- On Friday the 13th, different people meet on Grand Cayman - a US money launderer and his daughter, a lawyer, a young fisherman in love with a rich man's daughter, other high school students, a crime gang etc.
- In Cayman Island, the daughter of a powerful man - Andrea - and the fisherman Shy are in a deep but secret love, hidden from Andrea's parents. When Andrea's father sails in a fish-trip, they have a night of love at Andrea's home; however they sleep and are surprised by the arrival of her family in the morning. Later, Andrea's brother Hammer throws acid on the face of Shy and spends four months in prison. In Miami, the dirty businessman Carl Ridley is chased by Federal agents and escapes with his teenage daughter Pippa to Cayman Island trying to reach his lawyer Mr. Allen. Pippa meets the small time thief Fritz sleeping in her room and he invites her to go a party. Before leaving the condo, Fritz sees Carl counting lots of money. Fritz owes money to the dangerous drug dealer Richie Rich and tells him about the fortune Carl has. Along a Friday 13th night, their lives entwine in a chain of tragic events.—Claudio Carvalho, Rio de Janeiro, Brazil
- A corrupt and greedy businessman, Carl Ridley (Bill Paxton), is running from the government, with his 18-year-old daughter Pippa (Agnes Bruckner) in tow. Pippa is not happy to leave her friends and comfortable life in Miami for the Cayman Islands.
Arriving in the islands, Ridley is preoccupied. Banks are rapidly closing and he must find a clean place to store his stolen money. Meanwhile, Pippa finds native Caymanian Fritz (Victor Rasuk) sleeping off a late night in her bed. He flees out the window, leaving his wallet behind. She later finds Fritz on the beach to return his wallet and befriends him, in spite of his ridiculous come-on attempts.
Fritz is yearning to show her the island, including its wild parties. But he owes money to island gang leader Richie Ritch (Raz Adoti), and when he peeks in on Pippa's father unwrapping a massive amount of cash that he had taped around his torso, Fritz begins scheming. Pippa is completely unaware that she's leading her father into even more trouble than he had in the United States.
A parallel storyline involves Shy (Orlando Bloom), a Cayman native. He is in love with Andrea (Zoë Saldaña), the daughter of his boss, Mr. Sterling, a very influential person in the island. But for an unknown reason, Andrea's brother Hammer (Anthony Mackie) despises Shy. To protect their secret affair, whenever Shy would visit Andrea at home his good friend Kimo (Mpho Koaho) would watch the house in case Andrea's father were to arrive. On Andrea's birthday Shy visits her house and has sex with her, but Kimo falls asleep and fails to warn Shy of Sterling's arrival. Shy escapes out the window, but not without being identified by Hammer. Later on, to avenge his sister's lost womanhood, Hammer attacks Shy with acid which leaves a permanent scar on Shy's face. Hammer is sent to jail for four months.
Physically and emotionally scarred, Shy becomes a recluse. Andrea is emotionally broken and gives in to drugs and sex. Shy has his friend Patrick, the son of Mr. Allen (Ridley's lawyer), take him to Richie's birthday party to find Andrea. Finding her in the bathroom having sex with a stranger, he runs into the front yard and vomits. She runs after him but he pushes her away knowing that she is high. Hammer sees Shy and begins to beat him up with help from his friends. Shy finally breaks free and runs down the street as Hammer curses at him, telling him to stay away.
Meanwhile, at the same party, Fritz gets pulled in to see Richie while Pippa talks to a few other white girls doing drugs. Upset after smoking some pot, she finds Fritz and demands that he take her home. Having just told Richie to go to her home to steal the cash, he instead takes her to Mr. Sterling's yacht. As they sit down inside, they find that the alarm has been set off; the police arrive shortly and arrest both of them. Pippa is taken to the police station, while Fritz is transported to a laundromat where a local cop who knows him delivers a lecture and a beating for acting disobediently throughout his life.
After his own beating, Shy obtains a gun and returns to the party to find Hammer. After firing the gun to clear out the party, he corners Hammer and explains what a mess Hammer has made of his own sister's life. He says that he will spare Hammer's life so that he can watch the trouble that he has caused in Andrea's life. Hammer replies that he would rather see Andrea become a whore than be with Shy. Enraged, Shy pulls the trigger. Shocked by what he has done, he apologizes and runs off.
Over the next few hours, Andrea asks Patrick to take her to find Shy. He is disgusted with her and kicks her out of his car, but tells her that Shy is at the docks. When she finds him, she expresses her desire to be with him, regardless of others' feelings. When he confesses to killing her brother, however, she leaves him in disgust, forgetting her shoes in her hurry.
When Allen and Ridley go to the police station the next morning, Ridley soon realizes that he has been betrayed and is taken into custody by the FBI. When Allen goes home to retrieve the money that he believes he tricked Ridley into leaving in his safe, he discovers that the bag contains only sand and a conch shell. At her own condo, Pippa discovers the million dollars under her mattress.
In the final scenes, Andrea prepares for Hammer's funeral with her father, Kimo comforts Shy's mother, and Shy sits on the dock where Andrea left him. He then gets into his boat, cuts the rope and motors away, throwing the gun into the water.
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