The Culver sailing team is one of the best supported and equipped high school sailing programs in the country. The program supports advanced racers as well as novice sailors who are beginning to sail in high school. Qualifying students can earn U.S. Sailing Certifications. The Culver racing and novice squads are entirely co-ed, with girls and boys having an opportunity to learn and compete on an equal basis. The Team has competed in the Midwest Interscholastic Sailing Association in and around the Great Lakes as well as national regattas in New Orleans and the U.S. Coast Guard Academy.

Its state-of-the-art facility includes the recently renovated Naval Building (with a ventilated sail locker, staff offices, and class and conference rooms), winter storage barns, and over a mile of frontage on beautiful Lake Maxinkuckee. Culver's total sailing fleet includes a newly replaced fleet of over 18 Vanguard 420s, over twenty Vanguard Lasers, Sunfish, Interlakes, Lightnings, MC Scows, E scows, Capri 21 keel boats, Boston Whaler safety boats, and two pontoon committee/observation boats. The program is supported by a U.S. Sailing trained coaching staff and a professional boat crew. The fleet’s flagship is the R. H. Ledbetter, a fifty-six foot, three-mast, square-rigger that is the only boat of its kind on an American inland lake. Students from both the Naval School and the Academies have an opportunity to climb the Ledbetter's masts in harnesses, unfurl and set the fourteen sails, and steer the helm of this boat whose design has stood the test of time. Culver’s sailing program offers extraordinary opportunities for learning, competition, and fun on the water.