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Yachtapalooza 2026 Returns to Crowley’s Yacht Yard ⚓

Visitors walking at Yachtapalooza gathering
03/18/2026 | Boat Safe Chicago | , , ,

Chicago’s boating community is ready to shake off the winter chill as Crowley’s Yacht Yard prepares to host the highly anticipated Yachtapalooza 2026. Taking place on Saturday, March 21, from 8:00 AM to 4:00 PM, this event has become the unofficial kickoff for the Great Lakes boating season, blending education, safety, and a whole lot of nautical fun.

A Growing Tradition: Boat Safe Chicago’s 3rd Year

Boat Safe Chicago returns for their third consecutive year at the event. For those looking to elevate their time on the water, the Boat Safe Chicago booth is a must-visit. Their team will be on hand to discuss a wide array of professional services, including:

  • On-Water Boat Training: Perfect for new owners or those looking to sharpen their skills. Let’s schedule a boat training class!
  • Charters & Captaining Services: Ensuring your next outing is stress-free and professional. Book with Chicago’s best captains!
  • Vessel Relocation & Surveys: Essential services for the logistical side of boat ownership

Insights from the Experts: The Seminar Line-up

One of the core draws of Yachtapalooza is the high-caliber seminar schedule. This year, local legend Geoffrey Baer will dive into “The Harrowing History of Chicago’s Lakefront” at 11:00 AM, while Captain Lisa D. Dixon takes the stage to tackle the practicalities of modern boating.

Captain Lisa photo courtesy of Dixon Enterprises Master captain lisa women captain woman captain boat safe chicago crowley's yachtapalooza
Captain Lisa photo courtesy of Dixon Enterprises

“I’m looking forward to speaking at Yachtapalooza this year,” says Captain Dixon. “My presentation will cover safe navigation in Chicago, an overview of key U.S. Coast Guard regulations and Chicago ordinances, and I’ll share a few sea stories along the way to bring those topics to life.” 

Other notable sessions include David King from the National Weather Service on marine preparedness and  Madeline Crispell on the history of Great Lakes sailing.

Gear, Goods, and Great Food

Crowley’s owner, Grant Crowley, promises an event that caters to every type of mariner. 

“We’re excited for another incredible Yachtapalooza,” Crowley says. “The event will feature great food from the Tamale Spaceship, live music from the Chicken Dolphin Band, and our popular Nautical Donations Flea Market.”

For the gear-heads, this year marks a significant milestone in the industry. The event features the Boater’s Closet pop-up store, which will host the official reintroduction of Henri-Lloyd foul-weather gear to the U.S. market. Between the Ship Store sales and the vendor area, there is no better time to outfit your vessel for the 2026 season.

Plan Your Saturday

Whether you’re hunting for a rare find at the flea market or looking to learn the “Ins and Outs of Rebedding Deck Hardware,” Yachtapalooza 2026 is designed to be a “fantastic celebration of Chicago’s boating community.”