10 Books to Read Before a Caribbean Beach Vacation

When Canadians Ann Vanderhoof and her husband Steve quit their jobs in the mid 1990’s to pursue their dream of a Caribbean sailing adventure, they probably weren’t imagining that their life would become one of the most enjoyable travelogues in modern literature. After renting out their house and changing from business attire to shorts and flip-flops, the couple set sail on a 42-foot boat named “Receta” that they would call home for the next two years. An Embarrassment of Mangoes* is the amusing chronicle of their spectacular journey across sixteen countries and no less than forty-seven different islands in the Caribbean. Apart from sunbathing on white-sand beaches, hiking through colorful rain-forests and savoring local rum on deck, Ann Vanderhoof takes a special interest in the region’s exotic cuisine. A few pages into the book, it becomes clear that the boat’s name—translating to ‘’recipe’’ in Spanish—was definitely no accident. The narrative encompasses tips for shopping at local markets, accounts of some of the most peculiar dishes the author came upon, as well as detailed recipes for heavenly meals, all written in a refreshing, enchanting style.

Back in the early 1960’s, Trinidad’s government invited Nobel prize winner V. S. Naipaul to revisit his birthplace and document his experience. The result was The Middle Passage*, the author’s first travel narrative of many to come that takes readers on a sentimental year-long journey through Trinidad, Jamaica, Martinique, Suriname and British Guiana. Naipaul paints a realistic picture of the modern Caribbean societies while explaining how profoundly colonialism and slavery affected them in the past and analyzing how the indigenous cultures, languages, values and politics have been shaped and defined by foreign civilizations through the years. An excellent read for those that want to get a better understanding of Caribbean’s past and develop a more educated perception of its present.

Set in the 17th century, Pirate Latitudes* invites readers on a fearless, treasure-hunting, swashbuckling, bootlegging piracy adventure in the Caribbean seas. The story begins on the island of Jamaica, a distant Crown colony and more specifically in Port Royal, a town of shady taverns frequented by notorious, cutthroat, backstabbing, groggy pirates with questionable morals. The plot follows Captain Charles Hunter, a Harvard graduate-turned-privateer who tries to make a living for himself in this rather hostile environment. When Jamaica’s governor hires Captain Hunter to investigate a rumor that has a galleon loaded with unimaginable treasure waiting to be repaired in a nearby port, all hell breaks loose. Crichton’s New York Times best-selling novel is a suspenseful tale of skulduggery, theft and betrayal, with useful insight on Caribbean’s maritime history and its legendary piracy era.

In a wonderful blend of fiction and history, James A. Michener undertakes the extremely demanding challenge of squeezing hundreds of years of history in a few hundred pages – and easily comes out on top. The story* begins in the 14th century and goes on to cover the most critical points and periods of the region’s turbulent past. Tales of cannibal tribes, the Mayan Empire, European settlers, pirates, politicians and revolutionaries unfold in a masterful, beguiling prose that celebrates Caribbean culture and its boundless diversity.

What happens when an unsuccessful vacuum-cleaner salesman gets recruited by the secret services to gather intelligence on nuclear facilities during the Cold War? The answer is ingenious comedy in the form of political satire. Walking a tightrope between an espionage thriller and a ludicrous parody, Greene’s classic novel is the tale of James Wormold, an everyday store-owner who becomes a spy in order to sustain his daughter’s lavish way of life. Wormold is more than happy to collect paychecks for filing fictitious reports about imaginary undercover spies and nuclear weapons, until he comes face to face with the most disturbing truth—all of his lies are somehow turning into reality and coming back to haunt him. Our Man in Havana* is not only an entertaining read with brilliant storytelling but also a kaleidoscopic depiction of the Cuban capital’s society in the 1950’s, with insight on culture and lifestyle that is still relevant today.

Jelly-Schapiro’s Island People takes the readers on an insightful voyage to Haiti, Barbados, Trinidad, Cuba, Jamaica, Puerto Rico and everyplace in-between with the scope of re-discovering the islands’ cultural identities and reinstating their significance in how modern civilization was shaped. Starting with Christopher Columbus—who set foot on a Caribbean island mistaking it for an Asian shore—the author argues that the region has repeatedly been defined by a series of misconceptions and false assumptions by outsiders. Sandy beaches, exotic food and a tropical climate might be more than enough to spark a flame in a traveler’s imagination, but this masterpiece comes to show that there is much more to the Caribbean than that. Jelly-Schapiro examines the region’s politics, languages, religions, music and culture and explicitly demonstrates how the place “where globalization began” and its peoples contributed to the making of the modern world as we know it.

It’s not long after freelance journalist Paul Kemp moves from New York to San Juan, Puerto Rico for a new job that he finds himself hilariously entangled in a web of mystery, lust and deceit. The author sets the tone from the beginning of the story, by having the protagonist drunkenly board the plane to Puerto Rico and instantly fall in love with a woman that he soon finds out is a colleague’s girlfriend. What ensues is a fascinating, rum-drenched tale of secrecy and corruption against the backdrop of palm-tree-lined beaches and tropical landscapes. Hunter S. Thompson’s very first novel is considered to be semi-autobiographical in a way, as the author himself moved from New York to Puerto Rico in the 1950’s to pursue a career at a local newspaper. Whether or not the rest of the plot was based on real-life events or was just a figment of his imagination was never clarified, but one thing is for sure—The Rum Diary* will leave you with the bittersweet taste of a rum cocktail and an appetite for adventure.

The title says it all. This is one of the most entertaining, humorous books set in the Caribbean. For those of you who don’t know her, Dear Miss Mermaid is a very popular blogger that had been living in the Caribbean for over twenty years, before relocating to the US. She has been writing in two blogs in a style that she defines as “the comedy of living on the edge of reason in the Caribbean”. This book is a collection of sixteen hilarious short stories based on real-life events that are guaranteed to put a smile on your face and make you start planning your own trip to a tiny tropical paradise.

Florida-based author Carl Hiaasen is indisputably one of the funniest crime fiction novelists of the last decades. Even though his books are usually set in Miami, Bad Monkey* takes us to the Bahamas, where inspector Andrew Yancy tries to solve a rather bizarre murder case. His only lead is a frozen human arm and his allies are the most heterogeneous cast of characters ever imagined: the victim’s widow, two real estate agents, a berserk fugitive, a quirky coroner, a local voodoo witch and, last but not least, a very bad monkey. Once again, Hiaasen amazes readers with a fast-paced plot, a dark sense of humor and exquisite storytelling.

No list about books related to the Caribbean islands could ever be complete without having at least one Hemingway title on it. Instead of going with the obvious choice of The Old Man and the Sea, however, we’ve decided to highlight one of the author’s lesser-known works. First published in 1937, To Have and Have Not* is the story of Harry Morgan, a poor fisherman who agrees to run contraband between Key West, Florida and Cuba in order to provide for his family. In doing so, he gets involved with some dubious characters and finds himself enmeshed in a peculiar love affair. This classic novel is a razor-sharp account of the Caribbean’s harsh realities and social relations during the Great Depression, filled with historical references and astute analogies. It has been—loosely—adapted for the big screen several times, most notably in 1944, with William Faulkner co-writing the screenplay.