1. The novel opens with the tragic death of Tess and Greg MacAvoy; as it develops, we see how the lives of their six best friends are forever altered. How do you think the relationships of each couple within the group would have developed if Tess and Greg had not died on their sailing trip?
2. The heart of the novel explores the dynamics of a close- knit group of four couples, the complexities of their friendships, and how they get along with each other. What are the dynamics like in your circle of friends? Have you faced similar struggles?
3. The Castaways is set mainly on the island of Nantucket. How does this setting contribute to the story’s insular nature as the novel portrays a tight- knit group of four couples?
4. The novel occasionally leaves the Nantucket setting to travel back in time to the group vacations taken by the Castaways. Discuss the importance of the setting for each of these trips and how it plays a part in the development of the characters and the plot.
5. Hilderbrand describes how each of her eight main characters came to live on Nantucket. Which characters seem the most at home on the island? Discuss the factors that brought you to settle where you live now.
6. The Castaways is told from multiple points of view. With which character did you feel the most connected, and why? Did that change in the course of the story?
7. The surviving members of the Castaways are all grieving in their own way after losing two of their best friends. Discuss how grief manifests itself in each character and how each handles that grief. How have you handled grief in your own life?
8. Delilah says at one point that honesty should be met with honesty, yet then she makes an important decision not to share the truth. Discuss the role of honesty and dishonesty in the novel and the ways in which moral ambiguity creates confl ict for the characters.
9. By the end of The Castaways, grieving has led many of the characters to reach an acceptance of the tragedy and an absolution in their lives. Discuss how each character achieves this absolution and learns to move forward.
10. What do you think the future holds for the three surviving couples and their children?