- Hugely influential in 20th-century literature, Orlando is considered one of Virginia Woolf"s most accessible and exciting works. Roundly considered Woolf"s most playful work, Orlando is the "biography" of a unique individual; a protagonist whose search for satisfaction, for a full and all-encompassing life, is entirely unbound by convention. Starting out as an Elizabethan boy, Orlando travels through distant lands and through centuries on a quest to find self-expression, before becoming a twentieth-century female writer. Conceived as a cryptic love letter from Woolf to Vita Sackville-West, Orlando is an ambitious and revolutionary epic that experiments with form and character to create a work that is at once challenging and exuberant.