A docking station for a portable electronic device comprises a device receiving recess including a device receiving bottom surface and at least one device guiding structure sized to slidingly receive therein a device to be docked in the docking station and to guide the device toward, and maintain the device in, a desired position within the device receiving recess in which an electrical connector of the device mates with an electrical connector of the docking station and a well formed in the bottom surface of the device receiving recess, the well extending downward from the electrical connector of the docking station to a drainage opening formed at a lower-most point of the well in combination with a first lumen extending from the drainage opening to an outlet at an exterior of the docking station.