Cuba: How I Spent The Revolution

At 1:30 a.m. Saturday, Sept. 27, 1958 I flew aboard a Capital Airlines Vickers Viscount aircraft non-stop from Detroit’s Willow Run Airport to Miami International, then via National Airlines to Havana, Cuba, arriving at the luxurious Habana Hilton Hotel at 9:30 a.m.

As I waited for my luggage in my room on the 19th floor, overlooking the hotel’s artistic entryway, I watched a local school marching band parade past a growing crowd in front of the hotel – while Fidel Castro and his band of revolutionaries prepared to march from the Sierra Maestra Mountains in Oriente Province to Cuba’s largest city, to overthrow Fulgencio Batista’s corrupt and oppressive regime and form a revolutionary government. In August 1958, the Fidelistas began their approximately 550-miles long march from Santiago to Havana. 

Cuba was a surprise, unique, exciting, beautiful, friendly, sensation-filled, life-changing and, ultimately, frightening experience for a 26-year old, skin-diving-crazy, unattached, adventure-seeking copywriter from the Motor City. Unknown to me at the time, Havana was the sex capital of the world, a haven for Meyer Lansky and his friends, home to the famous Tropicana’s topless dancers, 18-to-20 year old beautiful women in every bar, and all only 90-miles from Miami Beach. I thought I had died and gone to heaven—until that became a very real possibility. No one mentioned to me during my trip planning that there was a very real, bomb-throwing, gun-shooting, revolution in progress!

Castro was on his way, and the Cuba I visited was about to disappear forever.

Still, I made wonderful friends there. Some were killed soon after I left. Some of my memories bring tears to my eyes and my heart. Sights, smells, sounds, voices, I will miss forever. Scuba diving off Miramar under the watchful and threatening eyes of Batista soldiers; my room and luggage searched while I was distracted by a Cuban girl at the hotel bar; dinner at the home of a Cubana Airlines pilot and President of the Pan American Skin Diving Association; meeting—in passing—a 10-foot shark in the bay off Morro Castle; a local fisherman’s son who hugged me when I gave him the gratuity his father had earned but refused to accept. And the bomb that shook the ground the night I left.

At 1:30 a.m. Monday, Oct. 6, 1958 I reluctantly, sadly, somewhat fearfully fled Cuba. Fulgencio Batista ran for his life on Jan. 1, 1959. On Jan. 8, Fidel Castro arrived triumphantly in Havana.

The adventures of Jac Flanders are available in an e-book titled, What I Learned On The Way Down on Amazon.com.