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Traveling to Cuba is easier than ever. Will that change if a Republican becomes president?

Tourists take in the sites from a double-decker tour bus of Havana a day after the second round of diplomatic talks between the United States and Cuban officials took place in Washington, DC, on February 28, 2015, in Havana, Cuba
Tourists take in the sites from a double-decker tour bus of Havana a day after the second round of diplomatic talks between the United States and Cuban officials took place in Washington, DC, on February 28, 2015, in Havana, Cuba
Joe Raedle/Getty Images

It’s the holiday season, which means you’ve probably headed out of town. Or perhaps you’re prepping for an upcoming trip, or contemplating when and where you might take your next one.

If so, Cuba might come to mind: One year after President Barack Obama announced he had begun the process of normalizing relations after half a century of official hostility, travel to the island nation has become easier than ever.

Americans are still technically forbidden from traveling to Cuba as tourists — it would take an act of Congress to formally lift the ban. But since the start of 2015, the American government is allowing individuals to travel there, so long as the purpose of their trip falls loosely under one of 12 broad categories.

Since Obama’s announcement, Americans in the tens of thousands have flocked to the once off-limits island for a new glimpse into its culture and — because this is America — its potential for business ventures. (Vox just recently published a helpful travel guide to Cuba.)

So far, Americans wishing to vacation in the island nation must do so on costly charter flights leaving primarily from Miami and New York. (The average cost of a Miami-Havana charter flight is about $450, and flights from New York go for about $800.)

But just this month, the US and Cuba reached a deal to allow commercial flights to once more operate between the two countries, easing the process and lowering cost of travel. Already, four major airlines – American, JetBlue, United, and Southwest – announced plans to operate as many as 20 daily flights between the two nations, from airports in New York, Los Angeles, and across Florida.

Politicians and interest groups across the political spectrum have voiced support for normalization, with groups as disparate as a bipartisan group of House Representatives, the US Chamber of Commerce, and even Cuban-American business leaders applauding increased ties.

But a prominent group of Republicans, including several presidential candidates, are holding out. They strongly oppose any easing of official hostility, viewing it as a concession to a dictatorial government with a dismal record on human rights.

Sen. Marco Rubio, a Cuban American who’s in the lead to capture the Republican establishment in this year’s primary, has said that rolling back President Obama’s détente with Cuba would be a top priority on day one.

"The statute passed by Congress specifically prohibits many of the things he [Obama]’s now undertaking," Rubio told the Guardian’s Sabrina Siddiqui. "It says those things can only happen after certain conditions have been met, none of which have been met. As president, I will follow the law."

Such a reversal would once more severely curtail travel to Cuba for everyday Americans, who are rapidly warming to the idea of making the Caribbean nation their next vacation spot.

Strong rhetoric aside, it is an open question whether Rubio, if elected, will have the political backing to reverse the course on Cuba and rebottle the curiosity, from both citizens and businesses, that this rapprochement has welcomed.

How did Americans go to Cuba before President Obama normalized relations?

Before Obama’s announcement, legal pathways existed that American citizens could take to reach Cuba — though they were limited in scope.

In 1998, President Bill Clinton — who had wanted to end the embargo early in his presidency — opened several new avenues of travel to Cuba, allowing citizens to apply for visas under one of several categories, including humanitarian, religious, and educational missions, among others. This is the program under which the Cuban national baseball team played the Baltimore Orioles in an iconic 1999 exhibition game.

Under the program, citizens were asked to submit detailed itineraries ahead of time to demonstrate that their time would be spent on purely professional activities. Licenses were sufficiently difficult to obtain, and the majority of Americans entering Cuba ended up doing so through organized programs licensed through the US government.

When George W. Bush entered office, he put an end to this "people-to-people" form of contact as part of a larger effort to choke off any revenue stream to the Cuban government, in hopes that would weaken its hold on power.

Obama once more renewed the program when he was first elected, but made no major alterations to travel policy until 2014.

Of course, many Americans traveled to Cuba illegally, both before and after President Clinton made travel a legal possibility. These Americans would simply fly through a third country, typically Canada or Mexico, and obtain a visa through one of those airports. Cuban officials knew not to stamp the passports of American travelers.

Even so, this sort of travel required logistical hoops. American banks were never permitted to do business with the Central Bank of Cuba, which is operated by the government, preventing Americans from withdrawing any money. That policy is changing under Obama’s policy shift.

It’s clear Cuba has become a partisan political issue. But how did it happen?

It’s difficult to pinpoint exactly when opinions on America’s policy toward Cuba grew polarized — or why, exactly, hard-line supporters of the embargo tended to vote reliably for Republicans.

The embargo was first put in place by a Democrat, President John F. Kennedy, during a period of heightened tensions with the newly communist nation. It was originally put in place to starve the Cuban government of cash and, with any luck, hasten its demise.

But even then, traces of partisanship can be found, according to Christopher Sabatini, a scholar at Columbia University’s School of International and Public Affairs. In 1961, Kennedy authorized the Bay of Pigs invasion — a CIA-led operation to topple communist leader Fidel Castro that failed in a disastrously public way. Hard-line Cuban Americans, who supported any attempt to topple Castro’s government, grew furious when the Kennedy administration — which had sent in the initial fleet of 1,200 rebels to carry out the revolt — did not then send in air support to bomb Castro's forces that surrounded them.

They believed the moment of military restraint had cost them the opportunity to regain the island, and from that point, Cuban Americans developed an affinity for the Republican Party.

By the late 1970s, however, it had become clear that tough American policy had failed to oust Castro from power. During a period of détente with the Soviet Union, President Jimmy Carter allowed parts of the embargo, notably travel restrictions, to expire without renewal.

But in 1980, something happened that had a lasting influence on presidential politics. In a move aimed at quieting dissent, Castro allowed anyone wishing to leave the island to do so. Cuban Americans orchestrated for refugees to come to the United States, and between April and October 1980, about 125,000 Cubans landed in Florida.

Florida was then, as it is now, a swing state — and Ronald Reagan pledged toughness on the Castro regime to win votes. When he entered office several months later, he reinstated restrictions in full, as part of an amped-up global effort to weaken the Soviet Union and its allies.

In an arguably more important move, Reagan also helped set up — along with prominent, virulently anti-Castro members of the Cuban-American community — a political action committee called the Cuban American National Foundation. The forceful, politically savvy organization sought to place a deep freeze on Cuban-American policy by corralling votes in Congress. The organization, supported by a prospering Cuban community, drafted anti-Cuba legislation and donated to candidates in return for pledges to vote against any move toward normalization.

When Clinton came into office and signaled a desire to end the embargo, CANF rallied members of Congress to oppose him, believing that after the Soviet Union and other communists had fallen, Castro’s government would topple at any moment.

Several years later, in 1996, the Cuban government shot down two private planes flown by members of a refugee organization that had reportedly dropped fliers on the island. The shootdown killed four Cuban Americans and outraged the nation, dampening any appetite for opening relations.

In response, CANF pushed through the Helms-Burton Act, which prohibited the president from ending the embargo without congressional approval. Clinton signed the bill into law. It was an election year, and he couldn’t afford to alienate the large Cuban-American community in the politically crucial state of Florida.

These politics, taken together, cemented the notion that supporting any loosening of the embargo amounted to political poison. "It was a third rail of politics that no one wanted to touch, because they worried the gains wouldn’t be as big as the potential risks," said Alana Tummino, head of the Cuba Working Group at the Americas Society.

The Helms-Burton Act determined Clinton’s Cuba policy for the remainder of his time in office, and President Bush was of course not eager to shift the needle. But in the meantime, views within the Cuban-American community were evolving.

Children of Cuban-American immigrants, perhaps removed from the Cold War politics that shaped their parents’ worldview, are increasingly breaking with previous generations’ staunch support of the embargo. And more recent Cuban immigrants of the US, motivated to leave for economic rather than political reasons, don’t harbor the same zealous hatred of the Castro regime.

What, exactly, did the president change?

President Obama’s announcement, on December 17, 2014, marked the furthest any president has gone in walking back the embargo and restoring a relationship with Cuba.

By January, the Obama administration had lifted significant restrictions on travel, dropping the requirement to apply for a license to travel in advance.

Now Americans wishing to travel must check one of 12 boxes on a visa indicating the nature of their trip, but beyond that, the American government takes them at their word. Travelers are still technically required to carry an itinerary, in case agents ask to check — but of course no one does.

"[Obama administration officials] really want people to be engaging with the people of Cuba — eating at private restaurants, meeting with entrepreneurs," Tummino said.

Since then, the Obama administration has removed Cuba from the government’s state sponsors of terrorism list, and the two countries reopened embassies in each other’s capitals.

Perhaps more importantly, Obama has permitted American companies to reenter Cuba, particularly to work with private enterprises on the island. Airlines will once more resume flights, and Airbnb, the room-sharing service, is now representing private lodgings across the nation.

American internet providers have moved onto the island, and two cellphone companies, Verizon and Sprint, have already signed roaming agreements with Cuban cell carriers.

But the regulations that allow these companies to operate in Cuba, and allow tourists to visit there, exist purely under executive action. That means, legally speaking, without help from Congress, the next president can simply choose to alter or drop them if he or she so chooses.

Will a Republican president reverse normalization?

That’s exactly what several presidential candidates, Rubio chief among them, are pledging to do.

To these Republicans, Obama’s deal is taking a perilous gamble — that by bringing economic liberalization to the country, a relaxation of political authoritarianism will follow. They point out – and they are correct – that nothing in the deal Obama struck with the Cubans actually requires them to change their structure of government or curtail human rights violations.

If a Republican with hard-line Cuba policy gets elected in 2016, it’s likely he will at least tinker with the Obama administration’s regulations, perhaps closing embassies or putting light restrictions on travel.

But taking any further action might prove politically untenable. Not all Republicans even agree anymore on the orthodoxy of the embargo; Rand Paul, for example, opposes it on libertarian grounds, and Donald Trump has declared it bad for business.

Overall, 59 percent of Republicans surveyed in a July Pew Research poll favor ending the embargo altogether, which could put pressure on the eventual Republican nominee.

Public opinion aside, pledges to roll back the steps the US has taken toward normalization ignore the deep business interests that have sprung up in the short time since Obama made his initial announcement. It’s one thing to stand in opposition to Democrats; it's another to alienate America’s business community.

"The toothpaste is out of the tube, and you cannot put it back in," Columbia's Sabatini said. "You can make some marginal changes, you can make some noise – but there are too many interests who have a stake in this to go back."

So if you’re contemplating spending a future winter break in Cuba, it’s a good bet your plans are a go.