A jump enhancement system is provided for use while riding upon a water or snow planing apparatus towed behind a boat or snowmobile. The system includes an aerodynamic lift generator, such as a parachute, coupled to the user. Most preferably, a flotation or padded/insulated vest is provided which includes leg harnesses and which can be worn by the user with a cord collector coupled to the flotation vest and securing a cord to the flotation or padded/insulated vest which also extends to the parachute. The cord collector is biased to cause the cord to be collected adjacent the user when no drag forces are exerted upon the parachute. When any such drag forces are experienced, the cord is deployed out of the cord collector so that the parachute is deployed. The parachute is thus in position to enhance a height and duration of jumps off of the surface.