Have you ever gone 84 days without taking a fish?
Whether you have writer’s block or you’re lacking inspiration in general, you may identify with the hero of Hemingway’s The Old Man and the Sea.
Of course, this wasn’t the only great work by Ernest Hemingway. He also wrote classics like For Whom the Bell Tolls, A Moveable Feast, and Islands in the Stream.
Where did all this inspiration strike him? The beautiful island nation of Cuba, where he lived for over 20 years.
What drew Hemingway to Cuba? What was his life like while he lived there? And what remains of his legacy on the island today?
In this post, we’ll delve into these questions and more. We’ll also reveal details about our Ernest Hemingway tour of Cuba–and why you’re sure to love it!
Hemingway and Cuba: Love at First Sight
Ernest Hemingway first set foot in Cuba in 1928.
He left his home in Key West, Florida on a ship bound for Spain. En route, the boat docked in Havana, where Hemingway and his family spent three days at the Hotel Ambos Mundos.
Four years would pass before Hemingway returned to his beloved island. In 1932, he and several friends cruised down to Havana for the city’s annual Marlin run. It was on this trip he got “hooked” on the sport from his friend and master fisherman, Carlos Gutierrez.
The following year, Hemingway bought his own boat, “Pilar,” and began making annual trips to join in the Marlin run. He even wrote articles for Esquire magazine about his fishing adventures in Cuba.
In 1939, shortly after the outbreak of World War II, Hemingway bought a house in Havana with his third wife Martha. The couple lived happily at Finca Vigia (“lookout house”) with their many cats, whose descendants live on today.
During his years in Cuba, Hemingway wrote and published some of his greatest stories. No doubt the island’s beautiful surroundings and the magical atmosphere was the perfect setting for his inspiration.
After Hemingway’s death in 1961, his home passed to the Cuban government. In recent years, it has been restored and turned into a museum that delights visitors from around the world.
Interesting Ernest Hemingway Facts
In many ways, Ernest Hemingway seems larger than life. What else is there to know about this fascinating man?
Here are some fun facts you’ll appreciate before your tour.
1. He Was (Almost) a Cellist
Hemingway’s mother was obsessed with the idea of her son becoming a musician. She even kept him home from school one year and forced him to learn the cello.
The result? Hemingway proved more stubborn than his mother, with no desire or ability to play. As he put it, “I played the cello worse than anyone on earth.”
2. He Had Terrible Eyesight
During World War I, Hemingway’s poor eyesight limited what he could do on the battlefield.
Instead, the military made him an ambulance driver, where he saw plenty of action and received many combat wounds.
3. He Won a Nobel Prize While Living in Cuba
In 1954, Hemingway received a telegram informing him he was being awarded the Nobel Prize in Literature.
He won the award for his story The Old Man and the Sea, which he wrote during his time in Cuba. The gold medal remains at the Catholic Church at El Cobre to this day.
4. He Was Married Four Times
Hemingway loved women–sometimes a little too much. Always in and out of love, the writer was married four times and divorced three.
The names of his wives were Hadley, Pauline, Martha, and Mar Welsh. His longest marriage lasted 15 years.
5. He Was a Bit of a Superhero
During his lifetime, Hemingway experienced more than most people ever will.
On the short list, he managed to survive two plane crashes, a ruptured spleen, exposure to anthrax, a fractured skull, and malaria. The only thing that could stop him was himself–he took his own life in 1961.
What to Expect on an Ernest Hemingway Tour
An Ernest Hemingway tour is the perfect way to follow in the writer’s footsteps and see Cuba through his eyes.
At the same time, a tour gives you the freedom to customize your itinerary to include other things that interest you too.
Your tour will begin with a pick up at your hotel or cruise port in one of our stunning classic cars. During the morning, you can choose between visiting Havana’s Old or Modern Districts–or a little of both!
When hunger strikes, you’ll enjoy lunch at a local paladar. One taste of those delicious black beans and fried plantains and you’ll understand why Hemingway stayed for 20 years.
With a full belly, you’re now ready to visit Hemingway’s favorite bars and eateries. El Floridita and Bodeguita del Medio still look almost the same as they did when the writer sat in their bars.
No Ernest Hemingway tour would be complete with exploring Finca Vigia, his residence during his years in Cuba. This rustic bungalow is filled with mementos of the writer’s life, from hunting trophies on the wall to his beloved fishing boat in the backyard.
At the end of the tour, you’ll be returned to your accommodation via the same authentic classic car. Could there be a better way to spend a day in Havana?
Ready to Be Inspired?
The facts are clear: Ernest Hemingway loved Cuba. You will, too, once you visit and experience an Ernest Hemingway tour and all this beautiful island has to offer.
From Hemingway to Havana and classic cars to mojitos, Cuba has something for everyone to enjoy.
Are you still in the process of planning your trip? Do you have questions about where to go, what to do, and how to get around?
Check out our Info & FAQ page for more helpful information. We look forward to seeing you soon!

