The present invention provides an improved self draining boat plug which does not need to be repetitively removed and reinserted into a boat. The boat plug is specifically designed to allow water to escape from the boat while the boat is at cruising speed or removed from the water. Additionally, the drain plug blocks water from entering the boat while the boat is in the water. The drain plug is designed for durability, and continued performance when exposed to the hazards typically encountered in its working environment.