Carefree Boat Club was founded on the principle that adventuring on a boat is always more fun without the chores associated with ownership. Over time, the owners gathered a huge fleet of speedboats, pontoons, and sailboats, launching them into prime boating waters from 27 harbors around the nation. They also assembled a team of maintenance experts to care for the vehicles, removing cleanup and repair responsibilities from club members' agendas. Then, they set their membership rules, keeping a strict ration of ten members to every one vehicle in their fleet to ensure easy boating access.

Today, the company maintains a fledgling branch of their operation out of the 31st Street Harbor in Chicago. Their growing fleet already includes a variety of speed boats ready to zip across the smooth surface of Lake Michigan, such as the Sea Ray 240s, 260s, and 270s. In addition to providing unlimited vessel access for members and rentals for non-members, they also arrange a variety of club events at each location. Members go on annual picnics, gather together on holidays, and host seminars for boating-related subjects such as safety, navigation, and how to trick everybody into calling you admiral.