Nantucket writer Madeline King couldn't have picked a worse time to have writer's block. Her deadline is looming, her bills are piling up, and inspiration is in short supply. Madeline's best friend, Grace, is hard at work transforming her garden into the envy of the island with the help of a ruggedly handsome landscape architect. Before she realizes it, Grace is on the verge of a decision that will irrevocably change her life. Could Grace's crisis be Madeline's salvation?

After a string of bad dates and no prospects, Sophia Othonos has finally hit the jackpot: an actual nice guy. When he suggests a romantic getaway, she’s sure they’re about to take the next step toward their future. A rustic cruise to the Galápagos Islands isn’t exactly her idea of a vacation, but Sophia is ready for anything…until her boyfriend has to cancel. Now she’s all alone on a trip that was meant for two. Sophia finds herself at a crossroads about who she is, what she wants, and whether her relationship is really everything she thought.

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.

Meredith Martin Delinn just lost everything: Her friends, her homes, her social standing - because her husband Freddy cheated rich investors out of billions of dollars. Desperate and facing homelessness, Meredith receives a call from her old best friend, Constance Flute. Connie's had recent worries of her own, and the two depart for a summer on Nantucket in an attempt to heal. But the island can't offer complete escape, and they're plagued by new and old troubles alike.

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.