Hollis Shaw, creator of the popular food blog, Hungry with Hollis, is shocked when her heart surgeon husband, Matthew, is killed in a one-car accident on a snowy morning. The cracks in Hollis’s perfect life—her strained marriage and her complicated relationship with her daughter, Caroline—grow deeper. So when Hollis hears about something called a “Five-Star Weekend”—one woman organizes a trip for her best friend from each phase of her life: her teenage years, her twenties, her thirties, and midlife—she decides to host her own Five-Star Weekend on Nantucket.

In this moving story about losing and finding love again, a woman sets out to find the perfect matches for those closest to her. Forty-eight-year-old Nantucketer Dabney Kimball Beech has always had a gift for matchmaking. Some call her ability mystical, while others, her husband, celebrated economist John Boxmiller Beech, and her daughter, Agnes, who is clearly engaged to the wrong man, call it meddlesome. But there's no arguing with her results: With 42 happy couples to her credit and all of them still together, Dabney has never been wrong about romance.

Adrienne Dealey has spent the past six years working for hotels in exotic resort towns. This summer she has decided to make Nantucket home. Left flat broke by her ex-boyfriend, she is desperate to earn some fast money. When the desirable Thatcher Smith, owner of Nantucket's hottest restaurant, is the only one to offer her a job, she wonders if she can get by with no restaurant experience. Thatcher gives Adrienne a crash course in the business...and they share an instant attraction.

The Carmichaels and the Grahams have gathered on Nantucket for a wedding. Plans are being made according to the wishes of the bride's late mother, who left behind The Notebook: specific instructions for every detail of her youngest daughter's future nuptials. Everything should be falling into place for the beautiful event - but in reality, things are far from perfect. While the couple-to-be are quite happy, their loved ones find their own lives crumbling.

On a perfect June day, Vivian Howe, author of 13 beach novels and mother of three nearly grown children, is killed in a hit-and-run car accident while jogging near her home on Nantucket. She ascends to the Beyond where she's assigned to a Person named Martha, who allows Vivi to watch what happens below for one last summer. Vivi also is granted three “nudges” to change the outcome of events on earth.

Claire has a problem with setting limits. All her life she has taken on every responsibility, assumed every burden, granted every request. Claire wants it all—and in the eyes of her friends, she has it: a devoted husband, four beautiful children, even a successful career as an artist. So when she agrees to chair the committee for Nantucket's social event of the year, she knows she can handle it. Claire can handle anything. But when planning the gala propels her into the orbit of billionaire Lock Dixon, unexpected sparks begin to fly.

When Mallory Blessing's son, Link, receives deathbed instructions from his mother to call a number on a slip of paper in her desk drawer, he's not sure what to expect. But he certainly does not expect Jake McCloud to answer. It's the late spring of 2020 and Jake's wife, Ursula DeGournsey, is the frontrunner in the upcoming Presidential election. There must be a mistake, Link thinks. How do Mallory and Jake know each other?

Welcome to the most tumultuous summer of the 20th century. It's 1969, and for the Levin family, the times they are a-changing. Every year, the children have looked forward to spending the summer at their grandmother's historic home in downtown Nantucket. But like so much else in America, nothing is the same.

A warm June evening, a local tradition: The students of Nantucket High have gathered for a bonfire on the beach. But what begins as a graduation night celebration ends in tragedy after a horrible car crash leaves the driver of the car, Penny Alistair, dead and her twin brother in a coma. The other passengers - Penny's boyfriend Jake and her friend Demeter - are physically unhurt, but the emotional damage is overwhelming, and questions linger about what happened before Penny took the wheel.

Birdie Cousins has thrown herself into the details of her daughter Chess's lavish wedding, from the floating dance floor in her Connecticut back yard to the color of the cocktail napkins. Like any mother of a bride-to-be, she is weathering the storms of excitement and chaos, tears and joy. But Birdie, a woman who prides herself on preparing for every possibility, could never have predicted the late-night phone call from Chess, abruptly announcing that she's cancelled her engagement. It's only the first hint of what will be a summer of upheavals and revelations.