A system for one person raising and lowering the mast of a sailboat wherein the mast is less than about forty feet in length and in the down position the mast is laid horizontally along a median line of the hull of a sailboat. The system includes rigging to raise the height of the mast from the hull and then to pivot the mast with the pivot being near the lowest point of the mast. Means is provided to pivot the mast about the lowest point of the mast until the mast is in a vertical position. The mast is then brought down into an upstanding vertical position with means to support the mast on the sailboat at the mast's lowest point and upwardly therefrom. The same rigging may be used to lower the mast to the horizontal. The operations occur by a winch located towards the rear of the sailboat to either pay out a line thereon when lowering the mast to the horizontal or conversely to take up the line when the mast is pivoted to the vertical.