The remarkable spring unfolding in Cuba this year had its biggest moment on Sunday, as President Obama became the first U.S. leader since 1928 to visit the communist island nation, just 90 miles south of Florida.

For the past 55 years the target of economic embargoes intended to punish the dictatorial Castro brothers — for nearly 50 years, Fidel, and for the past eight, Raúl — into submission, Cuba has suffered tremendously, its people enduring poverty that in the collapse of its benefactor state, the Soviet Union, became particularly extreme in the early to mid 1990s.

More recently, President Obama and the United States have opted for a new relationship with Cuba, under a simple and straightforward philosophy: More than five decades of quiet hostility have benefited no one, least of all the long-suffering Cuban people, so it’s time to approach the relationship directly with fresh ideas and an openness to dialogue.

And so as President Obama descended the steps of Air Force One on Sunday, the most significant remaining remnants of the symbolic wall that has long separated the two nations crumbled. As the president and his family toured Old Havana on foot, it seemed the perfect illustration of the new era beginning for U.S./Cuba relations.

There are plenty of other signs of that new beginning. There was the arrival four days ago of Hawaii’s famed canoe, The Hokulea, which sailed into Havana for the first time, making the journey from the British Virgin Islands. Due in town later this week: The Rolling Stones, who plan to play a massive free outdoor concert this Friday in Havana for an estimated 500,000 fans.

Arriving Monday morning were the Tampa Day Devil Rays, which became the first Major League Baseball team to travel to Cuba since the Baltimore Orioles played an exhibition game there 17 years ago. Also in Cuba with President Obama’s Washington entourage: Rachel Robinson, widow of the legendary Brooklyn Dodger Jackie Robinson, who played in Cuba in 1947, the same year he broke baseball’s color barrier. Robinson’s historic first paved the way for many black Cubans in the big leagues, and the baseball-loving country remembers him fondly.

Government, Policies Stuck In The Past

But if the recent symbolism has been breathtaking and the number of firsts extraordinary in Old Havana, much has also, sadly, remained the same since President Obama announced resumption of diplomatic relations with Cuba last summer.

A joint press conference Monday afternoon featuring Obama and Raul Castro offered pointed examples of how much Cuba’s government and public policies remain stuck in the revolutionary politics of the late 1950s, when Raul’s older brother led an overthrow of the U.S.-backed dictator, Fulgencio Batista.

Castro seemed defensive and uncomfortable — a vivid reminder of the lack of press freedom that characterizes civic dialogue in Cuba and how unfamiliar he is with having to deal with honest inquiry from media he doesn’t control.

Confronted on the issue of political prisoners by CNN’s Jim Acosta, whose own father fled Cuba decades ago, Castro denied his government has such prisoners, though their existence has long been documented by Cuban ex-pats, human rights organizations and others.

For a government that in its first several years executed thousands of individuals who opposed Fidel Castro’s revolution, such ongoing unwillingness to acknowledge troubling realities that are well known to the rest of the world shows how far Raul Castro still has to go to shed the deserved label of shameless dictator.

But Monday’s press event also showed the United States has work to do. Castro used the opportunity to demand that the United States give up the Guantanamo Bay land on Cuba’s southern tip that is home to an American military base and to end its longstanding economic embargo against Cuba.

He also pointed out the shortcomings of what passes for equality in the United States, noting that, “In Cuba, women get the same pay (as men) for the same work.” He also referenced what many believe has been one of the successes of the Cuban government — universal health care. In Cuba, he said, “All children are born in a hospital. … It doesn’t matter if they live in far away places, or in the mountains.”

‘The Road Ahead Will Not Be Easy’

For many who fled Cuba or are the sons or daughters of others who did, including more than 700 Cuban Americans living in Hawaii, it is undoubtedly painful to see an international spotlight shine on Raul Castro as he criticizes others about equality and human rights.

That this moment comes not after the Castros have been driven from power, but with the regime still very much in place serves as a bitter reminder of the families, homes, businesses and more taken from them through a revolution they’ll never be able to see in anything other than quotation marks or with anything other than a great sense of loss.

But for the 11.27 million people who live in Cuba today and those interested in having a relationship with them and their country, the emergence of a new era of interaction and normalization holds great promise.

As the United States divines a path forward within this new context, it must not waver in pressuring Cuba to accept and implement democratic reforms, including free elections, press freedom and a cessation of harassment and imprisonment of Cubans who oppose the Castro government. The economic embargo remains in place, and Castro must acknowledge that without his embrace of freedom for the Cuban people, many in the United States will remain doggedly committed to keeping it there.

As President Obama acknowledged at Monday’s news conference, “The road ahead will not be easy.”

But the first steps on that road at least look as though they can take us to a new and better destination, far away from the stationary, hostile silence of the past 50 years.