On a barren landing strip in Agramonte, in central Cuba, a swayback horse nosed for scraps in the weeds. Off to one side, the decaying hulk of a Russian tractor—its wheels long gone—stood rooted in place by rust. In the distance, rows of green sugar cane waved in the breeze. On a 10-day journalist visa in 1999, I traveled to what had once been busy grass airfields and paved landing strips all around Cuba. In Agramonte, some 435 miles from Havana, I walked the length of the old runway, kicking at the grass and looking for tie-downs, landing lights—any hint that aircraft had ever landed here at all.

Almost 50 years before, on a warm fall day, I had stood on the edge of the same strip, holding my mother’s hand as we watched a DC-3 float down for a landing on what was a lush, manicured grass field beside a central, or sugar mill. The cargo airplane gleamed in the heat waves as it settled. I was just four, but the image of that day was burned into my memory—the shiny silver fuselage, the wisp-wisp of the propellers slicing the air, and my mother’s perfume mixing with the smell of the freshly mowed grass as she leaned down to tell me, “That’s your uncle and father in that plane.”

Ours is a family of pilots. All four of my mother’s brothers were aviators. Two died in airplane crashes. The others were Cuban military pilots, as was my father. Born at a military hospital at Campo Columbia airfield near Havana, I still remember the lines painted on taxiways, the roar of the Allison engines in my father’s P-38 Lightning, and the forest-green airstrips at places like Agramonte.

What none of us could have known on that day in September 1957 was how dramatically our lives—and aviation in Cuba—would soon change. For even as my father and uncle brought that DC-3 down for a landing, a powerful force was taking shape in the slate-blue mountains surrounding the field. There, guerrillas loyal to Fidel Castro were fighting to overthrow the regime of Fulgencio Batista, whose three decades in power had spanned the golden age of aviation in Cuba. Castro’s forces would take control on New Year’s Day 1959, and with their arrival began the chaotic, downward spiral of aviation that, in less than three years, would result in the grounding of virtually all private airplanes in Cuba.

Of course, other authoritarian regimes around the world—in the Middle East, in Africa, in Asia—have either tightly restricted private flying or banned it altogether. But Cuba is unique in that, for more than 40 years, it had a vibrant flying community. Three schools taught hundreds of Cubans how to fly. Numerous airstrips were laid down all over the island, usually near large sugar plantations. And because of Cuba’s close relationship with the United States, a steady supply of private aircraft flew in, out, and around the island.

Cubans had embraced aviation with a passion from the beginning, when in May 1910 a French aviator, Andre Bellot, astonished Havana residents by flying his 60-horsepower Voisin biplane over a grassy plain in the city. Three years later, two Cuban pilots—Domingo Rosillo (with a naval escort) and then Agustin Parla (with only a compass)—made the 90-mile flight from Key West, Florida, to Cuba and were hailed as heroes. In 1919, the Compania Aerea Cubana set up the first flying school in Cuba, using Farman F-40s. The following year brought the first Cuban airline service and the first airmail flight. Charles Lindbergh stopped by on his goodwill tour of the Caribbean, landing the Spirit of St. Louis in Havana on February 8, 1928.

In the 1940s, Benigno Diaz—now 96 and living in Miami—set an aviation record of a different sort: He put together Cuba’s first homebuilt, assembled from plans in Popular Mechanics, with the help of a childhood friend, Roberto Gude. In 1938, Diaz and Gude used wood from fish crates and poplin from a fabric store to begin constructing the island’s first experimental aircraft. “It took us years,” Gude says. “We had to beg for every nut and bolt and piece of fabric and wood. Everything on that plane was improvised.”

The landing gear was crafted from automobile exhaust pipes. One friend, a pilot, donated a 65-hp Continental engine and the tires off a Piper J-3 Cub. After seven years, the airplane dubbed La Estrella Errante (Wandering Star) was finished. Diaz’s father was there for the 1945 maiden flight. He approached his son, put his arm around him, and said, “Benigno, are you sure you tightened all the bolts on that thing?” Diaz nodded. He climbed into the cockpit, turned the aircraft onto the grass field, and gave it power. Gaining speed, the little airplane bounced and lifted off. “It flew very well,” says Diaz, who still has a small model of his handiwork. “It was the first flight of the first homemade plane on the island.”

La Estrella Errante joined many other airplanes to take part in an annual celebration in Havana called The Day of the Aviator. The festival, which had begun in 1953, was held every May to commemorate the Florida-to-Cuba flights of Domingo Rosillo and Agustin Parla. As part of the festivities, private aircraft landed on public streets, then taxied parade-like down the capital’s coastal boulevard, the Malecon. Hundreds of people lined the sea wall, and pilots would wave at the admiring crowds like princesses on May Day floats.

“It was wonderful, like a dream,” recalls Diaz’s daughter Alba. “The airplanes and the sea wall, the crowds of people. I remember someone lifting me up and into the little plane to sit on my father’s lap. We taxied around the Malecon in the parade.”

Luis Palacios, 67, who soloed in a Piper J-3 Cub when he was 19, remembers the heart-stopping landings the pilots had to make. “You had to land the plane directly on the street,” he says. “Sometimes it was tricky with the crosswinds coming off the water. The planes were mostly tail-draggers. Then all the planes would taxi the length of the Malecon with people hanging onto the wings, helping guide the plane through the crowds. It was spectacular. I’ve never seen anything like it anywhere else in the world.”

Such bravado was typical for the pilots. In those days, private pilots in Cuba flew unencumbered by airspace regulations or control towers, says Palacios, who flew for Eastern Airlines after coming to the United States in 1961. “You could take off from one town, fly along the coast, and see a beach and land on it. Many pilots used to land on hard-packed sand beaches, have lunch or a swim, and get back in the plane and take off. Of course, if you do that today [in the United States], you have the FAA and the NTSB and everybody else on top of you in minutes.

“Some pilots never bothered with actually getting a license,” Palacios says. “Somebody taught them the basics of flying and they just flew. There were no sectionals [charts], no radios, and no electrical systems. The planes were hand-propped, and it was basic stick-and-rudder flying. But many of those pilots without licenses were a bit reckless. There were times unlicensed pilots would fly under bridges or do barrel rolls over houses. I think there might have been an element of machismo at work there because it wasn’t very safe.”

Palacios’ most vivid memories from that time were simply of the romance of flying in Cuba. “There was a fragrance,” he says. “Not just a smell. It was a fragrance that would waft in through the open windows of those small planes. If you were flying into coffee fields or sugar cane fields and especially tobacco fields—it was wonderful.” While some Cuban pilots flew for the sheer enjoyment, many others were training to become airline or cargo pilots. They wanted the glamorous position of airline captain, and they had several flight schools in Cuba to choose from—one in Havana, one in Santiago de Cuba, and the third, a floatplane school, on the Rio Almendares, Havana’s main river.

Several factors Spurred the growth of general aviation on the island, chief among them Cuba’s proximity to the United States. “In those days, Americans and Cubans traveled back and forth from Cuba and Miami the way we do now between Miami and Fort Lauderdale,” Palacios says. “Cuba was only an hour or so away from the States by plane. There were all the flight schools in Miami. There was the Pan Am base in Miami. Many pilots trained in flight schools in Miami, bought planes there, and flew them back to the island.”

During the 1940s and ’50s, more and more American pilots made the crossing to Havana; airports and grass fields all over Cuba were crowded with private airplanes. One travel brochure of the time had a drawing of a leather-helmeted pilot flying a small airplane from Florida. The headline read: “Just a ‘plane’ hop and you’re in Cuba.” Another, which read “For Private Pilots Only,” had a goggled pilot playing the maracas with a comely senorita, her skirt billowing as she dances. The brochures offered an image of an exotic paradise of casinos, nightclubs, and dance halls, where rum flowed like water and women were always available. One flight school airplane sported an advertisement on the underside of its wings: “Drink Bacardi Rum.”

But in January 1959, everything began to change. Within weeks of Castro taking over, a new guerrilla war broke out in the mountains of central Cuba, pitting “counter-revolutionaries” against the new government. Sensing danger, some Cuban and American pilots began flying their aircraft off the island. The first to leave were the professionals. “It was the upper and middle class that could afford the private planes that left Cuba right away: doctors, lawyers, bankers,” says Jorge Rodriguez, editor and publisher of On Cuban Wings, a history of Cuban aviation.

But where some saw turmoil, others saw opportunity. Cuban expatriate pilots began flying their airplanes in from Miami to drop anti-Castro leaflets all over the island or bring guns and ammunition to the counter-revolutionaries, just as Castro’s forces had flown private airplanes against Batista’s regime. Several anti-Castro exiles even flew impromptu sabotage missions, dropping homemade bombs from their Cessnas and Pipers. Though the missions had little effect, the flights angered the Cuban government, which promptly began grounding civilian airplanes. The Day of the Aviator parade was canceled. Orders were given to shoot down any unauthorized airplane in the skies over Cuba, and Castro—fearing an invasion was imminent—drew closer to the Soviet Union.

Throughout 1959 and 1960, Castro began nationalizing everything on the island, from banks and oil refineries to Cuba’s airline, Cubana de Aviacion. As the split with the United States grew, the exodus of private aviation accelerated. Like flocks of migrating birds, airplanes quietly lifted off from grass fields and small airports all over the island. Cuban and American businessmen and tourists piloted Beechcrafts, Luscombes, Cessnas, and Pipers back to the States. Mobsters fled aboard Lodestars and DC-3s.

“Pilots were escaping with anything that flew,” says Rodriguez. “Castro tried limiting the amount of fuel for private planes to try to keep them from having enough range to reach the U.S., but pilots still found gas and opportunities [to escape].”

Finally, in early 1961, the United States broke off diplomatic relations with Castro’s government. Commercial flights between the two countries—including airmail—ceased. Airplanes, private and commercial, were being hijacked at gunpoint all over Cuba by pilots or passengers desperate to leave. At least 19 aircraft were hijacked from early 1959 to the spring of 1961, according to Rodriguez. Those who made it to the United States were officially welcomed and given asylum. “Anyone escaping Castro’s Cuba was considered a political refugee,” says Palacios, who flew away in his Cessna 310 that summer from Rancho Boyeros airfield near Havana.

I remember my own flight from Havana as a seven-year-old in early 1960. A friend of the family and an airline captain helped my mother and me get visas under assumed names. Like all departing Cubans, we were searched, and whatever personal items we carried were confiscated. As we waited in line to board the Aerolíneas Cubanas DC-3, our pilot friend put his arm around my mother’s trembling shoulders, stuffed a forged ticket in her purse, and whispered: “Los turistas no lloran”—Tourists aren’t supposed to cry.

Wearing green uniforms and carrying rifles, rebels with beards and shoulder-length hair watched the line of passengers, looking for counter-revolutionaries. If the people were just turistas, the thinking went, they would not cry. If they cried, they were escaping. If they were escaping, they would be caught and jailed. After we were seated, my mother’s arm tightened around my shoulder as the bearded men boarded the airplane and, after a few moments, pulled a middle-aged man in a starched white guayaberra from his seat. There was a nervous pleading in the man’s eyes as he walked down the aisle, between the rebels. My mother could not stop trembling. A little less than an hour into the flight, the pilot came back to get me. He brought me forward to sit in the cockpit for the landing in Florida. As the DC-3 descended through a thunderstorm, past the blur of windshield wipers, I saw the coastline of Key West. My mother, alone in the back of the plane, could finally cry without the fear of being seen either by the rebels or by me.

My father, Rafael Sr., and uncle, Luis Rojas, would join us later in Miami’s Little Havana neighborhood. As pilots in Batista’s air force, they were jailed as enemies of the state after Castro came to power. My father would spend a few weeks in prison before escaping with the help of a rebel soldier and the Brazilian Embassy. My uncle didn’t fare as well; he spent 23 years in political prisons before making it to Miami, and is mentioned in Armando Valladeres’ book Against All Hope: A Memoir of Life in Castro’s Gulag. (My hopes of revisiting Cuba for this story were dashed when I learned earlier this year that a videotape of my documentary on Cuba’s 1960s political prisoners had been smuggled into the country and viewed by a group of independent journalists at a clandestine meeting in Havana. The Cuban government rejected my repeated attempts to obtain a visa.)

After the failed April 1961 Bay of Pigs invasion, in which a CIA-backed force of about 1,500 armed Cuban exiles tried unsuccessfully to invade a beach in south-central Cuba, Castro aligned his government firmly with the Soviet Union and confiscated all remaining private airplanes. “With the Russians coming in right after the Bay of Pigs, everything
became Soviet,” says Rodriguez. Cuba’s air force got new MiGs, while its domestic airline got old Antonov An-2s and Ilyushin Il-14s. Almost at once, U.S.-built airplanes on the island were endangered: Spare parts were almost impossible to get, and without spare parts an aircraft is practically useless. “The Cuban government sold some to Latin countries,” says Rodriguez. “What planes had not been flown from the island were cannibalized and finally sold as scrap aluminum.”

Perhaps the last private airplane out of Cuba was a single-seat Air Tractor that flew from Havana early in the morning of October 26, 1961, according to Rodriguez. A pilot and mechanic escaped in the airplane, which was fitted with cropdusting gear on the wing’s trailing edge. As the pilot checked the ailerons, tires, and oil level, the mechanic found a comfortable position to lie on top of the wing. The pilot took a rope and looped it around the mechanic’s wrists and waist, strapping him to the wing. The cropduster lifted off the grass field and into a rosy dawn. Some three hours and 40 minutes later, the aircraft and its hog-tied mechanic touched down to safety in Key West.

At the height of general aviation in Cuba, there might have been as many as a thousand private and student pilots on the island, Rodriguez says, and “probably hundreds of private planes, if not a thousand.” But since many logbooks and flight records stayed on the island, it is difficult to get an accurate number. In the end, any airplane that was not hijacked, used in anti-insurgency operations, or shot down was grounded—in most cases permanently—and seized as the property of the Cuban government.

“I would say it only took one, maybe two years to completely end general aviation in Cuba,” says Palacios. “The counter-insurgency, then the mass exodus of Cuban pilots, the Bay of Pigs, and finally the Soviet involvement. Not to mention that there was no more private property. You couldn’t own a private car, much less a private plane.” Adds Rodriguez: “Cuba is still a centralized Soviet style system where the state owns and runs everything. There is no private anything.”

When I last saw it in 1999, the grass field near Havana where Diaz and La Estrella Errante took flight was a weed-strewn open lot, and the fate of that homebuilt airplane was unknown. Some say it was shipped to a military airfield in Cuba. “We heard it was there in mothballs,” Alba Diaz told me later. “But we don’t know for sure. Someone else said the plane had been left outside on a tie-down and simply rotted.” Covered with house paint, its primitive construction “would not have stood up very long outside,” her father agreed.

All around the island, the airports and flight schools that once sparkled with the glint of painted canvas were gone. The 10,000-acre sugar, tobacco, and coffee plantations that were the unofficial homes for private airplanes were portioned into small, peasant-farmed agricultural collectives. At Jose Marti airport in Havana, I saw no private airplanes, save the occasional European corporate jet hissing to a gate, carrying a diplomat. The few American pilots were mostly with charters, although it is legal—with permission from both the U.S. and Cuban governments—to land private American aircraft in Cuba.

Flight in Cuba today is military aviation. The Cuban military makes no secret that it owns Gaviota, the Cuban tourism agency, which in turn owns the hotels and night clubs on the island. Gaviota also owns the domestic airline, whose Antonovs and Ilyushins are flown by military pilots, the only type of pilots still trained in Cuba. “When you step aboard a Cuban airline,” Rodriguez says, “the air crew will be MiG pilots.”

Across the island, American cars from the 1950s—wire-tied and cannibalized—still sputtered along the roads. Left behind by their owners, the cars had become the property of the state, on loan to those the government favored. But in the skies over Cuba, there were only jumbo commercial airliners, the old Antonov and Ilyushin transports, and the contrails of MiG-29s.

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