Challenging Devil’s Isle


Finding Light in the darkness at Bermuda’s premier paddle race

It was still dark at the start line of the 2017 Devil’s Isle Challenge. Headlamp rays wafted above the check-in table like beams of miniature UFOs casting a dreamy mood for the pre-race hustle. A modest handful of brave endurance athletes hovered around the beach, somber silhouettes prepping their boards and alternating sips of Carbo Pro with coffee. The humid morning air clung with anticipation that felt thick enough to chew. Wind whipped the palm fronds above the beach. If it weren’t so dark, we would have seen whitecaps writhing outside the shelter of Snorkel Park. Twenty-five knots howling from the south was hardly the forecast we had hoped for—especially after flying halfway across the world for an endurance race around Bermuda.

I tugged my wrist hairs to make sure I wasn’t conjuring a nightmarish twist to the imminent race; no such luck. It was set to kick off at dawn to ensure a finish before dusk. No one hoped to spend the day’s entire span of sunlight at sea. But, given the conditions, no one could rule out the contingency. Thirty consecutive miles under heaving wind on the tip of the Bermuda Triangle awaited; unfortunately, I was wide-awake.

Clockwise from lower-left: Annabel Anderson. Photo: Greg Panas // Gordon Middleton checks racers in by headlamp for the pre-dawn start. Photo: Greg Panas // Darrell Horton finds his zone before the race. Photo: Andrew Stevenson // The Oracle boat checks in on a weary paddler. Photo: Greg Panas

I stood by my borrowed heap of a board, glazed eyes pointed toward Nova Scotia somewhere out there in the darkness. My mind was already racing. As much as I wanted to do this race, I was not prepared. I hadn’t trained enough and I knew it. Prospects of pain or death from pain floated toward me like specters from the void.

Out of the black Atlantic came a mysterious figure hammering straight toward me. A real one. It was Annabel Anderson, one of the fastest female paddlers on earth, coming in from her twilight warmup. She’d signed on last-minute to do the Devil’s Isle Challenge after finding a brief window in her busy schedule and reckoning one of the world’s longest ocean races could be a fun way to fill it. Anderson parked her board next to mine. It looked like she’d just paddled 100 miles and was ready for 100 more.

I tugged my wrist hairs to make sure I wasn’t conjuring a nightmarish twist to the imminent race; no such luck.

“I have good news for you,” she grinned with her unmistakable Kiwi accent. “The Oracle boys want you on their relay team.”

Perhaps only a world-class athlete like Anderson would have the bravado to call the men of the U.S. sailing team for the America’s Cup “boys.” Or maybe it’s just a Kiwi thing. Anderson had been staying with her pal Jimmy Spithill, world-famous skipper for the team, who was stationed on Bermuda with his crew—Oracle Team USA—to train for the America’s Cup, the prestigious international races that would take place in Bermuda three weeks later. Rumor had it, if the wind was too rowdy for his team to practice, Spithill would spend his down day competing in the Challenge. Just another training day for a superstar, I supposed. For me thirty punishing miles felt pretty damn daunting.

Oracle Team’s athletes are the sailing world’s elite. And much to my relief, as Anderson informed me, Spithill wasn’t the only member of the squad set to compete in the Challenge. They also arranged a relay crew comprised of token grinder, Graeme Spence, as well as Revelin Minihane, a blunt Irish cyclist with a penchant for pain who doubled as Oracle’s chase-boat operator. That relay team needed a third. Salvation! Along with my team, I also got to upgrade my board, and my chances for survival.

Racers lined the water’s edge as the sun began to rise. Warm rays haloed the horizon and the nightmare vanished. I took the opening leg for our team and dug hard out of the cove. Anderson shot off like a rocket, leaving the pack behind as we rounded the point into a ruthless quartering wind. The sea turned to bucking chop at the edge of the lee and I broke focus to take a look around. The pack was scattered. The few paddlers I could see above the whitecaps had dropped and were gunning from their knees.

Photo: John Singleton

SPLASH! I took my first plunge. Nerves rinsed away in the turbulent water and I remounted the board with a deep breath of pure air. Forget the chaos. Forget the fear. Remember where you are and why you’re doing this, I thought. It was still the morning’s golden hour and the seascape was ablaze in a pink hue that mimicked the island’s sand beaches in the distance.

My invitation to the Devil’s Isle, more commonly known as Bermuda, arrived a few months earlier with a call from Christian Shaw and Gordon Middleton, the altruistic young upstarts behind Plastic Tides, a grassroots nonprofit that uses SUP to spawn environmental and social change. Shaw and Middleton had been visiting Bermuda since 2014 to draw awareness to the island’s environmental issues and educate the local youth through their paddling program, SUP’r Kids Bermuda.

“The goal is to use paddling and plastic as a gateway drug to being environmentally minded on a bigger scale and give people a sense of stewardship.” –Christian Shaw, Plastic Tides

Their island crusade against plastic is an ambitious one. Bermuda sits alone in the direct path of the North Atlantic Trash Gyre (the Atlantic’s equivalent to the North Pacific Garbage Patch), a flotilla of mostly submerged marine debris roughly the size of Texas. Outside the tourism brochures, it’s not uncommon to find bottle caps, cigarette butts and candy wrappers half-buried across the island’s majestic beaches.

“We don’t just want to clean Bermuda up one piece of plastic at a time,” Shaw explains. “The goal is to use paddling and plastic as a gateway drug to being environmentally minded on a bigger scale and give people a sense of stewardship.”

Left to right: Royal Naval Dockyard is a tourism hub in Bermuda, hence the massive cruise ships docked across the harbor. It’s also home to the start and finish line for the Devil’s Isle Challenge. Photo: Andrew Stevenson // The many shades of Bermudian blue. Photos: Greg Panas // The salty and stoked Christian Shaw of Plastic Tides. Photo: Greg Panas

In 2015, after paddling around the entire island on a whim—a 40-mile, 20-hour sufferfest that nearly lost the duo at sea—Middleton and Shaw dreamed up a way to simultaneously raise money for their onsite programs and draw global attention to the area’s environmental issues. That dream became the Devil’s Isle Challenge, Bermuda’s first-ever SUP event. The 2016 Challenge was one of the longest ocean SUP races in the world. For the 2017 rendition, the guys invited me to cover, and experience, the action first-hand. A trip to Bermuda and all I had to do was compete. Why not give it a shot?

Any kind of serious training would have been wise. Halfway into the race, I cursed myself, having spent the past four months overworking and undertraining. After 12 trips into the drink, I started to lose count. Slogging at what felt like negative knots, we rounded out of Hamilton Harbor and headed back east with the south wind still beating. Our team took 20-minute shifts to evenly distribute the pain. I couldn’t imagine how the solo paddlers felt.

Beyond pride, my main motivation was to not let down the team, which was clearly being carried by Spence. A quippy six-foot Aussie with a larger-than-life presence, his boyishly playful demeanor betrayed his behemoth physique. Spence was merely a casual paddler but he stroked with more fervor than many of the racers on the course, most of whom were behind us.

The author warms up during the calm before the Challenge’s storm. Photo: Greg Panas

Compared to my centaur-like teammate, I stood all of 5-foot-8 and felt like a wet noodle. Love for the water gave us our common ground though, and between slogs the three of us swapped stories and jokes to keep our minds off the grind. Spence and Revelin’s singular drive was contagious; I felt empowered with them at my back. I passed one of a half-dozen contenders ahead—and even gained some distance before handing the paddle back over to Revelin.

Back on our support boat, Spence filled me in about a downwind stretch a couple miles ahead, a quick dash from Five Star Island to our turning point at Somerset Bridge.

“See my house? It’s right over there,” he said, pointing to a yellow waterfront speck. “On days with good south wind I sometimes downwind to work at the Oracle base in Dockyard. It’s a straight shot from my dock and it can crank! We’ll be on it soon.”

Not a bad commute. I had all the reason to believe Spence’s claim. This was just one of many zones around Bermuda with incredible potential for standup paddling. On the low-key, Bermuda is a seldom-tapped paradise for paddlers. A sliver of land surrounded by warm water and outer reef, the island stretches roughly 15 miles as the crow flies and is shaped like a massive fish hook. Wrapped in scattered offshore reef, it’s fringed with quaint coves, secluded bays, empty beaches and little islands with something on tap for every paddler. You can paddle downwind from Five Star to Dockyard in the morning, surf Horseshoe Bay in the afternoon and tour between the boats moored in Hamilton Harbor by sunset.

Graeme Spence engages in full-blown beast-mode. Photo: Greg Panas

Spence wasn’t lying. He handed the paddle back to me just in time to take on the same downwind stretch he had just praised. Gliding instead of digging, connecting little bumps atop translucent water that glowed turquoise beneath the capping wind swell, I lucked into a standout section. Undoubtedly my best leg of the race, the prime conditions didn’t last long.

Downwind bliss came to an abrupt halt when I realized I’d passed the keyhole I’d been shooting for at Somerset Bridge, a tiny stone span connecting two fingers of land that form Cavello Bay and separate the island’s eastern bay of Ely’s Harbor from the Great Sound. Turns out I’d get my best leg of the race and then my worst, back to back.

“The goal is to use paddling and plastic as a gateway drug to being environmentally minded on a bigger scale and give people a sense of stewardship.”

The support boat had run off to check on Spithill racing solo in the front pack, and I was left to my own devices. The task at hand was to paddle east a mile or so into Cavello Bay with quartering 20-knot wind threatening to clash my borrowed board into the rocks just north. I dropped back to pivot, lifting the nose of my board. The wind pinned it and twisted me off course. I spent the next half-hour hammering on my right side, barely moving. I dropped to my knees. Then to my stomach. Then back to my feet. Then fell in. When I finally made the lee, I slowed my clip and drank in a few extra deep breaths as I passed through the shelter of bridge. Momentarily relaxed in what felt like a European canal, I admired the well-crafted stone undercarriage of the bridge, thinking about the area’s cultural singularity.

Oracle Team USA skipper Jimmy Spithill aims for the keyhole at Somerset Bridge. Photo: John Singleton

The Bermudian beat is something different: warm and inviting locals mixed with classic architecture and postcard-perfect beaches. The accent spoken is one of its own—a punctuated and rhythmic melding of island tongue with English swagger that mirrors the odd complementary blend of cultures on the British island colony. This mashup dates back to the early 1600s when a ship sent to colonize Virginia crash-landed on the island’s outer reef. The full load of 150 passengers (and one dog) survived and set up camp, forming a British colony that quickly enveloped the island. Relics of British invasion and rule—archaic bastions, cannon-clad stone fortresses and red London-style phone booths installed across the subtropical setting—still dominate views in locations like Royal Naval Dockyard, the dreamy starting point of the Devil’s Isle Challenge.

With the bridge behind me it was time to synch up with my super-team for the final stretch of the race—a blustery five-mile jaunt back to the beach at Snorkel Park. I tapped Spence to paddle the next leg and hopped on the boat as he hammered off toward Dockyard. The stoic Revelin had warmed up to me over the course of the day and gave me the helm of his chase boat. I pushed the throttle forward to catch up with Spence.

Windy much? A paddler finds refuge in the island’s lee. Photo: Greg Panas

As we finally neared the finish after nearly seven hours at sea, I thought about my doubts on the dark and stormy beach that morning. How the ripple effect of Anderson’s little plot twist of adding me to the Oracle Team had carried a hopeless paddler through. Like my pushback to the bridge, I realized that no matter how big the obstacle ahead, if you just go for it, there’s always a chance. In a sense, that’s the same gist as Plastic Tides’ mission taking on the massive challenge of cleaning up the environment one race, one person, one stroke at a time. Go for it, because there’s really nothing else you can do. Small strokes can sometimes yield big results.

In the end, Anderson finished first with a time of 6 hours, 2 minutes, more than eight minutes ahead of Spithill, who took first place in the unlimited class on his 17-footer. Garrett Fletcher followed to win the Men’s 14-foot division. Our team won the relay division and watched from shore as the rest of the paddlers trickled in. The final two racers landed in just under 10 hours—plenty of time for a well-earned Dark and Stormy rum cocktail, or two, before dusk. Of the 20-odd racers to start the race, only three didn’t finish it.

Thanks to Oracle Team USA, I wasn’t a fourth. –MM

Learn more about Plastic Tides and their mission in Bermuda by visiting 


Gallery and Recap: Reliving the 2017 Devil’s Isle Challenge

Giving Back in Bermuda: The Plastic Tides SUP’r Kids Program

The article was originally published on Standup Paddling

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