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You know the story (we’ve written it here): Cuba boasts the Caribbean’s most intoxicating and history-filled capital, the region’s finest collection of undeveloped beaches and twice the landmass of all the other Caribbean islands combined. It is “a place that has been so divorced from the world market economy that a certain ​purity​ and innocence has thrived,” to quote Cuba specialist and CT+L contributor Christopher P. Baker. And though, 50 years into a U.S. trade embargo, the Treasury Department’s Office of Foreign Assets Control (OFAC) still insists that Americans spending money in Cuba are violating the Trading with the Enemy Act of 1917, that’s no reason not to hold a conference dedicated to figuring out how to get American tourists spending money in Cuba the moment that embargo is lifted.

This March, the U.S.-Cuba Travel Summit convened in Cancún, Mexico, attracting tour operators and hoteliers who want to be ready. They have both reasons for hope and reasons for frustration.

Americans have been traveling to the island for years – as many as 176,000 in 2001 (the last year for which figures are available), many of them Cuban-Americans,​ others covertly traveling through Canada or Mexico. When G.W. Bush launched a clampdown on unsanctioned visits, fines were issued to those caught entering the United States. While some say enforcement of the ban has begun to ease under the Obama administration, the White House hasn’t made concrete moves toward legalizing travel – though President Obama used the 2009 Summit of the Americas, in Trinidad, to say, “The United States seeks a new beginning with Cuba.”

Cuba: Then and Now...

“President Bush’s veto pen is gone,” said Philip Peters, an advisor to the Cuba Working Group of the House of Representatives. “But if we want the right to travel to Cuba, it’s going to have to be legislated.” In February, Rep. William D. Delahunt of Massachusetts and Sen. Byron L. Dorgan of North Dakota introduced bills to allow travel between the two countries.

 “Our country allows Americans to travel to North Korea and Iran, but Americans who travel to Cuba without a license face fines and up to 10 years in prison,” explained Dorgan, addressing the Summit by phone. “The Office of Foreign Assets Control is supposed to be tracking assets of terrorist groups, and instead they have been busy chasing people who go to Cuba. In the previous administration, up to a quarter of their time was spent trying to track Americans suspected of taking a vacation to Cuba. It is pretty absurd, it seems to me.”

It also sounds absurd to businesspeople who cater to Cuba-hungry travelers.

“There are many countries in the world that the U.S. has political differences with, but there’s only one country in the world we can’t travel to,” says Bob Guild, vice president of Marazul Charters. “The Supreme Court decided in the 1950s that, under the Fifth Amendment, there’s a right to travel by U.S. citizens.”

Cuba on the Horizon...

Marazul is a Miami-based charter operator licensed to provide travel to Cuba to individuals and groups licensed by OFAC. But Guild feels that U.S. tourism dollars are being held out like a carrot to encourage the Cuban government to improve its human rights record and other issues. “But we have a right to travel – I don’t believe the U.S. government has the right to use that right as a foreign policy tool,” he says.

“What if we were to treat Cuba as not our best friend but the way we treat other communist countries?” asked Peters. “We could work together today on things like disaster relief, environmental issues and immigration.”

For many of the Summit attendees, the bigger concern was whether Cuba was ready for a flood of Americans. Although Americans make up the majority of travelers to the Caribbean, Cuban tourism has been doing just fine. The island received 2.4 million tourists in 2009, making it the region’s second most-visited destination (after the Dominican Republic). One of every seven hotel rooms in the Caribbean is in Cuba, yet only 20 percent of the island’s beaches are in use today, said Miguel Figueras, senior advisor to Cuba’s minister of tourism.

But the island’s 50,000 hotel rooms are barely sufficient to meet the current demand, suggested Baker, author of Moon Cuba and National Geographic Traveler: Cuba guidebooks. “Today, Cuba competes head to head with the D.R. for snowbirds from Canada and Eastern Europe,” said Baker. “But when it opens up for Americans, there’s going to be far more demand than Cuba can supply. My sense is the Cubans will maximize the returns they can get per head. Prices will escalate.”

Cuba Vacations...

Baker also noted there is going to be a real distinction between Cuba’s current visitors and the Americans: “Lifting the veil after six decades being held apart, you can’t expect them to come and just lay their towel on a beach. For Americans, the early emphasis will be on people who want to walk the streets of Old Havana and rent a car to explore the hinterlands.”

But Americans have been waiting to walk those streets for decades now, and they start packing bags whenever Castro so much as sneezes. Why hold out hope?

“This is not pie in the sky; it’s not some fantasy,” said Guild. “Someday there will be a rational decision made by Congress and the administration, and the travel restrictions will be abolished.”

Order us a daiquiri, Bob, and save us a seat at El Floridita.