In order to become a Sail Chicago skipper, a member must take the four-session Advanced/Skipper-Prep course. Successful completion of the course and course tests will qualify you as a Sail Chicago skipper and enable you to take out Sail Chicago boats as well as makes you eligible to obtain U.S. Sailing Basic Keelboat certification. NOTE: Private boat use is granted based on an instructor's evaluation of your skills. For 12 months following your skipper certification, you will be required to sail with another Sail Chicago skipper on board.