A week before his friend Jack is to be married, best man Miles and the prospective groom head off to wine country for a week of fun, relaxation and - of course - wine drinking. Miles is the oenophile and does his best to teach Jack a bit about the art of appreciating great wine. All Jack cares about is drinking and carousing, something he accomplishes when he meets the attractive Stephanie at one of the vineyards. Miles is something of a sad sack, a high school English teacher who is a failed writer at heart. He has yet to get over the fact that his wife has divorced him and that she has remarried and he now faces that nerve racking wait for word from a prospective publisher. Miles has an opportunity to start anew when he meets Stephanie's friend Maya but when he let's slip that Jack is about to be married any hope of a relationship seems to be lost.
Miles Raymond is a hopeful but struggling writer who also happens to be a wine connoisseur. Jack Cole is a fading actor and his soon-to-be married friend. To celebrate Jack's concluding days as a bachelor, they will embark on a wine-tasting road trip through California's renowned vineyards. As they travel through the countryside, the two men confront their trepidation about what their futures hold and contemplate the paths in which they want to follow.
Miles is a failed writer living a meager existence in San Diego as an English teacher. With his career seemingly fading and the fate of a book hinging on a publisher's decision, Miles is depressed with himself and what he hasn't achieved. Jack is a television actor whom some recognize but not many do, as if he were a minor actor who got a taste of success. With his best friend Miles, the two embark on a road trip through California's wine country. Miles wants to give his friend a nice sendoff before married life, while Jack simply wants to have a fling beforehand. As they're both nearing middle age with not much to show for it, the two will explore the vineyards while ultimately searching for their identities.
A week before the marriage of his great friend, the decadent actor Jack, the bitter frustrated writer divorced oenologist English teacher Miles Raymond travels with him to the wine country of California to spend a week together. While Miles intends to drink wine and play golf, Jack indeed intends to score and get laid with as many women as possible. While hosted in the Windmill Inn, they meet the waitress Maya and the attendant Stephanie, and they spend some time together, visiting different wine makers and and Miles and Maya disclosing their inner secrets and falling in love for each other.
Miles Raymond, a failed writer and divorcé who teaches junior high school English takes his best friend, former hot actor Jack, on a weeklong drive up to California's wine country. There they explore the nature of their failures and question their relationships. Jack, about to get married, has an affair with a woman and wonders whether he should call off his wedding. Miles questions whether or not he made the right choice while trying to form a relationship with the woman's best friend, a fellow oenophile who is a waitress at a restaurant that he frequents often when visiting that part of the country.
Two men reaching middle age with not much to show but disappointment embark on a week-long road trip through California's wine country, just as one is about to take a trip down the aisle.
- Miles Raymond (Paul Giamatti) is an unsuccessful writer, a wine-aficionado, and a depressed middle school English teacher living in San Diego, who takes his soon-to-be-married actor friend and college roommate, Jack Cole (Thomas Haden Church), on a road trip through Santa Ynez Valley wine country. Miles wants to relax and live well. However, Jack wants one last sexual fling.
In the wine country, the men encounter Maya (Virginia Madsen), a waitress at Miles's favorite restaurant, The Hitching Post, and her friend, Stephanie (Sandra Oh), an employee at a local winery. They arrange a double date without revealing that Jack is to be married. Jack has an affair with Stephanie while Miles and Maya connect. Miles accidentally tells Maya that Jack is to be married. Enraged by the dishonesty, Maya dumps Miles and tells Stephanie, who breaks Jack's nose using her motorcycle helmet.
Upon finding out his manuscript has been rejected again, Miles makes a scene at a wine tasting room, and Jack hooks up with another waitress named Cammi. Jack gets into deeper trouble when Cammi's husband comes home unexpectedly & has to flee without his clothes and wallet (which contains the wedding rings). Miles sneaks into Cammi's house and barely escapes with Jack's wallet. To explain the broken nose to his fiancée, Jack runs Miles's car into a ditch to create front-end damage and tells her that he was hurt in an accident.
At the wedding, Miles runs into his ex-wife Vicki and meets her new husband. After learning that she is also pregnant, Miles faces the fact that Vicki will never return to him. Alone, he drinks his prized wine, a 1961 Château Cheval Blanc from a disposable coffee cup at a fast-food restaurant. Later, he receives a message from Maya, who says she enjoyed his manuscript and invites him to visit. The last scene in the movie shows Miles back in Santa Ynez, knocking on Maya's door.