Treasure Island
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1. Jim is probably around 12 or 13 years of age, a naive and impetuous boy. How does he change during the novel to achieve a level of maturity and perspective? Can you find some examples of how he vacillates between the worlds of childhood and adulthood? 

2. How would you describe Jim as a narrator? Why might Stevenson have chosen a boy to tell the story rather than, say, Dr. Livesey or Squire Trelawney? What does Jim's narration bring to our understanding—and enjoyment—of the tale?

3. What do you think of Long John Silver? Is he thoroughly evil, a stock villain? Or is he something more complicated? Does he possess any semblance of nobility? Many readers have considered him the most story's most compelling character. What do you think?

4. Both Captain Smollett and Long John Silver lead teams of men. How do their leadership abilities differ from one another? What do their styles suggest about their characters?

5. Jim sees Dr. Livesey as a good man...but not a grand one. Why? How do you see Livesey?

6. Talk about role models, one of the central ideas of the novel. Who best serves as an inspiration for Jim as a pattern for his life? What aspects of Dr. Livesey and Squire Trelawney does Jim admire? What about Long John Silver—does he offer any kind of a role model for Jim?

7. How might Ben Gunn stand as a cautionary example of someone too long separated from civilizing influences of society?

8. Talk about the presence of flags in Treasure Island. What is their symbolic significance to the story?

9. Discuss the role of greed in Treasure Island—a book all about unfettered desire. How does greed motivate the different characters...and how does finding the treasure affect them? What is Jim's attitude toward the treasure at the end of the book? Why do the gold coins evoke nightmares rather than pleasurable dreams? Why does he have no desire to return for the silver that was left behind?

10. Why would Stevenson reveal his characters' religious sides near the end of the adventure?

11. Why does Jim wish Long John Silver happiness in the last paragraphs of the novel?

* Some questions from LitLovers.