They will meet on the resort island of Sentosa, which is "conveniently isolated" from the rest of the Southeast Asian country of 5.9 million, noted Sung-Yoon Lee, professor of Korean studies at the Fletcher School at Tufts University.
"So it's one-time, it's a one-time shot, and I think it's going to work out very well".
What can we expect from the summit? Kim, whose organization helps defectors escape North Korea and China and assists them once they reach South Korea, said that, even now, the situation is much the same; North Koreans know their government is lying.
Instead, Trump acknowledged, the summit is unlikely to achieve a major breakthrough, stating that at minimum he would like to "start a dialogue" with Kim.
"Id like to accomplish more than that", Trump said.
President Trump predicted Saturday that he will know nearly immediately when meeting Kim Jong Un whether the North Korean dictator is serious about negotiating a nuclear deal, suggesting his intuition is enough to size up the leader of the worlds most opaque authoritarian regime.
Is Libya the right model for North Korea denuclearization?
In 1997, Kim and his father left the country in the midst of a four-year-long starvation and economic crisis that some estimates suggest claimed the lives of between 240,000 and 3.5 million North Koreans, out of a population of 22 million.
Kim Jong Il, the current leader's father who died in 2011, violated past global deals aimed at curbing the North's nuclear program and ballistic missiles by launching new weapons tests. Pyongyang's ICBMs have the range to hit the U.S.
North and South Korean soldiers glare at each other across the line that Kim Jong Un historically stepped across for his recent summit with South Korean President Moon Jae-in.
That changed in one stroke at end of April when North Korea's Kim announced that the isolated country would immediately suspend nuclear and missile tests, scrap its nuclear test site and pursue economic growth and peace, said T.C. Koh, group managing director of the company.More news: Pres. Trump signals support for legislation easing US ban on pot
"But It depends on what they're talking about it and it depends on their willingness to take time and work around the periphery and ultimately to get to the really hard cards in the pack; human rights and nuclear weapons". How long will it take?
"He might as well have said, 'Carry on, '" Lee said.
She said if the outcome was denuclearisation in North Korea, "we all need to celebrate that".
To achieve this long-held desire he has dramatically shifted in character from isolated angry strongman to global statesman.
Still, questions remain about what a deal on the North's nuclear weapons could look like.
But it's not completely barren territory for students of North Korean media.
Should the agreement be binding?Lacking one can result in arrests.
Trump expressed hope that the summit would be good for world peace but also for the dictatorship. "I think I'll also know whether it will happen fast".
"I'll speak very frankly, I think Australia needs to press its own diplomatic stance on this issue, rather than align itself with the United States".
"This being said, a treaty is not ironclad and usually contains clauses that allow each side to withdraw from the treaty", Aum said.
Yet many close observers doubt the once hostile leader's appetite for peace. The Lowy Institute's global security director Euan Graham says Mr Kim has relied on the classic North Korean playbook, swinging predictably from provocation to engagement. "At the same time, Trump, by having signed or agreed to it himself, will become a captive of the agreement, and will find it politically hard to scuttle the deal".
Since the first inkling that a Trump-Kim summit could be on the cards, Japan has repeatedly insisted that Washington be mindful not to let its guard down with the nuclear-armed regime in Pyongyang.