Charlie St. Cloud is a sailor who wins a boating race on his sailboat, the ''Splendid Splinter'', along with his younger brother Sam. In 2005, he receives a sailing scholarship to Stanford University. Charlie graduates from Winslow, Washington and after returning from his graduation ceremony, Charlie promises Sam that they will practice baseball every day until he leaves for Stanford. That night Charlie is supposed to go to a graduation party with his friends, but his mother makes him babysit Sam while she picks up another shift at her job.