Cuba has inspired a rich body of writing — history, memoir, fiction, and photography. A few recommendations for before and during your trip.
Our Man in Havana by Graham Greene (1958) — Greene's spy comedy set in the last years of Batista's Cuba. Funny, sharp, and still the best literary portrait of Havana's faded glamour. Essential reading.
Cuba Libre by Elmore Leonard (1998) — a novel set during the Spanish-American War of 1898. Vintage Leonard: fast dialogue, morally complicated characters, and a good feel for the period.
Waiting for Snow in Havana by Carlos Eire (2003) — a memoir of childhood in pre-revolutionary Havana and the chaos of the 1959 revolution. Won the National Book Award. Beautiful and painful.
Cuba: A New History by Richard Gott (2004) — a serious, readable one-volume history from pre-colonial times through the early 2000s. Good for understanding how the country arrived where it is.
Trading with the Enemy by Tom Miller (1996) — an American journalist travels Cuba illegally in the mid-1990s. Vivid street-level portraits and a useful corrective to both pro- and anti-Castro mythologies.
Dirty Havana Trilogy by Pedro Juan Gutiérrez (1998, translated 2002) — raw, explicit fiction set in 1990s Special Period Havana. Not for the squeamish, but nothing captures the desperation and black humor of that era like this.
The Old Man and the Sea by Ernest Hemingway (1952) — technically set off the north coast of Cuba at Cojímar. Hemingway lived in Cuba for 20 years and is inescapable in Havana; this is his best work, and the setting matters.
Birds of Cuba by Garrido and Kirkconnell — the standard field guide, useful if you're heading into the Zapata wetlands or the eastern mountains.