Two middle-aged men embark on a spiritual journey through California's wine country. Miles Raymond (Paul Giamatti), a depressed teacher and unsuccessful writer, and Jack Cole (Thomas Haden Church), a past-his-prime actor, take a week-long road trip to Santa Barbara County wine country to celebrate Jack's upcoming wedding. Along the way, they dine at wineries, play golf, and indulge in good food and wine, with Miles teaching Jack how to appreciate the nuances of wine tasting.
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