Cuba: What Everyone Needs to Know by Julia Sweig. This is the most up-to-date book on what lead to the revolution and how we got where we are today—if you only read one book, this is it.
If you want to know what led up to the Revolution read Havana Nocturne: How the Mob Owned Cuba and Then Lost It to the Revolution by T. J. English.
If you want to know what is happening in Cuba today read Without Fidel: A Death Foretold in Miami, Havana and Washington by Ann Louise Bardach – not as up-to-date as Sweig’s book, but Bardach’s analysis is spot on.
The story of the rise of the Bacardi family is integral to understanding the modern history of Cuba. This book will fill in the spaces between Without Fidel and Havana Nocturne. This is a deeply entertaining historical narrative.
For more in-depth reading
Voices From The Other Side: An Oral History Of Terrorism Against Cuba by Keith Bolender and Noam Chomsky.