The book describes the adventures of a poet who changes sex from man to woman and lives for centuries, meeting the key figures of English literary history.

[2] This had its British premiere at the Edinburgh Festival in 1996, with Miranda Richardson playing the title role;[3][4] Isabelle Huppert performed in the version in French, which opened at the Théâtre Vidy-Lausanne in Lausanne (Switzerland) in 1993.

This episode, of love and ice skating against the background of the celebrated Frost Fair held on the frozen Thames River during the Great Frost of 1608, when "birds froze in mid air and fell like stones to the ground", inspired some of Virginia Woolf's most bravura writing:Great statesmen, in their beards and ruffs, despatched affairs of state under the crimson awning of the Royal Pagoda ...

The old bumboat woman, who was carrying her fruit to market on the Surrey side, sat there in her plaids and farthingales with her lap full of apples, for all the world as if she were about to serve a customer, though a certain blueness about the lips hinted the truth.

A period of contemplating love and life leads Orlando to appreciate the value of his ancestral stately home, which he proceeds to furnish lavishly.

Only on the ship back to England, with her constraining female clothes and an incident in which a flash of her ankle nearly results in a sailor's falling to his death, does she realise the magnitude of becoming a woman.

Orlando engages energetically with life in the 18th Century, holding court with great poets, notably Alexander Pope, Joseph Addison, and Jonathan Swift.

Once the book shifts to the 20th century, she again encounters critic Nick Greene, apparently also timeless, who reappears and promotes Orlando's writing, promising to help her publish The Oak Tree.

[12]: 60  Woolf also intended the novel as compensation for the sense of loss often felt by Sackville-West who lost her beloved childhood home Knole.

[12]: 63  Sackville-West in a letter praised Woolf for compensation for her sense of loss, saying: "I am in no fit state to write to you...I only tell you that I am really shaken, which may seem to you silly and useless, but which is really a greater tribute than pages of calm appreciation...Darling, I don't know and scarcely even like to write how overwhelmed am I, how could you hung so splendid a garment on so poor a peg...Also, you have invented a new form of narcissism-I confess-I am in love with Orlando-this is a complication I had not foreseen".

[12]: 66  The recurring image of the grey goose that Orlando chases after, but never captures over the centuries is an allegory for the ability to write a truly great novel that Sackville-West longed to do, but never managed.

[12]: 68  When Orlando attempts to define love, he says to himself: "Every single thing, once he tried to dislodge it from his place in his mind, he thus cumbered with other matter like a lump of grass, which after a year at the bottom of the sea, is grown about with bones and dragon-flies, and the tresses of women's hair".

[12]: 69  Woolf intended the book to be therapeutic, to address the sense of loss felt by Sackville-West as well as herself, to provide a "spark" of hope to keep herself from drowning in what she called in her diary "a great sea of melancholy".

[12]: 70 Woolf was often critical of British historiography, which at the time was largely concerned with political-military history, which she accused of neglecting the lives of women, which with the exceptions of leaders like Elizabeth I, Anne, and Victoria, were almost totally ignored.

[13]: 63  Woolf's father, the historian Sir Leslie Stephen, whom she both loved and hated, had proposed in his book English Literature and Society in the Eighteenth Century, a theory that what writers choose to write about reflects contemporary tastes, a "return to nature" as "literature must be produced by the class which embodies the really vital and powerful currents of thought which molds society".

[13]: 65 At the same time, Woolf, though she was critical of many aspects of British life, felt a deep sense of affinity in her country, where the past seemed to live on in so many ways.

[13]: 70  During the course of their visit, a farmer came in with a wagon full of wood to be chopped up to heat Knole, which Sackville-West said had been done for hundreds of years, which gave Woolf the idea of the English past was not dead, but still alive, a theme that is expressed in Orlando by the ageless, timeless nature of the eponymous character.

[13]: 65–66  As part of her attack on Victorian values, Woolf satirized the theories of the influential critic John Ruskin who saw the Renaissance as a period of moral and cultural decline, which he called a "frost".

[13]: 67  On the contrary, Woolf depicted the parts of the book set in the Elizabethan-Jacobean era as one of rebirth and vitality, of a time when "the moon and stars blazed with the hard fixity of diamonds".

[13]: 67  It is during this period that Orlando first falls in love with the Russian princess Sasha, which leads to "the ice turned to wine in his veins, he heard the water flowing and the birds singing".

[13]: 67 That it was in Constantinople that Orlando become a woman reflects the city's status in the 17th century as a melting pot of cultures with a mixed population of Turks, Greeks, Armenians, Sephardic Jews, Circassians, Sudanese, and other peoples from all over the Ottoman Empire, in short a place with no fixed identity that existed half in Europe and half in Asia, making the city the perfect backdrop for Orlando's transformation.

[14]: 180  Furthermore, Constantinople had been founded by the Greeks as Byzantium in 7th century BC; had become the capital of the Roman empire in 324 AD when the Emperor Constantine the Great renamed the city after himself; for centuries had been seen as a bastion of Christianity against Islam; was taken by the Ottomans in a siege in 1453, becoming the capital of the world's most powerful Muslim empire; and was renamed Istanbul in 1924, making the city itself into a metaphor for shifting identities, whatever they be national, cultural, religious, gender, ethnic or sexual.

The American scholar Urmila Seshagiri wrote that the "fixed British hegemonies" of the early chapters set in London and in the English countryside seem "fragile" when Orlando is confronted with the vast, teeming, wealthy city of Constantinople with its multi-ethnic, multi-religious population that appears as a far more powerful and greater city than London, which was Woolf's way of undermining the assumption widely held in 1928 Britain that the British Empire was the world's greatest empire.

The novel's title has also come to stand in some senses for women's writing generally, as one of the most famous works by a woman author that directly treats the subject of gender.

A British film adaptation was released in 1992, directed by Sally Potter and starring Tilda Swinton as Orlando and Quentin Crisp as Queen Elizabeth I.

[21] The play had a major New York revival in 2024 at Signature Theatre Company directed by Will Davis, with Taylor Mac in the title role and featuring an ensemble of LGBTQ+ and gender nonconforming performers.

[24] The League of Extraordinary Gentlemen comics feature Orlando, starting with a mention in The New Traveller's Almanac and short story and cameo in Black Dossier.

[26] In 2023, writer and theorist Paul B. Preciado directed Orlando, My Political Biography, which freely adapts the novel into a documentary about contemporary transgender life and identity.