Abstract: A launching assembly designed to be used in combination with a rider support connected to a parachute and a tow line which is movably secured so as to connect the rider support to a towing boat which is typical of para-sailing activity. A line guide assembly includes a winch mounted on the towing boat and movably connected to the tow line and adapted to extend and retract the tow line as well as the rider support attached thereto wherein the line guide assembly includes a guide means mounted in spaced relation to the winch and adapted to movably engage and guide the towing line along a path of travel of the towing line extending between the winch and the rider support regardless if the rider support is in the launched or retracted position.