A cockpit covering system for a small boat comprises a tent or cover comprising a plurality of wall portions and a base, and wherein the tent is sized to extend over a recessed area of a cockpit and to enclose an interior that extends from above deck height to below the height of a base layer. A compressible gasket is below the base for resting on a deck of the small boat around the cockpit outer perimeter. A plurality of webbing straps extend from the outer perimeter of the boat to the tent. A plurality of webbing straps extend from the cockpit outer perimeter to the tent covering system. Tension applied to the plurality of webbing straps compresses the compressible gasket to form a seal along a cockpit recessed area. Pole housings can be provided on webbing straps or on the tent base to secure tent poles at deck level.