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Cuba: You Can (Soon, Maybe) Get There From Here

A view of Plaza Vieja in Old Havana, Cuba
Brian Snelson

It’s been more than five decades since you could hop a commercial flights here in the U.S.A. and head south to Cuba. But if you’ve ever imagined yourself perusing the colonial squares of old Havana, maybe ordering up a daiquiri at El Floridita like you’re Ernest Hemingway, you might soon be able to. And in a twist on an old New England adage, "you might even be able to get there from here."

Despite the warming relations between the U.S. and Cuba, Americans do still need to meet one of a dozen criteria to visit the island nation. But getting there, which today you can only do by charter flight, is about to get a whole lot easier. 

In a deal signed last week, the U.S. government is set to soon approve 20 daily commercial flights between the U.S. and Havana—and up to 90 daily flights to smaller airports in other Cuban cities. It's kicked off a scramble among major airlines eager to add Cuba to their portfolio. In all his years covering the commercial airline industry, Seth Kaplan, editor for Airline Weekly, says he's never seen anything quite like it.

"This big bang where Cuba goes from this almost untouchable place to a place where suddenly Americans can travel there rather freely is unprecedented," Kaplan said. "Most of the major U.S. airlines—so we’re talking more than a half dozen—are going to be trying to get their hands on these permissions to fly to Cuba."

American, Southwest, Jet Blue and Delta have all said they want in. Kaplan says that regulators at the U.S. Department of Transportation, who will determine which routes get approved, will likely award a good chunk of them to flights that originate in cities with large Cuban-American populations, like Miami, Fort Lauderdale and New York City. But not all of them.

"If anything, that’s really Boston’s hope. Just the fact that [regulators] are going to make that concerted effort—probably—to spread the flights around not just give them all to one or two places.

Thomas Glynn, CEO of Massport, which operates Boston Logan International AIrport, says they’re doing more than just hoping for one of those flights. They’re planning for it. Back in December, Logan was one of 22 U.S. Airports to secure approval from U.S. officials for travel to and from Cuba.

"We took the initiative to make sure that we were being designated by [U.S.] Customs and Border Protection, so we’ve been gearing up for this for a little while," Glynn said. "We are ready to go."

Now all they need is for one of the airlines to select Boston as a location for one—or more—of their flights.

"A lot of the major airlines are looking at Cuba and a lot of the major airlines are looking at Boston as a possible location," said Glynn. 

Glynn said that, for the airlines, it’s all about the potential profitability of a Boston to Havana route. And he says that Boston is rife with organizations whose employees and constituents would put plenty of passengers in the seats.

"The group of folks working on the Ernest Hemingway House, Catholic Charities of Cuba, the Road Scholar organization, the large number of universities we have," he said.

Add to that the many Bay State biotech firms interested in developing relationships with researchers involved in Cuba’s innovative healthcare industry, and Glynn says a Boston-to-Havana flight would be a smart bet for airlines.

"I think we have a strong market here and I think that if any of the airlines to select us as one of their pilot locations they’ll be very pleased with the enthusiastic response that their gonna get," he said.

While Glynn declined to say which airlines were including Boston in their application, Airline Weekly's Kaplan said that if he had to bet on one airline that would be eager to fly from Boston to Havana, he’d bet on blue.

"Logically Jet Blue, as the largest airline there, you can certainly imagine them wanting to step forward and be that airline," he said. 

We won’t have to wait long to find out how this all plays out. The deadline for applications from the airlines is March 2, the Department of Transportation is expected to announce which routes have been selected in mid-March, and flights could be up and running by the end of the year.

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