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Preparing for a Cuban vacation after Castro

Have you always wanted to visit Cuba? Travel columnist Peter Greenberg explains how soon a Havana holiday may no longer be off-limits.
/ Source: TODAY contributor

Quietly, deliberately, and quickly, the travel industry is preparing for Cuba after Fidel Castro.

Major U.S. cruise lines won’t publicly admit this, but each has now charted at least seven, and perhaps eight viable Cuban harbors. So it stands to reason that the cruise ships will be first in when the travel rules are changed. And U.S. hotel companies — through their foreign subsidiaries — already have been "prospecting," doing handshake deals on properties throughout Cuba, and signing quiet conditional deals to kick in the minute things change and they are allowed to do business.

But there are plenty of Americans already there. Despite U.S. administration efforts to the contrary, on any given day in Cuba, there are as many as 2,000 American tourists. No, these aren't the folks who are Cuban Americans visiting friends and relatives. And they're not officially licensed travelers on humanitarian missions. They are American tourists who fly in from any of five secondary countries: Bahamas, Jamaica, Canada, Mexico or the Cayman Islands. All are eager to experience Cuba before Fidel checks out.

How are they doing this? After all, aren’t U.S. citizens banned from travel to Cuba?

First, some history. There’s a law, still on the books called the Trading with the Enemies Act. It’s been around since 1963. And for more than 43 years, it’s officially banned American tourists from Cuba. Or has it? There are those who would argue that the legislation was specifically aimed at U.S. firms trying to do business in Cuba. Indeed, if you read the law it doesn’t specifically bar American tourists from going to Cuba, but it does ban Americans from spending U.S. dollars there.

So what about those 2,000 American tourists in Havana? Are they in violation of the law? Certainly they are in violation of  the spirit of the law. What they’ve done is book all-inclusive travel through those five other countries. They’ve paid local tour operators there in U.S. dollars to cover their airfare, hotels, transfers, taxes, tips, meals. So, officially, these American tourists prepaid their trips in another country, so they are not spending U.S. dollars in Cuba. In addition, Cuban authorities do not stamp U.S. passports. Officially, you visited that secondary country and never left that country, when, in fact, you transited to Cuba.

And, since 1963, how many have been fined or arrested for doing this? It’s actually tough to find any. Why? Some would argue that for the American government, which is surely aware of this long standing practice, to crack down on U.S. tourists, it would also have to acknowledge how many there are. (It’s as if the U.S. government is Claude Rains' character, Captain Renault, in the legendary movie “Casablanca,” who was “shocked” to find out there’s gambling in Rick’s casino, before he collected his winnings from the night before.)

So American tourism in Cuba goes on, despite even more tightened travel restrictions imposed by the Bush administration in 2004. In fact, American tourists are not only staying in Cuban hotels, many are even sailing their pleasure boats into Havana and staying in the Hemingway marina.

I am not endorsing travel to Cuba for Americans; I'm simply reporting that it is being done. One note of caution: Should you buy anything in Cuba that would be evidence that you actually were that country. So you would be dangerously flirting with a stiff fine, at the very least. By the way, U.S. credit cards are not accepted in Cuba.

However, times are changing. This past march, Congressmen Charles Rangel (D-N.Y.) and Jeff Flake (R-Ariz.), cosponsored HR 654, a bill calling for an end to restrictions on Americans traveling to Cuba. The bill would also allow all U.S. companies to compete in booking trips to the island. This may mark the first time such a bill gets strong bipartisan support.

With the Cuban leader's health fading, Flake noted that now is an appropriate time for a new approach to Cuban-American relations. “For nearly 50 years our current Cuba policy has done little to bring democracy to Cuba,” said Flake, in a statement. “Far from hastening democratic reforms, our current policy has given Fidel Castro a convenient scapegoat for his own regime’s failures. With the Cuban government taking new shape, we shouldn’t give the new leader the same excuses we’ve given the old one.”

The bill reads: “The president shall not regulate or prohibit, directly or indirectly, travel to or from Cuba by United States citizens or legal residents, or any of the transactions incident to such traveling.” In other words, the travel ban would disappear.

Of course, all of this is having a big ripple effect throughout the rest of the Caribbean. For the first time in nearly 44 years, Cuba may be no longer officially off-limits. And tourism officials from just about every country in the region are worried — as they should be — that the minute Castro goes, their tourism numbers could drop as much as 20 to 25 percent.

Stay tuned….