It's the summer of 2002, and Sarah Harris has experienced enough heartache this past year to last a lifetime. In the shadow of 9/11 and the wake of her own personal tragedies, Sarah escapes to the solace of her aunt's beach cottage on Cape Cod. She only has one plan for the summer: to work as many hours as possible waitressing at a swanky golf resort on Pleasant Bay, saving up enough money to put herself through her final year of college. But then, she finds herself falling head-over-heels for Luke, a baseball player who's also on the Cape for the summer - definitely not part of her plan. Especially because when the summer is over, they'll have no choice but to go their separate ways, and she's not sure her still-shattered heart can handle another break. Nearly two decades later, sixteen-year-old Madelyn is going through some struggles of her own - mainly with her overworked single mom, who doesn't approve of Madelyn's older boyfriend and is too overprotective to give her the freedom she so desperately wants. More and more, she finds herself longing for the father she's never had, the father her mom refuses to tell her anything about. When the friction between the two of them reaches a boiling point, Madelyn's mom sends her to Cape Cod to spend the summer with her grandmother in her little cottage on Pleasant Bay, where she stumbles upon clues to her absentee father's identity. But as she begins to consider reaching out to him, she's faced with an impossible choice: risk breaking her mother's heart, or her own. As their storylines converge, both Sarah and Madelyn must confront the far-reaching consequences of their choices - not only on themselves, but on the people around them. Is it too late to ask forgiveness from the people they've hurt? And more importantly, can they find it in their hearts to forgive themselves? Spanning two summers and nearly two decades, Pleasant Bay is an intimate portrait of the unwavering bonds of family, the beauty of second chances, and the journeys we take to find our way back to ourselves.