Six lifelong friends—Abby, Rebecca, Catherine, Naomi, Val, and Jenny—set off on a weekend getaway to Napa Valley to mark the occasion of Rebecca's fiftieth birthday. Despite Rebecca’s insistence that it’s merely a vacation, the group is keen to celebrate. Recently, Abby lost her job but chooses to keep this from the others. Meanwhile, Catherine, a successful TV chef, is bombarded with work-related calls, and Naomi, a mother of four, is avoiding calls from her doctor.
Upon their arrival at the rental house, they meet the quirky owner, Tammy, who gives them a warm welcome and humorously warns that they might spiral into a drunken feud—a suggestion the group brushes off. Abby is particularly uptight, adhering closely to their planned schedule. Their first evening leads them to a posh local restaurant where they are served by Jade, who shares her recent breakup story, catching Val’s interest. To their surprise, they also spot Brené Brown and can't resist the urge to approach her for questions, only to be kindly asked for some privacy.
As the night progresses, Catherine comes with the idea of taking molly pills, but the friends express concerns about their respective medications, ultimately deciding to indulge in more wine and dancing instead. The following day, Abby is startled by Devon, who "comes with the house" as their personal chef and driver—a detail that Tammy forgot to mention. Despite their hangovers, Abby sticks to the itinerary and has a tarot card reading scheduled. Lady Sunshine arrives to conduct the reading, revealing insights about their individual lives and emphasizing the need for the group to shed their past skins to maintain their friendship.
Their wine-tasting adventure continues with Devon driving them to various vineyards. Catherine continues to get interrupted by work calls, Val finds herself concerned about her earlier messages to Jade, and Abby frets over Rebecca’s reluctance to confront her significant birthday. At one vineyard, Naomi, under the influence of wine, takes to the microphone and begins singing "Eternal Flame" before dramatically falling from the piano.
As tensions rise later, Abby attempts to gather everyone for a drone photo, losing patience when the friends stray from her planned schedule. A moment of confrontation arises when Rebecca tries to share her thoughts, prompting Abby to vent her frustrations on the group. Ultimately, Abby musters the courage to confess her job loss, which leads her to discard the weekend agenda. Val receives an invitation from Jade to attend her art show, so they decide to check it out together. The exhibit turns out to be an homage to Fran Drescher and "The Nanny," leading to sharp critiques from the wine-loving ladies. Meanwhile, Catherine, while speaking with Tammy, is reminded that if her friends dismiss her job, they may not fully appreciate who she is.
As the night falls, Abby and Devon share a moment, while Rebecca experiences a physical mishap and confides in Naomi about her anxieties surrounding aging and her unsatisfactory marriage. Inspired by new realizations, Rebecca vows to embrace life and finally opts to follow through with the birthday itinerary, whimsically seated in a rolling chair. Catherine’s absence leaves the group in disarray as they suspect she might have stepped off to pursue her career. The women decide to cheer Rebecca up by recreating their first job site, only for Catherine to storm in, upset at being excluded once again. Confessions lead to emotional turmoil, where Naomi reveals her anxiety about undergoing a genetic test.
In a dramatic turn of events, Naomi is bitten by a snake during a heated argument, prompting the women to engage in a comical effort to find help. In the midst of chaos, Catherine realizes the need for balance in her life and chooses to decline a new job opportunity, recognizing the value of living in the moment. Fortunately, Naomi's snake bite turns out to be a non-venomous encounter and the group rallies together, with Catherine finally connecting with her doctor.
With newfound clarity and resolve, the friends unite, inviting Tammy to join them in a relaxed evening filled with wine and laughter. Abby and Rebecca both confess their romantic interludes with Devon. In a heartwarming conclusion, they celebrate Rebecca’s birthday, grateful for the cherished moments they’ve created during this unforgettable escape.
