Orlando buys herself English women's clothes and gets aboard the ship to take her home to England. She reflects upon her new gender and the penalties and privileges it holds for her. She thinks how she can no longer swim now that she wears so many petticoats and she questions whether she feels good or bad about needing manly protection. She feels a tingle when Captain Nicholas Benedict Bartolus offers to cut her meat for her. She questions whether the man's or woman's sexual ecstasy is greater, whether it is better to pursue or flee. She decides it is most delicious to yield and see the Captain smile. But Orlando is dismayed at the time and energy it will take her to make herself presentable (obedient, chaste, scented and appareled) as a woman each day. As a person who has been both sexes, she concludes by censuring both sexes equally; women for their limited role and power in society, men for the way they prance about like lords and become fools the second they see a lady.
The ship anchors off the coast of Italy and Orlando agrees to accompany the Captain onshore. When she returns the next morning, she speaks more like a woman than a man, and it is clear that her romantic interlude with the Captain has made her more feminine. She rejoices in being a woman, happy to take on the blights of poverty and ignorance in order to be free of the manly pursuits of power, happy that she may spend her time on contemplation and love. She finds that even though she is now a woman, she is still in love with women, and she realizes she can understand Sasha better than ever before. But Orlando remains conflicted; she does not want her new gender to require her to hold her tongue and "fetter her limbs" remaining powerless to man.
The ship makes its way to England and Orlando stands in wonder at the sights of St. Paul and the Tower of London, which she has not seen for such a long time. London is much different now in the late seventeenth century than she remembered it more than a century ago. There are shops, paved streets, and many people walking about, talking, and shopping. At a coffee shop, she thinks she sees Mr. Dryden and Mr. Pope (English authors) stopped for a drink. She returns to her home to find happy servants awaiting her (who seem confused but content to serve their mistress as they had their master), and to find that several lawsuits have been brought against her. The chief charges are that one) she is dead, and can therefore own no property, two) she is a woman, with much the same consequences as being dead, and three) that she was an English Duke, whose three sons by Rosina Pepita claimed her property. Orlando does not think much of the charges at the moment, and once at home, she takes to reflecting on her religion (poetry) and her history. She concludes: "I am growing up. I am losing my illusions perhaps to acquire new ones." She decides to start fresh upon her poem, "The Oak Tree."
Orlando looks out her window and sees the Archduchess Harriet, the woman whose seductions led her to flee the country. She laughs at Harriet's appearance, thinking she resembles a "monstrous hare." She invites Harriet in, thinking women annoying, and when she turns around, Harriet has turned into a tall man dressed all in black. The "Archduke Harry" asks Orlando to forgive him for the way he has deceived her. He explains that he has always been a man, and he merely dressed as a woman because he was so in love with Orlando when he was a man. Now he asks Orlando to marry him and travel with him to his castle in Romania. Orlando does not give him an answer, but Harry is persistent, returning day after day, though the two can find nothing to talk about. They take to playing a game in which they each bet money as to where a fly will land. Orlando grows so bored with Harry that she cheats in the game, hoping he will catch her. After the twentieth time, Harry finally catches her cheating and is appalled. Orlando, who is relatively new at being a woman, drops a small toad down his shirt. This enrages Harry and he drives away. Orlando is relieved she does not have to marry him.
Orlando does not really care about her title or fortune. All she desires is "life and a lover." She takes off for London in her coach. Here, the narrator takes a moment to point out that Orlando is changing because of her sex; she is a little more modest about her writing, more vain in her appearance. Her outlook on the world changes because of the clothes she wears, because of something intrinsic to the gender.
When Orlando arrives in London, it is not long before she finds a lover. She goes out for a walk on the mall one morning, when suddenly she finds herself surrounded by a mob of people who know her from reports of the lawsuit. She is distressed as the mob closes in, when suddenly the Archduke Harry arrives to whisk her away. He has forgiven her for the frog incident, and has even made a jewel in the shape of a frog to give to her. Orlando is slightly annoyed that she cannot even go for a walk without Harry asking for her hand in marriage. She returns home to find the cards of many great ladies who desire to make her acquaintance; she is thrust into London society.