Pirate Diary: The Journal of Jake Carpenter

Written By: Richard Platt

Illustrated By: Chris Riddell


For parents of independent readers, we provide a set of questions that should give you insight into what your child is reading and help you engage him/her in meaningful conversations about literature. We recommend using the questions provided here as a springboard for deeper conversation about Pirate Diary: The Journal of Jake Carpenter and what your child takes away from the book. Enjoy!


Jake’s father wants him to study medicine but is convinced that he needs to see more of the world first, so he sends him off to climb aboard the Sally Anne with his Uncle Will and embark on the journey of a lifetime. Jake can’t wait to become a real sailor like his uncle, but he has no idea what is in store for him out on the open sea. Upon arriving in Charleston where the Sally Anne is meant to depart, they discover that it has already set sail so they sign on to another ship, the Greyhound, that is seeking crewmen as well. It doesn’t take long for them to realize that things are not right on this ship. Not only is it transporting smuggled goods, but the captain is a ruthless, horrible man who will find any reason to flog a man or set him adrift out to sea, which is precisely what he does to Uncle Will. Jake is left to fend for himself but when the ship is captured by pirates, he comes to find that he has some useful skills that have yet to be utilized. He joins the pirate company and learns what it means to live the life of an outlaw, raiding settlements, chasing treasure, and much more. Upon his return back to Charleston, he is reunited with Uncle Will and they decide to return home before setting out again to join the crew of another ship. This incredible story provides a historically accurate account of what it would have been like to be a pirate in the year 1716.

Discussion Questions

  1. Why did Jake leave his life as a landsman to be a sailor? Do you think you would have made the same decision if you were in Jake’s position? Why or why not?
  2. Why did Jake and Uncle Will have to set sail on the Greyhound instead of the Sally Anne? Do you think Jake’s experiences would have been different if he had been onboard the Sally Anne? How so?
  3. What did Jake discover about the Greyhound and its captain once he got onboard? What happened to Uncle Will?
  4. What were some of Jake’s duties as a sailor? How is being a sailor different from being a pirate?
  5. How did the pirates take over the Greyhound? Why did Jake decide to join the pirate company? Did he have any other options if he didn’t join the company?
  6. What happened during the raid to find the Spanish Treasure? Why was Jake considered a hero?
  7. Jake wrote detailed descriptions of the things that he saw and did while on his journey. How is the way he wrote different from the way you write? Why are they different? Try writing a journal entry about an exciting day in your life using his writing style.

Above all, be sure to engage your child in a discussion about the plot line and his/her thoughts and feelings about the book. Ask what s/he likes, encourage exploration related to the book, and every now and again, offer to read parts of the book aloud, just for fun!