Gather initial thoughts and broad opinions about the book.

1. The author builds Grace O’Malley’s story from a blend of critical English state papers and celebratory Irish folklore. How did this mix of historical fact and legend affect your reading experience? Did the novel feel more like a biography or a mythic tale, and how does this compare to other historical fiction you’ve read, such as Hilary Mantel’s Wolf Hall or Philippa Gregory’s The Other Boleyn Girl?

2. What was your initial reaction to the novel’s nonlinear structure, which jumps between Grace’s life as a “Maiden,” “Mother,” and “Matriarch”? Did you find that this approach enhanced the story by building thematic connections, or did it make it more challenging to follow her journey?

3. What aspect of Grace’s story will stick with you the most? Is it a specific scene of defiance, a moment of surprising vulnerability, or her final, audacious appeal to Queen Elizabeth I?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Grace is shaped by several mentors, from her pragmatic mother, Maeve, who teaches her about power, to Richard Bourke, who teaches her to fight. Think about a mentor in your own life; what kinds of lessons did they teach you, and how do they compare to the guidance that Grace receives?

2. From cutting her hair as a child to defying her abusive husband and even the Queen of England, Grace’s life is marked by acts of rebellion. Can you recall a time when you felt compelled to challenge a rule or expectation that you believed was unjust? What did you learn from that experience?

3. The novel explores The Burden of Family Legacy, where personal desires are often sacrificed for the clan. Grace has a complex relationship with this idea, both upholding and defying it. How do you think about the concept of legacy in your own life? What pressures, if any, do you feel from your family’s history?

4. Grace inspires fierce loyalty in her followers, like the Murray twins and Gutty, who become her chosen family. Think about the leaders you’ve admired in your own life, whether in your community or at work; what traits do they share with Grace?

5. Grace’s relationship with Richard is presented as a partnership of equals in contrast to her oppressive first marriage. Do you see a similar dynamic in your own partnerships with others, romantic or not? What elements do you feel are essential for any relationship to be a true partnership?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. The novel frames the Tudor reconquest as Imperialism as Cultural Erasure, where English law was violently imposed on the Gaelic people. What specific examples of this cultural clash stood out to you in the story? In what ways do you see similar conflicts over cultural identity and sovereignty playing out in the world today?

2. Grace and Queen Elizabeth I are presented as parallel figures: two women wielding immense power in patriarchal worlds. How does the portrayal of Elizabeth in this novel compare to other depictions you’ve seen in films or books? What does their meeting suggest about the unique challenges that women in leadership face, both in their time and in ours?

3. The story contrasts the decentralized Irish Brehon law, which allowed for trial marriages and divorce, with the rigid English common law. How did the novel’s exploration of these competing legal systems shape your understanding of the central conflict?

Dive into the book’s structure, characters, themes, and symbolism.

1. The sea is a central motif representing Grace’s freedom and identity. In what ways does the author use Grace’s connection to the sea to define her character in contrast to the confining castles on land? How does her “Sense” of the sea function as both a literal skill and a symbol of her unique power?

2. In what ways do characters like Grace’s gentle brother, Donal “of the Pipes” O’Malley, and her abusive first husband, Donal O’Flaherty, serve as foils to highlight different aspects of her personality and journey?

3. Sir Richard Bingham is portrayed as more than just a political adversary; his campaign against Grace feels like a personal vendetta. What do you think truly drives his obsession with destroying her? Is it pure ambition, a rigid sense of English superiority, or something more personal stemming from their childhood encounter?

4. How does Grace’s relationship with knives evolve throughout the novel? Consider the kitchen knife she steals as a child, the dagger Richard gives her, and the blade she ultimately uses to threaten Bingham and cut her own hair. What does this evolution reveal about her journey?

5. What effect did the anachronic “Maiden,” “Mother,” and “Matriarch” structure have on the storytelling? For instance, how did knowing about “Matriarch” Grace’s losses impact your reading of her younger, more optimistic self in the “Maiden” sections?

6. The Author’s Note explains that the story is built from biased English records and Irish folklore. Where in the novel did you feel the influence of folklore most strongly? How does blending these sources create a more compelling character than a strictly historical account might have?

Encourage imaginative and creative connections to the book.

1. If you were casting a film adaptation of The Pirate Queen, which actors would you choose to play Grace at different stages of her life, Richard, and Bingham? What qualities would you look for to bring these complex characters to life on screen?

2. The novel spans decades, and much happens off the page. If you could add one scene to the book from another character’s perspective, whose would it be? You might consider Richard’s perspective during his and Grace’s long separation, Tibbot’s in captivity, or even Queen Elizabeth’s after her meeting with Grace.

3. Imagine you had to choose a single object to represent Grace’s legacy. Would you pick her flagship, the Niamb; the compass she chose as a child; her ever-present dagger; or something else entirely? What makes your chosen object the best symbol for her life and spirit?