Virginia Woolf's early impression of the aristocratic, free-loving woman of letters Vita Sackville-West was not exactly complimentary: 'Not much to my severer taste – florid, moustached, parakeet coloured, with all the supple ease of the aristocracy, but not the wit of the artist.' Her opinion soon changed, however, and she found herself falling in love with the patrician dynamo who had already caused a scandal by eloping with Violet Trefusis, daughter of a mistress of Edward VII. The sexual aspect of the affair between Virginia and Vita was brief, but the emotional side was intense and longer-lasting.

In 1927 To The Lighthouse had just been published to mostly complimentary reviews. Virginia was struggling with a non-fiction book and wondering what to write next. In a letter to Vita she wrote: 'Yesterday ... I couldn't screw a word from me; and at last dropped my head in my hands: dipped my pen in the ink, and wrote these words, as if automatically, on a clean sheet: Orlando: A Biography. No sooner had I done this than my body was flooded with rapture and my brain with ideas.' What emerged from this moment of inspiration was one of Virginia's most popular works, a cod biography, a satirical history, a rumination on gender, sexuality, and creativity, a love letter to Vita, and an attempt to woo her away from her latest conquest, Mary Campbell – A book that Vita's son, Nigel Nicholson, called Vita in Wonderland.