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Catalina Fleet 21

Catalina Owners Association, Chicago Region

Welcome to Catalina Fleet 21

Why you should join today!

We’re an association of Catalina sailboat owners in the Greater Chicagoland region. We’re one of America’s most active Catalina fleets, and celebrated our 50-year anniversary in 2023. Members have boats of all sizes, from 22 to 42 feet.

You’ll enjoy social and online opportunities to meet with other Catalina skippers who own boats just like yours. We share ideas, experiences, discuss problems and solutions, and our individual modifications. You’ll learn things about your Catalina you never expected, and maybe teach others a thing or two.

Great programs and sailing outings

Our fleet regularly has interesting sailing-related programs on topics relevant to the whole sailing community. Recent programs include DIY boat maintenance, cruising tips, marine weather, ecological lectures and much more. Programs are offered remotely via Zoom, and we also have in-person gatherings.

The summer calendar includes outings to many of our members’ harbors. Some of our most popular have been a season-opening Margarita party, shrimp boils, Kenosha overnight, and sail-in and Ribfest in Michigan City. Longer cruises along the Michigan or Wisconsin shores are often on the calendar. And even when the boats are on the hard, the activities and programs don’t stop.

We sail from all harbors

We’re primarily a cruising fleet, with members from all around southern Lake Michigan: Belmont, Burnham, DuSable, Hammond, Kenosha, Michigan City, Monroe, Montrose, North Point, Racine, Waukegan, St. Joseph and Wilmette.

The absolute best sailing club around

Come join us for sailing and making lifelong friends. For more information, please visit the Membership page

Also check us out on Facebook Groups.  Click link at top of page.

Upcoming Events

  • Apr 15, 2025, 12:00 AM – 11:59 PM
    North America
    The deadline to be included in the 2025 Fleet 21 directory is April 15. The registration form is available under the Membership tab.
  • Sat, Apr 26
    Apr 26, 2025, 5:30 PM – 9:00 PM
    Chicago, 601 W Montrose Ave, Chicago, IL 60613, USA
    Join Fleet members Saturday, April 26 at Corinthian Yacht Club for drinks, a delicious Mediterranean buffet and a presentation by renowned Chicago photographer Barry Butler. He’ll show and discuss his amazing photography. Price: $35
  • Sun, Jul 06
    Lake Michigan, United States
    Jul 06, 2025, 8:00 AM – Jul 12, 2025, 12:00 PM
    Lake Michigan, United States
    South Haven, Saugatuck, Grand Haven, Holland, St. Joseph. Join us for all or part of it. Contact the Commodore for more info.
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