Sail for Your Life: A True Story

I have a confession and it’s not a pretty one. I’m a terrible dinghy sailor.

Sure, I can put on a good act of hauling in sheets, raising halyards, splicing the main brace and doing all kinds of salty talk, but when it comes down to it, I capsized the only dinghy I ever sailed while leaving Scott Scanlon’s Barcelona Beach Blast about a thousand years ago, and had to be towed home. It was a major embarrassment, especially since I’d borrowed the dinghy from a friend without asking permission.

Years and years later, two people died when that tippy little dinghy tipped them out of the boat into the waters outside the Sag Harbor breakwater. Really. They weren’t even sailing it. They were just trying to board their sailboat after a night of bar-hopping. Everywhere you went in Sag Harbor in the weeks after their death, you’d hear people saying ‘yep, that was a tippy little dinghy.’ I count myself lucky to be alive.

The truth is, any sailor worth their salt can sail a dinghy. You have no business calling yourself a sailor if you can’t. It was with that in mind that, with a heavy conscience and a healthy dose of fear, I agreed to crew on what would turn out to be one of the most bone-chilling and exhilarating experiences of my brief life.

The mission was simple: Meet my sailing buddy and get in a Sunfish on the beach in Greenport. Sail west until we land on the shore alongside the old Galley Ho in New Suffolk. Do a little sailor dance and go home. It seemed like a straightforward little task. I studied the chart at home for about five minutes and we headed out the door with the sheets and the blocks and the daggerboard and the tiller and rudder. I never sailed a boat with so many detachable parts before. I was in proverbial uncharted waters. It was time to take them on the chin.

We put in at Gull Pond in Greenport. The wind was doing a thing that it does only occasionally in late August, when it blows fairly steady, not too strong, and is actually warm even though it is coming from the bitter northeast. Our sailing voyage was looking like a straight-ahead downwind run. We smiled as we assembled our new boat. We tied a small bit of nylon rope in a braid around the handle on the foredeck, for good luck, and sailed right off the beach. Within minutes, we’d passed the breakwater at the entrance to Stirling Harbor and sailed straight through the ferry passage, easily timing our crossing to avoid causing a traffic jam in the closest thing to a shipping lane in these parts.

I claim to be an expert on the East End waters, but the truth is that I’ve never before sailed between Greenport and Cutchogue, even though I’ve studied these waters on the charts for years. I’ve never before been in a boat looking across the water to see the brickmaking tower behind Goldsmith Boatyard, the backyard of my landlubber childhood in an apartment above the old Mill Creek Inn, or seen a sailor’s view of the gazebo at Camp Quinipet on Shelter Island, which stands on the far shore from where a little kid me sat on the beach and conjured seafaring dreams.

Nearly all of my sailing has been as delivery crew, either hurriedly motoring the boring stretch of water from Newport, R.I. to Block Island to Sag Harbor, or in a creaky old 24-foot sloop in the waters surrounding Sag Harbor, Noyac and East Hampton. You can do a lot of serious sailing in a 24-foot sloop without getting wet.

This video below was on the homepage of the website for Intensity Sails up in Rhode Island, where I bought the parts to outfit the Sunfish. I watched it over and over, shivering all the while, as I weighed the cost of each block and each deck fitting. So this is what dinghy sailing is really all about. Yikes!

We were still sailing downwind under sunny skies on the same tack on which we’d left Gull Pond, when I began a glazed-eye squint at the unfamiliar shore. A wisp of white sand jutted out into the bay, but our little crew, our eyes aging from too many years of staring into the sun, couldn’t tell if the white sand was on the Greenport shore or the Shelter Island shore. The chart memory I’d stored in the hard drive of my brain said it was Conkling Point, just east of Brick Cove and my childhood brick chimney, but my eyes just panicked the way the eyes of landlubbers panic.

We pushed our heading southward, hoping to make it around the spit of land, if it was a spit of land, without being whipped overboard by an accidental jibe. I’ve done some accidental jibing out sailing alone, but never in a dinghy and never with someone else’s life at risk other than my own. I could hear the sound of boom cracking on skull, reverberating inside my skull, which has already been whacked by more booms than I care to recall. If Albert Einstein was a terrible sailor, I justified, I could be a terrible sailor too.

The gooseneck on the boom creaked around the mast. The sail held steady on our heading. We rounded the point, waving at the seagulls basking on their spit of sand, and then stared befuddled at the expanse of Southold Bay.

Southold Bay was big and it was wide, and there was bound to be some chop, I thought, as the wind whistled over that expanse of open water. Sailors call the distance from one shore to another the “fetch,” and the bigger the fetch, the more time wind has to rustle up the water. It’s one of the big reasons the waves are bigger on the ocean than they are on the bay. They’ve traveled that much farther and built up that much more energy.

We weren’t quite sure where we were heading, but our heading was pushing us over to Shelter Island. It was at that moment that both of us realized our dyslexia would prevent us from being able to turn around into the wind and tack, so we jibed instead. The sail sang and the boom sang as they crossed our little ship. The little fish printed high up on the sail laughed and sang because the wind was suddenly stronger on our new tack, stronger than you could ever guess if you spent your whole life heading downwind. We began to heel over. The sheet whistled through my hand as I thought of the Intensity Sails video and panicked. For just a second. Really.

We had a problem. I saw it before my sailing buddy could. I worry about everything, but he worries about nothing. It’s why we work well together. The outhaul line attaching the sail to the back of the boom had come loose and it had come loose because, after so many years on land, I don’t remember how to tie a rolling hitch. It was too far away to reach and it was getting looser every second. We were headed straight for Paradise Point but we may as well have been heading for a collision course with the moon. It would take another tack or another crazy, ill-conceived jibe to get us around the point of paradise.

We jibed because the wind had entered our heads and there was no room left for thought. The outhaul line disappeared into the bay and the sail began flapping. The flat fish printed on it laughed and laughed, but the boom missed us. Our heads were still intact and it looked like we might just round the point. We took a heading, gritted our teeth, and watched the edge of the sail creep up the boom, flapping more and more as the wind tugged harder.

If there’s one thing that always seems true about being at sea, it’s that little problems quickly become big problems if they’re not fixed. It’s that way in life too. And if there’s one thing that’s true about life, it’s that bad fortune comes in threes.

We were perpendicular to Paradise, watching the point, and we knew we were moving fast because all we could hear was the wind whistling through our ears. The boat lurched and was suddenly stopped, hard ashore on the sand bar off the point, while our little crew lurched forward. Our stomachs lurched forward and then our bodies lurched and then we were grabbing at the daggerboard and yanking for our lives and Einstein was in the clouds laughing above us at the simplicity of inertia. I wouldn’t be surprised if the great physicist himself had run aground on Paradise Point because his essence is in the air all around that place, whipped up in the irony that there is no paradise in this treacherous spot.

The daggerboard came up easy but our sail was still getting looser and the boom end was still out of reach and the outhaul line was still somewhere miles back drifting on the sea. The boom tried one last time to kill us on another accidental jibe. Green water began pouring in over the lee rail and both of us became monkeys, climbing out the windward side of the boat, mast in the sea, paradise drifting beyond our transom and the daggerboard pointing out of the bottom of the boat toward the mid-morning sun. We were on the boat bottom, clawing pushing and crawling, when the Sunfish suddenly popped upright and began sailing again as if nothing happened.

My shoe and two sandwiches floated around in the cockpit. A sleeve of Ritz crackers pretended to be a floatation device. The sail was still flapping and we were headed straight for two fishermen, a father and a small boy, pointing at us in amazement from the shore of Cedar Beach. We beached just south of them, our legs quaking and our stomachs around our necks, as we crawled to shore and kissed the ground.

I quaked and shivered and opened up the soaking sandwiches and decided to chicken out and call my mom. My sailing buddy poured the sea out of his shoes and walked around the Cedar Beach point to investigate the lee shore. Across the water, a hairy head of land jutted out at me, like the middle finger of the South Fork stretched far out into the sea.

Jessup’s Neck! Of course! I’d never seen it from this angle before. On the charts it looks like a finger of land, but out here, in the real bay, it was covered in hills and trees. It seemed the ghost of Elizabeth Morton, the girl on the salt box, was wandering through those woods, feeding salt to the deer and the birds and watching us from her family’s wildlife preserve. I waved and then I thought about where we were and what the water must be doing as it funneled through the land between Paradise and Cedar Beach and Jessup’s. This was not a pretty place for novice sailors.

My sailing buddy was running back toward me around the point.

“It’s another world on the other side!” he said, then untied our lucky braid from the bow handle, tightened up the sail outhaul, bailed out the boat and pushed us offshore. We were going to try to reach our destination and if we didn’t succeed we were going to die trying. It was no different than the rest of life.

We were out now in the big Hog Neck Bay and the sun smiled on us but we had a new problem: The winds were different over here and we were afraid to tack. Nothing made sense. The sheets and sail, boom and wind, were all a jumble in our heads. Our vision was clouded by the memory of that daggerboard pointing to the sun as we capsized. We were almost to Nassau Point before we worked up the courage to tack.

Along the cliffside shores, new bulkheads and plantings shored up houses that had come perilously close to falling off the edge during Hurricane Sandy. The shore was a massive construction site and we, in our foolish innocence, were alone in a 14-foot boot on the sea that had ravaged the East End last October. What morons we were!

In the distance, children played with buckets and shovels along the beach while their parents lounged in chairs reading and keeping just one eye on the monster sea that was playing with their precious children. We finally worked up the courage to tack and their faces faded quickly.

We were bound for the long spit of land at the end of Nassau Point, halfway to the South Fork, before we braved the crossing of that sandbar. We still ran aground, but, no longer novice sailors, we quickly pulled up the daggerboard and drifted into a familiar sea, Robin’s Island to our left and the Galley Ho directly ahead as the sun crept low into the late afternoon sky. By the time we beached our legs were rubber mushes, like the legs of trans-Atlantic veterans. We wandered down First Street to find someone to tell our tale.

The first shopkeeper to hear it didn’t believe, so the story of the great Sunfish delivery has remained a secret until now.

“That’s too far to go in that little boat,” he said. I don’t think we learned our lesson yet.