Plot

A recently orphaned heiress meets a young racing yacht captain in the Long Island Hamptons. He shows interest in her, but love may not be the reason.

Young heiress Olivia Lawrence seems to have everything: good-breeding and a two-hundred-million-dollar fortune. But behind the serene façade of her East Hampton seaside estate, something is missing: passion. Enter Timothy Whalen, the young sailing instructor and playboy who isn't ashamed of sleeping with his boss' insatiable wife or social-climbing for sport. And when he sets his sights on Olivia, she falls under the spell of this handsome stranger, unaware that he has his eye on more than just her beauty--and his mind on something unimaginable. When the two run into a problem, the local policeman, who happens to be a childhood friend of Olivia's, seems to be turning a blind eye to incriminating evidence.—Rob Hartill

Young sailing captain Timothy Whalen (Rob Lowe) is having an affair with Brooke Morrison (Kim Cattrall), the wife of his boss Granger Morrison (Brian Davies) in the upscale town of Southampton, Long Island. Timothy is the new captain of his boss' racing sailboat Obsession. Following the recent death of her mother, young heiress Olivia Lawrence (Meg Tilly) returns home to Southampton after graduating from college. At a party, Olivia is introduced to Timothy, who asks her to dance. Impressed with her knowledge of sailing, Timothy asks her to go sailing with him, and she accepts.

Olivia is residing in the family mansion with her alcoholic stepfather Tony Gateworth (John Glover), and his live-in girlfriend Anne Briscoe (Dana Delany). Her mother's will provided that her Gateworth retain access to shit the family's eight properties. Olivia has nothing but contempt for her stepfather, who married her mother for her money. At her family attorney's office in New York City, Olivia learns she cannot restrict Gateworth's access to her homes, and the nearly one million dollars a year he receives from the estate barely covering his gambling debts.

Olivia and Timothy go sailing on her sailboat Masquerade, which was her late father's pride and joy. Later at Olivia's mansion, they are confronted by a drunken Gateworth who insults Timothy, his former sailing competitor. In the coming days, Olivia and Timothy began dating and eventually fall in love. However, Olivia's newfound happiness is soon offset by another confrontation with Gateworth who informs her as her guardian, she wants Timothy out of her life. Olivia confides to her aunt that Timothy is the first man she has felt comfortable with and that he isn't interested in her money. Later that day, at a lobster house on the outskirts of town, Gateworth and Timothy meet surreptitiously to discuss their conspiracy to murder Olivia for her money. When Timothy expresses doubts, Gateworth threatens to expose of his past. He informs him the text step is to gain Olivia's confidence by having Timothy defend against him.

That weekend, Olivia and Timothy have passionate sex in the mansion. Afterwards, a drunken Gateworth breaks into Olivia's room as planned, but Timothy kills him with his own pistol. Believing they will be accused of killing Gateworth, Olivia covers up Timothy's role in the murder by claiming she killed Gateworth in self-defense. Timothy establishes an alibi with an unsuspecting Brooke by resetting her bedside clock. During the investigation, Officer Mike McGill (Doug Savant) -- a childhood friend with a romantic interest in Olivia -- finds evidence that Timothy may have been involved in the murder, but does not report this to his captain, presumably because of his feelings for Olivia.

Gateworth's girlfriend Anne Briscoe begins questioning to investigation's findings, and informs the authorities about Olivia and Timothy. Meanwhile, Timothy breaks up with Brooke, who later confirms Timothy's alibi to the police. Not long after, Anne Briscoe informs McGill that her friend saw Gateworth at a diner with Timothy, she is found hanged in an apparent suicide, McGill requests an autopsy.

While sailing aboard Masquerade, Olivia asks Timothy to marry her, but he is unwilling, informing her he once spent 30 days in prison for writing bad checks. He also informs her about her affair with Brooke Morrison. He honestly convinces Olivia he is the right man, and the couple are soon married. Later, Olivia reveals she is pregnant. That night, Timothy drives to the marina where he meets secretly with McGill, who was part of the original conspiracy - who actually planned everything. Timothy is unwilling about killing Olivia, but McGill insists she must die in a stage car accident. He threatens to put away Timothy for Gateworth's murder if he doesn't cooperate.

When McGill learns that Timothy has no intention of killing Olivia and that they are planning to set sail for Florida on Masquerade the next day, he sabotages Olivia's sailboat and plans incriminating evidence in Timothy's linen drawer. Timothy discovers McGill's treachery and races to the marina to save Olivia, but is killed in the gas explosion meant to kill Olivia. In the marina office afterwards, Olivia discovers a newspaper clipping of Timothy, Gateworth and McGill, just as McGill enters the office. Seeing that she has figured out the conspiracy, he tries to kill her. In the ensuing struggle, Olivia pushes McGill out of a window causing his death.

At Timothy's funeral, Olivia learns from her family attorney that Timothy recently insisted that he be removed from Olivia's will, and however this may have started, he came to love Olivia in the end.