Alvin develops an alter ego after Brittany rejects his invitation to the Valentine Ball. In a dream state, he becomes a dashing Don Juan, the Valentine heartbreaker extraordinaire, Captain Chipmunk. Brittany is quickly won over and eagerly accepts his offer to the dance. Alvin wakes up at the dance and realizes he's not the dashing, debonair Captain Chipmunk anymore.

A compilation of some of Alvin's most hilarious hijinks, as he goes to Hawaii, boot camp, skiing, and much more.

When Dave embarks on a business trip to Europe, Simon, Theodore and Alvin are left at home in the care of the accident-prone Miss Miller. But soon Alvin and the boys become jet-setters of their own as they participate in an around-the-world hot-air balloon race! Their main competition will be the Chipettes, but their real opponents turn out to be Klaus and Claudia, two international crooks who are using the race as a front for their worldwide diamond...