A stacked arrangement of travel coolers including a plurality of travel coolers arranged in a series of stacking pairs and a method of stacking the travel coolers. Each travel cooler includes a base with a bottom surface, a pair of wheels mounted to the base, an insulated container, a front end of the base and a rear end of the base. Each stacking pair includes an upper travel cooler disposed on top of a lower travel cooler. The bottom surface of the base of the upper travel cooler rests upon the bottom surface of the base of the lower travel cooler. Alternatively, a surface of a lid of the upper travel cooler rests upon a surface of a lid of the lower travel cooler. The front end of the upper travel cooler is disposed over and generally aligned with the rear end of the lower travel cooler.