been at sea for a month. Our food stores were so low that we were making a can of beans last three days. Valparaiso was still an incomprehensible distance away, through storms and currents and headwinds. We had no idea how much longer we’d be at sea—or how much longer we’d be able to operate effectively at such a fatigued state—but we knew that, if we could get that oversized fish over the stanchions and onto our boat, we’d be okay. 

            The contrast between its yellow-tipped fin and twilight body was the most beautiful sight I’d seen in weeks. There was an endless supply of food: especially if we sun-dried the meat for jerky. We weren’t just going to be okay – were going to eat like kings.

            Taylor went hunting for a tool to help heave the fish onboard. He came back a minute later with his phone and a speargun. The yellowfin had remained beside the boat, tamed and downcast. We thought we had him defeated. Taylor even took a photo with his phone before readying himself for the haul. It wasn’t until John started to reel him in that we realized how wrong we were. 

            A good fifteen minutes had passed since we’d felt any real resistance. But no tuna gets that big, and lives that long, without a fighter’s instinct. This guy knew it was now or never. He could sense our excitement above deck, strategizing how to hoist him over the railing. He could hear us working out who was going to pin him down and who would swing the bat. This was his moment. We were distracted.

            The line snapped in an instant. Our catch, the largest tuna I’d ever seen, went from docile and defeated to frothing water like a speedboat propeller. The wire connecting our lure broke before we could react, and a white crater replaced the clear saltwater separating us from our salvation. I didn’t even see him fade into the depths. One minute he was there, and the next, all that was left of him was a splash of sea salt from his thrashing.

            Our fantasies of grilled filets, fresh sushi, seasoned ceviche, and dried jerky dissipated much slower than that yellowfin did. But the uncertainty of our situation came on stronger than ever. Our food stores were finished. A tuna had just swam away with our last fishing lure. And we had no idea how much longer it would take to close the gap between us and Valparaiso.


Despite the many dangers of our voyage, it wasn’t all doom and gloom. There were days without sleep or food—there were snapped lines, fires, and flooding—but there were also sunsets over a horizon of glass, and starlit nights that looked like a scene straight out of Life of Pi. On some days, the winds were so steady we could lash down the helm and go nap on the deck. An ocean breeze tempered the equatorial sun, and bronze skin contracted around raised hairs. We’d glide over those gradual pacific swells, and on most nights the Ole Lady rocked us to sleep.

            Our morale came and went with the winds. But we had some influence over that. And, in the same way that one person’s energy can bring up the whole group, so could they bring it down.

            Taylor was the most effective in this department. He was our captain and, generally speaking, the most dominant personality on the boat. When he’d replace me at the helm, I would hold my breath to see which Taylor would break through the companionway. Would he be tired and grumpy? Back aching from a poor nights sleep, body fatigued from an exhausting day at the helm? Or would he be fresh off a good rest, riding the high of a caffeine pill, and eager to make the best of another day at sea.

            More times than not, it was the latter. Taylor would lure us on deck with music and positive energy. He’d start a conversation with whomever passed through the cockpit, and the other would join in. At his very best, we’d congregate around Taylor during his shift to swap stories and share communion over the sparse almonds and peanuts we had left. 

            “People back home are never going to believe this,” he’d say. “They’re never going to understand.” He could be talking about a gorgeous day on the water—about sailing in general—or he could be talking about something as small as a seabird swooping between the swells like a propeller-plane, threading a mountain range.

            John and I would nod, listening behind our rum-stained mugs. “Preach, brother,” we’d say, drinking him in.

            At his worst, Taylor would keep to himself. Days passed off the coast of Colombia where I hardly got more than a word out of him. The same happened during our Pacific crossing. More than once, he came into the cockpit to trade shifts with his headphones already in. He’d move to take the helm, brushing me aside without a word. At times like these, it was hard to ignore the darkness that enveloped our boat. I’d retire below deck and lie in my birth with my eyes wide, staring at the ceiling for hours. 

            That’s not to say John and I were starling constants. I remember shifts when I snapped  at John or Taylor for something small they had done, or not done. I had one particularly miserable shift about halfway through our journey, in the middle of duldroms. It was the 4am-8am “sunrise” shift. I hadn’t slept at all before my shift, the boat pitching and rocking in the glassy rollers. When I finally took the helm, I was determined to get us moving.

            The wind wisped to life early in my shift, but our sails wouldn’t hold it in the swells. The rocking of the boat generated it’s own kind of wind, the top of the mast swaying back and forth like an upside down pendulum. And without an engine, the next worse thing you can do is let the sails chafe and, eventually, tear. The occasional drafts of wind taunted me, though. I thought for sure they would grow steady enough to hold the sails, and so I hoisted the sails time and time again. I tried to get us moving five times during that shift, lifting and lowering the sails, so that by the end of it my hands were numb and raw.

            I lowered the sails for the last time right before Taylor’s shift began. He climbed into the cockpit, full of energy and cheery as ever (probably to compensate for my grumbling), but I cut him short. I was furious and exhausted and miserable with our entire situation. I don’t think I said more than two words to transition him in. I went below deck and tucked into my sleeping bag with my last thoughts being, “It’s his problem, now.”

            I woke up not ten minutes later to an air horn blowing on deck.

            “ALAS,” called Taylor from the deck. “YOU HAVE CROSSED INTO KING NEPTUNE’S TERRITORY!”

            I groaned, loud enough for Taylor to hear, but he pressed on.

            “Any Landlubbers or Polywogs aboard this ship must report to the deck immediately before his highness, King Neptune.”

            I wasn’t fast to get up. I was tired, beat down, and we were a thousand miles offshore. I knew that my shellback ceremony was something Taylor had been looking forward to ever since we left Florida, but months had passed since we’d crossed the equator. When I finally crawled through the companionway, squinting into the daylight, I found myself standing before King Neptune himself.

            Taylor had wrapped a roll of tissue paper around his face for a beard, and was holding a boat hook in his right hand like it was a trident.

            What followed was an ultra-secret, clandestine ritual known as a Shellback Ceremony. It’s a recognition that’s been passed down from sailor to sailor for centuries, and serves as a rite of passage for seamen everywhere. Mine involved crawling around on the deck, groveling before the king of the sea (Taylor), and stripping down naked, only to jump into the freezing water of the south pacific – with nothing but my emaciated frame for insulation. It was the most fun I had that entire leg.

            Once the ceremony was over, Taylor brought me a towel and John made me some hot rum with a splash of tea. We were still laughing and congratulating in the cockpit when the wind whipped the hair from my face. Then the skies had cleared before a wall of blue and the sun was coming out. We scrambled to raise the sails, and for the first time in days began cruising along at 6 knots, on course.

            “Poseidon is appeased!” said Taylor, laughing. “The ceremony worked!” And, for a flickering moment, I believed him. Of course I did. We all wanted to believe it. We wanted to believe that our streak of bad luck was over, and that it was going to be smooth sailing the rest of the way to Valparaiso.

            If only I’d known how wrong we were.


The fire occurred about a week later, when we were 600 or more miles offshore. The transmission was in pieces, but we’d still been able to run the engine to charge batteries. We were also able to charge our Garmin, the satellite phone, and other electronics, like our phones and kindles.

            I was fast asleep when it happened. Sleep, even at that point, was practically all I could do when I wasn’t at the helm. We could be in 30ft rollers, with the boat heeled forty-degrees or more, and I’d be knocked out like a baby in a car seat. This was concerning mostly because it reflected our state of mental and physical deterioration, but also because it was disabling. When Taylor burst into the salon screaming, “FIRE, FIRE, FIRE!”—for instance—it took me a good ten seconds to pull myself out of a deep, trance-like sleep.

            Taylor woke up to a cabin filled with smoke. By the time he was yelling “FIRE” into the companionway, he’d already lunged for the battery switch. The fire extinguisher had been knocked loose of its hold by the engine compartment long ago, and the closest one was across the cabin by the entrance to the v-berth. Sparks were shooting off the burnt oil lines and showering the pool of oil in our bilge. There was no time to get to the fire extinguisher. Instead, Taylor ducked back into the head and wrapped his bare hand around the burning oil lines to kill the flame.

            Few sailors experience a fire in their engine and live to tell the tale. If not for the improvised sacrifice of Taylor’s hand, and the crack in our hull that was filling our bilge every 3-to-4 hours—sloshing water to extinguish the falling sparks—our entire boat would’ve undoubtedly gone up in flames.

            Taylor called us into the cockpit the next day. We were becalmed and surrounded by a glassy, windless ocean. He was composed, tranquil even, in his delivery. “It’s time to call it,” he said. “This boat’s not going to make it. We’ll scrap her in Valparaiso, use the money to fly home.”

            More was said. Something about a “Swiss Cheese Effect” and our long list of malfunctions. You punch enough holes into a foundation and the block crumples.

            We called our families, hung our heads, and bowed inland. We never imagined, even then, that it would take two more weeks—and all of our provisions—to reach the shore. There was a series of low pressure systems lining up to break against the Ole Lady, and if not for some mid-sail improvisations, they would’ve easily succeeded.


We were a few days from Valparaiso when our furling line snapped.

            Our boat shuddered, then jerked sideways. I’d barely had time to perk up to the whip-crack noise of it before the jib unfurled, grabbing 40 knots of wind and yanking us into the water. I panicked.

            With both of my hands cling to the helm, it was all I could do to try and turn us upwind. Drenched and frozen, I fought to keep us alive.

            I had shouted for Taylor and John when it happened, but there had been no need. Headlamps were flashing in the cabin below deck, and my efforts were focused on keeping us afloat. The cockpit was still draining out when Taylor and John rose up through the companionway, harnessed and ready for battle.

            “Let out the jib sheet!” said Taylor.

            I’d been struggling so much to hold the helm, I hadn’t thought to use my hands for anything else. I let out the line. Then, like brothers, Taylor and John rushed the bow. Neither of them hesitated. Six years of training and practice culminated in that single moment of action. Waves crashed over the boat, jib sheets lashed the deck with enough force to knock a man overboard, but they pushed forward. When the reached the bow, they began to roll in the headsail. With their bare hands.

            We’re talking about a feat of incomprehensible proportions. Imagine them at the bow in forty-foot waves, slamming down the backs of swells with enough force to knock them off their feet, heeled over at 45 degrees or more, with waves crashing over their heads throughout. They had to twist the entire foresail, which had filled with wind and was holding thousands of pounds of tension, with frozen fingers, in a wet and biting cold.

            What they accomplished in that moment was nothing short of a miracle. And it took time. It was hard for me to know what they were doing, or how long it would take. Meanwhile, we were sitting ducks for a rogue wave to catch us on our beam and toss us like a toy. We were helpless, with the jib loose and flapping in the wind, but I clung to the helm anyway, hoping against hope that our rudder might be able to hold our angle into the swells until they finished.

            It might’ve taken minutes, it might’ve taken an hour, but—eventually—they did it. After rolling it a few times, John was able to grab a stub of the shorn furling line and together they hauled in the jib back to a quarter sail. They cleated that line right there at the bow, and by the time they returned to the cockpit, the Ole Lady had leveled out. Control returned to the helm. We eased forward, a steady rhythm returning to our progress. Climbing one swell to its crest, and surfing down to meet the next. It was a temporary solution. An improvisation. Another hole to crumple the block.


We rigged a new furling line after the sun rose, and three days later we limped into Valparaiso. It was a confusing landfall. We were relieved and ecstatic and filled with a sense of accomplishment for having survived. We were alive! And yet we had failed. We would be flying home soon. Closer to Patagonia than ever, but Cape Horn had never been farther away. We were also desperate for food and rest. It was tempting to collapse from the exhaustion, but we had to get to shore. Our bodies needed sustenance.

            John found us a pub with WiFi using his international data plan, and we tendered to shore. The reality of being on land, of hot food and a cold beer, swept over us in the form of raw ecstasy. We had survived. We’d made it! And soon we would be warm, showered, home.

            We took turns washing our hands in the bathroom – looking at the alien features of our reflections. Then we huddled into the dry warmth of a corner booth. It took time for our cellphones to charge enough to awaken, and even longer for the messages and notifications to pour in. There was going to be a summit with North Korea, John said. Taylor announced that his sister was having another baby. John’s little brother had been accepted into university. Amy Flannery, a producer of documentaries in the States, wanted to help with our documentary. Glasses were raised, pints were drained.

            Then Taylor read a message that checked all of the rest.

            “Serna’s dead,” he said. The words fell flat on the table. Tears were already blinking out of his eyes. “He committed suicide.”

            “No,” John said. He turned to his own phone for confirmation. “No. Not him, too.”

            Serna was a former rescue swimmer. He had deployed with Taylor and John, but he was more than a fellow veteran. He was a friend. He was charismatic. He was the life of the party. Serna had enlisted because he believed in a man’s duty to serve his country, his fellow man. He became a rescue swimmer because he wanted to help people. He was the embodiment of patriots everywhere, but – most of all – he was a good man.

            Serna was the fourth of Taylor’s friends to commit suicide. Each one drove the stake deeper into our hearts, and our morale. We should’ve reached out. We weren’t doing enough. We had failed them. The futility of our efforts sunk in, and the pain of cutting our journey short hit harder than ever.

            There had been a handful of other times when we’d bent to the point of breaking. In the middle of the Gulf, for instance, and on either side of the Panama Canal. It happened again in Ecuador, when our revived engine quit just twelve miles west of Isla de las Platas. We not only should’ve given up on each of those occasions, but we wanted to, and would have, if we hadn’t been prevented by some small reminder—donations from a stranger; John (a fellow rescue swimmer) flying out to join us; bundles of letters from a Texas Middle School—of the purpose behind our expedition.

            But this was different. Serna’s death hurt.

            No decision was made that night. There was no conversation about continuing on, despite the risk to our lives. John flew home a week later, having booked his tickets long ago, and Taylor and I spent the next month trying to piece together our lives in Chile.

            The choice was made gradually. We were broken, we were broke, and we had no reason to believe that we’d succeed. But we weren’t going to give up. Because this trip wasn’t about just us. We were in a position to make a difference, to help our friends and peers—men and women dying by the dozens because of neglect—and to do nothing at all would’ve been worse than to die and to fail.