Monroe Community Sailing: Doubling Capacity, Doubling Opportunity
May 30, 2025
by Diane Foote
2025 welcomes the new J/100 sailboat Charlotte Ann, joining her sister vessel Whaat’s Up in Monroe Harbor and doubling the CYC Foundation’s ability to introduce sailing to Chicagoland youth. Whaat’s Up, generously donated in 2024 by Paul and Susan Herer, was the Foundation’s inaugural boat. This donation enabled the start of the Foundation’s Monroe Community Sailing Program, helmed by Program Manager Caroline O’Malley. The Chicago Yacht Club generously enabled the Foundation to use one of its 23-foot Sonar sailboats to complement Whaat’s Up, but it has been a longtime goal of the Foundation to build out its own fleet. Read an article in UK Sailmakers' newsletter about the Herers and their donation here.
The CYC Foundation purchased Charlotte Ann through a generous gift from Captain Dave’s Foundation, whose president, Robert Bied, is also a CYC Foundation board member. She is named after Captain Dave Truitt’s own schooner of the same name, at the time the largest sailboat on Lake Michigan. Captain Dave passed away in 2024, but his legacy lives on in this program and in numerous organizations that have benefited from his tireless and generous support, and continue to benefit through the foundation that bears his name. Read the Foundation’s Donor Spotlight on Captain Dave here.
This year, the Foundation is using these two J/100s to launch the City Sailing League, in addition to continuing week-long sailing camps throughout the summer. The City Sailing League is an after-school keelboat program for high schoolers to build skills, teamwork, and comfort on sailboats on Lake Michigan. Its programming has already begun, even through the unseasonably cold month of May.
Teen participants in these early early stages of the 2025 boating season have already caught the boating bug, several claiming their favorite part is helming. “Driving the boat, for me, was my favorite part,” said Rashad, a student from Curie Metro High School. When asked how he was so naturally drawn to driving, he replied, “Just being confident and having fun. It’s the best life!” Linyla and Amyra from DRW College Prep–A Noble School, concurred, Linya saying “My favorite part was when I got to sail the boat,” and Amyra following with “My favorite part of the day was probably steering. It was awesome!” Linya also observed how refreshing the lake can be, something longtime boaters may take for granted: “I loved touching the water. It was so cold!” Students from these two schools, as well as Excel Academies of Englewood and Roseland, are participating in the program via the community organization My Block, My Hood, My City, with which the Foundation regularly partners. Teens from the Instituto Justice and Leadership Academy join the City Sailing League in June.
“In the early stages of this program, the kids have absolutely loved their time on the water," says Caroline. “Many of the high schoolers have requested to come back during My Block, My Hood, My City’s summer camp week! We see this program growing into a three-day-a-week event for the kids through the fall and spring. We are planning on layering in tutoring, mentorship services, and maritime career experiences for the participants to have a more wrap-around approach. We are so excited to be partnering with My Block, My Hood, My City to make City Sailing League happen!”
The Chicago Yacht Club Foundation’s portfolio of year-round programs is structured around four progressive stages. Introduction-level programs provide safe, fun, and educational first-time experiences. Induction-level programs include tuition-free sailing camps that build comfort and familiarity on the water. Development-level programs focus on more intensive skill-building programs and financial support enabling sailors to attend the program of their choice. Finally, Inspiration-level programs support post-secondary education and sail racing at the highest levels, in order to reduce financial barriers to long-term success.
Week-long summer sailing camps at the Monroe Community Sailing Program are in the Induction category, with the spring and fall City Sailing League at the Development level. Regardless of which level Chicago-area youth come to the Foundation, there is something for everyone.