Rich Peelman gives his wife Linda (Keener) the gift of a lifetime for her birthday: a trip through the Caribbean on a sailboat with all six of their kids and their partners. Stubborn, competitive and overly confident in his sailing abilities that are clearly out of sync with reality, Rich is determined that the vacation be run on his terms. But things do not go according to plan.

His "father knows best" attitude clashes with the rest of the Peelman clan. And by the end, even the most patient of the bunch are ready to throw Captain Dad overboard, bringing new meaning to the idea of the dysfunctional family.