When her Great-Aunt Jessabelle passes away and leaves her home to Samantha, Sam and her daughters, Darcy and Rachelle, begin refurbishment on The Jessabelle House, a glorious house not far from the town of Siasconset on Nantucket. Once there, Samantha discovers her aunt's diaries, which reveal dramatic secrets from the past—and still more reasons not to trust the Colemans.

The Copperfields were once the most beloved family on Nantucket Island. Twenty-five years ago, their lives changed forever. And they never saw one another again. Not until now. In the spring of 1997, Julia watched as a judge sentenced her father, the renowned novelist, Bernard Copperfield, to twenty-five years in prison for conning, swindling, and stealing millions of dollars from his dearest Nantucket friends and fellow artists. With her family in ruins around her, seventeen-year-old Julia packed up her bags and ran away, pledging never to return to Nantucket ever again.

Susan Sheridan knows Martha’s Vineyard like the back of her hand. She grew up there as the eldest of the three Sheridan Sisters, their father the longtime owner of the Sunrise Cove Inn in Oak Bluffs. The Inn, the water, the sun all spun with laughter, and love, with the most important people—her family and friends. It was her glittering, perfect life—until it wasn’t. Tragedy struck over twenty years ago, and Susan has hardly said a word to her sisters or her father or anyone else she ever loved. Not until now.

Janine Potter grew up on the other side of the tracks. Her mother, Nancy, struggled with just about everything—alcohol, men, money—and Janine made a pledge to herself that she would never be like her. At age nineteen, Janine met Jack Potter, the son of an oil tycoon, and never looked back. Her life became a series of cocktail parties and multi-million-dollar apartments all across the world, and rubbing elbows with celebrities. Slowly, memory of her mother faded, although the trauma never really did.

When the Chambers sisters receive an invitation from their jet-setting aunt to spend the entire month of December at the family's cabin in Asheville, North Carolina, they have one question—why? The retreat, tucked into the Blue Ridge Mountains, may be the site of many happy childhood holidays and summers, but it also holds sad memories. The sisters and their aunt have spent twenty-five years avoiding the cabin and renting it to strangers. Why would Aunt Elizabeth want her "dearest darling" nieces to put their busy lives in three different states on hold and spend a month in the mountains?

As the owner of Twisted, Seattle’s best salons, Erica knows that the sharpest cuts come from the people we love. She’s terrified that she’s losing her teen daughter, Summer, to her “other” family. Summer disdains Erica’s career as shallow, and she's growing close to her stepmom, Allison. All it takes to blow up Allison’s happy life is one collect call. From prison. Her beloved husband, Peter, has been arrested, leaving Allison pregnant, scared and alone with a toddler, with no money for rent or, hey, food.

Margaret Dane Clayton has spent her entire life at the Dane Crown Inn, the beautiful resort in the quiet beachside town of Emerald Bay. But the inn once hailed as the "gem of Florida's Treasure Coast" is showing its age, much like its fiercely independent owner. Margaret swears she'll keep the doors of the inn open forever—until an accident forces her to accept that she can no longer cater to guests on her own. After reaching the most difficult decision of her life, Margaret asks her daughter and nieces to grant her one final wish before she places the property on the market.

Brooklyn-based Hannah is a bestselling author struggling to write her second book after personal losses. Her older sister, Sara, still lives in Chatham, Cape Cod, where they grew up, and is married with four children. Once a dedicated librarian, Sara dreams of reviving her love affair with literature, but instead, she is stuck with too many family responsibilities and a fizzling marriage.

Oona Kelly Webster has much to be grateful for. A striking woman with red hair and green eyes, she has a loving family and a job she adores, editing a prestigious line of books. To celebrate their twenty-fifth wedding anniversary, she and her husband, Charles, have planned a visit to France. But then Charles drops a bombshell. He has been living a lie—hiding an affair for a year—and he is leaving Oona for a younger male lover.

Five former sorority sisters, all in their 50s, undertake the adventure of a lifetime when a mysterious invite reunites them at an exclusive resort set on a private island.