In 1600, a young nobleman, Orlando, is visited by the aging Queen Elizabeth I who bestows upon him an estate, on one condition: he must remain forever youthful. Magically, Orlando obeys, not aging a day over the centuries. His journey starts in the Elizabethan era, where he navigates the complexities of court life and poetry, while trying to understand the nature of love as commanded by the Queen. Orlando's loyal heart falls for a Russian princess, leading to an icy romance that ultimately teaches him the first of many lessons about the fluid nature of relationships and gender roles.

Over the course of his eternal life, Orlando transitions from the role of a duke to that of an ambassador in 17th-century Central Asia, embodying various iterations of gender and class. Amidst wars and changing social norms, Orlando adapts while maintaining an introspective quest to find meaning and passion. The film explores the protagonist's transformation across four centuries, shifting genders from male to female in a society rigid with its expectations. Orlando experiences the constraints and privileges of both genders but continues throughout to pursue intellectual and romantic fulfillment, questioning the true essence of identity and the eternal human spirit.