Good Sports: Sailing

Aspen Recreation Department's Sailing Program
The air feels dead calm, and the water is as smooth as glass.

It’s hard to imagine that the kids who are setting up the rigging on a small flotilla of Sunfish sailboats will be able to get their vessels moving without a big gust of wind. However, in a matter of moments, the kids are sailing steadily out of the Aspen Yacht Club harbor into the open expanse of Reudi Reservoir.

Following close behind, keeping a watchful distance, is a pontoon motor boat driven by Taylor Hale, the program director.

“You’re never stuck. You can always find some kind of wind,” Hale says, watching as his students manipulate their sails, tightening or loosening the lines until their boats begin cutting swiftly through the water.

“Don Sheeley taught me to read the winds, which are way more unpredictable in the mountains than on the ocean,” Hale says, speaking of the man who started the Aspen Rec Department’s sailing program nearly 50 years ago in 1971. “Well, Don didn’t actually teach how to read winds, as in giving chalk time or lectures. Instead, he gave me the ability to figure it out for myself. He trusted me to find my sense for the wind and the water.”

The Don Sheeley Sailing School

There are four Sunfish sailboats in the program.  Eight kids. Two on each boat. Some are return students in their second or third year. Several are in their first week, fourth day of lessons. Hale has paired them well. Experienced sailors captain each boat. New sailors follow directions about when to duck as the boom swings from side to side, when to pull rope, how to position the rutter, and how to manage the sail so it captures the wind.

One boat has stalled, “luffing.” Hale explains what it means when a boat is steered so far windward that the sail is no longer full. He takes the support boat closer to the sailboat, gently teasing the brothers manning the vessel that their sail is flapping.

“Try to see what you can do to help it become tight,” he says. His mustache curls with the shape of his joy as a small adjustment sends the boat, as they say, sailing.

“I’m pretty much a big kid,” Hale explains. “I see these kids as equals, so I don’t talk down to them, or yell.  The only time I yell is to be heard. That’s how Don did it. He trusted us and had confidence in our intelligence. Don gave us the gratifying experience of learning that we could rely on ourselves. We could figure it out.”

Getting Onboard

In the early nineties, when Taylor Hale’s parents signed him up for sailing lessons with Aspen Rec, it wasn’t out of any particular interest in sailing. He had simply tried and loved nearly every rec program offered, and his mom figured he’d enjoy some summer days on the water. No one guessed that this program would help him chart his life course.

“I loved it,” Hale recalls, “Right away, I felt a kinship with Don, and it was mutual. I think I might have reminded him a little of himself.”

After three years in the sailing school, Don asked him to coach, making Hale, at age 14, the youngest-ever employee of Aspen Rec.

Meanwhile, Don and Jill Sheeley’s daughter Courtney grew up around sailboats, playing on the shores of Ruedi and at the Aspen Yacht Club. She was intuitively comfortable at the helm of a sailboat, but she weighed so little that she couldn’t gain a lot of speed. So Don paired her with Taylor and the two started winning every race. They became lifelong friends. She is now married to one of Taylor’s best friends, Chris Wyckoff, and their son is often a passenger on the support boat, along for the ride while Courtney and Taylor coach the kids.

Courtney Sheeley Wyckoff
Taylor Hale and his longtime friend, racing companion and fellow sailing coach Courtney Sheeley Wyckoff with her son. “My dad touched a lot of people through this program and it is so great to see his legacy live on through the program and the kids,” she says.
Full Sails = Full Life

When Don Sheeley passed away in 2017, the City of Aspen named the sailing school after him, and there was no question about who should step into Don’s role.

Only thing – Hale is a career chef. He is head sushi chef and co-owner of Maru, an extraordinary  foodie hub. Anyone who’s spent time in the front or back of a restaurant knows that to run a successful and innovative dining spot  in the heart of downtown Aspen usually means you don’t have much time in the summer. One may assume that Hale would be too maxed to also run a rec program.

Add the fact that Ruedi is a solid hour-fifteen from Aspen – but Hale doesn’t seem at all weighted by work stress or the time factor as he motors around Reudi. He will later drive the van of kids back to Basalt and Aspen before heading to work for 8-10 hours. Again, none of this seems to invade Hale’s time on the water.

He pulls a wide arc around the bouys marking the sailing race posts. He talks about the tactical choices of the various teams with Spencer Perley, a fifteen-year-old graduate of the school whom Hale has tapped to start coaching.   

His words of wisdom? Hale pauses for a moment, then shares something Don Sheeley used to say:

“The only time you’re completely certain

that you can do something is when you’re doing it.”

This explains why the absolute chill chef and sailing coach can do so much – and it explains how he goes about teaching without teaching.

Case in point – a happy squeal from across the water tells us that a boat’s been flipped, likely on purpose. These boats are designed to flip. The mast turns quickly underwater, pointing straight down toward the bottom of Reudi. The hull is upside down. 

Soon, a girl is shimmying up on top of the hull, balancing by clinging to the centerboard – which, on a Sunfish, comes in and out. Her boatmate quickly pulls himself from the water, joining her on the hull, and together they lean back on the centerboard until the hull starts to turn toward them.  The sail pops up out of the water and the kids quickly step up onto the topside of the sailboat. This is how they learn how to right the boat. This is how they learn that there’s nothing to be afraid of, nothing that they cannot figure out.

“These lessons translate into every area of my life,” Hale says. “That’s another thing that Don taught me. Everything is intertwined. If you think you can do something, you can. If you put everything you’ve got into it – just like how it takes throwing your whole weight into righting a flipped sailboat – then you’re going to succeed.”

LEARN MORE about Aspen Recreation Department’s programming.
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