The Race to Puerto Sherry

A rainbow for good luck

Race to Puerto Sherry

We set off from Portsmouth with all the optimism of a family at Disney World, ready to conquer whatever the sea might throw at us. For a while, we were doing okay, hanging around in the top five, But then, as though the universe had just noticed we were doing well, things took a turn. We fell back into last place with the grace of a kid tripping over a curb while carrying an armful of groceries.

At first, it was the usual boat stuff: getting into the groove, figuring out the watch system, and pretending to be comfortable in the company of people you barely know, much less trust with your life on a floating metal deathtrap. So far, so... not disastrous. But as the weather picked up and the waves grew into terrifying, rolling mountains, I began to feel like I was in a live-action version of The Exorcist.

Charlie and me at the helm

Down below, I became a walking (or rather, swaying) biohazard. Anything I ate or drank decided it had better things to do than stay in my body. I’d try to eat, and my stomach would immediately reject whatever I put in it. If you’ve ever wondered what it feels like to be a human bottle of Pepto-Bismol, I can tell you it’s not pleasant.

But when I crawled into my bunk, I’d pass out, completely unaware of the chaos unfolding above deck. Sleep, it seemed, was my only form of escape from the relentless storm and my body’s bizarre rebellion. But the moment my watch came up—POOF—back to reality, where getting dressed in the tiny galley area felt like preparing for a high-stakes game of Twister. The space was cramped, the air was thick with sweat, and there were eight other people also trying to squeeze into their gear like sardines in a can. All while the boat pitched and rolled like a carnival ride gone horribly wrong.

Then you finally emerge on deck, and the wind at night is so cold it feels like it’s been harvested from the heart of a glacier. The other watch sits there, their faces blank, as if they’ve seen it all before and have decided to accept their fate. And you? You immediately freeze into the same state of stupefied resignation. Until, of course, it's time to change a sail. That’s when all hell breaks loose, and you work like a mule for an hour, only to slump back into your trance, shivering and dazed, until the next shift.

The leg from Portsmouth to Puerto Sherry was, without a doubt, one of the most miserable experiences of my life. right up there with the time I was stuck in an elevator with an accordion player. We had 50-knot gusts and seas that looked more like a child’s drawing of a tidal wave than anything you’d expect from nature. Meanwhile, I was busy contemplating how quickly I could get my entire entry fee refunded, pack up my dignity, and walk away from the whole thing. Every wave that hit felt like a personal attack. And just when I thought it couldn’t get worse, it did. Kitemare—yes, that’s a thing now—happened. The big, glamorous spinnaker, which we had all looked at like a shiny new toy, came crashing down too late and wrapped itself around the forstay, ruining the sail in the process. I have only vague memories of this event, mostly because I was too busy wondering why I was still alive and whether I could get someone to recommend a good therapist.

Somehow, despite all the chaos and vomiting, we managed to finish fifth—just nine minutes behind fourth place. Which is almost like winning, if you squint and lower your standards just a bit.

But before we could disembark, we had to wait for the tide to come in. So we circled the Puerto Sherry marina like a lost dog in front of a donut shop. After a couple of hours, we finally docked, and were greeted with a glass of Sherry and a bouquet of carnations, as if we had just finished a leisurely cruise and not spent the last several days vomiting our way across the Atlantic. The Sherry, I must admit, was an inspired touch. There’s something particularly sweet about drinking at 9:00 in the morning, especially when you’ve just survived what can only be described as a floating hell.

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Getting ready to sail to Punta

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The start of the race