This is Sydney Pollack's first feature since his Academy Award-winning Out of Africa in 1985 and his seventh film with Robert Redford. This time the versatile actor plays Jack Weil, a middle-aged gambler going to Havana for one last big score at the high stakes poker table. On the boat, he meets and is mesmerized by Bobby Duran (Lena Olin), an exotic and alluring beauty. When she pays him to drive her car off the ferry, he discovers she is smuggling radios into Cuba. It turns out that she is married to Arturo (Raul Julia), an aristocratic left-winger who supports the revolutionaries under Castro fighting to bring down the Batista regime.
In Havana, Jack tries to arrange his card game through Joe Volpi (Alan Arkin), a world-weary casino owner. While Jack makes the most of the city's decadent pleasures with two American women, Arturo is apparently murdered, and Bobby is tortured by government police. Jack is not convinced that Castro's revolution will bring justice to Cuba, but he soon believes in this idealistic woman. In a shimmering moment of love, this self-centered gambler and confessed hedonist changes the course and direction of his life, and he can never go back again.
Robert Redford's performance captures the vulnerability in Jack's cool, controlling nature and his willingness to risk all for Bobby's love. Havana is an old-fashioned and bittersweet tale of romance about the most exhilarating and excruciating of human passions.