RedactedNarrative: Vessel 1 was eastbound under sail just west of Fairport Harbor in 20 mph west winds and six foot high seas.  The Operator reported that the main sail rigging tangled and the Operator was unable to start the motor due to either fuel pump fare or lack of fuel.  Vessel 1 then began taking on water and drifted into the breakwall.  The local USCG responded but was unable to secure a tow onto Vessel 1.  The Operator, who was on board alone, was able to climb the mast and jump off onto the breakwall without injury.  The USCG vessel then approached again at which time the mast of Vessel 1 broke off over the USCG boat.  Vessel 1 then drifted north along the breakwall and drifted across the main entrance to the harbor until it came to rest on the east wall and sank.  Vessel 1 suffered extensive hull and rigging damage, took on water, and sank.