Port Anna

An enchanting debut novel exploring second chances and blossoming romance in a charming port town in Maine, perfect for fans of J. Courtney Sullivan’s The Cliffs and Catherine Newman’s Sandwich.

Just about everything has gone wrong for Gwen Gilmore over the past year. She’s lost her mother, her teaching job, and been dumped by her—albeit not that great—long-term boyfriend. Adrift and out of options, she packs her life into her barely functioning car and makes the lonely drive north, to the only place she can think of going: her family’s aging cottage on the Maine coast, Periwinkle, which she’s recently inherited.

The cottage and Port Anna, the foggy Maine town of Gwen’s childhood, are unchanged in many ways. For Gwen, they are full of the ghosts of her past—boyfriends, forgotten creative dreams, and painful memories of a sister lost too young. Periwinkle is also home to some more literal ghosts: The Misses, friendly spirits who have long watched over the cottage, but who now seem strangely unsettled, slamming doors and moving furniture in the night. And behind its charming façade, Port Anna has not escaped the realities of modern life. Family homes are being razed to make space for garish condos, the cottage, coveted by a relentless local realtor, is about to be condemned, and the unsolved disappearance of a teenage girl has set the town on edge. On the face of it, it’s an odd place to try to make a new start.

But there are glimmers of hope everywhere, if only Gwen can open herself up to possibility. Sparks fly with Leandro, an Argentinian artist, as aloof and witty as he is wildly attractive. Old friends and former flames come out of the woodwork, bringing with them new opportunities and chances to laugh again. Even in the face of potential happiness, though, it seems some secrets refuse to stay buried. As the summer crowds return to the city and the locals hunker down for another harsh Maine winter, Gwen will be forced to make choices that will change her life forever.

These discussion questions were provided by the publisher, Simon & Schuster.

Book club questions for Port Anna by Libby Buck

Use these discussion questions to guide your next book club meeting.

Following the loss of her job and relationship, Gwen returns to the place where she suffered a life-altering tragedy, a site of tremendous pain. In your opinion, what made it almost inevitable that she would be drawn there?

In Port Anna, Gwen immediately encounters her childhood friends. Each of them has undergone significant changes, some in surprising ways. Have your oldest friends evolved over the years in similar ways? If so, how does this impact your adult relationship or your understanding of the person when they were young?

Hugh demonstrates from the start that he and Gwen have little in common. Why do you think she trusts him?

From the first chapter, Gwen finds solace in the various moods of the sea at her doorstep. As winter approaches, she spends time taking in the beauty of the frozen harbor and the frosted trees. How does this contribute to Gwen’s evolving sense of herself and her new life?

Shania is an enigmatic figure in the first two parts of the book. What do you make of her once she starts to speak? How do you understand Gwen’s fascination with her?

The community of Port Anna welcomes Gwen with open arms, but it is also a very small town. Early in the book, Gwen alludes to gossip: how news of her arrival spreads rapidly and that the old stories of her teenage escapades were common knowledge. This is a common trope of life in a remote, rural village. But was there anything you found surprising about the interactions between the residents of Port Anna?

Gwen talks a lot about the person that she was before the tragedy and the person she became after that. How do you understand those changes? Have you ever had an experience that severed one part of your life from the other?

Port Anna relies upon the financial support of summer visitors, the from-awayers, people who spend considerable time there but who don’t quite belong. This tension is a common situation in resort communities where outsiders arrive with unreasonable or foreign expectations of how things should be done. Have you ever had experience with a community like this? Was there anything unexpected in those interactions described in Port Anna?

There are several love stories embedded in the narrative. How many can you name? How do they serve Gwen and her new life? Which ones contribute best to her healing?

Some readers have characterized this book as a fairy tale. What elements of the story or the writing contribute to that interpretation?

Port Anna Book Club Questions PDF

Click here for a printable PDF of the Port Anna discussion questions