Dave takes the family on a trip to visit his parents in Florida because it won't cost him anything. However, Mike hates to fly, Vicky hates his parents and Hillary wants to stay in town so a boy won't forget her. The only one excited about going is Larry, who has started on a weight-loss program so he will look good in his Speedo. Things go from bad to worse when their ride to the airport cancels, Hillary's new nipple ring is discovered by security in front of a furious Vicky and Dave is searched by security. At the condo, Dave is continuously belittled by his dad, similar to the way he treats his own son Larry, and he wants to turn around and fly home minutes after arriving.

When Dave takes Hillary out for driving lessons and she gets pulled over for reckless driving, Dave takes the blame, thinking that Hillary will be forever grateful. When this fatherly act leads to a DUI arrest for Dave and Hillary isn't appreciative, Dave goes to court to straighten things out. Meanwhile, Vicky forgets to register Larry for Shakespeare camp, and Dave and Mike take up online poker.