Matthew "Matt" King is a Honolulu-based attorney and the sole trustee of a family trust of 25,000 acres (100 km2) of pristine land on Kauai. The land has great monetary value, but is also a family legacy. While Matt has ably managed his own finances, most of his cousins have squandered their inheritances. With the trust expiring in seven years due to the rule against perpetuities, the King clan is pressuring Matt to sell the land for hundreds of millions of dollars. Amidst these discussions, a boating accident has rendered Matt's wife, Elizabeth, comatose. With Elizabeth hospitalized, Matt is forced to cope with his two troubled daughters, 10-year-old Scottie, who seeks attention by bullying other children, and 17-year-old Alex with a history of substance abuse who is away at a private boarding school on the Big Island. Doctors determine that Elizabeth's coma is irreversible and her living will directs all life support to be discontinued. When Matt tells Alex, she reveals she learned Elizabeth was having an affair during her last visit, causing a major rift between mother and daughter.
Two close family friends, Kai and Mark Mitchell, tell Matt that Elizabeth was unhappy and loved Brian Speer, a real estate agent, and wanted a divorce. After Matt informs friends about Elizabeth so they can say goodbye, he decides Speer should also have an opportunity. He and the girls, along with Alex's slacker friend Sid, travel to Kauai to find Brian. While there, Matt's cousin, Hugh, mentions that Brian is brother-in-law to Don Hollitzer, the developer to whom the family wants to sell the land. Brian stands to make a small fortune from the sales commission. Matt privately confronts Brian and informs him Elizabeth is dying, and offers him an opportunity to say goodbye. Brian says Elizabeth loved him, but he only loves his wife and children, then apologizes to Matt.
Frustrated and fragile from recent events, Matt asks Dr. Johnston to explain Elizabeth's inevitable death to Scottie. Elizabeth is disconnected from life support. Elizabeth's father, Scott, admonishes Matt for failing to be a more generous and loving husband. Withholding his wife's affair, Matt agrees with him, but Sid and Alex unexpectedly defend Matt. At the King family meeting, Matt overrules the majority of his cousins, who favor selling to Hollitzer. Matt decides to keep the land and look for a way around the rule against perpetuities. Shocked, Hugh tells Matt that the family will take legal action, but Matt is undeterred.
After learning about Brian's affair with Elizabeth, his wife, Julie, comes to the hospital. She tearfully tells Elizabeth that she wants to hate her for "trying to destroy" her family, but that she forgives her. Matt comes to terms with his wife's infidelity and impending death. He kisses her goodbye, followed by Alex and Scottie. They later scatter Elizabeth's ashes in the ocean off Waikiki.
George Clooney as Matthew "Matt" King
Shailene Woodley as Alexandra "Alex" King
Amara Miller as Scottie King
Nick Krause as Sid
Beau Bridges as Hugh King
Judy Greer as Julie Speer
Matthew Lillard as Brian Speer
Robert Forster as Scott Thorson
Patricia Hastie as Elizabeth King
Mary Birdsong as Kai Mitchell
Rob Huebel as Mark Mitchell
Milt Kogan as Dr. Johnston
Laird Hamilton as Troy
Michael Ontkean as Cousin Milo
Matt Corboy as Kaiba