Reading and discussing Beyond Beauport by James Masciarelli? Here are is a handy discussion guide to enrich your experience! Click on the image at right to view/download a full discussion guide pdf, or enjoy the questions below…


Beyond Beauport introduces us to a place of simpler times. What places like this remain? Do you hold an imagined Arcady to cure the blues or salve for the human condition? Where have you found it in literature or travel?

What places, real or imagined, do you yearn for? What places would you like to visit, explore or return to?

If you have not visited Gloucester or Cape Ann (one hour north of Boston), how do you now picture it in your mind? How would you describe its physical and cultural attributes? If you have visited Gloucester/Cape Ann, how do you feel Beyond Beauport immerses you in setting and in the characters of Shannon Clarke and her friends? What makes Shannon a compelling lead character and a product of her environment?

What symbolism does the sea provide in the story? What imagery and emotion does it provide?

Which story locations did you enjoy most? Gloucester, Charleston, Barfield Bay, Lovers Key, Key West, Jamaica, Eastern Caribbean? Sailing in deep blue water?


Shannon, at 46, suffers deepening depression as she battles past traumas and recent abandonment from her grown children and a straying husband. She questions her life just as her uncle Paddy arrives and their nautical quest begins.

How do you react to the term ‘midlife crisis’? Is it a cynical reaction? Is this what Shannon is experiencing? How does one take a positive or negative turn in midlife? See it as an opportunity?

What types of barriers or choices prevented Shannon from achieving her childhood dream to become a sailing captain?

Shannon’s childhood trauma left deep emotional scars. What strategies did she use to mask and cope with her traumatic past? How does this play out in the story?

What parts of Shannon’s character resonate with you?

Paddy is a seafaring man in his early seventies who may be ready for a change in his life. How do Paddy and Shannon facilitate each other’s life transitions?

Do Paddy’s three Ls—living, loving and learning—comprise a cogent philosophy and meaning for human life/existence?

Paddy brings a wealth of wisdom and knowledge from his life’s experiences and his own reading/research. Shannon is evolved, with practical knowledge gained mostly from experience. In your life, have others surprised you with their depth of knowledge and understanding, despite limited formal education? What does that say for schooling in general?

Anne was an Irish-born pirate, born circa 1698. She sailed the West Indies and, although historical accounts differ, she was said to have avoided execution in 1720 and assumed a new identity as a wife and mother in South Carolina.

What did you already know about female pirates of the past? What was your impression of a woman like Anne Bonny living as both a pirate and then a wife and mother?

Do you have dreams of a more adventurous nonconventional life, or have an inner pirate that you need to manage?

What are the parallels between the lives and temperaments of Anne Bonny and Shannon, other than physical characteristics?


Does ancestry matter? Explore that in your group.

Shannon and Paddy search to understand their distant relatives, who are famous and infamous historical figures. In what ways do they search for identity, family and purpose?

Beyond Beauport employs Paddy’s notion of ancestral memories as a literary device with magical realism, particularly in Shannon’s lucid dreams of Anne Bonny and Privateer Captain Jonathan Haraden. Have you experienced vivid or lucid dreams? Have you ever dreamt you were someone else, living in a different time period?

How do you feel influenced by any of your ancestors’ experiences? Has anyone ever told you that you have the same personality traits or temperament as a parent, aunt, uncle, grandparent or great-grandparent?


When Shannon and Paddy are hijacked at sea by villainous Franco Torre, they faced death and physical abuse. How does Shannon survive it and rebound?

Shannon is appalled to learn that that her evil tormentor, Franco, is Caesar’s half-brother. She tells Caesar that “a family is like a hand; each finger is different.” How does this resonate in your own experience?

How did the pirate and privateer history in the novel support the story and offer a new understanding of the Age of Sail vs. Hollywood pirate movies and romance-focused pirate novels?

Is the hunt for authentic pirate gold primary or secondary for Shannon or Paddy? How do you imagine they would handle newfound wealth? What would you do with recovered pirate gold on public land?

How does the thought or experience of treacherous or balmy seas make you feel fully alive?


When Shannon and her husband, Eric, finally talk about being depressed with an empty nest and emptiness in their marriage, Shannon says, “Infidelity begins at home but changes everything.” What did she mean?

Shannon’s budding romance with younger Caesar is kept in suspense. What is going through Shannon’s mind and heart at this stage of her life?

Is it fear, common sense, or other goals that predominate?

Marriage and family is raised as a philosophical and practical question for Shannon, her friends, Daniella, Paddy, Jenny, Anne Bonny, and Caesar. Is a realistic view of modern marriage presented in the story?


Beyond Beauport is an example of cross-genre fiction, mixing elements of drama, nautical adventure, historical fact and fiction with a touch of romance. What scenes or aspects of the book resonated most with you?

Examine the meaning of the statement made by Captain Bill Davis of the schooner Vega: “It is natural to protect our vulnerabilities. Sometimes we bury shame with pride.” What does this mean to you?

How did themes resolve in the final two chapters, Dogtown and Halfway Rock? What was left to ponder? How do you feel about Shannon’s graveside “talk” with her mother, Regina?

At the conclusion of Beyond Beauport, did Shannon’s choice not to complete the race against the schooner boys show a change in her? In what ways has Shannon changed or stayed the same? How does Shannon’s character shape her destiny?

Which parts of the story evoked the strongest emotions in you?