"It is a message of love, this visit," said Jorgelina Guevara, 59, as she waited for the Mass to begin. "The Cuban people need it."
The trip comes 14 years after John Paul's historic tour, when the Polish pope who helped bring down communism in his homeland admonished Fidel Castro to free prisoners of conscience, end abortion, and let the Roman Catholic Church take its place in society.
Benedict's message as he arrived was subtle, taking into account the reforms that Raul Castro has enacted since taking over from his older brother in 2006 and the greater role the Catholic Church has played in Cuban affairs, most recently in negotiating the release of dozens of political prisoners.
The pope, who at the start of his trip said Marxism "no longer responds to reality," gave a much gentler message upon arriving on Cuban soil, saying he wanted to inspire and encourage Cubans on the island and beyond.
"I carry in my heart the just aspirations and legitimate desires of all Cubans, wherever they may be," he said. "Those of the young and the elderly, of adolescents and children, of the sick and workers, of prisoners and their families, and of the poor and those in need."
In his own remarks, the Cuban leader assured Benedict his country favors complete religious liberty and has good relations with all religious institutions. He also criticized the 50-year U.S. economic embargo and defended the socialist ideal of providing for the less fortunate.
Benedict's three-day stay in Cuba inevitably sparked comparisons with his predecessor's, when Fidel Castro traded his army fatigues for a suit and tie to greet the pope and where John Paul uttered the now-famous words, "May Cuba, with all its magnificent potential, open itself up to the world, and may the world open itself up to Cuba."
Benedict referred repeatedly to John Paul in his speech Monday, saying his visit was a "gentle breath of fresh air" that gave strength to the church on the island.
He also denounced the ills of capitalism - a theme that he has touched on often amid the global financial crisis but that took on significance in one of the world's last remaining Marxist systems.
Late Monday, Benedict celebrated an outdoor Mass in the colonial city's main square on a blue-and-white platform crowned by graceful arches in the shape of a bishop's miter. Benedict will spend the night in a house beside the shrine of Cuba's patron saint, the Virgin of Charity of Cobre, where he will briefly pray in a private.