From Camper to Coach

by Annie Thompson

June 17, 2026

This summer, three new junior instructors step onto the dock at CYCF, each of them once a participant in the programs they'll now help lead. 

Tony Olvera

Tony first came to CYCF in the summer of 2024, when he was sixteen. He arrived with friends from his St. Paul's cohort, which he says helped settle his nerves. One memory still stands out: the day his group tacked a J/100 without an instructor at the helm. "It felt good to take what they taught us and apply it ourselves," he said. "It's become a memory that we still talk about to this day."

Now eighteen, Tony is back at Monroe as a junior instructor. 

"It's rewarding to think that I started in the same position as many of the students I'll now be helping to teach," he said. "I hope I can pass along the lessons and experiences I've gained to others who may be inspired in the same way I was."

Johnathan Mondragon

Johnathan came to CYCF in 2024 alongside Tony, who'd told him about the sailing camp. He wasn't sold at first. "I wasn't the keenest on water, and sailing a keel boat seemed frightening," he said.

He came around fast. He still talks about the day he and Tony heeled a J/100 over hard enough that water splashed in over the rail. "I can't put into words that feeling," he said. "The sheer adrenaline and joy of the wind hitting our faces as we maneuvered the boat."
Two years later, he's returned to Monroe as a junior instructor. He wants other kids to feel what he felt.

"This program is representative of a directive to connect youth to sailing and spark a genuine interest in it, which they can hopefully use to pursue the sport further," he said. "If I can even spark a few kids' interest, that'll be enough."

Emma Sides

Emma first came to CYCF last summer as a Lead HER Ship participant, a five-day voyage aboard the 105-foot schooner Alliance with a crew of young women from across Chicago. Her clearest memory comes from the bow.

"We were all sitting and talking at the bow of the boat and truly connecting," she said. "I had the realization that these girls I had barely met a day ago are now some of my closest friends that I've made."

Now, she wants to help other kids find that same thing.

"Helping kids build bonds with the people around them is an amazing thing to do," she said. "Watching them open up and become more comfortable to be their authentic selves is so wonderful to watch. I'm happy to help them learn about the boat, but I'm more excited to watch them grow."