This reading group guide for Sailing Lessons includes an introduction, discussion questions, and ideas for enhancing your book club. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.

Introduction

Wrenn Bailey has lived all her life on Cape Cod with her mother, Lindy, older sister, Shannon, and younger sister, Piper. Growing up, life was dictated by the seasons with sleepy gray winters where only the locals stayed on, followed by the sharp influx and colorful bustle of summer tourists who swept up the elbow of the Cape and infiltrated their small paradise.

But it wasn’t just the tourists who interrupted Wrenn’s formative years; her father—brilliant but troubled photographer Caleb—has long made a habit of drifting in and out of his girls’ lives. Until the one summer he left the Cape and did not return again.

Now, almost twenty years later, Caleb has come back one last time, suffering from pancreatic cancer and seeking absolution. Wrenn and her sisters each respond differently to their father’s return, determined to find closure. But that means returning to the past and revisiting old wounds—wounds that cause the tightknit Bailey women to confront their own wishes and wants, and admit to their own wrongdoings over the years. In a place that brings both great comfort and great pain, the Bailey sisters experience a summer on the Cape that promises not only hard endings, but, perhaps, hopeful new beginnings.

Topics & Questions for Discussion

1. The book opens with the story of the Baileys’ boat capsizing when the sisters were very young. What did you think about the Baileys in these opening pages? In what ways do their personalities and relationships stay the same as they grow up, and in what ways do they change?

2. Sailing Lessons uses five different viewpoints to tell the story of the Bailey family. What do you think the novel would have been like if Hannah McKinnon had told it from the point of view of just one or two of the Baileys? Why do you think she chose not to use Lindy as a narrator? What is the effect of not hearing her narrative voice?

3. While each of the Bailey daughters is very different, they all share elements of their parents, Lindy, Caleb, and Hank. What family traits do they share and what trait is unique to each daughter?

4. Although there are characters with overt, diagnosed addictions in Sailing Lessons, there are also less obvious addictions that members of the Bailey family struggle with throughout the novel. What types of addictions do you see in the lives of these characters? Is there resolution and healing?

5. Compare and contrast the four Bailey women's romantic relationships. In what ways are their relationships influenced by Caleb's absence from their lives?

6. After Shannon's arrest, she remembers a nightmare she had as a child and her father's comforting words. How do you interpret this memory? What does it symbolize for Shannon?

7. Before the family scatters Caleb's ashes, Wren says a few words: "I like to think that when he finally came home to us, he gave each of us a piece of ourselves back." Discuss what piece of each of the Bailey women was restored by Caleb's return.

8. Which character's journey did you identify with the most? Did any of the characters frustrate you? Confuse you?

9. Cape Cod plays an important role in the novel; it’s not just the setting, it’s also a major influence on the lives of the characters. How does Hannah emphasize the importance of Cape Cod in the book? Pick a favorite passage describing the Cape and analyze the different ways the various characters think of their home. What does the passage reveal about the character?

10. Lindy, Wren, Shannon, and Piper all react to Caleb’s return in very different ways. Identify how each copes with their reunion, and the advantages and disadvantages of approaching it this way.

11. Caleb thinks that Shannon “inherited both the best and the worst from her father.” Do you agree? Do you think that could be said of all his daughters, or is this statement unique to Shannon?

12. What do you imagine or hope would happen for the Baileys after the book ends? What do you think their futures hold?

13. As much as this is a story about fathers and daughters, Hannah also delves into the relationship between mothers and daughters. What insights into the mother-daughter bond did you gain from reading Sailing Lessons?

Enhance Your Book Club

1. Take a relaxing group trip to your local beachy spot, whether it be ocean, lake, or poolside, and enjoy being outside together, like the Baileys do.

2. In addition to its natural beauty, Cape Cod has a rich maritime history. Research one of the Cape’s many charming towns and present its highlights to your book group.

3. All of Hannah’s novels feature families in beautiful waterfront locations. Read The Lake Season, Mystic Summer, and The Summer House and compare and contrast the families in each book.