President Obama arrived in Cuba on Sunday afternoon, a journey of only 90 miles from U.S. shores that took more than half a century to complete.

Stepping off Air Force One under drizzling skies, the president held an umbrella over his wife, Michelle, as he was greeted by senior Cuban officials.

The Obamas, including the president’s two daughters and his mother-in-law, were met on the tarmac by Bruno Rodríguez, Cuba’s foreign minister, and Josefina Vidal, the head of the U.S. section of Cuba’s Foreign Ministry, as well as Jeffrey DeLaurentis, the senior U.S. diplomat in Cuba. The official welcoming session will take place Monday morning when Obama meets with Cuban President Raúl Castro at the presidential palace.

Obama’s trip here — the first by a sitting U.S. president since 1928 — comes amid high anticipation and anxiety on the island within both the Communist government and its political opposition. The government hopes the two-day visit will allow it to reap benefits without ceding control, while dissidents on the island want it to speed the pace of change.

Since re-establishing diplomatic ties with Cuba, the U.S. has made it easier for Americans to travel to the island nation. Here is what you need to know about changes that make it easier to visit Cuba. (Claritza Jimenez/The Washington Post)

An affirmation of his larger foreign policy vision, Obama hopes that reaching out to Cuba will encourage a generational evolution in one of the United States’ most bitter and long-standing adversaries. Just hours before his arrival, there were familiar signs that change will not come easily.

As Sunday-morning Mass ended at Havana’s Santa Rita church, several dozen women in white T-shirts filed out, assembled in rows and began walking silently down the street. A block away, hundreds of uniformed security personnel and plain-clothed men and women stood waiting.

They met at the corner in a melee of shouting and manhandling. The women in white went limp on the pavement, shouting “Freedom! Freedom! Freedom!” and throwing leaflets into the air. The security teams half-dragged, half-carried them to waiting buses.

A number of men marching with the women were chased, thrown to the curb and handcuffed. As the buses drove away, the protesters lifted defiant fists through the windows while the plain-clothed crowd chanted “This is Fidel’s street!”

The Sunday-morning demonstrations of the Ladies in White dissident group are regular occurrences in Havana. The large size of the security force and the fact that the entire operation was conducted in front of international television cameras were not.

All the cross-currents and contradictions of Cuba and its changing relationship with the United States have been on display over the past two days. On Friday, the U.S. Coast Guard fished out 18 Cubans trying to reach Florida on homemade rafts. They reported that nine others had drowned on the journey.

Late Saturday, the Starwood hotel chain signed a mega-deal with the Cuban government to manage three hotels on the island, the first U.S. entrance into the tourist business here in more than 60 years.

On Sunday morning, Cubans crowded around their televisions to watch a hilarious phone conversation Obama taped Friday with the island’s best-known comedian.

Hours later, the Ladies in White were attacked.

“We want to see results” from the U.S. opening, said José Daniel Ferrer, head of Cuba’s largest dissident organization, the Cuban Patriotic Union. “But Obama himself has said not to expect spectacular results . . . and he has been exactly right.”

Ferrer and several other dissident leaders who gathered Sunday morning — all of whom have been invited to a private meeting with Obama on Tuesday morning — argued among themselves about the pace of change and the intransigence of the government. They agreed that they are not expecting short-term liberalization. But, they said, the combined weight of the U.S. opening and the coming generational shift replacing Cuba’s aging leadership would inevitably bring down the system here.

“It’s already easier to criticize Raúl than it was Fidel,” Ferrer said of the current Castro president, and his brother and predecessor. “The next will be easier still.” Raúl Castro has said he will step down in 2018.

“In the long run, this could be like a poison steak for the regime,” he said of normalization. “It will taste good, but you’ll eventually get a stomachache.”

The Obama administration “knows that Fidel Castro is about to turn 90,” and that Raúl is only a few years behind, said Guillermo Fariñas, head of the United Anti-Totalitarian Forum. “A new generation is coming, with ever less moral authority” to claim it is promoting a popular revolution that took place long before most Cubans were born.

Nearly a dozen dissidents are expected at the meeting with Obama. They have been told they will be picked up at their residences by U.S. officials and taken to the U.S. Embassy two hours before the meeting, presumably to avoid the past government practice of sequestering in their homes those it does not want meeting with prominent foreign visitors. At the embassy, they will watch and listen to Obama’s broadcast speech to the nation.

Most said they were going to wait to hear what he has to tell them before deciding what they want to ask the U.S. president. “Ten minutes will be enough for him to say a lot of things,” Ferrer said of the speech, scheduled to last 40 minutes. “It’s a unique opportunity,” he said. “Every Cuban is going to want to see if he projects an image of non-
complicity with the government, if he will be transparent.”

Far from Sunday’s protests, Obama and his family first traveled to the Melia Habana hotel in the upscale neighborhood of Miramar, where he met with the U.S. Embassy staff.

On his first day here, Obama tried out his Spanish. “¿Que bolá Cuba?” he tweeted on landing, using a particularly Cuban Spanish phrase meaning “What’s up?” To the embassy staff, he said “¿Como andan?” — “How are you doing?”

The Obamas took a brief walking tour Sunday evening of Old Havana, the capital’s 500-year-old historic quarter and a World Heritage Site. Images of their visit to its spiffed-up colonial plazas and colonnaded street­scapes are likely to stir up even more interest among would-be American travelers.

As they visited the Plaza de Armas with umbrellas under a steady rain, crowds nearby chanted “USA! USA!” Throngs of Cubans also watched as the family entered Our Lady of Immaculate Conception Cathedral to meet with Cardinal Jaime Ortega, who played a critical role in secret talks between the two countries. Afterward, the Obamas dined at San Cristobal, a privately owned restaurant.

The first family’s tour was limited to the renovated part of Old Havana. The larger, unreconstructed part of the neighborhood, which tourists rarely enter, is filled with families living in crowded, crumbling tenements.

Local resident Alberto Moreno, 35, a cook at a brewery, said earlier in the day that he thought Obama’s visit would show that “Cuba is not the disaster that people in the United States think it is.”

“This will probably be the first country Obama visits where there is no one protesting him,” said Moreno — and given that public demonstrations are banned, he is almost certainly right.

Obama seemed to have made a favorable impression ahead of his arrival by appearing in a skit with Cuba’s best-known comedian, Pánfilo. In a split-screen video shot Friday, the two discussed his trip by phone, and the dimwitted Pánfilo offered the U.S. president a ride from the airport and use of his double bed — warning Obama that Michelle would rest more comfortably on the side without a spring sticking out.

Havana resident Deroy Aponte, 28, who watched the video on Telesur, the Venezuelan network that is broadcast full time here, said he’d never seen a powerful political figure do something like that. “It made a big impression on me,” he said.

The U.S. president seems to be “open-minded, reasonable and someone capable of putting himself in others’ shoes,” said Aponte, who works as a repairman for cigar-making machinery.

But for Americans wanting to visit Cuba, the contradictions are stark.

As the Ladies in White began their ill-fated march, several held a banner that read “Obama: Traveling to Cuba isn’t fun. No more human rights violations.”

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