Most summer jobs don’t involve teaching kids how not to flip over in their tiny boats, but that is exactly what Maggie Ryland’s did, and she wouldn’t have it any other way.
Junior Maggie Ryland made waves this summer as the Miles River Yacht Club sailing instructor, using her life-long knowledge of sailing as well as her experience on the Hillsdale College sailing team.
Ryland, along with a few other college-age coaches, taught intermediate level children ages eight to 12 how to set sail. She took students with minimal sailing knowledge — some of whom had never sailed before — and showed them the ropes. By the end of the week-long camp, they were competing in regattas. Each student used his own optimus sailboat, a small, single-handed boat suitable for children under the age of 15.
She began with a classroom session, showing sailing techniques on the chalkboard before going out on the sailboats. Once aboard, Ryland created drills and set up courses to teach students how to sail. She adapted the training to the students’ young ages and incorporated a lot of games and swimming to break up the lessons. One week, she filled in for a coworker teaching 5- to 7‑year-olds.
“Each student could sail their own boat by the end of the week,” Ryland said. “It’s really rewarding seeing young kids learning real, concrete skills.”
The students are what made the job so great, Ryland said. It’s a Chesapeake Bay tradition to sail in 100-year-old log canoe sailboats every weekend in the summer in which sailors can use as large of sails as they want. To compensate for the size, sailors stick wooden planks on their boats. It’s very dangerous, she said, as people sit 10 feet outside the boat on the planks, commonly resulting in capsizing. One of her student’s fathers organizes the event.
“He’s a really precious kid, and one day he decided to bring in a miniature plank he made and tried to stick it in his tiny boat,” she said.
Before Ryland could stop him, he attempted to attach the plank to his sailboat, capsizing it in the process. The boat sank to the bottom of the river. Funny incidents like this, she said, kept her laughing the whole summer.
Some students returned each week to hone their sailing ability while some moved on after their week-long crash course. The area around the yacht club, Saint Michaels, Maryland, is a common vacation area. Ryland said many students were staying with their grandparents for the summer while their parents worked in Washington, D.C., or Boston, Maryland. Those are the students who typically enroll for the whole summer and who, she said, make the most progress. The program ran six weeks with two weeks off in the middle of the summer.
Head Coach Madison Iskra said the best sailing coaches aren’t just knowledgeable about the sport but also require strong communication skills to be able to teach children. This, she said, was why Ryland is such a good coach.
“All of the kids loved Maggie,” Iskra said. “She wasn’t just their coach, but also their friend. The kids trusted Maggie, which made lessons and time on the water easier for everyone.”
Ryland got the job after participating in the sailing program for the college her freshman and sophomore years. Sailing team commodore Kaitlyn Rowland said Ryland is among the more advanced sailors on the team and forwarded her an internship opportunity, which piqued her interest.
“I knew it would be really fun,” Ryland said. “Working outside with kids and working on keeping up my own skills — it’s just the best thing to do in the summer.”
She then went on a sailing website to explore the world of sailing instruction. After putting up her resume, Ryland got significant responses due to high demand for young, skilled instructors. Before this job, Ryland had completed five competitive high school seasons and two seasons of racing at Hillsdale.
As is commonly the case with summer internships, Ryland said she used the job as a way to dip her toes in the water of sailing as a potential career. She spent past summers tutoring and nannying for local families since she is also considering teaching. But teaching sailing, specifically, is something new.
“This is a passion and a skill I’ve had for a long time, and teaching rather than racing is just so great,” she said.
Part of her attraction to sailing long-term is the community that comes with it. Ryland spent some of her free time sailing with other staff members and said she is a better sailor for it. The majority of staff were locals who grew up sailing together, but despite being an outsider, she said she felt welcomed.
“Sailing people are just awesome,” she said. “We have a nautical connection.”
The sport, she said, typically attracts adventurous, outside-of-the-box thinkers who are mentally and physically tough. Ryland appreciates how grounded her coworkers and most sailors are and naturally finds her place among them. The feeling of belonging is true for her Hillsdale teammates as well. The camaraderie among the team is great, she said, and when they go to regattas at other schools, she always enjoys the parties they host, proving the fun and free attitude of sailors everywhere.
Rowland said she is confident Ryland’s experience this summer will benefit the team, not only improving her as a sailor but also as a teacher to her teammates. She serves as one of the team captains, requiring her to organize and lead practices. Many other team members are somewhat new to sailing, Rowland said, since the program is new. Coming from someone who has served as a children’s sailing coach for the past eight summers, Rowland said the skills Ryland gained in teaching children will help her teach adults.
“Whatever she taught still applies to adults,” she said. “Even if it’s taught as ‘watch out for the boom because when the boom hits your head it goes boom,’ it will benefit the team.”
Ryland said she is excited to bring her new skills to the team this fall season and looks forward to what the future holds. Even if her career doesn’t involve sailing, she said it was a good summer.
“I got to do what I love and got to teach kids how to do it too,” she said, laughing. “Just imagine the chaos of 8‑year-olds in their own boats.”