Protagonist of the film is Frank O'Brien (played by Denis Leary), small-time burglar whose girlfriend girlfriend Roz (played by Sandra Bullock) got tired of his criminal lifestyle and wants to settle down. In order to please her, Frank makes one last job that would solve couple's financial needs and steals valuable Matisse painting. In order to evade pursuing police and Frank's greedy partners, they take refuge in the small island community off the coast of New England. There they find vacant summer house, break in and later try to pass as its owners to the neighbours. One of the neighbours is refined and wealthy Evan Marsh (played by Stephen Dillane) who begins to charm Roz with his sophistication and opulent lifestyle. Confronted with alternatives to Frank, Roz begins to weigh her options, while FBI, led by Agent O'Malley (played by Yaphet Kotto) and Frank's former associate Wayne Callahan (played by Beano Robson) close in.

Sandra Bullock, mid-1990s queen of romantic comedies, and Denis Leary, comedian who built his charisma on the archetype chain- smoking foul-mouthed angry young man, don't mix well. But this is not the worst problem with TWO IF BY SEA. Characters played by those two actors are simply too dislikeable for the audience, mostly due to their utter stupidity - trait that they share with any other character in this sorry affair. If Leary and two of his co-writers thought that the audience would equate stupidity with hilarity, they were dead wrong. The movie is at times almost painfully unfunny. The only good thing about TWO IF BY SEA are Nova Scotia locations, but there are other, less painful ways to get familiar with them than to sit through 96 minutes of this disaster.