High School sailing closely parallels the collegiate sailing format. For fleet racing, teams are divided into A and B divisions comprising of different skippers and crews for each division. A team may substitute sailors as long as prescribe substitution rules are followed. Courses tend to be relatively short emphasizing starts and tactics. Teams also participate in Team Racing events where each team fields three boats to sail against three boats from another team. In team racing teammates work together to outmaneuver the other team so that their combined race scores are better than the other team’s combined scores.
Charleston sailing teams are part of the South-Atlantic Scholastic Sailing Association (SAISA) District. Teams participate in a number of regattas throughout the seasons which run from September to November and March to May. The end of each season culminates in a District Championship and in the spring, for those teams that qualify, the National Fleet Racing Championship (Mallory Cup) and National Team Racing Championship (Baker Cup).
Teams attend local events and travel to venues requiring overnight stays several times a season. Organization of all local and overnight trips is the responsibility of team captains and parents.
The following schools train at CCS: Academic Magnet, Ashley Hall, Bishop England, Charleston Collegiate, First Baptist, James Island Charter School, Porter-Gaud, School of the Arts, Wando, Charleston Day School, Mason Prep and The Citadel.