It's 1977 and Phoebe O'Connor (JORDANA BREWSTER), a recent high school graduate, lives in San Francisco with her mother, Gail (BLYTHE DANNER). Things are quieter in their home than in the past when Phoebe's father, Gene (PATRICK BERGIN), and older sister, Faith (CAMERON DIAZ), were still alive. It's been nine years since Gene died of leukemia, and six since Faith killed herself while in Portugal.
Feeling disconnected with the rest of the world and still obsessed with her sister and her death, Phoebe decides to follow Faith's path through Europe. Using her many old postcards as guides about her various thoughts and locations, Phoebe travels from Amsterdam to France where she runs into her sister's old boyfriend, Wolf (CHRISTOPHER ECCLESTON). No longer a hippie radical, Wolf is now engaged to a Frenchwoman, Claire (ISABELLE PASCO), and has tried to put his relationship with Faith behind him.
Nevertheless, Phoebe's presence and questions dredge up old memories and feelings. As Wolf eventually joins Phoebe as she continues on her quest, the young woman eventually pieces together the events that led to her sister's suicide and learns a thing or two about herself and life.