RedactedNarrative: Vessel 1 was operated by an operator who was brand new to boating. Operator 1 backed Vessel 1 and trailer without the drain plug in. Operator 1 drove Vessel 1 100 yards to a courtesy dock to load passengers. The engine of vessel 1 cut off and wouldn't start. Operator 1 then noticed that Vessel 1 had been taking on water. Two nearby PWC operators assisted in getting Vessel 1 and all occupants back to the west boat ramp. Vessel 1 took on water to the top of the open operation compartment. The propeller of Vessel 1 was also lost and damage occurred to the front starboard side trim at some point during this situation.