1. Early in the novel the narrator describes his mock battles with his friends and the submarine attacks upon Aruba and Curacao. How do these details help to prepare the reader for Phillip's later experience? What emotions are aroused by the destruction of the S.S. Empire Tern?
2. Henrik Van Boven is Phillip's closest friend in Curacao. How has Phillip's attitude toward Henrik changed after his stay on the cay?
3. Henrik and his mother are very different from Phillip and Grace Enright. Why does Taylor emphasize these differences?
4. Grace Enright hates living in Curacao. What are some of the things she objects to? Is Taylor's portrayal of Mrs. Enright largely based on gender stereotypes? Is the negative portrait balanced by the fact that she remains calm when the S.S. Hato is torpedoed?
5. Phillip always speaks admiringly of his father. How does Taylor indicate the closeness of their relationship? Does Timothy eventually become a substitute father? How are the two relationships similar? How are they different?
6. Phillip remembers life in three places: Norfolk (Virginia), Willemstad (Curacao), and the cay. How does he feel about each place? How does his life differ in these places? What part does each location play in his maturation?
7. At different times, Phillip considers his loss of sight both an advantage and a handicap. When is it a handicap? When is it an advantage? What changes Phillip's attitude toward his blindness?
8. Some critics have described The Cay as racist, alleging that Timothy is portrayed as a stereotypical black man. They object to the description of his physical appearance, the language he uses, and his "subservience" to Phillip. Do you consider any of these criticisms valid? Which? In what way(s)? Is there any other explanation for Taylor's inclusion of these details?
9. Critics have asserted that while Phillip's attitude toward Timothy changes somewhat, his "conversion" from racism is incomplete. Since the novel is set in 1942, are Phillip's attitudes representative of the time? Are his mother's? How does Phillip's attitude toward Timothy change? Are there similar changes in his attitude toward other blacks?
10. In the early part of the novel Phillip often acts childish and spoiled. What specific actions illustrate his immaturity? In what ways does Phillip mature during his stay on the cay?
11. Phillip returns to Willemstad almost one year after he left on the S.S. Hato. What changes does Phillip observe in Curacao, his friends, his parents, and himself?