Meet Orlando, living in England in 1586. He is young, attractive, noble, and playing a game called "attack a severed head" when we meet him. Being a noble, Orlando gets to meet Queen Elizabeth, and being tight with the Queen (not to mention good-looking and wealthy) gives Orlando some major credibility when chatting up the ladies. He does a lot of flirting until he falls in love with a Russian princess whom he decides to call Sasha. However, Sasha takes his heart, stomps on it with steel-toed boots, and before Orlando knows what hit him, she high tails it back to Russia.
Orlando goes back to his big castle to mope and write poetry. Eventually, Orlando decides to invite an actual poet to his house to get some honest feedback on whether or not he's got any actual writing skill. After six weeks of hanging out with the poet, Nick Greene, Orlando gets a very public answer. How public? Basically, Greene creates a South Park-style spoof of Orlando’s life and publishes it – not quite what our hero was hoping for.
Orlando reads the thinly-veiled spoof and promptly burns everything he’s been writing. He saves one piece called “The Oak Tree,” then orders a pack of elk-hounds, claiming that he is "done with men." Orlando tries to snap out of his blue funk by redecorating and refurnishing his whole castle, but pretty soon he figures out that the whole effect is lost without actual people to put inside his newly redesigned abode. Clearly, the solution is to start partying. Orlando invites all the neighbors over, but then decides to chill by himself and work on "The Oak Tree." After the same strange-looking woman walks back and forth in front of his window a couple times, Orlando realizes he's being stalked and invites the stalker inside for a cup of tea. Turns out the stalker is the Romanian Archduchess Harriet Griselda. Orlando falls in love; well, we (the readers) think it's love, but the narrator tells us that it's actually just lust. Orlando's not interested in anything long term, but unfortunately, Harriet is. Realizing he's a wanted man (pun intended), Orlando skips town.
He skips town…all the way to Constantinople, where King Charles has appointed him Ambassador. Next thing we know, Orlando is thirty-years-old and a woman. After cruising for a while with some gipsies, Orlando goes home to England, where she learns some of the advantages, limitations, and annoyances of her new gender. As soon as she gets home, she gets slapped with a bunch of lawsuits that all stem from the fact that she used to be a man. (Basically, at this point in time women weren't allowed to own the clothes on their backs, let alone their own castles.)
The Archduchess Harriet shows up at Orlando’s castle. Orlando invites her in, turns around to get some wine, and then turns back to find the Archduchess is now the Archduke Harry (there's nothing like a sex change to spice up a story). The Archduke declares his love, but Orlando doesn't want it. After some painfully awkward exchanges, Orlando finally manages to get rid of Harry. She also decides that she wants "life and a lover," and promptly heads to London to find both.
After arriving in London, Orlando parties with the other members of the nobility, but is soon dissatisfied and unfulfilled. She turns to the city’s literary circles in a quest to find great wit, spending time with the writers Pope, Addison, and Dryden, before realizing that, even though they may have great wit, they’re not exactly great people. After more wanderings, a cloud descends upon London and at the stroke of midnight, the nineteenth century begins.
Welcome to the Victorian Age. Orlando isn’t too happy in this age of repression; she constantly feels pressure to yield to the “spirit of the age,” which we learn involves getting married. Since there are no eligible men out there, Orlando turns to nature instead. In the process, she twists her ankle and meets Marmaduke Bonthrop Shelmerdine, Esquire (Shel for short). Two minutes later, they’re engaged. Great, except that Shel spends his time sailing around Cape Horn. After some happy couple time, the wind changes, the two get married quickly, and Shel takes off. We should also mention that the lawsuits’ verdicts restored all of Orlando’s property to her.
Remember that poem “The Oak Tree”? Orlando finishes it, hops into her car (invented when we weren’t looking), and drives off to London in search of someone willing to read the manuscript. She finds her old buddy Nick Greene, who is now a respected literary critic. He thinks the poem is wonderful and promises to get it published. Next, the novel’s style morphs into stream-of-consciousness. The novel ends with the image of Orlando in her backyard, baring her chest and shouting for her husband.