FLY THE SKIES TO HAVANA

In October of 1920, Aeromarine West Indies Airways was awarded the airmail contract from the U.S. Post Office for the Key West to Havana route. By November 1 of that year, it began the first scheduled international air mail and passenger service in the United States. Operating daily, the flight took one hour vs. eight hours by ship. The amphibious planes offered accommodations for eleven passengers, had a crew of three, flew at 85 mph, and could carry 300 pounds of freight.

As it was Prohibition, the flight was referred to as the "Highball Express." Aeromarine flew the Key West/Havana route in the winter and, in the summer, operated a New York City to Long Island flight, among others. By the time it ceased operations in 1924, Aeromarine had instituted a number of "firsts" beyond the first scheduled international U.S. passenger service, including "first in-flight movie" on a flight out of Chicago in 1921.

An Aeromarine flight from Key West landing in Havana harbor, with Morro Castle in the background.

Boarding in Key West for the flight to Havana.

In 1927, Juan Trippe picked up the slack by securing the air mail contract for the Key West/Havana route. He was 28 years old at the time. Trippe had attended Yale but quit, joining the Marine Corps as a flying cadet at the start of WWI. Unable to pass the eye test but anxious to fly, he asked his New York investment banker father to appeal to Franklin Roosevelt. Assigned to ground school for instruction in Miami, Tripp became a pilot. Trained and ready, the war ended before he could progress further but he'd gotten one thing out of the deal - his pilot's license. Trippe returned to Yale, graduated, and worked on Wall Street, but he couldn't forget his time in the air and was soon in Key West with his plane, applying for the air mail contract.

By January of the following year, he, too, was ready to add passenger service between the two island cities. That first passenger flight took off on January 16 aboard a Tri-motor Fokker and the manifest was full - all eight seats were occupied. Among those first passengers was the Cuban consul to Key West, Jorge Ponce, President Calvin Coolidge's aide, John Loudon, and Cuban baseball great turned Washington Senator, Baldomero Acosta. A one-way ticket cost $50.

(Left) Boarding that first flight in January, 1928.

But Trippe had problems regularly filling those eight seats for daily flights. So he hired a PR rep, Vick Chenea, to entice passengers. Chenea would board The Havana Special and bribe porters on board to point out which passengers were continuing on from Key West to Havana. He would then concentrate on convincing those passengers to buy a plane ticket.

It must've worked, for the airline did well, and soon adopted as its name Pan American Airways.

There remained a connection between Pan Am and the Florida East Coast Railway into the 1930's. Mail would arrive daily by train from Miami, then transferred to the plane and sent to Havana. And flights from Key West to Havana would be advertised in railway stations and on board the trains themselves.

The last airline to run regularly scheduled flights, Key West/Havana, was Aerovias "Q."

A copy of Cuba Airguide from 1956 containing all the information a traveler would need.

Next: Drive to Havana