Every Time I Go on Vacation, Someone Dies Summary, Characters and Themes

Every Time I Go on Vacation Someone Dies by Catherine Mack is a clever blend of mystery, dark humor, and interpersonal drama set against the vivid backdrop of Italy. 

The story centers on Eleanor Dash, an unexpected bestselling author whose literary fame is tied to the enigmatic and frustrating Connor Smith. Over a decade, Eleanor’s life becomes entwined with Connor’s through a series of true-crime novels chronicling their past adventures unraveling Mafia crimes in Rome. Now, Eleanor struggles to reclaim her own identity from the shadow of her creation while navigating threats, betrayals, and the dangerous consequences of their shared past. The novel skillfully balances suspense and character dynamics, creating a compelling narrative that explores fame, creative control, and the price of truth.

Summary

The story opens with Eleanor Dash in a Roman church, confessing her frustration with Connor Smith, a man she never intended to write about but who became central to her bestselling true-crime book, When in Rome. 

Their story began ten years earlier during a transformative trip to Italy, where Eleanor met Connor, a charming American expat investigating a series of bold bank robberies connected to the notorious Giuseppe crime family. 

Together, they solved the crimes, including a murder within the Mafia, and their collaboration blossomed into a passionate romance. Eleanor’s unexpected success as an author, fueled by their story, soon trapped her in a narrative dominated by Connor’s presence.

When Eleanor published her first book, she failed to inform Connor, who then demanded a share of her earnings under threat of legal action. This blackmail set a precedent: as the series expanded, Connor increasingly inserted himself into Eleanor’s public and private life, demanding larger cuts and manipulating their shared story for his gain. Ten years on, Eleanor feels imprisoned by the saga, likening her fate to fictional detectives who are only freed through death. 

Determined to break free, she plans to kill off Connor in her next book.

The narrative moves fluidly between Eleanor’s thoughts, her tense relationships with Connor and her sister Harper, and the unfolding mysteries in Rome. Connor insists that someone is trying to kill him, pointing to suspicious incidents like brake failure on his vintage car and near-death experiences around the Vatican. 

Eleanor is doubtful but intrigued. The danger becomes real when a nearby gunshot forces Connor to shield Eleanor, confirming the threat.

Harper, Eleanor’s sister and personal assistant, is a protective yet increasingly distant figure. 

Her own abandoned dreams as a writer create tension beneath their close bond, adding emotional complexity. Meanwhile, Eleanor must cope with obsessive fans—particularly the “BookFace Ladies” and a persistent stalker named “Crazy Cathy”—who invade her privacy and complicate her public appearances.

Adding to the tension is Oliver Forrest, Eleanor’s former lover and fellow author. 

Their unresolved history, coupled with Oliver’s dislike of Connor, fuels emotional friction. Eleanor confides in Oliver her plan to end the series by killing Connor’s character, hoping to regain creative control.

Suddenly, during a tour of Rome, Harper and Connor vanish after a scream, thrusting Eleanor and Oliver into uncertainty and danger. The story balances personal conflict, mystery, and suspense as Eleanor confronts threats to those she cares about and wrestles with her complicated feelings toward Connor.

Later, the story picks up near Trajan’s Column, where Eleanor finds Harper involved with Allison Smith, Connor’s ex-wife, revealing the complicated personal histories entangling the main characters. 

Connor’s dark reputation for manipulation and betrayal unfolds, including the exposé written by Allison. When Harper’s purse is stolen, suspicions of foul play grow, especially since Connor refuses police involvement.

The group attending a literary tour for the tenth anniversary of When in Rome includes a cast of characters linked to Connor: Guy Charles, Connor’s former business partner; Shek, a mystery author with a shady past; Emily Ma, a TikTok author accused of plagiarism; and Oliver. 

Eleanor surveys the guest list and suspects multiple motives behind the threats to Connor.

Tensions surface during a lavish dinner when Connor arrives with Isabella Joseph, a young Canadian woman. Conflicts arise over Connor’s entanglements with various women, and “Crazy Cathy” disrupts the evening, heightening unease. 

Eleanor nearly chokes on a fish bone, and Oliver saves her, deepening her awareness of mortality amid the ongoing dangers. Connor suspects this incident was an attempt on his life, tying it to prior threats and a recent near-fatal event near the Vatican.

Eleanor confides her plan to Oliver to kill off Connor in her next book, hoping to escape the tangled mess. Oliver cautiously supports her but warns of backlash. Meanwhile, Connor continues to provoke tensions, especially with Oliver.

The following morning brings tragedy: Harper discovers Connor dead in his hotel room, shocking everyone and confirming the deadly threat Eleanor feared.

As the investigation unfolds, Eleanor learns more about the conspiracy against her and Connor. 

She overhears a confrontation revealing Isabella’s ties to the Giuseppe crime family and a deeper vendetta led by Sylvie, the matriarch operating under an alias. Sylvie blames Eleanor and Connor for destroying her family’s criminal empire.

Eleanor confronts Sylvie atop a tower but ends up in a violent struggle. Sylvie falls to her death, and Eleanor is left unconscious, saved just in time by Harper. The aftermath is fraught with suspicion, despite Eleanor’s innocence.

Inspector Tucci reveals the breadth of the Giuseppe family’s plot, including blackmail by Shek and manipulations orchestrated by Marta, a publicist still at large. Though arrests follow, the conspiracy’s full scope remains partly unresolved.

Months later, Eleanor has resumed writing and reconciled with Harper. She attends a funeral for Shek, a mix of mourning and new beginnings. At a wedding with Oliver, a fresh murder hints that danger and mystery continue to shadow Eleanor’s life.

Throughout, the novel explores the challenges of fame, betrayal, the blurred lines between fiction and reality, and the struggle for personal freedom in the face of controlling forces—both real and imagined. Eleanor’s journey is one of reclaiming agency amid threats that are as personal as they are deadly.

Characters

Eleanor Dash

Eleanor Dash is the protagonist and narrator of Every Time I Go on Vacation Someone Dies. 

She is a bestselling author whose unexpected rise to fame began with her true-crime novel When in Rome, which centered on her adventures with Connor Smith. Eleanor is a complex character caught between her public identity as a successful writer and her private frustration with the narrative that has come to define her life—especially the hold Connor has on her story and career. 

She wrestles with feelings of resentment and entrapment, likening herself to authors trapped by their famous fictional creations. Despite her celebrity, Eleanor remains deeply human, grappling with fear, vulnerability, and the messy entanglements of love and betrayal. Her relationships with Connor and her sister Harper are fraught with tension, showing her as both fiercely loyal and conflicted. 

Eleanor’s inner world is rich with introspection, revealing a woman who is clever, determined, and sometimes overwhelmed by forces beyond her control. Her decision to kill off Connor in her next book reflects her desperate desire for autonomy and closure, even as real danger looms around her.

Connor Smith

Connor Smith is the enigmatic and charismatic American expat who became the central figure in Eleanor’s first bestselling book. He is a private detective with a murky past and a flair for manipulation, making him both fascinating and frustrating to those around him. 

His complex personality blends charm with a darker streak of self-interest and control. Connor’s attempts to insert himself into Eleanor’s career by demanding a share of her earnings expose his mercurial nature and his tendency to blur personal and professional boundaries. 

He is simultaneously a victim and a potential threat, claiming someone is trying to kill him while also provoking suspicion with his provocations and entanglements with multiple women, including his ex-wife Allison Smith. 

Connor’s presence dominates the narrative, serving as both a catalyst for Eleanor’s success and a source of escalating tension. His mysterious demise during the literary tour and the subsequent revelation of his many enemies deepen his portrayal as a man ensnared in a web of betrayal, crime, and revenge.

Harper Dash

Harper Dash, Eleanor’s sister and personal assistant, embodies a blend of loyalty and simmering resentment. 

She is protective of Eleanor, showing deep emotional investment in her sister’s well-being, yet beneath the surface, there is a growing tension fueled by Harper’s own abandoned dreams of being a writer. This jealousy and feeling of being overshadowed add emotional complexity to their relationship. 

Harper’s interactions reveal a woman torn between her love for Eleanor and her own unfulfilled ambitions, making her a nuanced figure in the story. Her sudden disappearance alongside Connor during the tour heightens the stakes and underscores her integral role in the unfolding drama. Harper’s loyalty is tested in the face of danger, and her presence as a stabilizing yet conflicted force adds depth to the family dynamics explored in the novel.

Oliver Forrest

Oliver Forrest is Eleanor’s former lover and fellow author whose arrival introduces both emotional tension and support in the story. 

His complicated history with Eleanor brings unresolved feelings into sharp relief, especially as he openly dislikes Connor, fueling conflict and alliances within the group. Oliver represents a contrast to Connor’s manipulative energy, offering Eleanor a sense of grounding and cautious support in her quest for creative freedom and personal safety. 

His quick thinking and protective instincts, demonstrated during the dinner incident when he saves Eleanor from choking, reinforce his role as a reliable ally amid chaos. Oliver’s presence adds layers to the interpersonal drama, embodying themes of past romance, loyalty, and the struggle for trust in a world rife with suspicion.

Isabella Joseph

Isabella Joseph is a young Canadian woman who enters the story as Connor’s latest romantic interest, arriving with him on the plane and becoming part of the tense dynamics on the literary tour. 

Her connection to the Giuseppe family—an infamous crime family central to the novel’s mystery—adds intrigue and danger. Isabella’s character straddles the line between innocence and involvement in the family vendetta that drives much of the plot’s suspense. 

Her interactions and overheard conversations deepen the conspiracy surrounding Eleanor and Connor, revealing hidden alliances and the complex web of revenge that fuels the narrative’s darker undercurrents.

Allison Smith

Allison Smith, Connor’s ex-wife, introduces additional layers of complexity through her past relationship with Connor and her own role in the story. 

As the author of a tell-all exposé on Connor, Allison represents a figure of confrontation and revelation, exposing the darker sides of Connor’s manipulations and betrayals. 

Her presence in the narrative highlights Connor’s tangled personal life and the repercussions of his actions on those closest to him. Allison’s involvement complicates the group dynamics and raises questions about trust and the blurred lines between personal history and the unfolding danger.

Sylvie / Sophia Giuseppe

Sylvie, later revealed as Sophia Giuseppe, the matriarch of the Giuseppe crime family, is the embodiment of the novel’s theme of vengeance and the destructive power of family loyalty. 

Her motivations are driven by a deep desire for revenge against Eleanor and Connor, whom she blames for the downfall of her family’s criminal empire. Sylvie’s confrontation with Eleanor on the Torre Maggiore escalates into a violent struggle that results in her own tragic death, marking a turning point in the story. 

Her character is a potent symbol of the long shadow cast by past crimes and vendettas, illustrating how the sins of one generation poison the lives of the next. 

Sylvie’s presence deepens the mystery and emotional stakes, making her a pivotal antagonist whose legacy continues to affect the characters’ fates.

Guy Charles, Abishek Botha / Shek, Emily Ma, Marta

Guy Charles, Connor’s former business partner, and Abishek Botha (Shek), a mystery author with a shady past, add layers of suspicion and rivalry. Shek’s role as a blackmailer entangled in the Giuseppe family’s vendetta intertwines crime, literature, and manipulation.

Emily Ma, a rising TikTok author accused of plagiarizing Eleanor’s plots, embodies modern literary tensions and competition, while Marta’s use of her publicist position to orchestrate deadly events shows the reach of the conspiracy against Eleanor and Connor.

These characters enrich the narrative’s complexity, each carrying motives and secrets that deepen the suspense and intrigue surrounding the literary tour and its deadly outcome.

Themes

The Burden of Creative Ownership and Control

In Every Time I Go on Vacation Someone Dies, the theme of creative ownership is explored through Eleanor’s fraught relationship with Connor, a man whose life and persona she has commodified through her bestselling true-crime novels. Eleanor’s initial unintentional capture of Connor in her narrative transforms from an accidental success into a prolonged creative and emotional imprisonment. 

The persistent intrusion of Connor into her life—demanding a share of her advances and manipulating her public image—symbolizes the loss of authorial control many creators fear when their work takes on a life of its own beyond their intentions. This loss becomes not just professional but deeply personal, as Eleanor wrestles with how her fiction shapes her identity and relationships. 

The book portrays how a character originally meant for storytelling becomes an oppressor in reality, illustrating the complex dynamics between a creator and their creations or subjects. Eleanor’s determination to “kill off” Connor in her next book represents a symbolic and literal attempt to reclaim agency over her story and her life. The narrative further probes the conflict between public expectation and private desire, where fan obsession, stalkers, and legal threats compound Eleanor’s sense of being trapped. 

Ultimately, this theme underscores the emotional toll and ethical complications of fictionalizing real people and events, revealing how storytelling can simultaneously empower and enslave its creator.

The Intersection of Reality and Fiction

The novel blurs the lines between reality and fiction, highlighting how narratives shape perception and influence the lives of both the storyteller and the subjects within the story. Eleanor’s career launch with a true-crime novel based on real events reveals the porous boundary between factual recounting and creative embellishment. 

The series’ growth, fueled by public fascination and fan obsession, intensifies this overlap, creating a feedback loop where reality informs fiction and fiction reshapes reality. This is evident in the complex public persona Connor adopts, manipulated both by himself and Eleanor’s portrayal of him, and the fan reactions ranging from adoration to hostility. Suspense and danger woven into Eleanor’s personal life stem from the fictional world she constructed, showing how stories, once released, influence real-world relationships, trust, and safety. 

The mysterious attempts on Connor’s life and the unraveling of the Giuseppe family vendetta underscore this theme by blending literary characters, personal histories, and criminal intrigue into one continuous narrative thread. This interplay raises questions about the responsibility of authors toward truth and the consequences when fiction’s allure entangles with real violence and betrayal.

The Complexity of Relationships and Trust

Relationships in Every Time I Go on Vacation Someone Dies are portrayed as deeply complicated and fraught with tension, betrayal, and unresolved emotional conflicts. 

Eleanor’s interactions with Connor, Harper, Oliver, and other characters reveal layers of loyalty, resentment, and unspoken fears. Eleanor’s bond with her sister Harper is characterized by both fierce protectiveness and subtle distance caused by Harper’s own sacrificed ambitions and growing bitterness. This dynamic adds emotional depth and vulnerability, showing how family relationships can strain under the pressure of fame and personal sacrifice. Eleanor’s romantic and past relationships, especially with Oliver and Connor, further complicate the narrative.

Oliver’s protective presence contrasts with Connor’s manipulative and sometimes dangerous behavior, forcing Eleanor to navigate shifting loyalties and uncertain motives. The atmosphere of suspicion during the literary tour amplifies the fragility of trust within the group, where every character harbors secrets, grievances, or hidden agendas. 

These interactions emphasize how personal and professional relationships can become battlegrounds where love, jealousy, ambition, and betrayal collide, underscoring the precariousness of trust in a world overshadowed by fame, danger, and hidden pasts.

Revenge and Its Consequences

Revenge is a driving force that propels much of the narrative tension in the story. The vendetta of the Giuseppe family, particularly embodied in characters like Sylvie (Sophia Giuseppe) and Isabella, illustrates how the desire for retribution for past wrongs can consume individuals and shape their actions in destructive ways. 

The violent struggle on the tower and Sylvie’s fatal fall serve as physical manifestations of how revenge spirals into tragic consequences, often blurring the lines between victim and perpetrator. The narrative reveals a cycle where past betrayals and criminal fallouts are neither forgotten nor forgiven but actively pursued, impacting innocent and guilty alike. This theme is tightly linked to the mystery and suspense of the plot, as the characters navigate threats born from grudges, blackmail, and long-held animosities. 

At a deeper level, the story explores how revenge affects the psyche—instilling paranoia, mistrust, and fear, as seen in Connor’s claims of assassination attempts and the characters’ mutual suspicions. 

The theme also exposes the collateral damage of vengeance, including fractured relationships, deaths, and the perpetuation of violence, offering a grim meditation on the costs of settling scores.

The Struggle for Personal Identity Amid Public Scrutiny

Eleanor’s journey highlights the tension between personal identity and public persona, especially for those thrust into fame unexpectedly. Despite her success as an author, Eleanor feels suffocated by the public’s fixation on Connor and the series, which has reduced her to a character in a story controlled by others as much as by herself. 

The “BookFace Ladies” and obsessive fans like “Crazy Cathy” embody the invasive nature of celebrity culture, where private lives are dissected and commodified for entertainment and gossip. Eleanor’s struggle reflects the broader challenges faced by individuals whose identities are co-opted by public narratives, leaving little room for authentic self-expression or escape from the spotlight. Her desire to end the series and kill off Connor symbolizes a desperate attempt to reclaim her privacy and redefine herself beyond the confines of the fictionalized narrative. 

The theme resonates with issues of autonomy, privacy, and the pressures of living under constant public scrutiny. It also examines the emotional cost of living with a persona shaped by external expectations, especially when the truth of one’s life is entangled with sensationalized stories and fan culture.

The Impact of Mortality and Fear of Death

Throughout the story, mortality is a recurring theme, approached both through direct threats and more subtle moments of reflection. The near-death experiences—such as the fish bone incident, Connor’s close calls with assassination attempts, and ultimately his murder—constantly remind Eleanor and the reader of the fragility of life. 

These incidents force Eleanor to confront her own fears and the unpredictability of death, which shadows her both personally and professionally. The juxtaposition of touristic Roman landmarks with moments of danger heightens this tension, suggesting that even amidst beauty and history, life is precarious. Eleanor’s calm acceptance upon realizing Connor’s intent to kill her reflects a complex response to mortality, where knowledge of impending danger paradoxically offers a sense of control or peace. 

The presence of death also catalyzes character development and deepens interpersonal bonds, as seen in Eleanor’s relationship with Oliver and her protective instincts toward Harper. This theme underscores the impermanence of life and the emotional weight that mortality imposes on human relationships, decisions, and creative expression.