Sailapalooza 2025: New Friends, Lasting Memories, and Fun on Lake Michigan
August 25, 2025
by Maggie Shea and Annie Thompson
During the last week of July, the Chicago Yacht Club Foundation hosted the inaugural Sailapalooza, a four-day sailing camp and evening cruise at the Chicago Yacht Club’s Monroe Station that welcomed more than 150 youth from neighborhoods across the city of Chicago. Participants took part in sailing, swimming, cruising, and fishing, all while making new friends and lasting memories. While most Foundation programs typically draw youth from a single community partner, Sailapalooza was intentionally designed to bring together young adults from various neighborhoods and age groups, creating a uniquely inclusive, citywide experience on the water. At the same time, the Foundation supported concurrent programs along the lakefront, extending opportunities to an additional 40 youth through Columbia Yacht Club’s Sailing School, the Judd Goldman Adaptive Sailing Foundation at Burnham Harbor, and Chicago Yacht Club’s Sailing School at Belmont Harbor.
One of the week’s highlights was the PALS Sailing Experience, an evening cruise for young adults with Down syndrome and their peer partners. More than 150 volunteers and youth set sail, filling Monroe Harbor with energy and joy. An event of this scale was only possible thanks to the generous collaboration of Columbia Sailing School, Sail Chicago, the Chicago Park District, and an army of dedicated volunteers––including boat owners and crew, Competition Fund recipients, CYC members, and facilitators––who came together to ensure every participant felt welcome, supported, and safe.
Sailing camp at CYC Monroe featured five Sonars, ideal for hands-on teamwork with small crews, and the Foundation’s two J/100s. First-time sailors learned the basics of boat handling and water safety. Returning sailors refined their technique, practiced coordinated maneuvers, and even worked on casually racing the other J/100 from point to point. Over the four days, sailors experienced the full spectrum of wind conditions, from glassy calm to a brisk 20 knots. When wind conditions became too strong for the Sonars, CYC members John and Cynthia Nedeau generously lent their boat, Cynthia Lyn, providing a safe and enjoyable afternoon on the water.
One of those sailors, Noah M., reflected on how the experience shifted their perspective: “I had a lot of fun learning to sail and growing more comfortable with uncertainty. I typically hate to be an amateur, but this camp helped me realize that it's okay to be a noob! Plus, sailing was cooler than I thought!”
By Thursday afternoon, the docks were filled with energy and a sense of pride. Sailors came off the water smiling and laughing about the unexpected waves that splashed over the rail as boats ventured outside Monroe Harbor in the strong Northerly wind. None of this would have been possible without the support of our community partners and generous donors, whose commitment makes experiences like Sailapalooza a reality. For the Foundation, the week was a true celebration of fun, growth, leadership, and community––proof that the lake is a place where all youth can find their footing, take the helm, and chart a course forward.