Dave Seville (Jason Lee), the chipmunks, and the chipettes are on a cruise with Dave for a family vacation. Dave discovers that his old boss, Ian Hawke (David Cross) is working as a pelican on the Cruise. Dave warns Alvin to not have too much fun but Alvin does not listen and him and the other chipmunks get blown away while holding onto a kite and they end up stranded on a deserted island. Dave tries to take a hanglider to find the chipmunks but after Ian tries to stop him and they both end up in the ocean.