Anna Brady from Boston is a planner that stages apartments for Realtors. Anna has been dating cardiologist, Jeremy, for four years and they are buying a high standard apartment in Davenport together. Anna expects Jeremy to propose to her on a dinner date but he gives her a gift instead, after which he travels to Dublin for a congress. Anna decides to meet him in Dublin on the February 29th and propose to him in accordance with an old Irish folklore tradition from the Fifth Century of leap-year proposals by women. However, her airplane is forced to land in Wales due to bad weather and she is not able to find a connection since the Dublin airport is closed. She decides to travel on a supply vessel but is forced to disembark in Dingle due to a storm. Anna walks to the only restaurant and inn and hires the unfriendly owner Declan to drive her to Dublin. Declan agrees to drive her as he needs the money to pay of his debts but their journey is fraught with many incidents.