Orlando A Biography is a novel by Virginia Woolf, first published on 11 October 1928. Inspired by the tumultuous family history of the aristocratic poet and novelist Vita Sackville-West, Woolf`s lover and close friend, it is arguably one of her most popular novels; Orlando is a history of English literature in satiric form. The book describes the adventures of a poet who changes sex from man to woman and lives for centuries, meeting the key figures of English literary history. Considered a feminist classic, the book has been written about extensively by scholars of women`s writing and gender and transgender studies.

The eponymous hero is born as a male nobleman in England during the reign of Elizabeth I. He undergoes a mysterious change of sex at the age of about 30 and lives on for more than 300 years into modern times without ageing perceptibly.

As a teenage boy, the handsome Orlando serves as a page at the Elizabethan court and becomes "favourite" of the elderly queen. After her death he falls deeply in love with Sasha, an elusive and somewhat feral princess in the entourage of the Russian embassy.