Abstract: A self-stabilizing floating cooler. The cooler includes a pair of upstanding, opposed end panels and elongated side panels extending therebetween to form a contiguous wall. A lid and a bottom panel are provided, and a floor panel is disposed between the lid and the bottom panel to define upper and lower compartments. The upper compartment is thermally insulated, and float members are detachably affixed to the side panels adjacent the floor panel exteriorly thereof. Perforations are provided in the lower compartment for filling the lower compartment with water to buoyantly stabilize the cooler in an upright position when the cooler is placed on water. Perforations also permit draining the water from the lower compartment when the cooler is removed from water.