Read Your Way Through Cuba
10 Books to Inspire and Inform
Cuba is one of my favorite places I’ve ever visited, so gripping it may never let me go. I dream of returning: to walk aimlessly once more, to talk with strangers, to linger over meals beneath the whir of ceiling fans. Cuba doesn’t reveal itself all at once. It gestures. It sidesteps. It sings its stories when it’s too dangerous to speak them aloud.
There’s no single way to understand Cuba, because Cuba, like the best literature, doesn’t want to be understood too quickly. It’s a country caught in the push and pull of memory and reinvention, where joy and hardship live side by side, not as opposites, but as neighbors.
I’ve wandered Havana’s Malecón at sunset. I’ve shared homemade meals in Cuban homes with conversations that go from boisterous to hushed. I’ve watched cigars being rolled by hand, the scent of tobacco hanging in the air. And if I’ve learned anything, it’s that Cuba unfolds slowly: on foot, in conversation, and, yes, on the page.
These books won’t decode the revolution or prepare you for the taste of a freshly rolled cigar. But they might help you listen more closely to the voices that have lived through it all, and imagine the ones still waiting to be heard. I’ve also included links to the writers featured here who are on Substack, so you can follow their work directly.
Non-Fiction:
The Cubans – Anthony DePalma
Ordinary people navigating extraordinary constraints. Through intimate portraits, DePalma captures modern-day Cubans as they wrestle with loyalty, hope, and survival.
Cuba Libre – Tony Perrottet
A wild ride through the Spanish-American War, featuring idealists, outlaws, and yellow journalists. History as adventure (with machetes and mustaches).
Trading With the Enemy – Tom Miller
Part travelogue, part cultural reportage. Miller wanders through 1990s Cuba with curiosity and wit, capturing the contradictions of life under embargo.
Havana Nocturne – T.J. English
Mobsters, mambo, and Meyer Lansky. A gripping account of how the American mafia turned pre-revolution Havana into Vegas by the sea, and how Fidel shut it all down.
Waiting for Snow in Havana – Carlos Eire
An elegiac memoir of childhood in pre-Castro Cuba and exile to the United States. Tender, furious, and unforgettable.
Fiction:
The Old Man and the Sea – Ernest Hemingway
A timeless novella of endurance and dignity, set off Cuba’s coast—sparse, symbolic, and deeply Cuban. Read it over a daiquiri (or a few) at El Floridita, Hemingway’s old haunt. Legend has it he once drank 13 double daiquiris in a single sitting.
Our Man in Havana – Graham Greene
Vacuum cleaner salesman turned reluctant spy. A razor-sharp satire of Cold War paranoia, set in Batista-era Havana with all its absurdity intact.
Cuba and the Night – Pico Iyer
An atmospheric tale of love and disillusionment in Castro’s twilight years. Written with moody, aching beauty by one of my favorite authors.
Dreaming in Cuban – Cristina Garcia
Family, exile, revolution, and reconciliation collide in this lyrical multigenerational novel. Magic realism meets political rupture.
Telex from Cuba – Rachel Kushner
Told through the children of American sugar barons, this novel captures the naïveté and complexity of a nation on the brink of revolution.
These books won’t chart the island’s streets. But they might help you feel their rhythm and stir the same desire I carry still: to be there, to listen, to wander, and to let Cuba keep unfolding.
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