Pope Benedict XVI arrives in Cuba from Mexico on Monday, a huge event for any small country, but particularly one ruled by a Communist party that banned Christmas until John Paul II visited in 1998.
The government has given workers time off with pay to welcome Pope Benedict and attend an open air mass in eastern Santiago upon his arrival, and again in Havana on Wednesday, the pope's last day on the island.
Hundreds of thousands are expected to turn out to see the pope. Signs of welcome line the freshly paved roads and avenues where the pontiff will pass. It is quite a contrast with other communist lands where he simply is not welcome.
Benedict, speaking aboard his plane to reporters as he flew to Mexico on Friday, said in Cuba "It is evident that Marxist ideology as it was conceived no longer responds to reality… So you have to find new models, with patience, and in a constructive way."
He said the church wanted to support that effort "in the spirit of dialogue to avoid trauma and to help bring about a just and fraternal society, as we want in the whole world."
But the visit has already caused controversy.
The government's most strident opponents at home and abroad charge the church is collaborating with a repressive regime. Supporters counter that it is part of the gradual economic and social change underway here that John Paul called for in 1998 when he said the island nation should open up to the world and the world to Cuba.
Thirteen dissidents took over a Havana church two weeks ago demanding Benedict intercede to end one party rule, only to be evicted by police. Dozens of activists were temporarily detained last weekend when they attempted to stage marches and warned off demonstrating when he is in the country.
Government opponents are demanding a meeting with the pontiff and are circulating a petition on the internet even as the Miami archdiocese brings hundreds of Cuban Americans home for the event.
"From the perspective of Miami Cubans, the visit presents another Elian Gonzales style dilemma because it pits two core values against each other. With Elian the values were family reunification versus hostility to the Cuban government. This time it's devotion to the Catholic Church versus hostility to the Cuban government," Jose Gabilondo, a Cuban American law professor at Florida International University, said.
Elian Gonzalez was the little refugee boy who survived a boat wreck in 1999 that killed his mother and nine others. Relatives in Miami refused to turn him over to authorities so he could be returned to his father in Cuba. Eventually, armed federal officers swept in and forcibly took custody of the boy and sent him back to Cuba.
President Raul Castro, who took over for his ailing brother Fidel in 2008, will meet Benedict upon his arrival in eastern Santiago de Cuba, where he will visit the shrine of Cuba's patron saint and Our Lady of Charity, the Caridad de Cobre.
The pope travels to Havana on Tuesday for talks with Castro, the country's bishops and most likely a retired, but still active, Fidel Castro.
Cuban authorities hope the visit will bring them further international legitimacy and repudiate the U.S. embargo and Washington's efforts to isolate the country.
Benedict will have with him gifts of symbolic importance to all Cubans, no matter their faith or place of residence, as the Vatican tries to turn the increased visibility it has achieved in recent years into more parishioners and clout.
His Holiness will bring a golden flower for the Caridad de Cobre to mark the 400th anniversary of the petite statuette's discovery by three fishermen in a Cuban bay, and the decree of venerability of 19th century educator and independence advocate Father Felix Varela, an important step toward his sainthood.
"Pope John Paul II's visit was the culmination of a period in which discrimination against people of faith ended, church membership grew, and religious expression became an accepted part of Cuban life," Geoff Thale, program director at the Washington Office on Latin America, said.
"Pope Benedict's visit marks a period in which the churches, particularly the Catholic Church, have become established actors in Cuban society. The churches have gained the social weight to intercede with, and dialogue with, the government about political prisoners, tolerance of dissent, and other issues," he said.
A dramatic improvement in the relationship between the state and largest independent organization in the land began two years ago when the church brokered the release of 130 political prisoners and periodic meetings got underway between Castro, Cardinal Jaime Ortega and the Archbishop of Santiago, Dionisio García, the head of the Catholic Bishops Conference.
The church has since opened cultural centers that double as classrooms and been given unprecedented, though still limited, access to state-run media. Religious processions in Cuba's streets, once banned, are now a common occurrence.
Castro has praised the church and condemned religious discrimination in just about every major speech over the last two years. Cardinal Ortega has praised Castro's efforts to reform the Soviet-style system.
"Benedict will arrive in a country in the process of transformation… begun precisely after a change of head of state and evidence of the exhaustion of the real, paternalist socialism… that John Paul II knew so well," Ortega's top aid and spokesman Orlando Marquez wrote in the Bishop Conference's web page.
"Relations between the church and government in Cuba today are at a qualitatively superior level than 14 years ago… There is a dialogue between different parties that has as its focus the common good of Cuban society as a whole."
An estimated 60 percent of Cuba's 11.2 million residents are baptized, but less than 500,000 systematically practice the faith, similar to the Protestant denominations.
Millions of Cubans are registered as Catholics but are practitioners of the syncretic, home-based Afro-Cuban religions that combine Catholic images with African gods and customs, best known as Santeria, and in which the Caridad de Cobre represents the Orisha (goddess) of love, money and happiness, Ochum.
"Syncretism exists when it comes to religion and in particular African religions and the Church through images, most notably the Virgin of Charity," the Rev. Jorge Palma, curator of the Basilica that houses the Caridad de Cobre, said earlier this year.
"Few Catholics regularly attend mass. To be Catholic in Cuba it is enough to be baptized and not join another religion," he said. "Cubans are idiosyncratic. There are few pure Catholics, pure Protestants, we are a small group."