East Wind

Written By: E. Sayre  De Castro

Doug was a screamer, but not that I can say in bed, only when on his boat, racing under sail, and that’s how we met. His wife urged him to switch from power to sail as a way to take the edge off his driven type-A personality.  An American success story, he started repairing cars in his parent’s garage, saved up for a gas station, bought homes, fixed them up and rented them, started an earth moving business with a backhoe and a truck, built it into an empire, sold it, and started a web site.

We are in the McKinnon Cup, which starts in New Suffolk, circles Shelter Island, and finishes back where we started. On the boat, Doug excels at the start where multi-ton vehicles jockey for position for that moment the gun goes off. Then it’s me on the wheel, and I always prefer the owner to do the start. If we crash into another boat, and there are moments when everyone is in a yelling match about who has right away and you think a crash is inevitable, at least he is on the wheel.

We are working our way upwind, Holmes Hill to our stern, and the salt spray misting my skin is refreshing. In thinking about it, I can say this is mostly true except the time when I was body surfing at Cooper’s Beach, and arrived home in bathing trunks to a phone call, whereupon the caller is a woman wondering why I have not picked her up for the August wedding and realizing in that moment I was off by an hour, and that only by jumping into the tropical grade wool suit with the salt still on my skin, and braving the heat wave of the day, that I could just barely make it on time.

Sometimes we switch off and I try to bend our sails into better wings. We were in the middle of the pack for the start – not good but not bad. We are not cracker-jack racers but enjoy the illusion that we can compete at a high level. We start a long run east through Little Peconic Bay. By the time we round the nature preserve at Jessup’s Neck we are making good time in moderate airs but the impact of a few wrong tacking choices drops us to the last third of the fleet. We shoot through the gap governed by Cedar Point Light and wade into an unending calm zone in Gardener’s Bay. As we drift aimlessly, sometimes slowly spinning to and fro, sail hardware clanging erratically, Doug goes nuts, like a caged stallion. He curses the gods, his bad luck, his desire to even race.  He curses a random boat that somehow catches a current eddy and drifts past us sideways.

Knowledge of the tides, how they come and go like a metronome, combined with the flighty winds is what makes sailing in general a challenge and racing filled with excitement. In 1854 Captain Eldridge published his ‘’ Eldridge’s Pilot for Vinyard Sound and Monomoy Shoals,” which included 32 pages on the dangers of navigating the waters from New York City up to Maine. But it was his son George W. that was constantly asked how the current ran with tides, as this is what was so mysterious to the seamen of that day. My father made a career out of moving cargo across the seven seas with state of the art navigation technologies, however, when he started it was a compass, sextant, wind up clock, and when on the east coast, Eldridge’s book.  Today, roughly 90% of Americans work indoors, and of those outside, the weather impacts only a few job segments.  Not for my father. The winds of eastern Long Island had additional meaning and feeling for him.  He would spontaneously tell me “It’s a two shirt day today. Southeast will bring in the humidity and rain.”  Sure enough, I’d sweat like a horse cutting the lawn and picking weeds at the East Hampton estate where I worked. “It’s northwest, finally will dry down and we’ll have good visibility.”  When you are on the water, being able to see far allows you to anticipate where to go and avoid bad things like running aground. During a storm he’d brighten up, “wind’s shifting clockwise and clear air’s on the way.”

I am with Doug coming back to north Shelter Island from Gardiner’s Bay, and we finally get the softest hint of a breeze, like a lover whispering into your ear. You can feel her breath more than you can hear the words. I get the boat moving, and it feels good to finally point and not drift.  But now the tide is at the maximum flood, current coursing into the bays, bringing fresh ocean water and renewal, which in a way was helping us as it pushes us in the direction we need to go.  Except for one buoy. According to the race course we have to pass that big red nun on our right hand side, to our starboard. If we do not make our turn to it at exactly the right moment we either undershoot it and will have to turn back against the relentless current, which in this lightest of wind will essentially put the boat in neutral, or we cut it too wide and lose critical ground against the rest of the fleet, who is also trying to figure out the same thing. An east wind from behind would have made it all easy, but that was not the case today.

We get closer to that moment when we need to make a decision: turn or stay. Time takes on a feeling like vertigo.

Doug says “when you gonna tack for that buoy?”

I reply softly “right,”

“When you tacking?”


I let that part of my brain that figures these things go without interruption or analysis by other parts of my brain.  The water slides by the white hull, but we are moving this 30’ boat hardly faster than a walk.

Doug can’t hide his anxiety to do something and not wait “See the blue hulled one? He’s tacking for it.”


My intuition fires up a red flare: too early.

I count off ten seconds to distract myself from Doug and everyone else.  It’s so tense in the boat it’s like watching that guy walk the wire in between the World Trade Towers. Midway through my count a green flare materializes. I give the order “ready to come about?”

“Ready,” Doug barks.

That the wind represents an underutilized source of clean power is lost on many in the Northeast. Nantucket residents battled a wind farm for years and only now Block Island has given the green light. Funny all that resistance when the east end of Long Island was dotted with critical windmills for grinding grains during our foundational years. Vestiges of these early clean power grinders punctuate the villages of Watermill and East Hampton.

Upon hearing Doug’s “ready” I ever so slowly spin the wheel, making sure not to turn us so abruptly as to lose whatever momentum we gathered.

“Move carefully to the other side,” I tell the guys in a direct but low voice so they can use their weight to help the sails change their set. We are making a line well above the buoy and Doug’s already worried, “you’re too high on it, we’re not going to be close enough.”  But then I see the blue hulled boat. They pass the buoy on the wrong side and now face the prison of trying to turn back against the current.

With the tide’s hands carrying us on, and the sails just filled, we creep past numerous racers that didn’t turn at that moment and come within a yard of the red buoy.  I see seagull droppings splattered Pollock-like over the rusted edges of the buoy.  All of a sudden, we emerge from being 20th in the pack to being three boats away from first.  More amazingly, since the pack had been drifting so long, the organizers move the finish line closer to us and we conclude with a fourth place.  When the gun acknowledges us crossing the finish line, our crew jumps up and down and slaps each other on the back as if we just won first place in the America’s Cup.  Doug is beaming ear to ear.

My wife asks me why there is wind. I think about high and low pressure fronts  telegraphed by Cirrus clouds, complex thermal zones of cement Islands like Manhattan and the cold Atlantic waters at the island’s doorstep, warm air’s love of the cold and how it rushes to meet and embrace it, but in the end tell her wind is the compromise born out of differences.  She seems happy with that and we move on.