We offer bowriders, cabin cruisers, tritoons, pontoons, fishing boats and sailboats that range from 22-31 feet. You’ll have opportunities to take your son or daughter out fishing, your coworkers out on a tritoon, your family out tubing on a bowrider, or your significant other out on a sunset cruise on one of the premium cabin cruisers! Our members love having options and never get bored because they are able to use a variety of boats, rather than taking the same boat out every time.

Carefree Boat Club Chicagoland & Wisconsin works closely with boat manufacturers year-round to buy and sell boats. This allows our members to always enjoy the latest and greatest models, including hard-to-find special order boats loaded with options not normally found in boat clubs - bow thrusters, cabin heaters, windlass anchors, upgraded performance packages, high hp engines, plush seating, and much more designed to provide more comfort and safety while allowing you to have more fun on the water! We're constantly upgrading our fleet with new boats throughout the year, so check out our fleet page often to see the latest additions.