Miles Raymond, a depressed and unsuccessful writer, and his soon-to-be-married friend, Jack Cole, embark on a week-long road trip through California's wine country to celebrate Jack's final days of bachelorhood. Miles, a wine aficionado, looks forward to educating his friend about the intricacies of wine tasting while seeking solace in the picturesque vineyards. Jack, meanwhile, has plans of his own, eager to indulge in a last fling before his wedding. This sets the stage for a journey filled with humor, misadventure, and introspection as the duo's contrasting objectives clash.

As they traverse the rolling hills and lush vineyards of Santa Ynez Valley, their escapade takes a more complex turn when they meet Maya, a knowledgeable and thoughtful waitress, and Stephanie, a spirited wine pourer. While Miles attempts to navigate his feelings for Maya against the backdrop of his personal and professional frustrations, Jack's flirtations with Stephanie threaten to derail his impending nuptials. Their interactions with these women lead to a series of unexpected and transformative experiences, forcing both men to confront their flaws and insecurities. Amidst the backdrop of serene landscapes and exquisite wines, their journey becomes one of personal discovery and redemption.