Fidel Castro probably never imagined a day when Americans would book flights to Cuba on their smartphones.

But, in a mind-bending example of just how quickly times have changed, that day has arrived. It's being ushered in via an Uber-style, on-demand flight app created by Victor, a private jet hire company.

In the wake of restored diplomatic ties between the U.S. and Cuba, few have been quicker than private jet chartering companies to make the most of the cordial, post-Cold War relationship.

Victor, for instance, was among the first private jet chartering companies to offer U.S. travelers direct flights to Havana from 19 U.S. cities. And more recently, the company began witnessing its customers booking flights to the island nation via the Victor app.

"The fact that you can book a trip to Cuba on a smartphone through the Victor app is really as contemporary as it gets," says David Young, senior vice president of North America for Victor. "It's a moment in history that will never come again. It's an exciting period. Visiting Cuba is going to be as commonplace as going to Mexico in the coming years."

While Cuba becoming the next Mexico remains a little hard to imagine, these are groundbreaking and fascinating times, particularly when it comes to the island nation's engagement with the world at large.

In just a few weeks, Cuba will host the first visit from a sitting U.S. president in 88 years, when Barack Obama descends on the tiny country for two days.


Shortly after Obama's visit, the Rolling Stones will hold a free concert in Havana at Ciudad Deportiva de la Habana, the first open air concert in the country by a British rock band.

One can only imagine what Fidel Castro, a dictator famous for jailing people for any actions that might be interpreted as dissent or criticism, must think of all the changes.

In perhaps the most notable recent development for average citizens, the U.S. and Cuba have agreed to re-establish scheduled air services between the two countries. The agreement creates the potential for as many as 110 daily, round-trip flights in and out of Cuba.

Not long after the agreement was inked, United Airlines submitted its formal application to the U.S. Department of Transportation to provide service to Havana from such gateway cities as Newark/New York, Houston, Washington, D.C. and Chicago. The airline's proposed service would include 11 round-trip flights each week, including daily flights from Newark Liberty.

American Airlines, meanwhile, is seeking to operate its own scheduled services, including ten daily flights to Havana from Miami. The airline is also hoping to offer additional service to Havana from hubs in Charlotte, Dallas/Fort Worth, Los Angeles and Chicago.


These are just a few of the airlines reportedly lining up to fly to Cuba. Alaska Airlines, Delta Air Lines, Southwest Airlines, and JetBlue have also submitted applications, according news reports.

The DOT will make the ultimate determination regarding which airlines are awarded routes.

"Flights to Cuba are opening in a big way," says Vinay Bhaskara, a senior business analyst for Airways News. "It's going to get a lot easier to fly to and from Cuba, compared to when there were just the few charter flights operating."

The renewed commercial flights to Cuba are not only a boon for travelers but also a welcome, and very lucrative, opportunity for the airlines, which stand to make millions of dollars from the new routes, notes Bhaskara.

"This is a genuine sort of boost to the U.S. airline industry," he explains. "It's a new source of revenue. This is a huge destination with lots of demand - there's a lot of Cuban Americans who all want to go back...This could add two to three million international travelers a year, and you're talking on the order of a couple hundred million dollars of revenue."

While large commercial airlines vie for a piece of the action, others have already begun figuring out ways to capitalize on present conditions.


CheapAir.com
, for instance, says it was the first online travel agency to sell direct flights to Cuba for qualified U.S. citizens.

The site started constructing itineraries that allowed travelers to get to Cuba as early as last February, says CEO Jeff Klee, by routing fliers through Mexico or Panama City. After that, CheapAir added charter flight inventory to its offerings.

"Once we added the charter flights, that's when it really took off," says Klee.

The site sells tickets for direct, charter flights departing daily from Miami International Airport, Tampa and New York's JFK.

While charters to Cuba are not entirely a new offering, being able to book such a flight online, or via an app like Victor jets for that matter, is definitely part of the emerging, more modern dynamic tied to the country. Each innovation is one more step forward in the march toward Cuban-American relations 2.0.

"This is a huge deal," says Klee of the easing airline industry regulations and increasing commerce. "This was the forbidden market. You couldn't get to Cuba. No one could fly there. Since I've been in this business and many decades before that, American airlines have not flown to Cuba."

One remaining obstacle amid in all of this historic momentum, thawing of relations, and ingenuity, however, is the still standing U.S. law prohibiting Americans from flying to Cuba purely to vacation.

U.S. visitors must continue to meet one of 12 criteria - such as family visits, government work, journalism, professional research, humanitarian work to provide support to the Cuban people or people to people travel.

"Nothing about opening the market to scheduled flights is changing one of those 12 reasons," emphasizes Klee.

Still, those 12 reasons haven't exactly kept U.S. travelers, or businesses offering flights to Cuba, at bay.

Magellan Jets, which offers clients private charter flights, began flying to Cuba within hours of the embargo being removed by President Obama, and business has steadily increased ever since. The company is currently booking about two flights a week to the country.

"After the embargo was lifted, people didn't know what to do, except for us, we were doing our research ahead of time," says Magellan's Joe Scanto.

Victor's Young, meanwhile, says the company has paired with Cuba Educational Travel (CET) to create acceptable itineraries for its U.S. fliers, which are specifically designed to allow American visitors to comply with those 12 regulations.

The customized CET trips include such activities as tours of Havana with urban planners to learn about the city's architectural past and future; dining with artists and musicians and meeting with diplomats to discuss the current political climate among other topics.

"CET creates the cultural exchange," says Young, a service that comes with a price-tag of about $1,000 per day, which covers two people. That fee is in addition to the cost of the flight, which can range depending on the type of plane and departure location from about $15,000 to $20,000 for a roundtrip flight from Miami, to $65,000 to $120,000 from Los Angeles.

While those prices alone will be prohibitive for many, it seems not to have dampened the enthusiasm of the average private jet customer.

"We're getting requests weekly to fly there," says Young. "I would anticipate that will increase to several trips a week in the coming months."

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