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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.