The Key West-Havana challenge
J.A.D. McCurdy, Domingo Rosillo and Augustin Parla cross the Florida Straits by air
A challenge is issued and answered
In 1911, Havana’s city leaders, together with the Havana Post, launched the first Cuban Air Meet, putting up an $8,000 prize for the aviator who could first cross the perilous Florida Straits by air.
In the early dawn of January 30, 1911, Canadian aviator J.A.D. McCurdy rose to the challenge. Flying a Curtiss biplane, and with U.S. Navy destroyers stationed 20 miles apart to guide his way by their smoke, McCurdy took off from Key West. He wore a pneumatic life preserver, relied on a small boat compass for navigation, and even had a special hinged recovery platform rigged on the stern of the USS Paulding in case of a forced water landing—an early experiment in shipboard aviation.
McCurdy lifted off at 7:22 a.m., passing over Key West and the destroyers in line. Crowds cheered as wireless stations relayed his progress. But after covering 90 of the 106 miles, his engine bearings failed from lack of oil. At 9:33 a.m., he was forced to alight gracefully on the water, where the USS Terry quickly rescued him.
Though short of Havana, McCurdy’s flight was hailed as a triumph of courage and skill. Later that day, when he arrived in Havana via destroyer, he was met by an ovation from thousands lining the Malecon. His feat proved that long-distance flights over open water were possible—a vital step toward naval aviation and the future of aircraft carriers.
The prize is claimed
Despite McCurdy’s near completion of the overwater flight, the challenge still remained up for grabs. Two years later, two men of Cuban heritage stepped forward, each determined to claim both the record and a new $10,000 reward.
The two contenders were Domingo Rosillo, born to Cuban parents in Algeria in 1878, and Augustin Parla, born in Key West in 1887, also to Cuban parents. Parla trained at the Curtiss Flying Academy in Miami but struggled to afford a plane, while Rosillo earned his license in Paris under Louis Bleriot, who in 1909 was the first man to cross the English Channel by air. By May 1913, both Rosillo and Parla had aircraft in Key West—Parla with a Curtiss seaplane, Rosillo with a Morane-Saulnier monoplane—and the race was on.
On May 17, Rosillo launched from Trumbo Point despite rough seas. Parla’s plane was damaged at takeoff, leaving Rosillo to claim the honor of making the historic first crossing. Accounts differ—some claim Parla fired a revolver in frustration, others that Rosillo carried a monkey mascot—but what is certain is that Rosillo, supported by Cuban Navy ships, landed after roughly 2½ hours, hailed as a hero.
Two days later, Parla succeeded on his second attempt, flying 117 miles to Mariel Harbor with only a compass for guidance. He earned $5,000 for second place and surpassed Rosillo’s distance record, carrying a Cuban flag once borne by José Martí.
Achievements are recognized
Both men were celebrated in Cuba, their rivalry remembered as El Vuelo de los Audaces—“The Flight of the Brave Men.” Rosillo was later honored on a Cuban stamp and monuments in Key West, while Parla’s memorabilia is housed at Key West’s San Carlos Institute. Though their achievements faded from memory, the Smithsonian restored their place in 1995 among aviation’s “Early Birds.” Today, busts and replicas commemorate their courage, reminding us of a time when crossing the Straits by air was a death-defying feat of courage and faith.