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How I Lost My Nautical Naivete

A teenager from Long Island reflects on her first experience aboard a sailboat.

I had yet to drive a car, but that didn’t stop me from steering the 31-foot sailboat through Oyster Bay Harbor. It was a morning in the middle of August, and I was having my first sail ever, off the North Shore of the Long Island Sound.

Along with two others named Peter and Doris, my mother and I had been invited onto a friend’s O’Day 31. The friend was named Bill, and the boat was called the Adele B, after his mother who’d been into the water and paddling sports. Over 30 years ago, Bill had taken up sailing. He was so experienced that Peter referred to him as, “our skipper.”

“This is the jib. You don’t want to sail into the wind, because then the sail would flap like a flag and we’ll get nowhere. You want to catch the wind in the sail. Do you understand?” our skipper asked me a short way into the sail.

I nodded.

“Alright. Take the wheel.”

I laughed at Bill’s joke. From what I’d gathered from watching pirate movies, sailing involved ships getting tossed about by waves. In those movies, sailing usually involved capsizing and becoming marooned on a deserted island.

I had just turned 18. I didn’t want to be the reason we got stranded.

“Go on,” Bill said.

I blinked. He was serious. I slowly took the wheel and steered the goliath out of the harbor. My fingers twitched on the wheel as I waited for a huge wave to knock us over. Maybe we would capsize and get eaten by a Kraken. No, I told myself. The Kraken was not native to Long Island Sound.

“Sailing has been compared to watching paint dry,” said Doris. The pirate movies had never mentioned that.

“It’s not the best form of transportation,” agreed Peter.

I looked around. The moment I realized that we had been bobbing up and down in the same place was the moment I realized that the pirate movies were wrong.

The breeze crawled along at 2 knots, and we continued to go nowhere beneath a faint layer of clouds.

“We are going to tack,” Bill declared.

“Tack?” I asked.

I learned that tacking was another term for turning.

“When you say, ‘Ready about,’ we will ready the sheets. When we say, ‘Ready,’ you say, ‘Helms alee,’ and turn the wheel to the left. Okay?”

I nodded. “Ready about?” It came out as a question. What else hadn’t the pirate movies shown?

The others yelled, “Ready!”

I took a deep breath, shouted, “Helms alee!”, and yanked the wheel to the left.

The jib glided from one side of the boat to the other. Sunlight glistened against the sail. I grinned. The boat was turning. We were moving once again.

Bill also gave my mother a chance to steer the boat. She had sailed before, so she wasn’t as hesitant in steering as I had been.

The shore receded into the mist. I marveled at the way the water glimmered like liquid metal. Who needed movies when you had real life?

After eating chicken for lunch, I felt some water droplets on my head. There was a 50 percent chance of rain that afternoon. We decided to head back. We moored the boat in the harbor, and Bill retrieved a walkie-talkie from the cabin.

“Oyster Bay Marine Center. Adele B. We need a pick up on CC42,” he said.

A launch arrived and we climbed in.

“Next time, when the wind is really good, you’ll see why sailing is so much fun,” Bill told me, his eyes shining.

I smiled. You never truly know someone unless you walk a mile in their shoes. The same could be said for boats.

“I can’t wait,” I said.


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