A canalphone system may include a high audio driver carried by a canalphone housing, and a low audio driver carried by the canalphone housing adjacent to the high audio driver. The system may also include an amplifier that amplifies an audio signal and delivers that amplified audio signal to the high audio driver and/or the low audio driver. The system may further include a passive audio crossover carried by the canalphone housing, the passive audio crossover receives the amplified audio signal from the amplifier and then delivers the amplified audio signal in a suitable frequency range to the high audio driver and/or the low audio driver.