A portable speaker system includes: a waterproof enclosure; a wireless communication element enclosed within the waterproof enclosure, the wireless communication element able to receive audio data from a mobile device; a pair of speakers enclosed within the waterproof enclosure that are able to generate an audio output based on the audio data received from the mobile device; and a set of connection ports located within a first recessed area of the waterproof enclosure, the first recessed area including a flexible cover that is able to expose the first recessed area when in an open position and form a waterproof seal with the waterproof enclosure when in a closed position.