A self-leveling boat bumper system attached to a nautical structure can include a floating bumper arrangement having a float element, a float extension, and a boat bumper; and a receiver, fixed to the nautical structure and moveably engaged with the arrangement, or fixed to the arrangement and moveably engaged with a guide fixed to the nautical structure. When floating within a body of water, the float element can provide a buoyancy force that maintains the boat bumper in a static position between, and including, first and second positions, and as the level of the water changes.