A long haul through the Bermuda abyss. Christian Shaw and Gordon Middleton enjoying the Bermuda blue from their custom catamaran SUP. Photo: John Singleton

Completing the First-Ever Circumnavigation of Bermuda – Part 2

This installment is continued from Part 1 of our Circumnavigating Bermuda series, the three-part story of the first nonstop SUP circumnavigation of Bermuda by Christian Shaw and Gordon Middleton of Plastic Tides. It was a brutal overnight attempt that resulted in lots of type II fun, a great campfire tale and Bermuda’s first SUP race – The Devil's Isle Challenge.

For ten minutes we simply stroked, concentrating on the task at hand. But even our strongest sea legs were no match for navigating the ruthlessly chaotic sea that hugged the island of Bermuda that night. Eventually Christian Shaw—cofounder of Plastic Tides and my partner in this wild first-attempt at an unsupported, nonstop circumnavigation of Bermuda—agreed with me: standing was no longer a viable option, at least for the time being. And so to our egos' dismay, we sat and stroked.

Sitting on a SUP for long periods of time sucks. You get sore in one position and switch to another. Then the same soreness soon overwhelms you and you switch again. For the hour or two that we paddled while sitting, we tried a constant rotation of positions to keep our feet and legs from falling asleep or our backs and knees from aching.

We paddled past Higgs and Horseshoe Island, Paget Island, and finally past Great Head Park. When we finally made it to the southeast shore, the chop and swell cleaned up a bit and so we stood.

After sitting for so long, our legs seemed incapable of functioning properly. The first five minutes were full of grunts, yells, and close calls. Even with the moon, darkness persisted as we struggled towards the most consequential pilotage of the trip.

Bermuda's south shore is full of boiler-head reefs and shoals, both of which you don't want to encounter on a SUP at night. We had our first sign of trouble at Pear Rock, nearly running aground as we tried to thread between the beach and the rocky face of an unnamed island. We managed to stay off the shore and the rocks. Correcting course, we paddled around the gnarled Pear.

The most dangerous pass on the island brought us through an unmarked channel between jagged outcrops and surging boilers. Navigating by ear to the gurgle of waves sucking off the reef; we finessed our way through and caught refuge between Castle Harbor and Charles Island.

After a quick break for some food, we left the comfort of the island's protection and paddled hard out to sea. Christian decided our best bet was to paddle far offshore for the entire stretch ahead of us as the reefs were invisible and their distance from shore varied wildly. After getting about two miles out, we turned to run parallel with the island.

This would be the most dangerous stretch of our trip, though we didn't know it yet.

The moon had finally risen high and the light gave us the confidence to stand, but occasionally a surprise set would jolt our boards out from under us. The wind and swell came out of the east, driving us simultaneously down and into shore. This meant we were limited to stroking on just our right side.

The real danger came with lack of sleep. For those wondering, yes, it is very possible to fall asleep while standup paddleboarding.

The overpowering need to sleep came in waves. My eyelids grew heavy. My strokes, lethargic. I pitched forward, lurching awake barely in time to catch myself before face-planting into the front of my board.

This cycle continued for what felt like an eternity. Pushing through each bout of sleepiness, I would feel renewed and able to paddle with confidence again. When the conversation waned, you knew someone was succumbing to exhaustion.

We had to keep talking.

The previous morning we'd woken at 6:30am for a full day of work and freediving prior to our departure. We hadn't slept in nearly 20 hours and yet here we were–paddling through the darkness–nearly two miles from shore in the middle of the Atlantic Ocean.

Between our micro-sleeps, we were plagued by shadows on the ocean that felt like circling sharks–ever-present and highly conscious of our struggle to stay awake and on our boards. An irregular splash from the chop would have us wide-eyed and suspicious; a shadow elicited a few yells…"Did you see that?!"

The atmosphere was tense and our wetsuits were soaked with sea spray and sweat. We tried to keep talking, to keep each other engaged, but lulls in conversation translated to closed eyelids, fleeting dreams and slaps across our own faces. We had to stay awake. We had to keep going.—Gordon Middleton

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