Winter in Paradise

Gather initial thoughts and broad opinions about the book.

1. The novel ends on a major cliffhanger, revealing that the helicopter crash was potentially not an accident. How did this final twist reframe the entire story for you, and did it make you eager to continue with the Paradise series?

2. Hilderbrand is celebrated for her Nantucket-based summer reads. How did you find the shift to a Caribbean setting in Winter in Paradise? If you’ve read her other books, like The Perfect Couple or 28 Summers, how did this story’s tone and atmosphere compare?

3. In what ways did the story live up to its title, Winter in Paradise? How did the novel effectively play with the contrast between the cold, emotional “winter” the characters experience and the idyllic tropical setting?

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

1. Irene discovers that her own design preferences are mirrored in the St. John villa, complicating her understanding of Russ’s betrayal. Have you ever learned a surprising detail about someone that made you see them in a completely new light?

2. The novel explores different ways of grieving. Irene’s process is complicated by betrayal, while Huck’s is very public and supported by his community. How do the different characters’ approaches to loss resonate with your own observations of how people cope with tragedy?

3. Cash feels a sense of relief that he doesn’t have to tell his father about his failed business. What does his reaction suggest about the pressure he felt to live up to Russ’s expectations? Have you ever felt a similar pressure to succeed? How did it affect you?

4. What did you think of Maia’s philosophy, inherited from her mother, that “love is messy and complicated and unfair”? Does it feel like a helpful way to navigate complex relationships, or more like an excuse for questionable behavior?

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

1. Consider the socio-economic divide the novel draws between St. John’s tourists and its locals. What does Hilderbrand’s story suggest about the relationship between privilege and power? How does the novel reflect contemporary conversations about extreme wealth and personal accountability?

2. Hilderbrand notes that she chose to depict the version of St. John she visited prior to the devastating 2017 hurricanes, despite setting the story in 2019. How does this authorial choice reflect a desire to memo?

3. Where else have you seen the dynamic between permanent residents and wealthy, transient outsiders play out, either in stories or in the real world? How does the novel use Ayers’s perspective to explore the impact of tourism on a close-knit local community?

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

1. How did the multi-perspective narrative, which shifts between Irene, Baker, Cash, Ayers, Huck, and Maia’s points of view, shape your experience as a reader? What crucial information or emotional insights did you gain from this structure that you might have missed otherwise?

2. Russ is dead before the novel begins, yet his presence dominates the story. How does Hilderbrand successfully build his character through the memories of others, the clues he left behind, and the contradictions between his two lives?

3. What specific details about Iowa and St. John are used to represent the different sides of Russ’s life? How does this geographical contrast work as a motif to highlight the emotional schism within the Steele family?

4. What is the significance of Russ’s island nickname, “the Invisible Man”? How does it evolve from a simple descriptor of a private person to a symbol of a much deeper, more corrosive secrecy as the story unfolds?

5. The Steele brothers, Baker and Cash, react very differently to the family crisis. What do their contrasting approaches to uncovering the truth and pursuing Ayers reveal about their personalities and their lifelong rivalry?

6. The premise of uncovering a deceased spouse’s secret life is a popular trope in fiction. How does Winter in Paradise handle this idea compared to other books or films you’ve seen with a similar setup, such as The Husband’s Secret by Liane Moriarty or Gone Girl by Gillian Flynn?

Encourage imaginative and creative connections to the book.

1. Write a short scene from Russ’s perspective, set a week before his death. What would it reveal? What do you imagine his thoughts and feelings were about juggling his two separate families and identities?

2. Imagine you’re casting a film adaptation of Winter in Paradise. Who would you choose for the key roles of Irene, Huck, Ayers, Baker, and Cash? What qualities would you look for in the actors to bring these complex characters to life?

3. At the end of the book, Huck and Ayers discuss getting matching petroglyph tattoos to honor Rosie and their island roots. Choose a symbol from the novel for a tattoo. What would it be, and what meaning would it hold for you?