Playing around while aboard a cruise ship, the Chipmunks and Chipettes accidentally go overboard and end up marooned in a tropical paradise. They discover their new turf is not as deserted as it seems. For a vacation, Dave and the Chipmunks (Alvin, Simon and Theodore) and Chipettes (Brittany, Jeanette and Eleanor) go on a cruise ship. The Chipmunks and the Chipettes end up creating trouble. Dave notices that his old boss, Ian Hawke is working as the ship's safety monitor dressed as a pelican, and is out to inform the captain if the Chipmunks and Chipettes cause more problems. Alvin goes para-sailing on a kite, but the kite flies away with him and the other Chipmunks. Dave goes on a hang-glider to find them but Ian stops him, and they both end up in the Pacific Ocean.