In Southport, Maryland, Susan Morrison (Teri Polo), recently divorced from her husband Frank (John Travolta) who is a struggling ship builder, is getting married to a younger and wealthier Rick Barnes (Vince Vaughn). Danny (Matt O'Leary), Susan and Frank's twelve-year-old son, is clearly unhappy that his mother is remarrying. Susan asks Frank to allow Rick to go sailing with him and Danny, to help Danny bond with and accept Rick as a stepfather.