Anchored in Tradition

From weekend pleasure cruises to iconic regattas, sailing is an iconic summer activity in Chicago and the Great Lakes.

Published: Thursday, May 28, 2026 9:00 am

To quote the Encyclopedia of Chicago, “before there were airports, expressways, and railroads, Chicago was a water city.” Sailing is as much a part of this city’s identity as its skyscrapers, including its world-renowned Race to Mackinac and numerous sold-out sailing and boating events. Now acting as part of the esteemed collection of Chicago boat shows, the Windy City Boat and Yacht Show offers something for every level of interest in sailing, from those getting on the water for the very first time to boat owners looking for new tips and tricks, to regular sailors interested in Chicago’s storied yacht club traditions.

“The masts of sailboats line the shore all along DuSable Lake Shore Drive,” says Larry Berryman, Show Director for Informa’s Windy City Boat & Yacht Show. “As we bring our premiere in-water boat show experience to Chicago this June, we knew the programming had to celebrate this Great Lake sailing tradition and provide opportunities to get new sailors on the water.”

“Sailing is an incredible way to experience the water whether on a calming excursion or a social cruise,” says Adam Cove, President of Sail America. “We are thrilled to partner with Informa at the Windy City Boat & Yacht Show to grow the love of sailing and bring people out onto the Lake Michigan waters.”

Attendees of this year’s show, starting June 12th and going until June 14th, have ample opportunities to see some of the best sailboat models and aligned products, experience them first-hand on the Great Lakes, and learn more about sailing from both experts and other boaters across these experiences.

Start Sailing Now: On-the-Water Lessons

Sailing lessons are the perfect way to try something new, build confidence, and see the city from a completely different perspective. The Windy City Boat & Yacht Show offers a new way to step aboard and experience sailing from a whole new POV, all three days of the boat show. In partnership with Sail America and SailTime, Start Sailing Now is a great opportunity for showgoers to get out on the water and discover what sailing is all about. Lessons start with a relaxed, 60-minute introduction on land in a classroom setting, teaching the basics before participants step aboard. Then, a certified captain will guide the small group out onto the water for a 90-minute hands-on sailing experience against the backdrop of downtown Chicago.

With no more than six participants per boat, every session is personal and designed to get you involved — from learning the ropes to taking the helm. No experience is needed. If you’ve always wanted to try sailing, this is your moment to get out there and experience it. Due to limited spots, we recommend registering before the show, visit at windycitybys.com/experience/on-water-sail-training/.

Cruiser Classroom to Enhance Your Boating Knowledge

Every level of boater/sailor will be at this show, and to help encourage the love and sailing, it helps to educate early and thoroughly. Presented by the Annapolis School of Seamanship, Cruisers Classroom features a series of engaging discussions and panels designed to help visitors become more confident, capable sailors and boaters. Whether you’re new to boating or looking to sharpen your skills, there’s something here for everyone.

Sessions cover essential topics for every stage of the boating journey, including navigation, docking, maintenance & safety, buying a boat, getting a license, and the cruising lifestyle. Each class session is followed by a deep dive into the safety equipment, training, and decision-making used by race crew — fascinating to all whether you’re a newbie or seasoned sailor who want to learn more about this legendary Chicago boating tradition.

Much of the show’s deep dives on sailing are focused around popular and regional interests. For example, on Saturday, June 13, the “Lessons from Mackinac Race” panel discussion shares an overview of the famous 300-mile race and offshore conditions. Widely recognized as one of the most prestigious yacht races in the world, the Mac Race is considered a bucket-list event for sailors across the United States and beyond, according to the Chicago Yacht Club, attracting global participants from Europe, Hong Kong, New Zealand, and beyond. This race, one which holds such a storied legacy that has evolved over time to now hold world records and reward inclusivity, is an iconic representation of what sailing can is and can continue to be.

Also, in response to popular interest, each day of the show will offer a “Docking De-Stressed” seminar, led by Captain John Martino of the Annapolis School of Seamanship, where boaters can learn the ropes, tricks, and techniques to make docking easy. Sessions will take place throughout all three days of the show and are included with show admission for all attendees. The full schedule at is available at windycitybys.com/experience/cruisers-classroom/.

Yacht Club Lounge

The Great Lakes is greatly connected by a passionate community of boaters, a community that has built itself up from meager beginnings. Many yacht clubs began in more humble iterations, from a 40-slip marina/restaurant/store location of the Bayshore Yacht Club in the 1950s to the floating barge clubhouse of Lakeside Yacht Club in the 1930s. With TLC, generous donations and hard work of its members and surrounding communities, yacht clubs have evolved into much more.

Inspired by Chicago’s prestigious yacht club tradition, the Windy City Show’s is hosting a Yacht Club Lounge, offering an elevated waterfront experience in a comfortable lounge atmosphere. Yacht club members and boating/sailing enthusiasts can meet representatives and learn more about our anchor clubs: Chicago Yacht Club, Columbia Yacht Club, Burnham Park Yacht Club and Chicago Harbors, all located on Chicago’s Lake Michigan coastline. Here visitors can learn about club programs, Chicago Harbors, show partners, and other membership benefits in an inviting, refined setting designed for connection and conversation.

Sailboat and Sailing Accessories Exhibitors

Among the stunning lineup of in-water boats, the Show will feature a wide variety of exhibitors, dealers, and manufacturers showcasing powerboats and sailboats, both new and brokerage, ranging from 20 to 75 feet, alongside the latest marine equipment, services, and lifestyle accessories.

Attendees can explore and board premium brands including Sunseeker, Boston Whaler, Chris-Craft, Sea Ray, Axopar, Regal, Riviera, Prestige, Cobalt, and Jeanneau from Great Lakes dealers including Jefferson Beach Yacht Sales, SkipperBud’s, Bay Marine, Gage Marine, Manitowoc Marina, and Spring Brook Marine. The show will feature everything from luxury yachts and center consoles to pontoons, sailing vessels, ski and wake boats, paddleboards, marine electronics, boating apparel, nautical décor, and more. This show has something for every boating enthusiast to enjoy and start their summer of boating at the Windy City Boat & Yacht Show.