For a vacation, Dave, the Chipmunks (Alvin, Simon and Theodore) and Chipettes (Brittany, Jeanette and Eleanor) go on a cruise ship heading for the International Music Awards. The Chipmunks and the Chipettes end up creating trouble, ending up with Dave grounding them to their room, only for them to escape to the casinos. 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 try to find them but Ian stops him and they both end up in the Pacific Ocean.
Meanwhile, the Chipmunks find an island and they sleep for the night. Dave enlists Ian’s help to find the same island and begin looking for the Chipmunks. The next morning, the Chipmunks go and find food and while doing so, an island castaway named Zoe shows up and sees the Chipmunks and Chipettes for the first time. They then go to Zoe’s tree house where Eleanor sprains her ankle and Simon gets bitten by a spider, the side effects including personality changes and loss of inhibition.
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