There's the issue of airport capacity: Currently, Key West is only approved by U.S. Customs and Border Protection to process 10 passengers and crew flying in from Cuba at any one time. The airport is working on an expansion that would eventually allow it to process about 70.
"If you would have a 30-seater, or a 25-seater that could do flights, that could be a profitable operation," said John Cabanas, former president of C&T Charters, which initially wanted to do the flights but has since closed.
Key West and Cuba have a long and intertwined history. So when President Barack Obama announced in 2011 that he was directing agencies to allow all U.S. international airports to apply to allow licensed charters to operate Cuba flights, Key West was among the first to apply.
There are now 19 U.S. airports authorized to provide flights to the Caribbean nation, which has had limited diplomatic relations with the U.S. since shortly after the 1959 revolution. Under Obama, travel to Cuba has increased. U.S. citizens can once again apply for so-called people-to-people licenses, which encourage cultural and educational exchanges. Cuban-Americans also have returned to visit the island in rising numbers.
Cuban officials have said they receive as many as 500,000 visitors from the United States annually, most of those Cuban-Americans visiting relatives.
The majority depart from big cities like Miami and New York. But Key West has long held a special place in the story of U.S. and Cuba relations.
Cuban poet and independence leader Jose Marti visited Key West to rally support from the island's large and wealthy Cuban population in 1892. He spoke to workers in the island's many cigar factories and at the San Carlos Institute, a stately building that still proudly hangs a large Cuban flag from its balcony.
The first flight ever to depart from the island left en route to Havana, as did the first commercial Pan American Airlines plane in 1928. And there were once daily ferries.
That history is still palpable today. Locals boast Key West has at least 20 Cuban coffee shops and just one Starbucks.
In October, it appeared the flights were just around the corner.
Mambi International Group, a travel agency, teamed up with charter operator Air Marbrisa Airlines to operate a flight. Mambi executive Isaac Valdes said the flights would be set to depart Nov. 15.
But one week before, Bob Curtis, the head of Air Marbrisa, wrote to Horton to say flights were being delayed. He said Mambi had failed to obtain a required certificate from the Department of Transportation. Curtis set the new date of departure as Dec. 15. He declined to comment when reached by phone.
Horton said companies have also faced delays with Cuban authorities. One interested charter agency said it had applied to the Office of Foreign Assets Control over two years ago and was still awaiting approval. Robert Valle, president of Florida AeroCharter, Inc., said he checks in periodically, including just three months ago.
Valle said he was told all the company's documents were complete and were being processed.
"In other words, 'Don't call us, we'll call you,'" Valle said. "Pretty frustrating."
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