Raul Castro's time in office has seen dramatic changes in Americans' ability to travel to Cuba, with a dramatic opening under U.S. President Barack Obama, then a partial reduction under President Donald Trump:
Before former President Barack Obama launched detente with Cuba in December 2014, most Americans without family ties to Cuba could travel to the island only on expensive guided tours dedicated to full-time "meaningful interaction" with the Cuban people and — in principle at least — avoiding activities that could be considered tourism, which is illegal under U.S. law.
"People-to-people" tour companies needed special licenses from the U.S. Treasury Department and were regularly audited and faced steep fines or loss of licenses for allowing travelers to engage in tourism.
In Cuba, U.S. tour companies were required to contract guides, tour buses and hotel rooms from the Cuban government, meaning U.S. travelers were effectively under the constant supervision of the government. As a result, they were often presented with activities and talks favoring Cuba government positions on domestic and international issues.
Obama eliminated the tour requirement, allowing Americans to travel to Cuba on individual "people-to-people" trips that were in reality indistinguishable from travel to any other country in the world. Travelers were legally required to maintain logs of their "people-to-people" schedules, but the Obama administration made clear it would not enforce the requirement.
Online lodging booker Airbnb was allowed into Cuba and commercial flights between the U.S. and Cuba resumed after more than half a century. As a result, U.S. travel to Cuba roughly tripled by the time Obama left office. U.S. travelers engaged in what amounted to illegal tourism, but also pumped hundreds of millions of dollars into independent restaurants and bed-and-breakfasts that drove the growth of Cuba's nascent private sector.
Trump re-imposed the requirement that "people-to-people" travelers could only come to Cuba with heavily regulated tour groups. Many Cuban entrepreneurs have seen reductions in the numbers of American travelers, whose business allowed many private Cuban businesses to flourish after the start of detente.
The policy also banned most American financial transactions with the military-linked conglomerate that dominates much of the Cuban economy, including dozens of hotels, along with state-run restaurants and tour buses.
Most individual American travelers ignore the ban or are unaware of it, and tour groups have found myriad ways of doing business with the Cuban government while respecting the letter of the regulation, for example by doing businesses with the Tourism Ministry and other organizations without direct military ties.
Individual American travelers are still legally able to go to Cuba for the purpose of supporting the Cuban people, a category that includes helping human rights organizations and non-governmental groups meant to strengthen democracy and civil society. In real terms, this sort of travel is largely undistinguishable from people-to-people trips, with Americans visiting the same private businesses, organic farms and musical venues they did under Obama.
Cuban government figures show that 2017 was a record year for tourism, with 4.7 million visitors pumping more than $3 billion into the island's otherwise struggling economy. Most were Canadians, Cuban-Americans and Europeans, who face no restrictions. Still, the number of American travelers without family ties topped 600,000, more than six times the pre-Obama level. But amid the boom — an 18 percent overall increase over 2016 — owners of private restaurants and bed-and-breakfasts reported a sharp drop-off.
In large part that's because much of the American travel since Trump's regulation has been in cruise ship passengers, a form of travel that the new administration did not restrict. Cruise ship passengers spend all or nearly all of their time in Cuba in activities organized by the Cuban government.
That means that so far, Trump's regulations are steering money into the hands of the Cuban government and away from private businesses, the opposite of their intended effect.