Start with The Baron in the Trees. A young Italian nobleman climbs into an oak in 1767 after an argument about a plate of snails and never comes down, living out an entire adult life in the canopy. It is funny, it has a plot, it moves, and it is Calvino doing what he does best — an impossible premise pursued with complete logical seriousness. Crucially, it is a novel. You can read it the way you read novels.
The two books people actually name when they name Calvino are Invisible Cities and If on a Winter's Night a Traveler, and both are wonderful and neither is a good first Calvino. Invisible Cities is a mosaic of prose poems about imaginary cities with almost no narrative pull; If on a Winter's Night a Traveler is a novel about failing to read a novel, made of ten interrupted openings. Come to them once you trust him, and they land as inventions. Come to them cold and they feel like being kept at arm's length.
The fables first
The Baron in the Trees belongs to a trilogy — the other two, The Cloven Viscount and The Nonexistent Knight, are not in this catalogue but are short and worth hunting down. Read Marcovaldo next: twenty small stories about an unlucky labourer chasing scraps of nature through a grey industrial city, one for each season across five years. It is the most immediately charming thing he wrote and by far the easiest way to see his method at short range.
The cosmic middle
Then The complete Cosmicomics, in which an ageless narrator called Qfwfq remembers the formation of the galaxies, the moment the moon was close enough to touch, and the last dinosaur, and turns each into a domestic comedy about jealousy or embarrassment. This is the pivot point: still stories, but the machinery is now openly visible.
Now you are ready for Invisible Cities — Marco Polo describing fifty-five impossible cities to Kublai Khan, each a compressed argument about memory, desire or death. Read a few at a time rather than straight through; treated as a book to finish it goes flat, treated as a book to keep by the bed it is inexhaustible.
Follow it with If on a Winter's Night a Traveler, which is the full metafictional performance and much funnier than its reputation suggests. It is also where some readers get off the ride for good — if a novel that keeps refusing to be a novel sounds like a chore rather than a joke, stop after Invisible Cities and lose nothing.
The reference shelf and the essays
Italian folktales is Calvino's two-hundred-story collection of oral tales gathered from across Italy, the Grimm project Italy never had. Nobody reads it end to end. Keep it and dip in.
The uses of literature collects his essays on writing and reading, useful once you have read enough of the fiction to argue with him. Then close with Six Memos For The Next Millennium, the Harvard lectures he was writing when he died in 1985 — five of the six were finished, on lightness, quickness, exactitude, visibility and multiplicity, and they are the best short statement of what he was trying to do. Read them last. They are a key that only works on doors you have already opened.
A note on order
There is no continuity between these books, so nothing forces a sequence. What the order above buys you is a gradient of difficulty: story, then story with visible seams, then seams without story. Reversed, Calvino reads as a cold formalist. In this direction he reads as what he actually was — a fabulist who kept finding new shapes for the fable. More literary paths sit on Discover.
Follow the full ordered path here: Italo Calvino Reading Order: Where to Start.