The story begins in the Elizabethan era in 1600 AD, shortly before the death of Queen Elizabeth I (Quentin Crisp) in 1603. On her deathbed, the queen promises an androgynous young nobleman named Orlando (Tilda Swinton) a large tract of land and a castle built on it, along with a generous monetary gift; both Orlando and his heirs would keep the land and inheritance forever, but Elizabeth will bequeath it to him only if he assents to an unusual command: "Do not fade. Do not wither. Do not grow old." The queen had treated Orlando as a son of her old age and her mascot, and she considered Orlando as her favorite.When Elizabeth dies, Orlando becomes attracted to Sasha (Charlotte Valandrey) in 1610, the daughter of a Russian diplomat. Orlando was engaged to an English nobleman's daughter at this time. Earl of Moray (Simon Russell Beale) had warned Orlando that his affair with Sasha will be taken as an insult to all English women. Orlando follows his heart and as a result his engagement is broken. Orlando is madly in love with Sasha, but one day he sees Sasha kissing a Russian sailor. Sasha insists that Orlando only saw shadows as the sailor was simply escorting Sasha across the deck of a ship. Orlando declares his love for Sasha and implores her to stay, but she decides to leave once the ice breaks. Orlando is heartbroken.by 1650, Orlando acquiesces and reposes in splendid isolation in the castle (he sleeps for one week straight) for a couple of centuries during which time he dabbles in poetry and art. Orlando tries to have his work validated by noted poets such as Nick Greene (Heathcote Williams), who ridicules him. His attempts at befriending Greene falls flat. He even offers Greene a pension of 300 pounds a yr, but Greene simply laughs at his work. Greene implies that he cannot insult his host as Orlando is rich, but Orlando understands his meaning and sends him away from the castle.Orlando then travels to Constantinople (in 1700) as English ambassador to the Ottoman Empire. The emperor The Khan (Lothaire Bluteau), asks Orlando for British Empire's help in war against mutual enemies. Orlando and the Emperor become good friends and share bread and wine together. After 10 years Archduke Harry (John Wood) arrives and informs Orlando that he has been promoted by his sovereign Queen Anne. At the celebratory dinner, the Emperor tells Orlando that the enemy is at their city gates and demands his help in war. Orlando is forced to pick up arms to keep his promise to the Emperor. Orlando witnesses too much death and blood in the war at the city gates. He falls unconscious. Waking seven days later, he learns something startling: He has transformed into a woman.The now Lady Orlando comes home to her estate in Middle Eastern attire in 1750, only to learn that she faces several impending lawsuits arguing that Orlando was a woman all along and therefore has no right to the land or any of the royal inheritance that the queen had promised. Archduke Harry offers to marry Orlando, to grant her respectability, but she refuses, which offends Harry.Orlando continues to nurse her love for poetry and meets several leading authors of the generation including Swift (Roger Hammond) and Pope (Peter Eyre). She finds that women are their muse, but they have no respect or admiration for females. They also consider a woman without a father, or a husband as "lost".The succeeding two centuries tire Orlando; Orlando falls in love with a US adventurer Shelmerdine (Billy Zane). She feels she has found her soulmate. She has sex with Shelmerdine. Meanwhile the British crown pronounces that Orlando is a female and will lose her property unless she bears a son. Orlando refuses to go with Shelmerdine to the US, the land of liberty and freedom.The court case, bad luck in love, and the wars of British history eventually bring the story to the present day (i.e., the early 1990s). Orlando now has a young daughter in tow and is in search of a publisher for her book. (The literary editor who judges the work as "quite good" is portrayed by Heathcote Williams-the same actor who played the poet who had, earlier in the film, denigrated Orlando's poetry.) Having lived a most bizarre existence, Orlando, relaxing with her daughter, points out to her an angel.