Book Club Discussion Questions for The Last Train to Key West by Chanel Cleeton

1. At the beginning of the novel, Helen says, "People are what circumstances make them." Do you agree with her statement? Why or why not? Are there places in the book where this sentiment seems to be true? How do the characters demonstrate this?
2. The hurricane hits Key West in 1935, during the Great Depression. What effect does the Depression have on the characters, on the setting? How do larger world events shape characters' lives in the book?
3. What parallels do you see between the effects the hurricane has on the characters and that of fighting in the Great War?
4. How is the treatment of the veterans of the Great War similar to the problems faced by society during the Great Depression? Were you surprised to hear about the veterans' lives after they came home from the war and some of the challenges they faced?
5. Helen and John have both experienced trauma. How does it shape them? What similarities do you see between their experiences and the way they cope with them? What differences?
6. Mirta and Elizabeth both come from wealthy families that have fallen on hard times. What similarities do you see in their personalities? What differences? How do those similarities and differences influence the choices they make throughout the novel?
7. The Last Train to Key West alternates between Helen's, Mirta's, and Elizabeth's perspectives. Which character did you identify with most? How do they grow and change throughout the novel?
8. Elizabeth tells Sam that the Depression has been particularly hard on women. What examples do you see throughout the book where women's lives are influenced by society's expectations for them? How do they react to these expectations?
9. During the Depression, marriage rates dropped significantly. At the same time, marriage plays an important role in the characters' lives. How do the heroines' views on marriage change throughout the novel? Do the women find power in their relationships?
10. Mirta and Anthony's marriage changes throughout the novel. What shifts do you see in their relationship? What roles do they take on and how do they evolve in those roles?
11. All of the main characters are searching for something at the start of the novel. Do you they ultimately find what they were looking for? How does the journey change them? What were they really searching for to begin with?
12. The characters' lives are largely shaped by the hurricane and its aftermath. Have you ever experienced a natural disaster? How did the experience influence you?

Unless otherwise stated, this discussion guide is reprinted with the permission of Berkley Books. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.