Thirty-three-year-old Abby Stern has made it to a happy place. True, she still has gig jobs instead of a career, and the apartment where she’s lived since college still looks like she’s just moved in. But she’s got good friends, her bike, and her bicycling club in Philadelphia. She’s at peace with her plus-size body—at least, most of the time—and she’s on track to marry Mark Medoff, her childhood sweetheart, a man she met at the weight-loss camp that her perpetually dieting mother forced her to attend.

Daisy Shoemaker can’t sleep. With a thriving cooking business, full schedule of volunteer work, and a beautiful home in the Philadelphia suburbs, she should be content. But her teenage daughter can be a handful, her husband can be distant, her work can feel trivial, and she has lots of acquaintances, but no real friends. Still, Daisy knows she’s got it good. So why is she up all night?

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.

The Kingsley family is American royalty, beloved for their military heroics, political service, and unmatched elegance. In 1967, after Joseph S. Kingsley, Jr. is killed in a tragic accident, his charismatic son inherits the weight of that legacy. But Joe III is a free spirit—and a little bit reckless. Despite his best intentions, he has trouble meeting the expectations of a nation, as well as those of his exacting mother, Dottie.

Six years after the fight that ended their friendship, Daphne Berg is shocked when Drue Cavanaugh walks back into her life, looking as lovely and successful as ever, with a massive favor to ask. Daphne hasn’t spoken one word to Drue in all this time - she doesn’t even hate-follow her ex-best friend on social media - so when Drue asks if she will be her maid-of-honor at the society wedding of the summer, Daphne is rightfully speechless.

Allison Weiss is a typical working mother, trying to balance a business, aging parents, a demanding daughter, and a marriage. But when the website she develops takes off, she finds herself challenged to the point of being completely overwhelmed. Her husband’s becoming distant, her daughter’s acting spoiled, her father is dealing with early Alzheimer’s, and her mother’s barely dealing at all.

For Kate Klein, suburbia's been full of unpleasant surprises. Her once-loving husband is hardly ever home. The supermommies on the playground routinely snub her. Her days are spent carpooling, and at night, most of her orgasms are of the do-it-yourself variety. So when a fellow mother is murdered, Kate finds that the unsolved mystery is one of the most interesting things to happen in Upchurch. She launches an unofficial investigation with the help of two friends and discovers the secrets and lies behind the town's placid picket-fence facade....

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.

It’s 2 AM on a Saturday night in the spring of 2001, and 28-year-old Cecily Gardner sits alone in a dive bar in New York’s East Village, questioning her life. Feeling lonesome and homesick for the Midwest, she wonders if she’ll ever make it as a reporter in the big city - and whether she made a terrible mistake in breaking up with her longtime boyfriend, Matthew.

Every summer the Newton family retreats to their beloved home on Nantucket for three months of sunshine, cookouts, and bonfires on the beach. But this summer will not be like any other. When Arch Newton, a prominent New York attorney, dies in a plane crash on his way home from a business trip, his beautiful widow, Beth, can barely keep things together. Above all, though, she decides that she must continue the family tradition of going to Nantucket, and at the same time fulfill a promise that Arch made before he died.