Editors' pick: Originally published July 15.

With so many developments emerging between the U.S. and Cuba these days, it can be hard to stay abreast of the latest rules for Americans hoping to travel to the Caribbean island nation.

For instance, just last week the Department of Transportation gave eight airlines tentative permission to offer regular from the United States to Havana.

That news followed an announcement in June that the DOT had approved routes to nine other Cuban cities: Camaguey, Cayo Coco, Cayo Largo, Cienfuegos, Holguin, Manzanillo, Santa Clara, Santiago de Cuba and Varadero

Flights from the U.S. are scheduled to begin in less than two months, ending restrictions that have been in place since the Cold War.

These are exciting times for the two countries as the new normal continues to take shape.

But does this mean average Americans will be able to just hop on a commercial flight and jet off to Cuba?

Yes and...not so fast.

Image placeholder title

The official line is that flying to Cuba from the U.S. for tourism is still not allowed. There continues to be one dozen approved categories, or acceptable reasons for travel. Among the categories are family visits; official business of the U.S. government; journalist activities; professional research or meetings; educational activities and people-to-people exchanges; religious activities; public performance, clinics, workshops, athletic or other competitions; support for the Cuban people; and humanitarian projects.

Most average travelers visit Cuba under the people-to-people or education category, which up until just a few months ago still required obtaining special approval from the U.S. government for such trips. And permission was only granted to travel companies authorized by the U.S. government to provide educational trips, not to individuals. In other words, if you wanted to visit, you needed to go as part of a group with a tour company that provided education oriented itineraries.

However, and this is a key point, in March the federal government relaxed that requirement.

In a move designed to significantly increase the ability of U.S. citizens to travel to Cuba and directly engage with the Cuban people, the Department of the Treasury's Office of Foreign Assets Control (OFAC) and the Department of Commerce's Bureau of Industry and Security (BIS) announced that individuals are now allowed to travel to Cuba.

A March 2016 fact sheet issued by the two agencies reads in part: "Individuals will be authorized to travel to Cuba for individual people-to-people educational travel, provided that the traveler engages in a full-time schedule of educational exchange activities intended to enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people's independence from Cuban authorities and that will result in a meaningful interaction between the traveler and individuals in Cuba."

Translation - no heading to Cuba, plopping on a beach and posting selfies to Facebook.

Image placeholder title

You may, however, head to Cuba to engage in a carefully planned itinerary that involves interacting with Cubans every day.
"As long as you meet the requirements of the people-to-people exchange, you can go to Cuba on your own," explains David Capaldi, president of Discover Latin America. "You still can't go for the purpose of tourism. But you can go for people-to-people interaction. But you must have a full schedule of people-to-people activities planned. You can't do three days of people-to- people and a day at the beach."


What's more, according to the new regulations, individuals must retain records demonstrating a full schedule of authorized activities, should there be any questions.

The essential takeaway here - those flights to Cuba beginning in September are pretty much aimed at you, the average traveler. As long as you have a trip planned that involves a full schedule of educational exchanges. To quote the new government regulations again:

"Previously, the general license authorizing educational travel required such trips to take place under the auspices of an organization that was subject to U.S. jurisdiction and required all travelers to be accompanied by a representative of the sponsoring organization. This change is intended to make authorized educational travel to Cuba more accessible and less expensive for U.S. citizens, and will increase opportunities for direct engagement between Cubans and Americans."

Now onto the intriguing new details regarding airlines and regularly scheduled flights, which were announced last week and last month.

Image placeholder title

The eight airlines that have been given tentative permission to fly to Havana are Alaska Airlines, American Airlines, Delta, Frontier, Jet Blue, Southwest, Spirit and United.

Alaska is the only airline that will fly from the West Coast (Los Angeles) to Havana. American meanwhile will be operating the most flights, four daily from Miami to Havana, and once daily from Charlotte to the island's capital city.

Additional notable routes include Delta offering one flight to Havana each day from New York City, Atlanta and Miami. United meanwhile will offer flights to Havana from Newark, N.J. and Houston, Texas.

Just six airlines, meanwhile, have been given permission to fly to Cuban cities beyond Havana. Those airlines are Frontier, JetBlue, American, Silver Airways, Southwest Airlines and Sun Country Airlines.

If you're curious what ticket prices are likely to be for a flight to Cuba, head over to the American Airlines website and get ready for a pleasant surprise.

The first to post its fares to Cuba, American is currently offering round-trip flights for as little as $262.

Billy Sanez, vice president of marketing and communications for FareCompare, says the intense competition among airlines flying to Cuba is likely to keep fares extremely affordable for the foreseeable future.

"When other airlines jump onto the bandwagon of loading up their fares online, it will be a great competition and fares will get even more competitive," says Sanez.

Already searches on the FareCompare site for flights to Cuba have increased 45% since the government's announcement awarding permission to airlines to begin regular commercial flights.

One last item worth noting - Starwood Hotels & Resorts recently announced the official opening of its 186-room Four Points Havana hotel, the first American hotel to open in Cuba in nearly 60 years.

The property is located in Havana's Miramar district-a business and financial center that's home to many international embassies.

The opening is particularly notable not only because Starwood is the first U.S. based hospitality company to enter the Cuban market, but also because accommodations for travelers in Cuba are in such short supply.

Four Points Havana is just the first of three properties the company will open in Cuba, according to Jorge Giannattasio, Starwood's senior vice president and chief of Latin America operations.

Later this year, or early next year, Starwood will complete work on two luxury properties - a 90-room hotel just 100 yards from the capitol building in Havana and a 27-room boutique offering in the center of Old Havana.

All of the hotels are conversions of existing properties that have undergone extensive renovations. Although he couldn't reveal exact amounts Starwood spent to rehab the aging Cuban hotels, Giannattasio said the price-tag is in the millions.

"We don't disclose exact numbers by property of how much was spent, but between the three properties it will be a multi-million investment to bring things up to standard," Giannattasio explains.

In addition to renovations, Giannattasio says the company has been working feverishly establishing training procedures for local workers to ensure the hotel provides the level of service that guests from around the world have come to expect. The Four Points Havana property, which has already begun accepting reservation, will only employ six expats. The remainder of the staff is local. That approach, of primarily employing local staff, is part of the company's continual effort to reflect the heritage of the countries in which their properties are located.

Like others, Giannattasio sees the approval of regular commercial flights from the U.S. to Cuba as one more positive step in the evolving Cuban American relationship, one likely to help fill the rooms at Starwood's properties on the island.

"The authorization of U.S. airlines to go to Cuba, beginning normal flights in mid-September, is great news," he says. "Today there's about 3.9 million visitors annually to Cuba and depending on how regulations continue to evolve, that number could grow to be 5 million."

Once those floodgates open, it will only be a matter of time before things change in Cuba, and some of the untouched charm it currently retains, is lost. Those who want to see the country before the American businesses and chains arrive, may want to start hammering out that people-to-people itinerary.

"It will change, but hopefully it won't change suddenly or quickly," says Capaldi.