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.