Woolf and Vita Sackville-West were both members of the Bloomsbury Group, which was known for its liberal views on sexuality. The two began a sexual and romantic relationship that lasted for a decade, and continued as a friendship long after that. Notably, this inspiration is confirmed by Woolf herself, who noted in her diary the idea of Orlando on 5 October 1927: "And instantly the usual exciting devices enter my mind: a biography beginning in the year 1500 and continuing to the present day, called Orlando: Vita; only with a change about from one sex to the other".
Nigel Nicolson, Sackville-West's son, wrote, "The effect of Vita on Virginia is all contained in Orlando, the longest and most charming love letter in literature, in which she explores Vita, weaves her in and out of the centuries, tosses her from one sex to the other, plays with her, dresses her in furs, lace and emeralds, teases her, flirts with her, drops a veil of mist around her.": 307