The narrator comments on the misfortune that so many documents regarding this important part of Orlando's life are destroyed. Orlando plays an important role in the negotiations between King Charles II and the Turks. While he is out of the country during the Glorious revolution of 1688, many of the records are destroyed.
Orlando finds Turkey quite different from the manor houses he has known in England, but he enjoys Constantinople's wild, exotic quality. He spends his mornings adding bows and flourishes to important letters of state, and his afternoons visiting other dignitaries with much pomp and ceremony. Yet this life tires Orlando, and he would sometimes take the opportunity to go out to the mountains and read his poetry. Though he has a magnetic quality that draws people to him, Orlando finds no close friends in Constantinople. But he carries out his ambassadorial duties so well that King Charles gives him a dukedom, raising him to the highest office of the peerage.
When the officer who carries his official patent of nobility arrives, Orlando throws a huge party. Thousands of people of every nationality are there to see the sight; the rumor has circulated that a miracle is to be performed there. The party is a sight to see. There are fireworks and many English people dressed in their most elegant attire. The narrator pieces the story together, she tells us, from fragments of reports of Lieutenant Brigge who watches the scene from a tree, and from the letters of Miss Penelope Hartopp. The letter reports that half the women at the party are dying of love for Orlando.
Just as Orlando kneels down to place the golden circlet of strawberry leaves upon his brow, a disturbance begins. An uproar arises as natives rush through the door. Luckily, British soldiers are there to quiet the disturbance. Later that night once all the guests are gone, a washer woman sees Orlando the Duke go out onto his balcony, let down a rope and pull a peasant woman up to his room. Then they embrace passionately. The next morning, Orlando's servants find him alone in his room, asleep, with all of his clothes and papers in a mess around him. They try to wake him up unsuccessfully. When his secretaries look through the papers on his desk, they find a marriage license to Rosina Pepita, a dancer.
On the seventh day of Orlando's trance an insurrection occurs. The Turks rise against the sultan and set fire to the town. They try to imprison or kill all the foreigners, but finding Orlando lying still in a trance, they think him dead and steal his robes. As Orlando lies in the trance, three figures enter: Lady of Purity, Lady of Chastity, and Lady of Modesty. They dance around Orlando's body and try to claim him, but trumpets sound. The figures are dismayed that no one wants them any longer. They decide that this is a place for Truth and not for them, so they leave. The trumpeters blast one note at Orlando, "the Truth" and he awakes. He stands upright, naked, and is now a woman.
Orlando is now a beautiful woman, with the strength of a man and a the grace of a woman. Orlando is not at all upset by this change. The narrator tells us that except for his gender, Orlando is in every respect "precisely what he had been." She remembers everything from her past, and the change has come about painlessly. The narrator confirms that up until age thirty, Orlando was a man, and now and ever after, she is a woman.
Orlando dresses, and calmly leaves Constantinople on a donkey with a gypsy. She rides to the mountains and allies herself with a gypsy tribe. The gypsies look upon her as one of their own. She had been in contact with them before the revolution and was now happy to join them at their camp. Her dark complexion and hair help her blend well with them. Though they accept her, the elders of the tribe notice that she often spends long periods of time staring into space. They believe the English disease, a love of Nature, has been bred into her. The old man of the tribe is angered because Orlando loves Nature so much and does not believe what he believes. She spends long periods of time writing blank verse poetry on her manuscript of "The Oak Tree" and she becomes less adept at her chores.
Orlando begins to notice large differences between the gypsies and herself. When she tells them of the enormous house in which she was born and of her ancestral lineage that is 500 years old, she senses their unease. Rustum, the oldest man of the tribe, takes her aside and tells her not to be ashamed of her background. Orlando realizes then that 500 years of lineage is nothing to these people whose ancestors helped build the pyramids. They scorn the person who claims land and builds grand houses because land and buildings are not important to them. They don't need any bedrooms to be happy. To them, her family seems to be an upstart, and even worse, nouveau-riche.
Orlando is upset that she and the gypsies have such different values: she treasures the sunset, they a flock of goats; she sees the value in multiple bedrooms, but they cannot. One day as she lies beneath a fig tree in the heat, Nature plays a trick on her, and she watches a hollow deepen in a rock. Inside the hollow, she can see visions of England, and then she sees her great house and great lawns swallowed up. She bursts into tears, runs to the gypsies and tells them she must return to England the very next day. It is good that she does this, because the young men of the tribe have been plotting her murder. They were happy to send her back to England, and with one of her pearls, she pais her way home and bids them farewell.
The narrative structure of Orlando values the personal over the political. While the main focus of the novel remains the story of the protagonist, we are constantly aware of the historical background of the events. Though the narrative defies a consistent chronological structure, it is possible to piece together the succession of Kings and Queens in order to roughly determine when events take place. During the Glorious Revolution of 1688, for example, when William of Orange usurps the throne from King James II, Orlando is in a gypsy camp far away in Turkey. Such a conflation of actual historical events with the story of a fantastic, fictional life, changes the nature of the biography. It evidences the interconnectedness of all events while allowing the personal, internal story to take precedence over "facts." Thus, Orlando's biography, much of it an internal monologue, exists alongside a framework of other, more 'definite' and more masculine history.
The description of Orlando's gender change is both poetic and sudden. The three ladies of Chastity, Purity, and Modesty attempt to control Orlando while he is in a trance, but the trumpeters of Truth frighten them away, waking Orlando from his deep sleep. When Orlando awakes, he is a woman. This passage may at first appear confusing, but the Ladies and the trumpeters are merely the narrator's means to describe the process of Orlando's change. Modesty, Purity, and Chastity work to cover Orlando, to prevent his new, true self from being shown to the world. But the strong duty to tell the Truth means that the narrator must reveal to the reader what truly happened to Orlando. Though it seems neither modest, nor chaste for Orlando to reveal his himself to the world as a woman, he does so nonetheless. This scene is a metaphor for the act of revealing one's true self to the world, no matter how different it may be from what people may expect. There are those, the narrator writes, who wish to hide the truth in darkness. Orlando as a novel, brings Truth to light, exposing the tenuous line which separates male from female, suggesting that the qualities of both may even be combined into one being.
We learn that Orlando's character hardly changes, except for the appearance of his body. Indeed, to Orlando, the change is so slight that she hardly notices it. She looks herself up and down in a long mirror, and walks calmly to her bath. Gender is not nearly so important to Orlando as the other qualities that make up a person. This idea is immediately apparent in the gypsy passage which follows the gender change. In the gypsy camp, Orlando reveals her deep love and reverence for nature, which is in stark contrast to the gypsies who treat nature as a harmful adversary. The difference between Orlando and the gypsies is likewise highlighted when Orlando talks of her enormous house with 365 bedrooms. Old Rustum takes Orlando aside and tells her that she should not be embarrassed for having so much of what she does not need. The gypsies do not share Orlando's strong English values of property and nature. Although Orlando can change her gender, it is these values that cannot be changed. No matter what her gender, she is forever English, and that remains most important.