A retractable cantilevered watercraft whip mooring system has a retractable canopy which covers the watercraft while moored to a dock. The system includes a pair of whips secured to the dock by a pair of mounts. Each whip includes a tie-down line. Each whip includes a tie-down line. The retractable cantilevered watercraft whip mooring system protects the watercraft from rubbing or bumping against the dock. In addition, a retractable canopy slides over and is secured by the pair of whips. The retractable canopy includes a support baten. The watercraft is secured by the retractable cantilevered watercraft whip mooring system to protect the watercraft from rubbing or bumping against the dock. The canopy slides over the pair of whips. The canopy is securable relative to an exterior side of the watercraft, enabling the watercraft to be protected during severe weather conditions while the watercraft is attached to the dock.