Introduction

“A radiant, sun-flushed summer novel packed with beaches, sisters, and secrets.” —Nancy Thayer, New York Times bestselling author

Martha’s Vineyard, 1978: After suffering through her first year of graduate school at Columbia following her senator father’s death, Betsy Whiting is hoping to spend the summer with her boyfriend…and hopefully end the summer as his fiancée. Instead, her mother—a longtime feminist and leader in the women’s movement—calls Betsy and her sisters back home to Martha’s Vineyard, announcing that they need to sell their beloved summer house to pay off their father’s debts.

When Betsy arrives on the island a week later, she must reckon with her strained familial relationships, a long-ago forbidden romance, and the complicated legacy of her parents, who divided the family even as they did good for the world. Following a dual timeline between 1965 and 1978, and filled with the vibrant, sunlit nostalgia of the cherished New England vacation setting, Our Last Vineyard Summer poignantly captures two generations of women navigating love, loss, and womanhood while trying to find the courage to stand up for what they believe in—and the strength to decide if the home they once loved is worth saving.

Perfect for book clubs interested in discussing mothers and daughters, the complex relationships of sisters, long-ago summer romance, the impact of birth order in a family, and the pull of our childhood homes.

Discussion Questions

1) Many of us have places in our lives that we return to because they help us connect to our authentic selves. Why do you think Betsy connects so closely to Martha’s Vineyard? Share your own special place with fellow book club members and discuss why this place figured so prominently in your life. Do you still return to it?

2) In a disagreement with her mother, Betsy brings up moments when she felt that her mother wasn’t there for her. Did Betsy hold her parents to the same standard? Are daughters harder on their mothers than they are on their fathers? How was your relationship with your mother different or similar to the one Betsy has with Virgie?

3) Betsy feels frustrated that her mother sometimes put her career before her family. Is it a fair criticism? How have you struggled with any of your choices as a mother—or with your mother’s choices that impacted you growing up? If you’re a parent, how did becoming one change your view of your own mother?

4) If you were to consider the three Whiting sisters—Louisa, Aggie, and Betsy—which one of them do you relate to the most and why?

5) Psychologists have long believed that birth order can play a role in a child’s development as they age into adulthood. How did their place in the family impact each sister’s identity? Do you think Betsy would have been a different person if she were born first? Think about your own siblings. How might you have been different if you swapped birth years with one of your siblings?

6) Sisters often have complex relationships—they love each other fiercely, but they may compete for their parents’ attention or categorize each other as the “smart” one or the “pretty” one. How has the baggage of their parents influenced the three Whiting sisters? How did it impact your own identity in your family?

7) Virgie is always trying to empower her girls with her feminist principles. Do you think she ever manages to balance her desire to be a great mother with her dreams of creating lasting political change for women? How do her viewpoints impact her grown daughters in ways that are both positive and negative?

8) Selling a house can bring forth a complex wave of emotions. In this story, the sisters uncover family secrets as they begin to pack up the beach house. Why do our childhood homes carry so much significance in our lives? Would you have tried to find a way to save the house like the sisters do or do you believe it was time to let go?

9) The author has said that her own family had secrets and that uncovering them was unsettling, but also freeing. Have you discovered any secrets about your family you’d be willing to share? How did it influence how you saw yourself and the people you love?

10) When Betsy runs into her old boyfriend, James, she’s brought back to her childhood palling around with him on the island. How did her relationship with James shape her, both good and bad? Would you have listened to your father if he forbade you to see a boy at that age—why or why not?

11) Why do you think Virgie and Charlie’s marriage is under strain? Why didn’t he turn out to the be the man she thought he was?

12) Charlie Whiting passes away before the book begins, but he looms large in the story. How did each of the Whiting women’s relationship with him color their view of their themselves and their family? How does that perspective change and evolve as the book progresses?

13) Forgiveness is an important theme in this novel. Have you ever been briefly estranged from one of your siblings or family members? Discuss what happened and the conversation that ultimately led to healing.

14) What do you envision happens next for Betsy and her longtime best friend, James? What about Virgie and Wiley? Do either pair have a chance at serious long-term love?