President Barack Obama arrived Sunday in Havana for a visit that he hopes will help end a hostile U.S. policy toward Cuba that he views as futile, lifting one of the biggest impediments to closer U.S. alliances across Latin America. Air Force One touched down at Jose Marti International Airport at about 4:19 p.m. Obama took an evening walking tour of Old Havana ahead of a formal arrival ceremony and a meeting on Monday with Cuban President Raul Castro. He told staff at the U.S. embassy, re-opened in 2015, that the visit was a chance to engage the Cuban people. “Having a U.S. embassy means we’re more effectively able to advance our values, our interests, and understand more effectively” the Cuban people’s concerns, Obama said. “This is a historic visit and a historic opportunity.” Obama led a U.S. delegation that includes lawmakers from both parties, corporate executives eyeing new business with and within Cuba, and prominent Cuban Americans. Over two days, he’ll sip Cuban coffee and will talk with dissidents and entrepreneurs. Offering a taste to Cubans of what a more open relationship could mean, Obama also plans to attend an exhibition baseball game between the Tampa Bay Rays and the Cuban national team. ‘A New Era’ Even with little chance that Congress will lift the U.S. trade embargo on Cuba before he leaves office in January, Obama is betting that a rapprochement, symbolized by his visit, has now become irrevocable, no matter who succeeds him. “It signals the beginning of a new era, more than anything that’s been done so far,” said Senator Jeff Flake, Republican of Arizona, who’s among the leading U.S. advocates of normalization. “Any Republican administration would be hard-pressed to reverse really any of this. This all feeds on itself. These changes are going to be permanent and expanding.” The president, first lady Michelle Obama and their daughters, Malia and Sasha, exited their plane and set foot on Cuban soil shortly after 4:30 p.m. in light drizzle and temperatures of about 85 degrees Fahrenheit (29 Celsius). They were greeted by Bruno Rodriguez Parrilla, Cuba’s minister of foreign affairs; Cuba’s ambassador to the U.S., Jose Cabanas; and Jeffrey DeLaurentis, chief of mission at the U.S. Embassy in Havana. A crowd greeted the First Family with shouts of “USA! USA!” as they arrived at the Plaza de Arms in Old Havana to walk through the city’s colonial center, a UNESCO world heritage site. The Obamas carried black umbrellas as they walked along the cobblestones and proceeded to the city’s cathedral. The president met there with Catholic leader Cardinal Jaime Ortega, a former 1960s labor-camp inmate who played a role in the secret negotiations leading up to the opening of relations between the U.S. and Cuba. They later dined at a privately owned restaurant, the San Cristobal, drawing crowds of onlookers as the presidential motorcade made its way through the narrow and crowded streets. Republican Opposition The president’s visit is the latest step in an effort announced in December 2014 to restore relations with the Communist-run island after a half century. Though embraced by many Americans, the prospect of reconciliation with the government of Raul Castro has drawn sharp criticism from some Republicans, including presidential candidates Ted Cruz and Donald Trump. In a concrete sign of the business opportunities emerging as a result of the thaw, Starwood Hotels and Resorts Worldwide Inc. announced a day before Obama’s arrival that it had agreed to convert three hotels in Cuba into Starwood-brand properties. Airbnb Inc. announced on Sunday that the Treasury Department had approved its plan to offer accommodations in Cuba for non-U.S. travelers. Marriott International Inc. also announced on Sunday that Treasury had approved its application to do business in Cuba. Marriott CEO Arne Sorenson is traveling with Commerce Secretary Penny Pritzker as part of the U.S. delegation accompanying Obama to Cuba. No Flags Other business leaders including Ursula Burns, CEO of Xerox; Brian Chesky, president and founder of Airbnb; and Daniel Schulman, CEO of PayPal also will travel to Cuba to participate in an entrepreneurship summit tied to the Obama visit, according to a list released by the White House. House Democratic Leader Nancy Pelosi of California and Senator Dick Durbin of Illinois, the second-ranking Senate Democratic leader, flew with Obama on Air Force One. He was was also accompanied by Rachel and Sharon Robinson, the widow and daughter of the late Major League Baseball player Jackie Robinson, whose Dodgers trained in Cuba. Two days before Obama’s scheduled arrival, there were few outward signs of the American president’s coming arrival in the historic Old Havana neighborhood or along the Malecon seaside strand. There were none of the banners, photos of Obama, or flag displays that often precede his arrival in foreign countries. Even in the neighborhood around the U.S. embassy, the only American flag visible was the one flying at the diplomatic outpost. Knots of Children Outside a school a block away from the theater where Obama is to make an address to the Cuban people, knots of children dressed in blue shirts and blue pants expressed excitement at the prospect of a U.S. president in the country but little hope they would see him in person. Interest in Obama’s visit is tempered by uncertainty over what might come next. Yoel Oliver, 29, and Nayla Montano, 32, friends and partners in a small art stand at a seaside craft market, personify the mixed feelings on the prospects of the opening with the U.S. The stand, which sells paintings of Havana cityscapes, antique cars and musical scenes to European and Canadian tourists, is struggling, they said. “To sell a painting is like winning the lottery,” said Montano, who said she’s never even had access to an Internet connection to use the hot-pink encased Samsung Android phone jutting out of her jeans pocket. Montano expressed little optimism that the Obama visit is a sign of improving times. Isn’t the American president in his last year of office anyway, she asked. And what is to stop his successor from retreating? Oliver, whose wrists show the scars of surgeries that have strengthened his hands to partly overcome disabling birth defects, counts himself among the optimists that the historic visit begins a path to better economic times. “A lot of people hope, and a lot of people don’t think so,” Oliver said. “I am one of the people who hope so.” Fidel Castro Obama will meet with Raul Castro but not with Fidel Castro, the 89-year-old architect of Cuba’s revolution. He’ll deliver a speech to the Cuban people and urge the nation’s government to improve its human rights policies as well as its business climate if it wants real U.S. investment. The Associated Press reported that counter-protesters and police on Sunday broke up an anti-government demonstration by the Ladies in White dissident group in Havana, hours before Obama was due to land. Offering a taste of what a more open relationship could mean, Obama also plans to attend an exhibition baseball game between the Tampa Bay Rays and the Cuban national team. He’ll miss by a couple of days another historic spectacle, a free Rolling Stones concert in Havana. Those images are not just for consumption back in the U.S. or in Cuba. The highlights of the trip will be beamed across Latin America. Latin American Friction Obama is making the connection between his Cuba policy and his aspirations for improved relations with the rest of Latin America explicit by flying from Cuba to Argentina. The last visit by a U.S. leader to Argentina, for a multination summit in 2005, ended with then-President George W. Bush rebuffed in trade talks by South American leaders and anti-U.S. protesters in the streets led by Argentine football legend Diego Maradona. While the friction between the U.S. and Latin America has multiple sources, the isolation of Cuba is a common factor. “The Latin Americans are really amazed by our enduring enmity to Castro,” said Jonathan Hansen, a Harvard University historian and specialist on Guantanamo, who is writing a biography about Fidel Castro. “Having a reciprocal, respectful recognition of Cuba as a country that’s struggling on its own terms, to treat them like they have a right to exist, is really important for Latin America.” Easing Relations Obama already has moved to restore the relationship, reopening the U.S. embassy, opening the way to commercial airline flights to Cuba, resuming direct U.S. mail delivery, and undercutting the embargo through a series of regulatory changes his administration has deemed legal to ease restrictions on remittances, travel, exports, banking and businesses. Obama, 54, wasn’t born when a group of Central Intelligence Agency-trained Cuban exiles stormed ashore at the Bay of Pigs in a failed effort to overthrow Fidel Castro, casting the die for more than a half century of antagonism between the U.S and its island neighbor. By becoming the first sitting U.S. president to set foot in Cuba in 88 years, Obama looks to unwind that legacy and build a new one. U.S. policy toward Cuba hasn’t worked “since I was born,” Obama said in an interview with CNN en Espanol last week. Giving Cubans more access to commerce and the Internet may bring about bigger changes than the embargo ever could, Obama said. In relation to the rest of Latin America, he said, it means removing “this one lingering irritant or perception that somehow the United States was trying to big-foot smaller countries in the region.” Partisan Fault Lines Obama’s track record on shifting U.S. foreign policy is mixed. He has yet to deliver on a 2009 speech in Cairo signaling a new framework for U.S. relations with the Muslim world. Obama’s attempt to put Asia at the center of U.S. foreign policy remains a work in progress more than seven years into his presidency. Obama’s Cuba outreach has also exposed clear lines in U.S. politics, particularly in the presidential campaign. While former Secretary of State Hillary Clinton and Senator Bernie Sanders, the two candidates for the Democratic nomination, have embraced improving relations with Cuba, the Republican candidates have generally opposed Obama’s actions. Trump, the businessman who’s the front-runner in the Republican race, more recently said he would close the U.S. embassy in Havana and instead negotiate more concessions from the Castro regime. Cruz, a Republican senator from Texas whose father came to the U.S. from Cuba, has called Obama’s approach “unconditional surrender.” And John Kasich, governor of Ohio and another Republican presidential candidate, has said he wouldn’t allow greater commercial ties without changes by the Cuban government. Dissident Arrests Even with growing U.S. public sentiment for normalized relations, the Cuban government’s human rights abuses—including arrests of dissidents and monitoring its residents’ communications—plus limits on direct hiring by foreign businesses, infrastructure shortcomings, and restrictions on foreign and private investment, remain significant obstacles to a full restoration. Ana Quintana, a Latin America analyst with the Heritage Foundation, a conservative research group in Washington, said Obama’s trip rewards continued oppression by the Castro government and signals to Cuban political prisoners that the U.S. cares more about commerce than their freedom. “Strategically and logically, the trip makes no sense,” she said. Obama “needs to refocus back on human rights.” Quintana said conditions for activists have worsened since Obama announced his move toward normalization, saying there have been 2,555 politically-motivated arrests in Cuba this year and a rise in religious persecutions. “It overwhelmingly benefits the Cuban government at the expense of the Cuban people,” she said.