Orlando, Virginia Woolf's 1928 novel, is a fantastical biography inspired by her close friend Vita Sackville-West. The story follows its protagonist across nearly four centuries, beginning in Elizabethan England as a young nobleman. After a passionate affair with the Russian princess Sasha, Orlando serves as ambassador in Constantinople, where he mysteriously awakens transformed into a woman. Living now as a female, Orlando navigates shifting eras and social conventions while pursuing her lifelong dream of writing. The novel culminates in 1928 when Orlando publishes her poem "The Oak Tree" and finds love with Shelmerdine. A playful, pioneering exploration of gender fluidity, identity, and time, Orlando remains a landmark of modernist literature.