Orlando is a beautiful young English nobleman born in the sixteenth century who physically transforms into a woman around the age of thirty. Possessing a deep, enduring passion for nature and literature, Orlando writes continuously, heavily revising a poem called "The Oak Tree" across several centuries. Aging incredibly slowly, Orlando experiences the shifting social expectations of different eras while seeking artistic inspiration and personal truth.

An unnamed narrator who attempts to compile the facts of Orlando's exceptionally long life. Claiming to value objective historical documentation, the narrator frequently struggles with missing records, damaged diaries, and the impossibility of capturing a person's inner thoughts. Consequently, they often insert personal opinions and imaginative descriptions to fill in the historical gaps.

A Russian princess whose ambiguous winter clothing initially obscures her gender from Orlando. Culturally distinct from the English court, she speaks French and maintains a guarded, independent demeanor. Her presence heavily influences Orlando's early understanding of romance and heartbreak.

A garrulous poet who complains extensively about his health and financial struggles. He frequently criticizes his successful contemporaries, asserting they write only for money rather than artistic glory. Benefiting from Orlando's financial pension, he prioritizes public reputation over genuine creative substance.

A strikingly tall noble figure who takes an intense interest in Orlando. Demonstrating an unusual mix of gender presentations and social behaviors, they persistently pursue Orlando's affections through daily visits and games, heavily parodying the traditional romantic heroes of English literature.

The oldest and wisest man in the Romani group that takes Orlando in. He holds a vastly different perspective on property, nature, and lineage than English nobility. Viewing long family histories tied to land ownership with pragmatic indifference, he offers an alternative philosophy to Orlando's heritage.

A seaman and adventurer who sails around Cape Horn. He possesses a temperament that mirrors Orlando's, freely embracing traits traditionally assigned to both masculinity and femininity. His arrival provides Orlando with a deep mutual understanding and comfortable companionship.

The aging English monarch who heavily favors Orlando. Weary from political unrest and conflict, she is drawn to Orlando's youthful innocence and classical beauty, elevating the young nobleman's status within her court.

An English noblewoman possessing a pristine family tree that aligns perfectly with Orlando's lineage. She embodies the traditional expectations for a nobleman's wife and becomes engaged to Orlando before the arrival of the Great Frost.

The captain of the vessel transporting Orlando from Italy back to England. He directs romantic overtures toward Orlando, prompting reflections on the newly experienced social expectations of womanhood.

A sex worker in eighteenth-century London. Initially assuming a transactional dynamic, she becomes a genuine confidant once she realizes Orlando's true identity, openly sharing her personal life story.

A Romani dancer involved in a brief, clandestine relationship with Orlando in Constantinople. This connection later causes legal complications regarding property claims back in England.

A famous poet in eighteenth-century London society. His physical presence and limited remarks disappoint Orlando, shattering the idealized illusion of literary genius.

A sailor on the Russian ship frozen in the river during the Great Frost. He helps Sasha retrieve her clothes below deck, sparking a significant conflict.