Miles Raymond, an ardent oenophile, eighth-grade school teacher and aspiring novelist, has arranged a tour of the Santa Barbara wine country with his old college roommate Jack to savor Jack’s last week of freedom before forsaking bachelorhood for the sanctity of marriage. Realizing that he is running late, Miles, who lives in San Diego, telephones Jack in Los Angeles and tells him that he is “just out the door,” but then indulges in hours of preparation. In Los Angeles, when Miles arrives to pick up Jack at the opulent house owned by the parents of his Armenian fiancée, Christine Erganian, he nearly becomes apoplectic upon learning that Jack has told the Erganians that his novel has been accepted for publication. As they drive off in Miles’s old Saab, Miles, who has been clinically depressed since his divorce from his wife Victoria two years earlier, continues to fume about Jack’s premature announcement of his success when in fact, Miles is anxiously awaiting word from his agent. Jack, whose career as an actor peaked eleven years earlier when he played a soap opera doctor and now finds himself faced with the prospect of working for his future father-in-law, is eager to savor every last moment of his freedom, and so opens the warm bottle of rare sparkling wine that Miles has been saving for the trip. As they approach Oxnard, Miles makes an unscheduled stop to wish his mother happy birthday, scribbling her birthday card as he walks from his car to her house. Dressed in a dowdy bathrobe, Miles’s mother Phyllis beams over her son’s unexpected visit and insists they stay for dinner. When Phyllis buoyantly announces that she has phoned Miles’s sister and arranged for a family brunch at a hotel the next day, Miles sullenly excuses himself from the table. Going to his mother’s bedroom, he peels several $100 bills from her secret stash, then notices the framed photos of his family and ex-wife on her dresser. Early the next morning, as Phyllis snoozes on the couch, Miles awakens Jack and hustles him out of the house. When they stop at a coffee shop, Jack flirts with the waitress and decides that, as a gift to Miles, his best man, he is going to “get him laid.” As they approach Santa Barbara county, Miles stops at a winery and is appalled when Jack chews gum as Miles tries to coach him on the fine art of wine tasting. After checking into their hotel, they dine at a restaurant where Jack sizes up Maya, an attractive waitress. Although Miles, a frequent customer of the restaurant, tells Jack that Maya is married, Jack assures Miles that she is attracted to him. At the end of the evening, when Maya stops at the restaurant bar for a drink, Miles screws up the courage to ask her to join them, and Jack brags that Miles’s novel is about to be published. When Maya expresses interest, Miles announces that he is going back to the hotel to sleep, earning Jack’s contempt. The next morning over breakfast Jack, fed up with Miles’s negative attitude, declares he is "going to get laid," offending Miles, who imagined an idyllic week tasting wine and playing golf with his old friend. At another tasting room, Jack ogles Stephanie, the saucy wine pourer, and asks if she knows Maya. Chagrined, Miles walks out to his car and soon after, a smiling Jack comes out carrying three cases of wine and informs Jack that he has set up a double date with Stephanie and the divorced Maya for that night. While stopping along the roadside, Miles rhapsodizes about Victoria’s extraordinary wine palate. When Jack shatters Miles’s reverie by disclosing that Victoria has remarried and plans on attending his wedding, Miles petulantly grabs a bottle of wine and slugs it down as Jack chases him through the fields. That evening, as they approach the restaurant where they are to meet Maya and Stephanie, Jack admonishes Miles “not to be a downer,” and Miles warns that if anyone orders a bottle of merlot, he is leaving. Using the excuse of Miles’s book deal, Jack orders intemperate amounts of wine. Becoming progressively drunker, Miles excuses himself from the table and calls Victoria from a pay phone. After a quarrelsome conversation, he returns to the table and Jack guesses that he “drank and dialed.” When Stephanie invites them all back to her house, Jack ecstatically hands Miles a condom. While Stephanie and Jack retire to a night of passion in the bedroom, Maya and Miles discuss wine, and Miles reveals that the prize in his collection is a bottle of 1961 Cheval Blanc that he is saving for a special occasion. Miles is impressed when Maya remarks that “anytime you open a bottle of Cheval Blanc it is a special occasion.” When Maya asks Miles about his fondness for pinot noir wines, he replies that they are thin-skinned and temperamental and require constant care and attention. Miles begins to feel a rapport with Maya when she defines wine as a living thing that continues to evolve until it peaks, then begins an inevitable decline. Later, as they drive off in their separate cars, Miles to his hotel and Maya to her apartment, Miles gives her the 750 page manuscript of his novel that she has requested to read. The next morning, Jack bursts into their hotel room, crowing about Stephanie’s sexual animalism, and informs Miles that he is spending the day with her. Later that afternoon, Jack joins Miles at the hotel bar and confides that he is thinking of putting the wedding on “hold.” When Jack begins fantasizing about moving to Santa Barbara and opening a vineyard, Miles regards him with disbelief. After Jack heads out with Stephanie, her mother Carol and daughter Siena, Miles settles in with his antidepressants, wine and a porn magazine. The next day, Miles, who has not heard from his agent, tells Jack he is a fraud and that his life is “behind him.” Jack then tries to reassure Miles that his book will be published and that Maya is romantically interested in him. At sunset, the foursome picnic in the grass and afterward, Miles follows Maya to her apartment where they make love. As they ramble around town the next day, Maya suggests that Miles stay through the weekend to attend a wine dinner. When Miles replies without thinking that they have to be back in Los Angeles by Friday for Jack’s rehearsal dinner, Maya realizes that he has been deceiving her and denounces him. Chastened, Miles returns to his hotel room and declares that he wants to go home. To lift Miles’s spirits, Jack takes him to a large commercial winery that peddles tee shirts and hats alongside their wines. Finding the courage to phone his agent, Miles learns that his book has been rejected. Devastated in both love and work, Miles starts to pop pills and swill wine, finally gulping down the entire bucket in which people have spit out their unwanted wine. When Miles and Jack return to their hotel, Stephanie, who is waiting for them in the parking lot, slams Jack with her motorcycle helmet, breaking his nose. Later, while waiting for Jack in the hospital, Miles phones Maya and confesses to her answering machine that his novel has been rejected. On the last night of their adventure, Miles and Jack eat at a restaurant where Jack flirts with their chubby waitress Cammi and arranges to go home with her. Later, the slumbering Miles is awakened by a pounding on his hotel room door. Upon opening the door, Miles sees Jack standing in the nude, ranting that Cammi’s husband came home in the middle of their tryst and that he was forced to flee, leaving his clothes and wallet behind. Because his wedding rings are in the wallet, Jack cajoles Miles into driving to Cammi’s house to retrieve the wallet. When Miles sneaks into Cammi’s bedroom, however, he finds her gleefully engaged in sex with her husband, who excitedly calls her a whore and “bad girl.” Snatching the wallet, Miles is chased from the house by Cammi’s corpulent, naked husband, whom he narrowly avoids by jumping into the car and speeding off. When they stop at a gas station on the road back to Los Angeles, Jack begs Miles to let him drive, and Miles reluctantly consents. Jack then deliberately crashes the car into a tree, intending to use the car accident as an excuse for his broken nose. Deciding that the car is not damaged enough, Jack places a cement brick on the gas peddle and sends the driverless car plunging into a ditch. At Jack’s wedding the next day, Miles encounters Victoria and her husband Ken. Upon discovering that Victoria is pregnant, Miles, shattered, deserts the wedding party and heads home for San Diego where he downs the bottle of Cheval Blanc with burgers at a hamburger stand. Some time later, Miles returns home from teaching school and finds that Maya has left a message on his answering machine. In the message, Maya thanks him for his letter and says that she found his book beautiful and painful and urges him to keep writing. With Maya’s words running through his head, Miles drives to her apartment and knocks on her door.