A multi-compartment modular cooler comprising multiple fully enclosed environments, including an insulated cold storage environment, a dry storage environment and an adjustable storage environment that may be either heated or cold storage. The fully enclosed environments may separate into self-contained individual containers. Each of the separate, self-contained enclosures may also recombine into a single unit, simplifying transportation of each section. Connection and disconnection of each section of the cooler may be facilitated by interfacing a plurality of pillars extending from a bottom surface of the upper section into one or more cup holder wells molded into the lid enclosing a lid of the lower section. The depth of the cup holder wells and the length of each pillar being inserted into the cup holder wells may provide significant stability for maintaining the upper section of the multi-compartment cooler in position while connected to the upper section.