The biographer begins Chapter III by stating regretfully that little is known about Orlando's time in Turkey because a revolution and a great fire destroyed many of the documents from the period. Orlando's daily routine involved relaxing in the mornings while looking at the exotic sites of Constantinople from his balcony, visiting with secretaries and high officials in the early afternoon, and then going on exaggeratedly formal social calls all evening. He continues to work on his poem, though people who hear him reciting it to himself think he is praying. He also continues to woo many people, no matter their gender or social class. However, Orlando remains a solitary person; he does not make any close friends. A "certain great lady" (113) follows him to Constantinople from England, but he does not give her his love or attention.
King Charles decides to make Orlando a Duke, and Orlando has the idea to throw an enormous party to celebrate. The biographer reiterates that little documentation from this period of history survived, but she puts together an account of the party from the diaries of an English naval officer and the daughter of an English General, as well as a newspaper story. The event is lavish and very crowded, and everything is going well until midnight when Orlando appears and is given the collar, star, robes, and crown of a Duke. As soon as Orlando puts the crown on his head, there is a great commotion; "natives" (117) run into the banquet hall, and people scream and run. The panic is stopped by British soldiers, and by 2 AM everyone leaves the Embassy.
The night of the coronation, Orlando goes to his bedroom. Accounts from common people living nearby say that he locked the door, which he didn't usually do, and brought a woman into his room by letting a rope down from his balcony. The next day, Orlando does not wake up; like in Chapter II, he seems to be in a deep trance. Orlando's secretaries search his room and find the poem "The Oak Tree," as well as a marriage contract between Orlando and a dancer named Rosina Pepita. On the seventh day of Orlando's trance, the insurrection that was hinted at the coronation begins in earnest: the common people rise up against the Sultan, the city is set on fire, and many foreigners are tortured and killed. When rioters break into Orlando's house, they believe him to be dead, so they rob him but do not harm him otherwise.
Here, the biographer laments that she cannot simply say that Orlando dies and finish the story. Instead, Truth, Candour, and Honesty, whom the biographer calls Gods, blow silver trumpets and demand the real story. The biographer describes a fantastic scene in which personifications of the values Chastity, Purity, and Modesty, who look like strange yet lovely ladies, introduce themselves in turn and then each plead "Spare, O spare!" (121). After each plea, the trumpets of Truth sound. The ladies try to cover Orlando and muffle the trumpets, but it is no use; they cry and run away. When they have gone, the trumpets blast a final time, and Orlando wakes as a woman.
The biographer says that Orlando, who stands naked, is the most beautiful human who has ever existed. Specifically, it is his androgyny that is so attractive: "His form combined in one the strength of a man and a woman's grace" (123). Chastity, Modesty, and Purity throw a towel to Orlando to cover his nakedness, but it falls short. Orlando calmly looks at his body in the mirror and then goes to take a bath.
The biographer pauses the narrative to say that Orlando has changed sex, but did not change mentally or in terms of facial appearance. She says that Orlando will now be referred to using the pronouns she and her. She also clarifies that a reader should not understand Orlando as always having been a woman or actually being a man at present: Orlando was a man until age 30 and is now a woman, as she will be until her death. The biographer then returns smoothly to the narrative, describing how Orlando continues to show no "signs of perturbation" (125) as she washes, dresses in a gender-neutral Turkish coat, feeds her dog, accessorizes with both a pair of pistols and strings of jewels, and moves from her bedroom out into the ransacked Embassy.
Outside the Embassy, Orlando finds a gypsy with two donkeys. Orlando gets on one; she and the gypsy ride out of Constantinople. They ride for several days together and finally reach the settling place of a tribe of gypsies Orlando had befriended before the revolution. Orlando settles into the routine of the gypsies and enjoys not having to do the boring duties she had as an ambassador. However, the gypsies are disturbed by some of Orlando's habits, such as calling things beautiful (or "good to eat" (127), in the language of the gypsies) and sitting quietly in thought for hours. The biographer specifies that it is a love of Nature that came from Orlando's English upbringing. As the gypsies become more fearful and skeptical of Orlando's views, Orlando begins to feel conflicted; she questions whether Nature is beautiful or cruel, and she longs to write poetry. She makes ink from berries and wine and writes in tiny script in the margins of "The Oak Tree," which she has taken with her. Orlando and the gypsies begin to clash even more; they become tense around her and think her presence bad luck, and she feels ashamed when they are not impressed by her lineage or possessions back in England.
Orlando wants to leave the gypsies, but she does not want to become an ambassador again. Lying under a tree one day, Orlando sees a shadow "though there was nothing to cast a shadow" (133). The shadow grows and becomes a hole in the mountain, and, through the hole, Orlando can see a scene of a summer day in England. As she watches, the scene turns violet and snowy. Finally, the hole darkens and disappears completely. Orlando bursts into tears and returns to the gypsy camp to tell them she has to return to England. The biographer notes that it is good that Orlando made this decision because the gypsies planned to kill her. Orlando finds a ship in the harbor that is returning to England and uses a pearl from her necklace to pay for her passage.
Woolf does not specify what exactly changes when Orlando becomes a woman. It is clear that the change is more physical than mental or emotional, since the biographer says that Orlando experiences the world in much the same way she used to before the shift (at least until she returns to England in Chapter IV). The biographer also notes that Orlando's face and body shape were similar enough to before the transformation that people recognize her easily, and some editions of the book corroborate this visually with pictures of Orlando before and after the transformation. A comparison of these pictures—"Orlando as Ambassador" (109) and "Orlando on Her Return to England" (139)—reveals that Orlando indeed looks much the same, with the major differences being dress and demeanor. Thus, it can be inferred that little besides Orlando's genitalia and secondary sexual characteristics, such as facial hair and breasts, were altered during the male-to-female transformation.
When Orlando wakes as a woman, Woolf, and her fictional biographer, make the literary choice not to immediately change the pronouns they use for the character. The author uses he/him pronouns for Orlando in the paragraph following Orlando waking up; for example, Woolf writes, "His form combined in one the strength of a man and a woman's grace...Orlando looked himself up and down in a long looking-glass, without showing any signs of discomposure, and went, presumably, to his bath" (123). In the next paragraph, the biographer grapples explicitly with the question of what pronoun to use for Orlando, writing, "In every other respect, Orlando remained precisely as he had been. The change of sex, though it altered their future, did nothing whatever to alter their identity. Their faces remained, as their portraits prove, practically the same. His memory — but in future we must, for convention's sake, say 'her' for 'his', and 'she' for 'he' — her memory then, went back through all the events of her past life without encountering any obstacle" (124). From this moment in the book onward, the biographer always uses female pronouns to refer to Orlando. This shift occurs for other characters in the book as well, such as Archduchess Harriet/Archduke Harry. In the 21st century, academics and the public alike still discuss the proper use of gender pronouns for people of various gender identities. Woolf's use of "they" as a gender-neutral pronoun is especially interesting, as its usage as the preferred pronoun for gender fluid or non-binary people is rising in popularity.
While Woolf's depiction of gender and sexuality in Orlando was progressive, if not revolutionary, she makes an effort to downplay the topic as the main focus of her novel. Soon after the biographer's discussion on pronouns, she comments, "But let other pens treat of sex and sexuality; we quit such odious subjects as soon as we can" (124). Woolf masks the political and social implications of Orlando's life experiences by focusing on the narrative and stylistic elements of the novel. By doing so, Woolf ensures that less politically inclined or socially progressive readers might become drawn into the story, rather than being pushed away by overt political ideology.
While Orlando is living with the gypsies, the biographer includes the second reference to a culture viewing something that the reader might perceive as normal as a disease. While in Chapter II this was Orlando's reading habit, which his servants and others in English society saw as a pathological desire to escape reality, in Chapter III the thing compared to disease is Orlando's love of nature. The gypsies particularly disapprove of Orlando calling things beautiful (or "good to eat" in the gypsy language (127)) and sitting idly in thought. While the comparison of reading to a disease was based on differences in class, this instance in which love of nature is compared to disease calls attention to differences in culture. When the gypsies confront Orlando about her strange behaviors and beliefs, Orlando starts to resent their culture for being different than her own. Likewise, the gypsies find the difference in culture so abrasive that they plot to kill Orlando, and she is only saved by leaving of her own accord for England.
Orlando's time in Turkey, and especially her time living with the gypsies, presents a foil for her life in England. Orlando's sex and gender transformation does not make much of a difference during her time with the gypsies, which gives her time to process the change within herself. Gypsy women in Turkey do many of the same jobs as men. In addition, men and women in the gypsy tribe wear very similar clothing, something that Orlando sees as a key element of performing and experiencing gender. In contrast, Orlando is treated differently in virtue of her womanhood as soon as she steps onto the boat back to England, especially with regard to her clothing. She is gazed upon and provided for, and, in exchange, she is expected to be modest and respectable. Orlando's power, status, and agency while in Turkey are directly contrasted with her lack of political, financial, and social stability upon her return to England due to her change in gender.