Cynthia Voigt grew up as the second child in a family of six. Her parents were well off enough to send her to an exclusive private school in Wellesley, Massachusetts near her family home in Boston. Voigt, according to Anne Commire, remembers her childhood as a happy one, marred only perhaps by competition with her older, more graceful sister. Though she began pursuing publication of her writing from the time she was in ninth grade, she did not persevere in her dream until many years later, as she labored under the illusion that if one publisher rejected a manuscript, it was, evidently, not fit to be published. Voigt majored in English at Smith College, lived in New York City for a year, and then married and moved to New Mexico, where she began to teach. Despite her initial reluctance to engage in such a conventional vocation for women, Voigt immediately fell in love with teaching. Voigt and her husband moved to Annapolis, Maryland not long after, where Voigt taught in public and private schools and where she and her husband were divorced shortly after the birth of their daughter. Several years later, Voigt remarried and, while pregnant with her son, began to devote more time to her writing. She found inspiration in the engaging young adult literature she taught to her middle school students, and when she found her daughter raptly reading her first manuscript, she sensed she had something that worked. The publication of Homecoming, which occurred only after it suffered rejections by an agent and several publishers, and the award of the Newbery Medal to its sequel, Dicey's Song, ushered both success and fame into Voigt's life. While she enjoyed the thrill of success and the immortality the Newbery would give to the Tillermans, little about her life and priorities actually changed as a result of the award. In an interview with theChristian Science Monitor Voigt asserts that she does not necessarily see herself only or even primarily as a writer: she sees both her family and her teaching as playing at least as large a role in her life as writing.
Critics have questioned whether the intensity of Voigt's writing and subject matter makes her books appropriate for young readers, but Voigt, in her Newbery Medal acceptance speech, expresses esteem for literature that "engages the imagination, sets to work the intelligence, fills the spirit," and believes that young people are much tougher than most adults imagine. She expressed her opinion to The Washington Post that young people are capable of handling realistic books that deal with difficult situations, theorizing that her books appeal to young people precisely because they depict young characters who are able successfully to negotiate the dangers of the adult world without the help of an adult. Voigt views not only her readers with deep respect, but also respects her characters: she asserts that she does not have a complete, final, and authoritative understanding of her characters, and that her characters retain a certain autonomy and inner life which even she cannot breach. In her Newbery acceptance speech, Voigt expresses delight that her readers themselves, in their comments and discussions with her, teach her about her characters. To Voigt, writing is a process through which she engages the world and her inner self in conversation and which results in her, like her characters, growing up and transforming.
According to Reid, the inspiration for Homecoming, the first book in the Tillerman cycle, came to Voigt one afternoon when upon seeing a station wagon full of children waiting for their mother, she found herself wondering what would happen to the children if their mother did not return. When Voigt completed Homecoming, she felt that she was not yet done telling the Tillermans' story, and began immediately to write Dicey's Song. Voigt uses both her familiarity with the Chesapeake Bay area and her knowledge of sailing and the ocean as a basis for her detailed description of the Tillermans' lives. According to Commire, the themes of reaching out, symbolized in song, holding on, symbolized in wood, and letting go, symbolized by the ocean and by sailing, guided Voigt as she crafted the entire Tillerman cycle. Dicey's Song picks up themes initiated in Homecoming, and Dicey, who struggled so fiercely to hold on to her family during their journey to Crisfield, learns more deeply in Dicey's Song what it means to reach out to her family members and friends, and also learns the importance of letting go of her painful past. Voigt views her characters as entities entirely independent of her, but admits that she sees an idealized picture of herself as an old woman in Gram, and an idealized picture of her childhood self in Dicey. Like Dicey, Voigt is tempted and soothed by the faceless, ever-changing and eternal call of the ocean, while remaining anchored by and rooted in the love of her family and her life upon land.