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Reality Check: In Cuba, The More Things Change, The More They Stay The Same

07/21/2016 03:35pm ET | Updated July 21, 2017
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"There are McDonald's and Starbucks all over Cuba now, right?" "I've already missed my chance to see the island as it was before the U.S. relaxed restrictions." "Now that I can fly a bunch of different airlines to Cuba, why shouldn't I go whenever I feel like it?" In my decades in the travel industry, I've never seen a destination become so popular so quickly or generate more questions and more misconceptions.

We're coming up on two years since the U.S. took the first steps to normalize relations, and it's time for a sanity check on what has and hasn't transpired. After all, according to some sources, more than 3 million visitors have landed on the shores of Cuba, the most ever until that point. But 2016 is on track to beat those numbers handily with around 2 million visitors in just the first six months.

I speak on a daily basis with leaders in the Cuban travel industry, my company introduces a steady stream of curious visitors to the country, and I've been lucky enough to make a number of visits to the island myself. With that feet-on-the-ground knowledge, let me give you a reality check to keep you up to speed and in position to win the cocktail party conversation.

First and biggest, let's talk airlines. Yes, a number of companies including Delta, American, JetBlue and United have preliminary clearance from the U.S. government to begin flights to a variety of Cuban airports. But wait a second. What the news doesn't always make clear is that the Cuban government hasn't matched this initiative with its own approvals. There's optimism that, as early as this fall, the number of seats and gateway cities will rise. Nevertheless, this is Cuba where a sure thing is never quite as sure as you'd like. Cuba will negotiate for some percentage of those seats to be set aside for Cuban people who travel back and forth to the U.S. Best estimates among my contacts are that we're still months away from the time when you'll be able to go online or pick up the phone and book the flight of your choice at will without fear of major confusion or practical problems. Right now, when we book flights for our guests, we're able to take care of the visa arrangements and the ticket price also includes health insurance, transfers and the like. How that may all change -- or get more complicated -- as the market opens up remains to be seen.

Another elephant in the room is the fact that the U.S. rules requiring Americans only visit Cuba as part of authorized "people-to-people" exchange programs are the same as they always have been. Plentiful flights or not, it remains easy to run afoul of this travel requirement. Only programs like the ones we run at Classic Journeys fastidiously negotiate the maze of rules about what is and isn't permissible. (U.S. citizens are still NOT allowed to go to Cuba for a beach vacation, for example.) While licensing of travel companies is not as closely monitored as it was several years ago when we began going to Cuba, the stated requirements are as stringent as ever. When, by how much, or even if those standards will be relaxed is even iffier at the due to the impending elections in the U.S. Without delving into the politics, suffice it to say that there are as many points of view about the wisdom of normalized relations. And whether or not things will continue on the same trajectory is, simply, unknown.

Business in Cuba has changed, but probably less than you hoped (or feared). For a while now, the Cuban government has been granting licenses to citizens so they can operate private businesses. Many of these enterprises are related to the travel industry. The paladares (privately-owned restaurants) are some of the greatest success stories of recent years. Their positive impact is compounded by the number of people they employ and pay at higher levels than the notoriously minuscule government wages. On the other hand, the environment remains largely unfriendly to American-owned businesses. The government does not allow totally free enterprise and demands majority stakes in businesses. As a result, many U.S. companies are still not ready to take the risk. Starwood now is involved in four Havana hotels, but there hasn't been a rush to erect golden arches, barista joints, or other chain stores. The fact is the Cuban population is still largely unable to afford such products; as much as travel has grown, relying only on visitors for revenue isn't a viable business model. The franchise invasion hasn't happened.

On the good news/bad news front, businesses in Havana can have trouble getting approval for an electric sign to attract customers. I call it qualified good news because it's part of an organized effort to protect the look and feel of the city. To maintain the character of historic facades, the City Historian regulates signage. Yet I can easily sympathize with the businesses that need every little advantage they can get, but which remain constrained by the top-down control that's characterized the government here since the Revolution.

There is no question that wonderful things have happened. I can see that Cubans are more hopeful. Many of them do have more opportunities to grow and develop. Incomes are higher and there is more independence, as well as better access to services and a greater range of choices. But still they have so very, very far to go. The idea of even owning even a '59 Chevy held together by baling wire is a pipe dream for most Cubans. The steady flow of visitors has certainly helped -- and I'm proud that my company and our travelers have contributed to that. The irony, though, is that I can promise you virtually the same cultural experience here that you'd have had if you traveled with us back in 2013. History is happening, but it hasn't yet passed us by. Cuba is changing, but by many measures it is substantially the same as the first time I visited.