First Flight Key West brewery
  • Key West's First Flight Island Restaurant & Brewery isn't just a popular eatery -- its historic building is known as the birthplace of Pan American Airlines. (Photo courtesy of First Flight)

     

  • By: Carol Shaughnessy
  • August 12, 2020

Legions of contemporary television viewers have been obsessed with the adventurous reality show “The Amazing Race.” Chances are, though, they don’t realize that more than 100 years ago, Key West was the site of one of the most amazing races in history.

In 1913, Domingo Rosillo became the first person to fly from Key West to Havana — in a plane some called “the motorized kite.” (All photos courtesy of Key West International Airport)

The year was 1913 — and the race was a competition between two early aviators to make the first flight from Key West to Havana, Cuba.

The competitors were Domingo Rosillo, who was born in Algeria and lived mostly in Spain, and Key West native Agustin Parla, whose father owned a toy store and had been a friend of Cuban patriot Jose Marti. According to Alex Pascual, author of an intriguing book on Key West’s Cuban heritage, Parla graduated from Miami’s Curtis School of Aviation in 1912 — becoming the first Key Wester ever to be certified as an airline pilot.

Naturally, when the city of Havana and the Curtis School announced a competition to determine who would become the first pilot to fly from Key West to Havana, Parla jumped at the chance to compete.

So did Rosillo. By May 17, 1913, each had acquired a plane and both were ready to attempt the flight — estimated at about 110 miles. As well as the honor of making the first crossing, they were vying for a $10,000 prize.

Around 5:10 a.m., Rosillo took off from Key West, battling significant winds in a plane some had reportedly dubbed “the motorized kite.”

About 45 minutes later Parla followed — but encountered mechanical problems almost immediately and was forced to return, ending his attempt.

Key West native Agustin Parla was forced to abandon the race when his plane developed mechanical problems — but he repaired it and successfully completed the flight to Cuba two days later.

Rosillo flew onward. Just over 2.5 hours later he landed in Havana, winning “The Amazing Race” and sparking wild celebrations.

Agustin Parla, however, was determined to repair his plane and complete the journey. On May 19, carrying a Cuban flag that Jose Marti had flown at Key West events, he took off for Havana without telling a soul. Though he narrowly avoided a crash landing, he reached Mariel, Cuba, and accomplished his goal.

The race of 1913 wasn’t the end of Key West’s pioneering role in flight. In 1927, the island was the birthplace of one-time aviation giant Pan American Airlines. And before that, it was home to Aeromarine Airways.

In 1920, Aeromarine began America’s first official international airmail service, between Key West and Havana. Aeromarine also inaugurated America’s first scheduled international passenger service — and strangely enough, passengers and sacks of mail were charged the same fare for the trip.

Pan Am’s first international flight was nearly as dramatic as the race between Rosillo and Parla.

By Oct. 11, 1927, the fledgling airline possessed a contract with the U.S. Post Office to deliver mail between Key West and Havana — but that contract required the first load of letters to be delivered by Oct. 19.

Today, Key West International Airport continues the island’s rich tradition as a leader in aviation innovation.

Unfortunately, Pan Am’s planes hadn’t arrived (despite being ordered 18 months earlier). Luckily, a seaplane pilot named Cy Caldwell was persuaded to make the flight.

At 8:04 a.m. Oct. 19, he left Key West with seven sacks of mail holding approximately 30,000 letters.

And while his journey made history as Pan Am’s first “official” flight, it was so brief that he landed in Havana about an hour before the cable from Key West arrived … announcing his departure.

Today, Key West’s unique place in aviation history is widely recognized — as is intrepid airman Agustin Parla.

Years after “The Amazing Race” with Rosillo, he helped develop the island’s Meacham Field, which later evolved into Key West International Airport. Fittingly, in 1957, a bust memorializing Parla’s accomplishments was installed in a place of honor at the airport.

(Heartfelt thanks to Alex Pascual for providing the background information about Agustin Parla and Domingo Rosillo.)

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