Orlando, Virginia Woolf's sixth major novel, is a fantastic historical biography, which spans almost 400 years in the lifetime of its protagonist. The novel was conceived as a "writer's holiday" from more structured and demanding novels. Woolf allowed neither time nor gender to constrain her writing. The protagonist, Orlando, ages only thirty-six years and changes gender from man to woman. This pseudo-biography satirizes more traditional Victorian biographies that emphasize facts and truth in their subjects' lives. Although Orlando may have been intended to be a satire or a holiday, it touches on important issues of gender, self-knowledge, and truth with Virginia Woolf's signature poetic style.

On January 25, 1882, Virginia Stephen was born to Leslie and Julia Duckworth Stephen. Her father, Leslie, a parson turned agnostic, was a man of letters who served as editor of Cornhill Magazine and later began compiling the Dictionary of National Biography, for which he is best known. Virginia's parents reinforced traditional stereotypes of men and women. Her father was stern and detached; her mother was more emotional and fond of poetry. Virginia had many brothers and sisters, only a few of whom she was close to. In 1895, after the death of Virginia's mother, the family moved to a home in Bloomsbury, London. Here, Virginia became the family writer. Virginia coped with mental breakdowns throughout her life, attempting suicide twice before 1904. Once in Bloomsbury, Virginia's writing career began to take off. With some of her brother's university friends, Virginia formed the Bloomsbury group, a group of young people who worked in different fields, but shared similar interests and had the same goal of rejecting conventional behavior. This group, which so highly valued independent thought, appreciated Virginia's talents.

In 1912, Virginia married Leonard Woolf. Although they had little physical intimacy in their marriage, Virginia respected her husband greatly. His opinion mattered most to her. Leonard supported Virginia by offering her a very controlled, regulated environment, one that was conducive to writing and helped her cope with her mental illness. Virginia's manic-depression was worst just as she was finishing a novel. Unable to handle criticism, Woolf was vulnerable to breakdowns. Leonard helped Virginia channel her energy by starting their own publishing company, the Hogarth Press. Working here gave Virginia some much needed mental relaxation. Writing was not always an easy task for Virginia. A perfectionist, she labored over her novels until the very last moment. But generally, her works were well-received, and Virginia soon became quite acclaimed as an author. Yet mental illness was a battle that Virginia could not win. On March 28, 1941, fearing another breakdown, Virginia committed suicide by filling her pockets with rocks and jumping off a bridge into the river.

Orlando was written at the height of Woolf's career. It was an extremely popular book when it was published. In the first six months after publication it sold over eight thousand copies, whereas To the Lighthouse sold less than half that amount. Woolf's income from book sales nearly tripled with the publication of Orlando.

After finishing To the Lighthouse in 1927, Woolf was prompted by an attachment to her lover, Vita Sackville-West, and by a strong interest in biographical literature to begin Orlando. She wrote in her diary that Orlando was to be "Vita, only with a change from one sex to another." Sackville-West, like the novel's protagonist, was a wealthy woman from a historic and noble family. In the novel, Woolf mocks her friend's brooding, poetic nature, and her family's history, which is detailed in Vita's book Knole and the Sackvilles (1922). Vita and her husband, Harold Nicholson, both openly bisexual, proved great models for Orlando. The novel, replete with lesbian and bisexual undertones, explores the nature of gender difference and sexual identity. It was not entirely unique for its time; Orlando was published near the time of Radclyffe Hall's trial for obscenity for her portrayal of lesbian love in her autobiographical novel The Well of Loneliness. While Woolf's novel skirts explicit description of homosexuality, her sex changes imply a love that reaches across gender. Vita's son, Nigel Nicholson, wrote that Orlando was Woolf's "love letter" to his mother.

While Woolf endeavored to explore Vita through the novel, Orlando also gave her the opportunity to try her hand at the genre of biography. Woolf's father, Leslie Stephen, had spent enormous amounts of time working on the Dictionary of National Biography, an "official" work which gives the facts about the lives of many important English people. In Orlando, Woolf mocks such an attempt to present the facts. By only presenting the external life, Woolf felt that an "official" biography fails to capture the essence of its subject. Although the 'biographer' in Woolf's novel claims to be limited by documents and records, she fully explains Orlando's internal thoughts, feelings, and reflections. In this way, Orlando challenges the traditional notion of truth in description.