By Kelly Phillips Badal
June 23, 2015
Cuba, Boy
Credit: Frederic Lagrange

Consider: Cuba is the only country in the world the U.S government has ever restricted its citizens from visiting. (Americans can even go to North Korea, so long as North Korea says it’s A-OK.)

Needless to say, relations between the U.S. and the Caribbean island have a complicated, tenuous past—made all the more complicated by the gradual abolishment of travel restrictions and increasing diplomatic ties.

To help explain where relations are heading, here’s a breakdown of the U.S.’s travel relationship with the “forbidden” land just 90 miles off the coast of Florida. This timeline endeavors to contextualize major policy adjustments and political milestones over the last 50-some years.

There are more developments and shifts than we could possibly list, but you’ll find the landmark moments here—many occurring just this year—as well as other significant events, too. After all, who can forget Jay-Z and Bey’s much-touted Havana jaunt?

February 16, 1959:

Fidel Castro is sworn in as Cuba’s Prime Minister after leading a revolution to overthrow Cuban dictator Fulgencio Batista.

October 19, 1960:

The U.S. implements an economic embargo against Cuba, which remains to date. It is the most enduring trade embargo in history.

February 8, 1963:

Shortly after the Cuban Missile Crisis, President Kennedy prohibits travel to Cuba and makes financial and commercial transactions with Cubans illegal for U.S. citizens.

Fast-forward nearly 50 years...

April 13, 2009:

President Obama eases travel restrictions for Cuban-Americans to visit their relatives in Cuba within his first 100 days in office, fulfilling a campaign promise. The new policy allows unlimited visitation and lets Cuban-Americans provide financial aid to their families there. Travel restrictions for American of non-Cuban descent remain; a special license from the U.S. Treasury is required.

November 4, 2010:

The American Ballet Theater performs in Havana for the first time in 50 years. The trip is seen to reflect a new openness between the U.S. and Cuba for cultural exchange.

January 14, 2011:

The Obama administration announces new “people-to-people” travel rules for Cuba. The broader measures expand the categories of who is allowed to travel—formerly Cuban Americans and few others—to those pursuing “purposeful travel” (academics, religious groups, students, do-gooders, etc).

April 2013:

Celebrity power couple Jay-Z and Beyoncé visit Cuba around the time of their fifth wedding anniversary. The trip is highly-criticized—the duo were accused of engaging in tourist activities illegal under the U.S. embargo against Cuba—but later declared legal as a properly licensed "people-to-people" cultural exchange trip.

December 17, 2014:

President Obama announces moves re-establish diplomatic relations between the U.S. and Cuba. The media calls it a “historic thaw.” Officials note that while the more liberal travel restrictions that are part of the plan still won’t allow for tourism, they will permit more Americans to visit.

January 16, 2015:

New rules put in place by the Obama administration greatly relax restrictions on travel to Cuba. It’s now easier for Americans to visit than it has been for the last half-century. Under these rules, U.S. citizens can visit Cuba without a license so long as the trip falls into one of 12 broadly-defined categories such as a family visit, professional research, cultural or religious reason, and others. Purely touristic travel—like stay at an all-inclusive beach resort—is still considered illegal.

January 29, 2015:

Travel search engine site begins offering searchable booking information for Cuba. Users cannot yet click through directly to booking links; options are only provided as information. But it’s a start.

February 19, 2015:

A Gallup poll reports that 59 percent of Americans favor ending travel restrictions as well as the trade embargo in Cuba. And, American opinion of Cuba is reportedly the highest it’s been in 20 years. The times, they are a’changin’!

March 1, 2015:

Mastercard becomes the first U.S. credit card to unblock usage in Cuba. Cigar shops, which have long accepted non-U.S. credit cards, are expected to be among the first to benefit; most restaurants and shops don’t yet have the facilities to accept them.

March 17, 2015:

The first regularly scheduled direct U.S.-to-Cuba charter flight departs. Sun Country Airlines 8891 flies between John F. Kennedy airport in Queens, N.Y., and Havana, Cuba; Cuba Travel Services offers the once-a-week round trip for $849, including Cuban medical insurance and taxes.

April 3, 2015:

Home rental site Airbnb introduces more than 1,000 listings in Cuba, mostly drawn from casa particulares (homestay) owners. The site estimates that 40 percent of the bookings available are in Havana, the other 60 percent scattered throughout the country. (To date, the available casas have doubled to more than 2,000.)

April 15, 2015: becomes the first online travel agency to book flights to Cuba for U.S. citizens. Its service routes run to Havana from Miami, New York, and Tampa, and from Miami to certain other Cuban cities.

May 29, 2015:

The U.S. drops Cuba from its State Sponsors of Terrorism list. Cuba is still subject to a wider U.S. economic embargo, but removal from the list allows private companies and banks more opportunities to do authorized business with Cuba—which ultimately will aid travelers. U.S. and Cuban officials are also currently sorting out details to re-open embassies in each others’ capitals.

June 5, 2015:

Congress votes to keep restrictions on travel to Cuba. One step forward, two steps back? This vote retains a Cuba-related provision in a transportation funding bill, which would block the rules issued in January that ease travel to Cuba and allow for regularly scheduled flights. The White House has threatened to veto the bill; in the meantime, travel rules put in place January still stand.

So, what’s next?

If given a green light from both the Cuban and U.S. government, JetBlue plans to become the first major U.S. carrier to resume scheduled service to Cuba from New York on July 3. Delta and American Airlines have also announced plans to begin serving Cuba. Ferry service between Miami and Havana—a 9-hour overnight trip—is also expected to start this year. And Google has already made a proposal to the Cuban government to bring better Internet service to the island, something that will completely change information available to visitors and Cubans.

It’s highly likely that all travel bans on Americans vacationing to Cuba will be eventually dissolved. The Cuban government is already predicting that 10 million Americans will visit each year after travel opens in full, turning the clock back to the 1950s—a time when Cuba was an inexpensive, casino-ridden, rum-soaked playground for American jetsetters. While that particular heyday may have passed, but the future of this “forbidden” land is still changing daily. And now, more U.S. citizens can be a part of it.