The film follows the story of Frank O’Brien (played by Dennis Leary) and Roz (played by Sandra Bullock), a young couple who are petty thieves living in Boston. Frank is a brash and impulsive thief, while Roz is his loyal girlfriend who dreams of a more stable life.
After pulling off a small heist, Frank and Roz decide to lay low in a beachfront cottage on Cape Cod that belongs to a wealthy family away on vacation. They plan to wait there until they can sell the stolen artwork from their heist and escape to a new life together.
However, their plans are complicated when Frank’s ex-partner, Evan Marsh (played by Yaphet Kotto), tracks them down and demands a share of the stolen artwork. To make matters worse, a local police officer, O’Malley (played by Mike Starr), becomes suspicious of Frank and Roz’s presence in the area.
As tensions rise and misunderstandings ensue, Frank and Roz find themselves in increasingly absurd and comedic situations. Despite their differences, they must work together to outsmart Evan and O’Malley and salvage their relationship.
In the climax of the film, Frank and Roz must confront their own insecurities and uncertainties about their future together. With the help of their friends and a newfound sense of determination, they come up with a risky plan to turn the tables on Evan and O’Malley and reclaim their stolen artwork.
“Two If by Sea” is praised for its charming performances by Dennis Leary and Sandra Bullock, who exhibit great chemistry on screen. The film blends elements of romance, comedy, and crime caper, offering a light-hearted and entertaining story about love, trust, and second chances. While it received mixed reviews from critics upon its release, “Two If by Sea” has since gained a small but devoted fan base for its quirky humor and endearing characters.