Orlando, a young man of sixteen, imagines himself slicing the head of a Moor, in the tradition of his father and grandfather before him. Now he is too young to ride with the men in France and Africa, but he vows to have adventures like them someday. His family is noble, and has been noble for as long as they have existed. The narrator describes Orlando's appearance: red cheeks, exquisite white teeth, an arrow-like nose, and dark hair fitted close to the head. He is beautiful. The reader is told he is marked for great things.
Orlando is a poet, and he writes drama, tragedy, description, and sentiment fluently. He goes out into nature to be alone. As he climbs a hill, he looks out over the spires of London and the vast properties of his father, his uncle, and his aunt. He lies down on the ground, imagining himself a part of nature. He awakes to hear a trumpet sound from his house in the valley: Queen Elizabeth I has come to visit them.
Orlando dashes home to change clothes and make himself presentable for the Queen. She immediately takes a liking to Orlando; to her, he represents innocence and simplicity. While he sleeps that night, she gives a great monastic house as a gift to Orlando's father. Two years later, the Queen summons Orlando to her court. She finds him the perfect image of a noble gentleman. She takes a ring from her finger, gives it to him, and names him her treasurer and steward. From then on, Orlando has everything that he wants; he travels everywhere with the Queen. As the winter grows cold, the Queen turns one day to see Orlando kissing a young girl. She is overcome with rage and breaks her mirror with a sword. But the narrator tells us that we must not blame Orlando for this act; the era and the morals are different from our own.
Orlando finds he also has a liking for "low company." He begins to hide his fancy clothes and look for adventures at inns and pubs. One night, the Earl of Cumberland finds him intertwined with a young woman named Sukey, and thinking them phantoms of drowned sailors, he vows repentance for all of his sins. But Orlando soon grows tired of these "low" manners and ways of life. Now that his Queen has died, he returns to court, this time the Court of King James I, and he is received with great acclamation.
He considers three Court ladies for marriage: Clorinda, Favilla, and Euphrosyne. Clorinda is sweet mannered and gentle, but she tries to reform Orlando of his sins and this sickens him. Favilla is graceful and much admired, but after Orlando witnesses her brutal whipping of a spaniel, he decides she is not for him. Euphrosyne has a deeply rooted family tree, much like Orlando, and he concedes that she would make the perfect wife of a nobleman. Their relationship goes so far that lawyers were busy making arrangements for the connection of their two fortunes. It is at this point that the Great Frost comes.
The Great Frost is severe in Britain and many people are dying from the cold. At Court, the King turns the Frost into a sort of Carnival, directing that the river, which is solidly frozen over, should be turned into a type of pleasure ground. One night at this Carnival, Orlando sees a seductive figure that takes his breath away. He is uncertain whether the person is male or female. As it comes closer to him, he finds that she is the Muscovite princess, Sasha. At dinner, he quickly becomes acquainted with her, as they are the only two people who speak French. He falls in love with her and is never far from her side, much to Euphrosyne's chagrin. They make love on the ice, but are not cold. Eventually, their passion cools and Sasha becomes tired of Orlando's melancholy moods.
Sasha and Orlando skate down the river to where the Russian ship is frozen in mid-stream. Sasha climbs aboard to reclaim some of the clothes she has left on the ship, and a young Russian crew member offers to help her find them. Orlando waits on deck for them to return, but when they take a long time, he goes down to look for them. He finds them in an embrace, Sasha upon the sailor's knee. He becomes irate, but Sasha denies that anything improper has occurred. He reluctantly believes her and apologizes for jumping to conclusions, but secretly he holds doubts about Sasha's faithfulness and social stature.
Night falls, and Sasha and Orlando go back to the town. He whispers a French phrase into her ear, which is their signal to run away together. At midnight they are to meet and take off on their flight. Orlando waits for her in the rain, but Sasha never arrives. He takes off on his horse along the river to the sea. There, as the sun rises, he sees that the frozen river has started to melt, and all the people who were on the frozen city are now stranded on icebergs floating down the river. All is chaos as the people trapped on the icebergs look to their doom. Orlando looks to the big ships and sees that the Russian ship is freely moving out to sea (he understands that Sasha is on it). In his rage, he yells insults at her as the ship moves further away.
From the very first chapter, the characters in Orlando are described as strangely androgynous. Orlando is beautiful. His red cheeks are covered with "peach down," lips drawn back to reveal teeth "of an exquisite and almond whiteness, an "arrowy nose," dark hair, and "eyes drenched like violets." His handsome body is accentuated by his "well-set shoulders" and "shapely legs." Although the narrator states that Orlando is a boy, his description is surprisingly feminine. The narrator implies that his appearance crosses gender boundaries. Similarly, Princess Sasha's gender is questionable at first glance. She is of "middle height," "very slenderly fashioned" in a tunic and trousers that disguise her sex. Orlando assumes that she must be a boy because she skates with such speed and vigor. The presence of androgynous characters foreshadows the gender changes that will occur later in the novel. Such descriptions imply that gender is of little importance to beauty or attraction. This theme reemerges throughout the novel.
The narrator is a vocal presence in the novel. Claiming to be a "biographer," the narrator exclaims her good fortune at having such a worthy subject: "Happy the mother who bears, happier still the biographer who records the life of such a one!" It is clear that the narrator will not be at all objective in her history of Orlando's life. In fact, the narrator writes in exactly the opposite way that she claims to be writing. Though she states that she never need "invoke the help of a novelist or poet," she writes in an extraordinarily poetic manner, describing Orlando's eyes as being "drenched like violets." Such conflicted intention and action highlights what Woolf assumes to be the impossibility of writing an "official" biography as fact.
The narrator frequently breaks the flow of the story to explain things from her point of view. When Orlando cheats on Queen Elizabeth with a young girl, the narrator implores the reader to consider the context of his actions: "It was Orlando's fault perhaps; yet after all, are we to blame him? The age was the Elizabethan; their morals were not ours..." The narrator is dismissive of Orlando's actions, excusing him because of circumstances of the time. Throughout the novel, she purposely intervenes to shape the reader's opinion of her subject. Thus, Woolf uses the narrator to challenge the truth of biography.