Plot
Charlie St. Cloud, with his younger brother Sam, wins a boating race on his sailboat Splendid Splinter, subsequently receiving a sailing scholarship to Stanford University. He graduates from Winslow High School and after graduation, Charlie promises Sam they will practice baseball every day until he leaves for Stanford.
That night, Charlie wants to attend a graduation party with his friends, but his mother makes him babysit Sam. Charlie tries sneaking out to the party, but Sam catches him and asks for a ride to his friend Tommy's house. While on the road, Charlie reassures him that his departure will not be like their father's abandonment.
The car later gets rear-ended by a SUV, pushing them into an intersection where they are T-boned by a 18-wheeler, killing Sam. During an out-of-body experience, but before dying, he tells Charlie to never leave him so that he will always be with him.
Paramedic Florio Ferrente revives Charlie but Sam dies in his arms. At the funeral, Charlie runs off, unable to put Sam's baseball glove in the grave. Running through the woods, he finds his spirit and discovers they can interact. Charlie fulfills Sam's dying wish by practicing baseball with him every day at sunset, even though it keeps Sam's spirit from "moving on."
Five years later, Charlie is a caretaker at Waterside Cemetery, having abandoned his scholarship. He continues to interact with ghosts, including his friend Sully who died in the Marines. Charlie runs into Florio, who is dying of cancer.
Florio encourages him to live his life more fully, in search of the reason why he was saved. At the docks, Charlie meets Tess Carroll, an old classmate and sailor planning to solo-sail around the world.
The following day, Charlie finds an injured Tess tending her father's grave. He tends to her at his home and they develop a relationship. Later, when Charlie arrives late to see Sam, he says he felt Charlie forgetting him and himself disappearing. Charlie explains his ongoing relationship with Sam to Tess, who has followed him, and breaks up with her to not lose Sam.
Charlie learns that Tess disappeared with her boat in a storm three days earlier. After meeting her on the docks, he believes he has really been interacting with her spirit as she appeared at the cemetery, and he assumes she died at sea.
Florio's wife Carla tells Charlie that Florio died the previous night, giving him his St. Jude medallion. Remembering that Florio believed there is no such thing as a lost cause, he becomes convinced that Tess is alive and that he was saved to save her now. With his friend Alistair and Tess's coach Tink, Charlie takes Tink's boat to find her.
At sunset, Charlie misses his game with Sam, causing him to move on from the living world, as the brothers affirm their love. Sam appears to him as a shooting star, revealing Tess' location. They find the wrecked boat and an unconscious Tess. Charlie uses his body heat to keep her warm until the Coast Guard arrives, protecting her against hypothermia.
Later, Charlie invites Tess to ride with him on an old sail boat he has bought. She is afraid, as she has had vivid dreams about them together. He tells her that these are memories, reciting a quote from her father's funeral that he discussed with her spirit. Charlie quits his job and makes his final peace with Sam's spirit. Some time later, they set off to sail around the world.
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