On a journey through California's wine country, two lifelong friends embark on a getaway before one of them's impending marriage. Miles, a literature teacher in crisis with an obsession for wine and a cynical attitude toward life, feels trapped in a whirlwind of insecurities, especially after a painful divorce. His friend Jack, a failed actor with a more carefree and laid-back approach, decides that it's the perfect time to celebrate his last days of bachelorhood while seeking a fleeting romance along the way.
As they tour vineyards, the two friends confront their own personal crises, the qualities of the wine becoming a mirror of their existences. While Miles seeks a connection with an attractive winery owner, Jack throws himself into a one-night romantic adventure with a local woman. The day turns into a whirlwind of emotions, laughter, and unexpected misadventures as the wines flow and so do their fears and longings.
Through moments of introspection and humor, the friends explore friendship, loneliness, and the meaning of love, all while trying not to ruin their getaway. This experience will teach them that sometimes there's more to life than meets the eye, and that deep down, everyone is searching for something genuine.