Grab your curated vacation reading list before traveling to sunny Florida and the tropical Caribbean islands.
Last updated: October 11, 2025
Explore Florida and the Caribbean through the Pages of Books
Perched on the southernmost peninsula of the U.S., Florida feels like another country. With its subtropical weather, tropical plants and wild animals, and a huge cultural and culinary influence from the neighboring Caribbean islands, Florida’s mainland and thousands of small islands or keys, as they are called here, promise a travel experience of a lifetime.
The connection between Florida and the tropical islands in the Caribbean Sea is stronger than it may appear at first. Key West, the southernmost tip of Florida, is located only 90 miles north of Cuba. In the old days, a fisherman could depart from the shores of the northern Caribbean islands and gauge how much he ventured into the sea by the dazzling lights of Miami in the distance.
Today, you can travel between Florida and the Caribbean in less than an hour or several hours, both by plane and boat, depending on your final destination.
With that being said, it’s hard to draw a line between the southern state of the U.S, and the predominantly Spanish-speaking islands. Nor was it necessary for Ernest Hemingway. The famous American novelist had resided in Key West, but spent many summers in the Caribbean, fishing and drawing inspiration for his books, before moving to Cuba.
A couple of books that Dylan and I picked up at the writer’s former abode, now the Ernest Hemingway House and Museum, prodded me to explore more of Florida and the Caribbean through reading. Here are some novels I would recommend that you read before planning a trip to semitropical Florida and the culturally diverse Caribbean islands.
BOOKS TO READ BEFORE TRAVELING TO FLORIDA AND THE CARIBBEAN
1. The Old Man and the Sea
A fiction book set in the Caribbean Sea by Ernest Hemingway
A highly-acclaimed novel, The Old Man and the Sea was the last book Ernest Hemingway saw published. The central character of the story is a Cuban fisherman. The old man is skillful at what he does. After years at the sea between the Caribbean islands and Florida, he is still in awe of the ocean. He respects and admires big fish he brings to his island.
But luck has eluded the old man recently. The fisherman loses his apprentice, a boy who learned to fish and mastered the tricks of the sea from the old man. Now under the pressure of his father, the young man goes to the sea with another, “luckier” fisherman.
The old man is on his own. But he is neither angry nor loses his hope to catch a big fish. He goes out to the sea by himself and faces his biggest opponent, a giant marlin, far out in the Gulf Stream.
2. Hemingway’s Girl
A fiction book set in Florida Keys and the Caribbean island of Bimini by Erika Robuck
The Great Depression is a hungry and hopeless time in Key West, Florida. Mariella Bennet, the daughter of an American fisherman and a Cuban beauty, knows it firsthand. After her father’s death and her mother’s submission to a soul and body consuming mourning, Mariella has to support her family.
On one of rare occasions, when the girl risks all her weekly earnings betting on a boxing match in the hope of winning money to pay monthly rent, Mariella attracts the attention of Gavin Murray. The WWI veteran is involved in the construction of the Overseas Highway in Florida. The man is smitten by the American-Cuban beauty. But he has a wealthy opponent, the famous writer Ernest Hemingway.
When Mariella is hired as a maid by Hemingway’s wife, Pauline, the charismatic novelist becomes an irresistible distraction. His flirtations and an off-island excursion to Bimini are dangerous. Mariella is at a crossroad. Will she cross the invisible line with the larger-than-life writer or pursue her and her father’s dream?
The book Hemingway’s Girl is a fictional work set in Key West, Florida. Many of its scenes take place in the mansion where Hemingway lived with his second wife. And if you’ve ever been to the now house-museum, the author’s attention to details will not be lost on you.
3. The Cuban Heiress
A fiction book set in Havana and at the sea between NewYork and the Caribbean by Chanel Cleeton
In 1934, wealthy Americans escape disruptions caused by the Great Depression onboard the luxury cruise Morro Castle. The massive ship departs from New York City and stops in Havana, Cuba, where its guests enjoy the festivities of the Caribbean before returning to the U.S.
A week-long excursion is filled with luxury, fine dining, dancing, and gambling. For some voyagers, however, the Morro Castle cruise is a means to smuggle people and weapons from and to revolution-racked Cuba.
On one breezy day, two women board the magnificent Morro Castle. Catherine, an orphaned heiress, is accompanied by her fiancé and his two-year old daughter. Elena Palacio travels alone. Two women can’t be more different, except both of them have their own secrets, secrets that can cost lives.
The book Cuban Heiress intertwines historic events with a fictional story set mainly onboard the historic Morro Castle during its last voyage from New York to the Caribbean.
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