Orlando uses money from the sale of another pearl to buy noble women’s clothing to wear on her journey home. She travels on a ship called the Enamoured Lady. Orlando reflects on how her clothing presents both limitations and privileges for her now.

Early in the trip, Captain Nicholas Benedict Bartolus approaches Orlando and offers to cut her a piece of roast beef. After considering the differences in sexual appetite and expectations across genders, Orlando decides to flirt with the Captain so that she can see him smile. Orlando bemoans the effort it takes for a woman to be both desirable and chaste.

When the ship anchors off the coast of Italy, Orlando accompanies the Captain onshore. After this romantic interlude, Orlando begins to act more femininely. She is happy to be a woman, despite the difficulties. It allows her to be free of manly pursuits of power, and to be free to “more fully enjoy the most exalted raptures known to the human spirit which are [...] contemplation, solitude, and love” (Chapter 4, Page 119). Orlando reflects on how all her lovers had been women. And despite being a woman, she finds that she still loves a woman, Sasha, though she can now understand her better.