Their highly anticipated meeting, which will be held on Tuesday, will mark the first time a North Korean leader has met a sitting US president.
Trump arrived at Singapore’s Paya Lebar Airbase at 12:30 GMT on Sunday, a few hours after Kim touched down at Changi Airport in an Air China 747 – almost 48 hours before the summit at the city-state’s Capella Hotel.
“Both sides have extensive advisory teams, so there is a lot of work going on behind the scenes,” said Al Jazeera’s Kimberly Halkett, reporting from Singapore.
“It’s not just the diplomatic aides and the audiences around the world, but even ordinary Singaporeans are feeling particularly special that history could be made right here on their soil,” she added.
Trump met Singapore’s Prime Minister Lee Hsien Loong on Monday, the eve of the historic summit.
They did not give any comment to waiting journalists, but as the two leaders took their seats Trump could be heard saying to Lee, “We’ve got a very interesting meeting in particular tomorrow, and I just think it’s going to work out very nicely.”
Since taking power in 2011, Kim had met no other foreign leader prior this year. After arriving in Singapore on Sunday, he held talks with Prime Minister Lee and thanked him for hosting the summit, according to Singapore’s foreign ministry.
“There is going to be a lot pressure on these two leaders to prove that this is more than just a photo opportunity, but something that can be achievable, starting with what the US president calls a dialogue,” said Halkett.
For Trump, who has withdrawn the US from several international agreements since taking office, much to the dismay of traditional allies, the hope is to achieve a legacy-making deal with North Korea to give up their nuclear weapons.
He has conceded, however, it may take more than one meeting.
“Hopefully, we will have liked each other and we’ll start that process. I would say that would be the minimal.”
It wasn’t always like this. Just nine months ago, Trump told the United Nations General Assembly that he was prepared to “totally destroy” North Korea if the US or its allies were attacked.
He also mocked Kim as “rocket man” and said he was on a “suicide mission”. In a rare statement directly attributed to him, Kim responded by calling Trump a “mentally deranged dotard”.
Diplomacy later kicked in, with North Korea sending a delegation to South Korea’s Winter Olympics in February; a landmark inter-Korea summit taking place at the demilitarised zone between the two countries; and a secret trip by then-CIA Director Mike Pompeo, the first of two visits by the current US secretary of state, to Pyongyang.
After what seemed like an endless back-and-forth, the Singapore summit itself comes after months of speculation and disputes between Washington and Pyongyang that led Trump to briefly cancel the meeting.
Following a flurry of diplomatic efforts – including a White House meeting between by Kim’s right-hand man, Kim Yong-chol, and Trump – the proposed summit was put back on.
Al Jazeera’s James Bays, reporting from Singapore, said Trump has been sending “mixed messages” to Kim in advance of their meeting.
“President Trump, last month, briefly called off this summit and he has repeatedly threatened to walk out if he doesn’t believe the negotiations are serious.”
Isaac Stone Fish, senior fellow at the Asia Society’s Center on US-China Relations, said Tuesday’s meeting with Kim is a “huge gamble for Trump”.
“If this meeting is a disaster, Trump will lose a lot of credibility and that is bad for American interests because if Trump feels like he needs to make a deal, it’s possible that Kim will be able to get the upper hand in those negotiations,” he told Al Jazeera, speaking from New York.
“I think the symbolic things that come out of this summit will be a lot more important than any sort of deliverables,” Fish added.
“Trump will really want to be able to sign something with Kim, so he can take that home and say, ‘Look, I was able to start solving the North Korean problem. Other past US presidents have not been able to do this, but I have.'”
At stake at the summit are North Korea’s nuclear weapons and peace on the Korean Peninsula.
The tests came amid a campaign of “maximum pressure,” led by Washington, that tightened economic sanctions against Pyongyang and raised the possibility of military action.
In a New Year’s address, Kim said his country had completed development of its nuclear programme and would focus on economic development, suggesting a meeting with South Korea.
After a flurry of contacts between the two Koreas, South Korean officials suggested to Trump in March that Kim would be willing to meet face-to-face.
The talks will focus on reaching an agreement on the denuclearisation of North Korea in exchange for the easing of economic and diplomatic sanctions.
Victor Teo, professor at the University of Hong Kong, believes “North Koreans are upbeat, but careful at the same time”.
He told Al Jazeera: “A meeting where the optics are positive, meaning Trump gets a handshake with Kim Jong-un and they both go home agreeing to some kind of denuclearisation deal would go a long way domestically for President Trump as much as it would for the chairman of the state committee.”
Authorities in Singapore imposed tight security around the summit venue and related luxury hotels, including installing extra potted plants outside one contender for Kim’s accommodation to obstruct reporters’ views.