In March, EverWalk proudly launched the 110.86 Mile Club — a virtual walking program that enables walkers to embark on an online adventure with walkers from all over the world. We named our club after the distance I swam from Cuba to Key West. Accompanying each milestone was an email describing my journey. For those of you who missed out on our inaugural adventure, I wanted to share it with you here — in this three-part blog.

Going way back to childhood, I had a buzzing mystique about that forbidden island just off the Florida shores. And I wasn’t the only one. Not only Floridians but people from all over the world have been intrigued and enchanted by the magic that is Cuba. This beautiful Caribbean island has one of the most complex histories of any country in the world. 

During the early 20th century, Cuba was visited by movie stars, foreign dignitaries, sports legends and the wealthy from around the globe. Lured by the Cuban culture, the beautiful weather, the gambling and alcohol, Cuba was the playground of the world’s elite. Frank Sinatra and his Rat Pack, Jack and Jackie Kennedy, would dance salsa into the night to the famous Buena Vista Social Club at the swank Hotel Nacional.  Cuba was also ruled by a dictatorship through that era. The rich were abundantly rich but most people were desperately poor.

When Fidel Castro overthrew the government to bring equality to the Cuban people, he also brought Communism and the Cold War to the Western Hemisphere. After the Cuban Missile Crisis was averted — avoiding nuclear war between the USSR and the United States, Cuba became an isolated nation-state, and to this day remains almost stuck in time. With its crumbling colonial architecture and beautifully-preserved vintage American cars, visitors to Cuba experience an extraordinary cultural time warp.

After trying the epic crossing over a 35-year period, I finally stumbled up onto Smathers Beach in Key West, having swum unaided the 110.86 miles, in 52hrs, 53mins, from the shore of Havana. 

I first tried the crossing back when I was young, in my 20s. That attempt was 42 hours of hell and circumstances just didn’t come together for me to make another go of it back then. Many years later, approaching age sixty, retired from swimming for thirty years, I went back to chase my big dream. Despite failing numerous times, nearly dying from deadly Box jellyfish stings in 2011, I simply refused to give up. My quote from the TED stage: “I don’t want to be the crazy woman who does it for years and years and years, and tries and fails and tries and fails and tries and fails, but I can swim from Cuba to Florida, and I will swim from Cuba to Florida.”

On Labor Day, 2013, at the improbable age of 64, I finally succeeded

For our first Walker Tracker 110.86 Mile Club, we created a route that “walked on water” on the very course I traveled over the surface of the sea — beccause Bonnie (the leader of the expedition Bonnie Stoll) and I wanted to share the Mother Nature on steroids we encountered. We wanted our walkers to drill down to your own true grit out on the road, as I did during the toughest hours. To feel the thrill of a world-class adventure. 

As Bonnie wrote to our group: “As you walk these 110.86 miles that Diana bravely stroked, imagine both the majesty of this particularly stunning azure Gulf Stream and the persistence it took for this individual to keep her mind focused on the other shore. You will be walking on water but let yourself sink into the story of one of the greatest endurance feats in history. The trip touched my very soul. Let it do the same for you.”



We embarked from Marina Hemingway, out on the western edge of Havana. We chose to leave from this famous marina because the waves pounding into the famous walkway, the Malecon, in Havana proper are on many days treacherous, not an easy departure point. At Marina Hemingway there are two lines of large boulders which serve as the entranceway to the Marina. It was there that our five expedition boats and all the Cuban boats could gather until I took the leap from the rocks. The Cuban press could also gather along the boulders for the start. 

As I was standing on the Marina boulders, staring out at the faraway horizon in a surreal moment of overwhelming emotion, my best friend Bonnie by my side, the inspiration behind this epic dream flooded my heart. To connect these two long-separated countries. To travel across a geography that had such rich history, by now called The Cuban Graveyard. We will never know how many Cubans perished to the bottom of that ocean, trying to escape to freedom in the middle of the night on flimsy rafts. The training through those thirty-five years was grueling, to understate it. To take the plunge and start on a 53-hour non-stop effort was the stuff of living life to the nth degree.

The best men and women ocean swimmers had made their valiant attempts. Now it was my turn.  Armed with scientific knowledge accrued from each previous failure, I stood on that Havana shore and represented to the 25 million people following us worldwide the bold attitude:  NEVER EVER GIVE UP.

Marina Hemingway is named after the American writer Ernest Hemingway — one of the most influential literary voices of the 20th century. Hemingway lived in Cuba for over 30 years, though his daughter-in-law and former secretary described him as a not belonging “to any country or person (though maybe to his alpha male tabby cat, Cristóbal Colón)”. 

He enjoyed the land, the sea, great ideas and small ones too, plus sports, literature and everyone who plied an honest trade. He let nothing interfere with his work, not even drink. He had an excessive love for animals and would show unusual kindness to people, but nothing could match his anger.” Hemingway’s Cuban legacy still looms large over the island — in his former finca (ranch), in the places he visited around the island, and in the museum dedicated to his legacy (which remains the most popular museum in Cuba). 

Ernest Hemingway’s legacy is also very much alive in Key West, where his former home is a museum and home to 40 or 50 of the famous six-toed Hemingway cats. Hemingway’s legacy forms a bridge between Cuba and the United States….and I admit I had always hoped, even way back in childhood, to somehow act in building that bridge myself.

As I swam away from Cuba, I could see Havana behind me. 

Old Havana has been endlessly photographed — its beautiful architecture, musicians playing on the streets with 1950s American cars behind them. The new wave of extraordinary contemporary artists in Havana capture its beauty in their paintings. 

It is a place where time and worlds collide. As Brin-Jonathan Butler has written: “In Old Havana, the names of the streets before the revolution provided a glimpse into the city’s state of mind. You might have known someone who lived on the corner of Soul and Bitterness, Solitude and Hope, or Light and Avocado.”

Over the course of my thirty years as a sports journalist, I traveled to virtually every corner of the globe, yet I’ve always considered Cuba my “heart place”. And I’m not the only one who has fell under the spell of Cuba. From every corner of the cobblestone streets, the charm of the people, their music, their pastel colonial buildings, oozes into sheer magic. 

I was in Havana at one time for National Public Radio: My audio man and I approached a man on a big Havana avenue and asked if he knew the American cars streaming by. 

He said: “I am Cuban. Of course, I know the American cars.”

I asked the gentleman:  “Would you mind describing of few of them as they pass by?”

He grabbed the microphone and started in with the next dozen or so beauties that passed.

“Well, here is coming the Chevrolet Bel Air. You will notice this one has the ornamentation on the hood that tells us this is early 1955. OH…here is coming now the dream of every Cuban, the Cadillac Sevilla. Lipstick red with white interior. Look closely the bucket seats with the red trim. AHHHH.”. We thanked him. What a personality. But he held onto the microphone to finish up: “As you can see, to stand on the street corner in Havana is to be in a moving car museum. Have a nice day!”

Cuba is pure charisma.

In 1978, then one of the top open-water marathon swimmers in the world, I made my first attempt to cross the straits between Havana, Cuba, and Key West, Florida. My team was well versed in the danger of the sharks of the tropics—the Oceanic White Tips, the Tigers, the Lemons– so  a $40,000, 20-by-40-foot catamaran with a self-propelling shark cage was created for the swim. 

That summer, I made what would be my first of five attempts over the next thirty-five years. I made it 76 miles over 42 hours before my team pulled me out due to man-o-war stings and strong swells. Career called, offers to work as a broadcaster for ABC’s storied Wide World of Sports. But for the next thirty years, I kept my eye on the swim of my dreams.


About Diana Nyad: 

 A prominent sports journalist, filing for National Public Radio, ABC’s Wide World of Sports, The New York Times and others, Diana has carved her place as one of our compelling storytellers and sought-after public speakers.