Catching the Winds of Change in Cuba

I head to Cuba on Saturday, joining a cruise in Cuban waters offered by the tour operator Group IST, in partnership with Variety Cruises. It’s mind-blowing to me that I will be flying from Newark, my closest airport, on an American carrier (United Airlines) all the way to Havana.

That is a new experience for most Americans.

Group IST has been offering Cuba cruises to Americans since 2013, more than a year before President Obama announced his move toward normalization of U.S.-Cuba relations—opening the door through which airlines, hotel companies and cruise lines rushed en masse.

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Funny that they use the word “normalize" because for well more than half a century "normal" was Americans being cut off from Cuba almost completely.

Under a stingy half-century embargo, no American was allowed to spend any money that would go to Cuba. This is normal. Not the new normal, the very old normal. The embargo is like a vestigial organ that no longer has a useful function.

Legally traveling to Cuba has only been available to Americans under special carveouts in the embargo that allowed people to travel for specific reasons. The category that has been most open to mainstream Americans is People to People travel—designed to allow cultural and educational exchange between Americans and Cubans.

People to People travel to Cuba was opened in 1999 under President Clinton, squeezed up again during 2003 under President Bush, then reopened by Obama early in his administration. He made his move to establish diplomatic relations with Cuba near the end of the his final term (in December 2014), further opening trade and tourism between the two nations.

The now-former president could only move within the parameters of the embargo, however, which will take an act of Congress to overturn. But he did establish some additional carve-outs, making it possible for American airlines, hotel companies, banks and some other industries to do business in Cuba.

Traffic to Cuba mushroomed after the well-publicized gesture toward reconciliation between the two countries. Prices for hotels also jumped. 

Since Obama’s 2014 executive orders, the paperwork for operators taking tours to Cuba has shrunken greatly. Operating in the Cuban tour market is not nearly as treacherous as it once was, when several major U.S. companies got hit with punitive fines for some error in their compliance with the regulations (often referred to as “onerous”) of the U.S. Office of Foreign Assets Control (OFAC).

Obama’s move toward opening trade and diplomacy was opposed by all Republican candidates for president in 2016, (in a gesture of loyalty to the anti-Castro Cuban exile community mostly residing in Florida and New Jersey).

READ MORE Traveling to Cuba On Your Own  

Trump was probably the most liberal of the Republicans on the issue, but even he claimed he would throw out Obama’s agreement and negotiate “a better deal.”  So, when Trump was elected, it automatically put travel to Cuba in question: Would it remain as open as it is now, and continue to evolve toward greater opening as it has in recent years?

Or will the Trump administration act as the last Republican administration did and cut it back again?

No one knows. And that uncertainty has also become normal for America's Cuba travel industry. The rules have gone back and forth and up and down for decades. It’s a political hot potato that no politician really wants to deal with but often cannot escape.

This requires ultimate flexibility and patience from tour operators in the business of travel to Cuba. Anything can happen at any time. Anything can change. Rules and regulations can be altered at any moment that will greatly affect an operator's ability to conduct business.

After the election, uncertainty came back into play and caused some U.S. travelers to hold back on booking trips until they see how things shake out.

As a matter of deregulation and free trade, it would seem to be a natural Republican position to further reduce the regulations and paperwork required of travel companies operating in Cuba. But politics is never simple.

I am optimistic that the Trump administration will not clamp down on travel to Cuba again. It does not seem like a good move for the administration at the moment. It would be throwing a monkey wrench into the businesses of major airlines and hoteliers that the administration has no reason to alienate.

Trump has many more pressing matters on his hands for now, and more urgent campaign promises to face up to. His promises about Cuba were vague anyway, only going so far as to say that he would get “a better deal.”

He doesn’t have to do very much to be able to say he has achieved that.

READ MORE What Travel Got Wrong About Cuba  

With the death of Fidel Castro, it already feels like the two countries have moved into a new era:  Raul Castro will step down in 2018, and the government of Cuba will pass to a new generation. Change is underway and no one can stop it.

So I am thrilled to be heading to Cuba, thankful to be able to legally travel there. It is not something to be taken for granted. I am looking forward to seeing what I can of the dynamic changes that are now taking place.

It will be my third trip to Cuba. (The first was in 2013; the second was early last year.) When I was last there, you could see and feel change happening. But after a period of time, it may be possible to observe the change more clearly from the perspective of a few years.

We know Cuba is changing dramatically. We can take that for granted with the influx of money from around the world as its government eases into free market reforms. The opening of trade and travel with the U.S. is bringing a lot of new business opportunities for Cubans. The standard of living for Cuban citizens is rising.

The privately owned inns and restaurants are a big step, a big opening of opportunities for the Cuban people to participate in the free market economy of the world. The significance of that reform can hardly be overestimated. It is a long way from the socialism that Fidel Castro instituted during the early days of his tenure as leader.

Cuba has changed enormously from the days when the curtain was lowered between our two countries in the early ‘60s, blocking the island from the view of Americans. It is changing dynamically now as we speak.

I am buzzing from the thought that I will be there in the middle of it this Saturday afternoon.

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