Orlando, a young nobleman and one of Queen Elizabeth I's court favourites, is the object of many ladies' attentions, but after suffering heartbreak he prefers literary pursuits to entertaining any thoughts of marriage. Having obtained an ambassadorial post in Constantinople, Orlando falls into a long sleep and wakes up suddenly transformed into a woman. Also blessed with the gift of never ageing, she embarks on adventurous travels throughout Europe and the following centuries, observing what it is like to be female.

A "fantastical biography" inspired by the life of the flamboyant writer Vita Sackville-West, Orlando is an amusing and eccentric jeu d'esprit, as well as a groundbreaking exploration of gender issues.