The first chapter begins by presenting Orlando’s physical appearance and by mentioning the fact that he is a young man from a noble family. Orlando hopes that one day he will be able to go on adventures just like his family did. Instead of being an explorer, Orlando is a poet who likes to contemplate nature and spend his time on the hills overlooking London. One day, Queen Elizabeth I comes to visit and she likes Orlando instantly. Two years after they first meet, the Queen makes Orlando her treasurer and steward. Orlando makes the mistake of kissing another girl, and he is caught by the Queen. Orlando also develops a liking for spending his time with ordinary people, but he soon becomes bored of it and decides to return to the court.
He finds out that the Queen has died and that she was replaced by King James I. Orlando thinks about marrying one of the ladies at the court. He decides to marry Euphrosyne, a woman coming from a noble family, just like him. The lawyers from Orlando’s side and from Euphrosyne’s side start to make legal arrangements, but the procedures stop when the Great Frost begins. It is during that harsh winter Orlando meets Sasha, a Russian princess, for the first time. They fall in love, but Sasha grows tired of Orlando’s moods and eventually runs off with another man.
Orlando begins to write extensively: plays, poems and other forms of literature. A few years later, he meets with Nick Green, a famous author whom Orlando admires. Green is described as being awkward, a short man who is out of his element inside Orlando’s big house. Orlando is disappointed by Mr. Green; after he finds that Green wrote a satirical story based on him, Orlando decides to stop writing and spend his time trying to find the answers to the big philosophical questions about life.
After a while, he decides to write again but for his own pleasure. He also begins to refurnish his home; after he finishes, he invites his neighbors over to see his house and to hear the poem he finished. One day, he sees a woman from his window and Orlando falls in love with her. Not wanting to be trapped in a relationship where he is only attracted by the woman’s physical appearance, Orlando asks the King to send him to Constantinople to be an ambassador. From the third chapter, the reader finds that Orlando played an important role in the negotiations between King Charles and the Turks but the records about Orlando’s deeds were lost. Orlando is well received by the people in Constantinople and he organizes parties frequently. After one such party, the servants see Orlando letting down a rope and bringing a woman into his room. They later find that he married a dancer named Rosina Pepita, but they are unable to ask him details as he falls into a trance from which he doesn’t wake for a few days.
While Orlando is in a trance, a civil war starts and the rebels find Orlando in his bed. Not knowing what to do with him, they steal his clothes and then they leave him be. After the rebels leave, three spirits appear around Orlando; each spirit tries to claim him but is unsuccessful. The spirits leave when they hear a trumpet blast; Orlando wakes up naked in his bed and in a woman’s body. Orlando is not scared and accepts the change that happened. Orlando leaves Constantinople with a gypsy on a donkey and then later joins a gypsy tribe. The elder of the gypsy tribe is displeased to see Orlando spending her time reading and contemplating nature, thinking that such actions are useless. One day, Orlando has a vision and sees her home in England destroyed. After that, she decides to return to England and leave the gypsy tribe behind.
Orlando buys female clothes and returns to England. While sailing to England, she slowly becomes accustomed to being a female. While Orlando is happy that she is now free to think about love and nature as long as she wants, she doesn’t like the feeling of powerlessness she has when she is in the presence of men. When she arrives home, her servants start to serve her again, but she also finds that some people have started lawsuits against her. Orlando sees Archduchess Harriet again, but she tells Orlando that she is actually a man called Harry and that he only pretended to be a woman so she could get closer to Orlando. Harry asks Orlando to marry him, but Orlando doesn’t answer right away. They begin to spend time together, but Orlando soon loses interest in him. Orlando goes to London and the narrator notes the changes that took place in her and how she changes more and more into a woman. While in London, she meets Harry again and Orlando is annoyed that she can’t get away from him. The ladies in London all want to meet Orlando, so she enters the London society. Despite this, she is unhappy and doesn’t find fulfillment in her life.
One day, the Countess of R- invites Orlando to one of her parties. Orlando goes, knowing that the Countess organizes parties where the best people are invited. It is there that Orlando meets Pope, and then she starts to spend her time with writers. She soon becomes unhappy because she realizes that the men around her don’t appreciate her for her intellect. Orlando begins to dress again in men’s clothes; then, one night, while she is in the park, she begins to talk with a prostitute named Nelly who invites Orlando to go with her. After Orlando reveals that she is a woman, Nelly and her friends tell her their life stories. From that point on, Orlando begins to switch from woman’s clothes to men’s clothes, depending on her mood and state. The end of the chapter presents Orlando sitting and watching the clouds over London at the turn of the century.
The fifth chapter begins with a description about London that creates the impression of excess to the point that it becomes suffocating. The action takes place 300 years after Orlando began to write his poem, and the world has changed a lot since then. Orlando goes home, but her home feels cold and empty; there, she meditates on how much she has changed in the last years. She feels like the age in which she lives is too constricting, but she realizes that she must conform to the age, so she decides to marry. Orlando goes and takes a walk; in nature, she finds happiness. She falls down and breaks her ankle when she is near a lake. She is saved by a man named Marmaduke Bonthrop Shelmerdine, and they get engaged immediately. They spend a lot of time together, and soon they realize that they are the opposite of what they said they are: Shel is a woman and Orlando was a man. Orlando and Shel spend almost all their time together, but their time comes to an end when the wind changes and Shel leaves to sail again. They are married in a simple ceremony before Shel takes off.
Alone, Orlando thinks about writing again but doesn’t want to submit to the spirit of the age. Despite this, she finishes her poem, The Oak Tree. Orlando goes to London where she meets Nick Green, now a wealthy writer and critic. He reads her poem and promises to publish it while assuring her that the poem will be well received. After that, she goes to the park where she has a vision of her husband’s ship sinking. She goes then and sends him a telegram. Orlando returns home and spends a good deal of time doing little there. When the narrator picks up the story again, Orlando has given birth to a son.
The year is now 1928, though Orlando is still in her mid-30s. Orlando is frightened by the present, but she is also amazed by the new inventions of the age. Orlando returns home; she thinks about all her past identities and how the house was always with her. She is thrust out of her reverie when she hears an explosion. Orlando runs to the oak tree and plans to bury her book of poetry there, but eventually she decides not to. Orlando knows that her husband will soon come home again and prepares for her husband’s arrival. When the clock strikes midnight, it is October 11, 1928.