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.

A kid walks into your bookstore and says to you, Guess what? I'm your son. The one you put up for adoption seventeen years ago. The one you never told anyone about. Surprise! His name is Matthew Walker, and he's come to spend the summer on the Cape with his parents. Why? Well, he wants to meet you before he heads off to college in the fall. Tiny detail—he didn't tell his adoptive parents about his plan. And while you hoped this day would come someday, you're so stunned, you actually faint.

Heather is happy . . . ish. She has a successful business, a cute but contemptuous cat, and best friends Daphne and Tori who know where she’s broken and love her anyway. So why does she feel crushed when her ex gets serious about someone new? No problem, she has a plan. More connections will hold her together while her world falls apart, so she finally reaches out to the stranger who might be her dad.

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.

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.