Winter in Paradise

Winter in Paradise (2018) is a contemporary family drama and mystery novel by Elin Hilderbrand—the first installment of the three-part Paradise series. When her husband dies in a helicopter crash in the Caribbean, a Midwestern woman discovers he was leading an elaborate secret life, forcing her and her two adult sons to travel to the island of St. John to uncover the truth. Winter in Paradise is set in early January 2019, alternating between Iowa City and St. John in the US Virgin Islands. The narrative uses a multi-perspective, third-person point of view, with each chapter focusing on one of five main characters: Irene, her sons Baker and Cash, and St. John residents Ayers and Huck. The novel explores themes of The Complexities of Living a Double Life, Paradise as a Façade Versus an Emotional Reality, and Redefining Family in the Wake of Tragedy.

Hilderbrand is a prolific New York Times best-selling author known primarily for her popular summer novels set on her home island, Nantucket, Massachusetts. Winter in Paradise represents a departure for the author, shifting the setting to St. John in the US Virgin Islands, a place the author considers a personal retreat. The book’s development was influenced by the devastating 2017 hurricanes that struck the region. Hilderbrand chose to depict a pre-hurricane version of the island, using the idyllic setting as a backdrop for the Steele family’s dark discoveries.

This guide references the 2024 Back Bay Books paperback edition.

Content Warning: The source material and guide feature depictions of death.

Plot Summary

On New Year’s Day in Iowa City, magazine editor Irene Steele learns from Marilyn Monroe, the secretary of Russ’s boss, Todd Croft, that Russ has died in a helicopter crash in the US Virgin Islands. Marilyn also reveals that Russ owned a secret villa on the island of St. John. Irene delivers the news to her two adult sons, both of whom are facing crises in their personal lives. In Denver, Irene’s younger son, Cash, confronts the financial failure of his chain of outdoor supply stores. In Houston, her older son, Baker, learns that his wife, a surgeon named Anna, is leaving him for a female colleague. On St. John, where the crash occurred, Ayers Wilson, a server and boat crew member, learns that her best friend, Rosie Small, died in the same crash as Russ. Rosie’s stepfather, a fishing captain named Huck Powers, is also informed of her death by the police.

Concealing the news of her husband’s death from his elderly mother, Milly, Irene travels to St. John with Cash and Baker to handle Russ’s affairs. Meanwhile, Huck and Ayers break the news of Rosie’s death to Rosie’s 12-year-old daughter, Maia, who is devastated. Upon their arrival, the Steeles are met by a property manager, Paulette Vickers, who takes them to Russ’s luxurious and secluded villa, which feels staged and impersonal, stripped of any personal effects. While exploring, Cash discovers a framed photograph of Russ with Rosie, which he hides to protect his mother from uncovering what he suspects is an affair. He questions Paulette and learns Rosie’s full name and the place and time for her memorial service.

Baker and Cash attend Rosie’s memorial reception, where they pretend to be vacationers crashing the funeral for the free food. Baker meets Ayers and feels an immediate connection to her that he later describes as “love at first sight” (271). Alone at the villa, Irene discovers the hidden photograph of Russ and Rosie. Confronted with evidence of his infidelity, Irene bursts into tears. Seeking distraction, Cash joins Ayers on a snorkeling charter, where they bond, and he confirms Rosie’s identity. Irene, who’s seeking answers of her own, tracks down Huck. They connect over their shared loss and spend a cathartic day fishing on Huck’s boat.

Irene and Huck’s bond deepens over dinner at the villa as they grill their catch from earlier in the day. Irene asks Huck to help her break into a locked room, which turns out to be a bedroom decorated for a young girl. When Huck shows Irene a picture of Maia, Irene is stunned by the girl’s resemblance to Russ and his mother, Milly. She realizes Maia is Russ’s daughter. Huck recalls that Maia recently told him Russ was her biological father, confirming the truth. At the restaurant where Ayers works as a server, Baker and Cash compete for her affections. Baker convinces Ayers to have dinner with him after her shift, and they kiss on a moonlit beach. Ayers wants to have sex, but Baker says he wants it to be special and invites Ayers to spend the night with him at a luxury resort the next day.

The family dynamics become more complicated when Anna arrives unexpectedly with Baker’s four-year-old son, Floyd, forcing Baker to cancel his overnight date with Ayers. Cash, who feels betrayed by Baker and rejected by Ayers, gets drunk and calls Ayers to reveal that he and Baker are Russ’s sons. Hurt by their shared deception and Baker’s lies about his wife, Ayers ends her involvement with both brothers. Shortly after, Russ’s ashes are delivered to the villa, prompting Irene to confront her sons about their own secrets.

Irene asks Huck to arrange a meeting with Maia. Maia agrees, on the condition that Ayers is also present. The meeting at the villa is tense. Ayers confronts the brothers for their lies, and the family, including Maia, scatters most of Russ’s ashes at the villa’s private beach. Irene saves a small portion for Milly and offers to support Maia financially, though Huck insists that he is Maia’s guardian and more than capable of supporting her. Disillusioned by the Steeles’ secrets, Ayers decides to reconcile with her ex-boyfriend, Mick.

Irene and Cash return to Iowa City, where they learn Milly is near death. She passes away shortly after their arrival. Baker returns to Houston with Anna and Floyd. While preoccupied with Milly’s death and their own affairs, Irene, Cash, and Baker each miss calls from an unknown number with a Puerto Rico area code. Back on St. John, Huck receives a call from FBI Agent Colette Vasco. She informs him that the helicopter crash is no longer considered an accident. The investigation suggests an explosive device may have been involved, and the FBI suspects foul play.