Sail Away

I fingered the yellow paper with its bold black type. “This license is only good for three years? Sheesh, what do they think is going to happen?” Flipping the card, I read the words on the front: Park District Sailing License. It was my badge of survival—I’d made it through 12 hours stuck in a 14-foot boat with five other clueless newbie sailors. My stalwart friend, Kathryn, had braved the waves of the local lake with me. We’d learned how to hoist and haul, how to rig and reef, how to beat, reach, and run. The difference between leech and luff held no mystery for us, and never again would we confuse a jib with a jibe.

“I don’t know,” Kathryn said, “maybe they’re afraid we’ll forget everything and need a refresher course.”

“People have been sailing the same way for thousands of years. What’s gonna change?” I tucked the card away. “Have you heard back from your dad about when we can go out?”

Kathryn nodded. “Yep, Monday. We’ll meet him in the city and then go to the harbor.”

Ah, the benefits of having a rich friend. Kathryn’s dad was a well-off businessman with connections to the skipper of a 35-foot sailboat on Lake Michigan.

A sudden thought struck me. “Oh gosh. You don’t think we’ll actually have to—like—help sail the boat, will we?” Shiny new sailing license notwithstanding, I wasn’t too keen on having any responsibility for a boat twice the size of a car.

Kathryn looked horrified. “I hope not. I mean, they have to know that we’re not actually competent, right?”

The boat was beautiful: gleaming white, trimmed with silver rails. It seemed like an even bigger risk to let me on it. The skipper welcomed us aboard and told us to get settled. As we carefully motored out of the marina to a place where we could catch some wind, the skipper called me over. “See that winch?” He pointed at a silver handle on top of a round spool. “Just turn it to the right a few times.”

Which right? I wondered silently as I wrapped my fingers around the handle. Right as I’m looking down at it, or—

“Not that way, the other way,” the skipper said, mildly enough, though I was pretty sure he was asking himself why he let a girl who couldn’t tell right from left onto his boat.

Once we had cleared the harbor, we began unfurling the sail. But instead of running it out on the boom and then hoisting it, the mainsail unrolled from inside the mast. Kathryn and I exchanged a glance. Swanky, she mouthed at me. I raised my eyebrows and nodded. It was impressive. And there was no need for us to do anything. Suddenly I felt a lot safer, knowing my fate was in someone else’s capable hands. The skipper cut the engine, caught the breeze, and we sailed out of Du Sable into a perfect day.

The sails soared above us, crisp and white against an endless sky. With just enough roll to give us a satisfying spray at the bow, the lake sprawled to the horizon.

“What’s that?” I asked, pointing at a tiny round structure in the distance.

The skipper squinted against the glare. “The Crib?”

I nodded.

“That’s where they used to pump water to the city,” he replied. “Tunnels run under the lake all the way in. The first one was built in 1865, and they used mules to cart the dirt out as they dug.”

I shuddered, thinking about being in a tunnel, 200 feet below the surface, with nothing but water above me.

We sailed into the wind for about an hour before swinging around and heading back towards the city. Chicago’s skyline spread out before us, gleaming in the afternoon sun, light flashing off a million panes of glass.

“Does anyone else want to take the wheel?” the skipper asked suddenly. My stomach dropped, and it wasn’t because of the waves. Why on earth would anyone want to do that? We were perfectly safe with things just the way they were. Letting someone else take the wheel seemed needlessly reckless…right?

“You mean like…steer the boat?” Kathryn squeaked.

“Sure,” was the response, “you want to?”

Kathryn shook her head. “Me? No. What? No. No thank you.”

The skipper shrugged. “That’s fine.”

There was a little silence. Then—“I’ll do it,” I said.

Kathryn almost fell overboard.

Maybe this was a bad idea. But all I could think was, If I don’t do this, I’ll always wish I had. I’ll always wish that, just once, I got out of my comfort zone and took a risk.

The skipper slid over and let me take his place at the wheel; the wheel that was huge and blindingly silver. “Just keep us pointed at the Presidential Tower,” he said. “You know which one that is?” He gestured at the Trump building.

I do now, I thought grimly. Clutching the wheel in a white-knuckled death grip, I saw with panic that we were beginning to slide too far to the right—excuse me, too far to starboard—so I tweaked the wheel the other way. Nothing happened. My jaw ached and I realized I was clenching my teeth. With an effort, I exhaled and nudged the wheel farther over. Farther…farther…Finally. The Trump spire slid back into view. Those few, insignificant seconds felt like I’d survived a major artillery battle. I’d better quit while I’m ahead… “Okay,” I said, “I think that’s enough for now.”

“You sure?” The skipper eyed me quizzically. “You don’t want to go longer?”

“Mm-hm.” Please, take it away from me before I capsize the pretty boat. “Yeah, I think I’m good. Thanks.” Longest two minutes of my life.

But I had done it. As I relinquished the wheel and stepped away over the swaying deck, I grinned like a fool. Maybe next time, I’d hold it for three minutes.

We ran before the breeze all the way back to Du Sable, and Kathryn and I sat on the bow with our feet dangling over the side. The sun had begun to slide down in the western sky, and Navy Pier shone in its vibrant golden warmth. We didn’t say much. As we approached the harbor, the masts of a hundred other ships in neat little rows began to tangle around us.

“You know what?” Kathryn asked softly as we pulled into our berth.


She smiled. “We have a pretty great life.”




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