The Obamas' tour of Old Havana was nearly a washout on Sunday evening as a deluge of rain came down minutes after they landed in Cuba for an historic three-day visit to the communist country.
The first family pressed on, despite the stormy skies, strolling through the Plaza des Armas as they huddled under umbrellas and they made their way to the Museo de la Ciudad, the museum of Cuba's capital city, and on to Havana Cathedral.
President Obama's family - particularly his daughter Sasha - looked less than pleased as they perched underneath their blue and black umbrellas.
As the Obama's taxied towards their motorcade, the president wrote on Twitter: '¿Que bolá Cuba? (What's up Cuba?). Just touched down here, looking forward to meeting and hearing directly from the Cuban people.'
Cuban dictator Raul Castro did not greet the Obamas on the tarmac, leaving the country's foreign minister to conduct the greetings and handshakes instead. Castro has a meeting with the U.S. president tomorrow morning, but Obama will not come face-to-face with former leader, Fidel Castro.
As he arrived in the country, Obama admitted that Cuba had work to do to correct its poor human rights record, but said: 'Change is going to happen.'
Obama told ABC News: 'The time is right. Obviously our intention has always been to get a ball rolling, knowing that change wasn't going to happen overnight. We felt that coming now would maximize our ability to prompt more change. And it gives us, I think, the opportunity before I leave office to continue to stay on track in moving things forward.
'Change is going to happen [in Cuba] and I think that Raul Castro understands that.'
He added: 'We still have some work to do. I think it is very important for the United States not to view ourselves as the agents of change here, but rather to encourage and facilitate Cubans themselves to bring about changes. We want to make sure that whatever changes come about are empowering Cubans.'
President Obama, his wife Michelle, children Sasha and Malia and the first lady's mother, Marian Robinson, touched down in Havana at 4:20pm ET on Sunday, with the first drops of rain falling as the Obamas walked down the Air Force One steps.
Obama is the first sitting president in nearly 90 years to visit the island, in a trip the White House says will 'deepen' America's relationship with the authoritarian government following more than half a century of tension.
Obama and his entourage were whisked off the runway to Melia Habana hotel to meet with U.S. embassy staff before their tour of Old Havana, a family excursion that was ill-fated, given the torrential downpour, but left on the schedule nonetheless as the U.S. president made a symbolic display of solidarity with the Cuban people.
Cuban and American flags flew from the president's car as it left the airport in the direction of central Havana.
'This is a historic visit and a historic opportunity,' Obama told embassy staff as he greeted them and reflected on the seven months since the embassy reopened in Havana last July. 'I want you to know, everyone we've accomplished so far, it's all happening because of you. Every day you're bringing the US and Cuba closer together.'
Obama was later cheered as he passed through a square outside Havana Cathedral, with hundreds of people erupting in applause and shouting the president's name as the first family stepped forward.
The Obamas then dined at a privately-owned restaurant in a bustling, working class neighborhood. Jubilant crowds surged toward the president's heavily fortified motorcade as it inched towards the San Cristobal restaurant.
After a short dinner, the Obamas headed to the ambassador's residence, where they are staying during their visit.
The first family will now spend three days on the island, then fly to Argentina for another two before returning to Washington, DC, just before the Easter holiday.
Republican presidential front runner Donald Trump accused Castro of disrespecting the United States by not meeting Obama at the airport.
'Wow, President Obama just landed in Cuba, a big deal, and Raul Castro wasn't even there to greet him. He greeted Pope and others. No respect,' Trump tweeted.
Senator Bernie Sanders, a Democrat seeking to replace Obama in the White House, meanwhile praised the president for 'making history by traveling to Cuba and moving relations between our two countries into a new era'.
'This is an approach that is long overdue....Fifty years of Cold War is enough. It is time for Cuba and the United States to turn the page and normalize relations,' Sanders said.
The president is scheduled to meet with dissidents of the oppressive government, as well as the country's leader, Castro, during his visit. He will also give a televised speech from Havana's national theater, Gran Teatro Alicia Alonso.
Amid the fanfare of Obama's arrival, as many as 50 protesters demonstrating against Cuba's poor human rights record were arrested in Havana, including the leader of women-run democracy campaign group who was arrested in a Castro regime crackdown.
Obama's first stop after landing in Cuba was meeting with staff at the recently re-opened embassy. The inclement weather meant the president chatted with workers at a nearby hotel instead of the consulate.
The president said: 'Back in 1928, President Coolidge came on a battleship, it took him three days to get here. It only took me three hours.
'Having a US embassy means we're more effectively able to advance our values, our interests and understand more effectively.
'This is a historic visit and a historic opportunity. I know it's been a pretty busy seven months. But I want you to know, everything we've accomplished so far, it's all happening because of you. Every day you're bringing the US and Cuba closer together.'
Speaking to diplomatic staff, he added: 'I'm so glad you brought your families here because I always like taking pictures with kids. Their future is what we all work for so hard and I'm so grateful to all of you for making it happen.'
The U.S. operated out of the embassy during the detente between the U.S. and the Castro regime from 1977 until the summer of 2015, but it was under the authority of the Swiss government, which served as the protecting power.
It officially assumed the role of the United States' mission in Cuba on July 20, 2015, when diplomatic ties were formally restored.
The president's spokesman on Friday said Obama will not shy away from using his 'bully pulpit' on the trip to address human rights violations in the communist country that the United States was estranged from for more than 50 years.
'For more than 50 years, we tried a strategy of saying, well, why don't we just try to ignore the Cubans and see if they change their mind on their own. Not surprisingly, that strategy didn't really work very well, so we're trying a new approach,' White House Press Secretary Josh Earnest told reporters on Friday.
Earnest. said: 'The President of the United States is going to get on Air Force One, he's going to fly to Havana, Cuba, and he is going to sit down with the leader of Cuba and say, you need to do a better job of protecting the human rights of your people.
'He's going to give a speech to the Cuban population, to the Cuban people, one that will be carried on TV, according to the Cuban government, where the President will advocate for better respect for human rights.
And while he's in town the president will 'visit with people who have previously been victimized by the government, and encourage them to continue to fight for the kinds of universal human rights that we deeply cherish in this country'.
'That is effective advocacy for American values,' Earnest added. 'That is effective advocacy for the kinds of principles that we cherish in this country and in our government. And it is, by the way, an approach that is strongly supported by the vast majority of the Cuban people.'
The first day of the trip saw the entire first family, including Michelle Obama's mother, Marian Robinson, take a tour of Old Havana.
As part of their 'cultural outreach' they stopped by Havana Cathedral to see Cardinal Jaime Ortega. The Cuban cardinal played a crucial role in the thawing of relations between the United States and his home country.
The first family's visit to his church was to 'mark the important role of the Catholic Church in the lives of the Cuban people', the White House said this week on a planning call, 'and in the increasing relations' between the two countries.
On Monday morning, the president will honor Cuban revolutionary José Marti, a hero in the Cuban revolt against Spain, by laying a wreath at his memorial, a 358ft tower, in Havana's Plaza de la Revolución, before his meeting with Raul Castro.
The president will be 'very candid about areas of disagreement' at their meeting, Deputy National Security Adviser Ben Rhodes said, 'including the human rights practices that have concerned us in Cuba and our support for universal values in Cuba'.
Both presidents are expected to deliver statements after the meeting and the White House indicated on Friday that Obama would likely take questions from the press, although a formal news conference has not been scheduled.
Obama will not meet with ex-Cuban dictator Fidel Castro while he is in town. The 1950s era Cuban revolutionary turned over power to his brother in 2006 temporarily for health reasons and made the transition permanent in 2008.
The 88-year-old has rarely been seen in public since handing over power, prompting rumors that he is in failing health. His last observed outing was in February.
'Neither we nor the Cubans have pursued such a meeting,' Rhodes said Wednesday.
Mrs Obama will meanwhile on Monday meet with female Cuban students, some of whom have studied in the U.S., as part of her Let Girls Learn initiative, the White House said.
The president and first lady will also participate in a State dinner hosted by the Cuban government at the Palace of the Revolution on Monday.
The following morning President Obama will give a speech, in which he will 'review the complicated history' between the countries, the White House says, 'but also to look forward to the future, and to lay out his vision for how the United States and Cuban can work together, to how the Cuban people can continue to pursue a better life.'
Afterward he will meet with political dissidents before attending an exhibition game between the Tampa Bay Rays and Cuban National Team.
'Americans and Cubans share a love of baseball, and this is yet another powerful reminder of the kinship between our peoples, as well as the progress we can achieve when we leverage those natural ties,' the White House's chief spokesman, Earnest, said Friday.