Frank O'Brien (played by Denis Leary) is a small-time thief who has been with his girlfriend Roz (played by Sandra Bullock) for seven years. They both want to retire from their life of crime, but need one last score to do it. The opportunity arises when Frank learns about a valuable painting that is being exhibited in a nearby town.
Without telling Roz about his plans, Frank steals the painting and takes her to a remote island off the coast of New England, hoping to sell it there. However, things don't go as smoothly as Frank had hoped. The locals on the island are suspicious of the couple, and the painting turns out to be more trouble than it is worth.
As Frank and Roz try to figure out what to do with the painting, their relationship starts to unravel. Roz becomes increasingly frustrated with Frank's lack of direction, and a handsome local named Evan (played by Yaphet Kotto) starts to catch her eye.
The situation comes to a head when Frank's criminal past catches up with him, and he is forced to confront his mistakes. In the end, he learns an important lesson about honesty and trust, and Roz discovers what she really wants out of life.
Two If by Sea was released in 1996 and was directed by Bill Bennett. Despite featuring two popular actors in the lead roles, the movie received mixed reviews from critics and was not a box office success. However, it has since gained a cult following among fans of romantic comedies and caper movies.