A portable cooler includes a first semicylindrical member defining a first aperture in a first side and a second aperture in a second side thereof. A second semicylindrical member is hingedly coupled with the first semicylindrical member. A cradle is removably positioned in the first semicylindrical member. The cradle can rotate with respect to the first semicylindrical member within the space defined by the first semicylindrical member. First and second wheels are rotatably coupled with the first semicylindrical member. First and second axles extend through the wheels and first semicylindrical member and into the cradle. The axles allow independent rotation of the cradle, the first semicylindrical member and the wheels to maintain a substantially horizontal rotational orientation of the cradle with respect to the first semicylindrical member.