Anna (Amy Adams) has to reach Dublin, Ireland to propose to her boyfriend Jeremy (Adam Scott) on February 29, Leap Day, as according to Irish custom, a woman can propose to a man on February 29. But on the way a gale ocurrs and the plane is redirected to Cardiff, Wales. Anna hires a boat to take her but due to heavy storm she has to stop her journey at Dingle Peninsula. There she solicits the help of an Irish innkeeper, Declan (Matthew Goode), to take her to Dublin so that she can be there to propose at the right time. After some persuasion, Declan accepts her request. But during the engagement party, Anna finds the behavior of Jeremy disappointing. Hence she has to take some important decisions about her marriage.