In advance: Make candies. Tint portions of melted white candy blue and red using candy colors. Mold sailboats using piping method. Chill until firm.
Bake and cool cupcakes; ice smooth. Attach disk candy faces to sailboats with icing. Pipe tip 1 dot eyes and outline mouth, tip 2 dot bandana (smooth with finger dipped in cornstarch) and pull-out ties. Add tip 1 dot trim. Position sailboats on cupcakes, support with icing in back if needed. Insert pick.