To Serve and Protect / Kickin' It Old School.To Serve and Protect: Simon becomes the school's safety supervisor and also gets to pick the location for the next family vacation: he chooses the Smithsonian. Alvin, desperate to escape the trip, starts misbehaving at school, hoping that Simon will either give him a citation or let him choose the vacation location, as Dave threatens to cancel the trip if one of them gets into trouble. Unable to make a choice, Simon resigns from his position, which leads to Alvin feeling guilty and talking to both the principal and Dave to fix everything. In the end, Alvin is grounded and does not get to go on the trip while Simon gets his position back, goes to the Smithsonian and has his teacher Miss Smith babysit him while his family is on vacation.
Kickin' It Old School: Willing to teach the Chipmunks how to live without technology, Dave takes them on a camping trip, only to discover that the once-thriving vacation spot is now in utter decay. After initial difficult moments, they actually start enjoying both their solitude and nature, and once back home, although quickly regaining their old habits, the Chipmunks now like to camp in the garden with only their sleeping bags and their imagination.