Things have yet to get going but keen North Korea-watchers will be pleased to know the Running Bodyguards have already made an appearance.
What's The Summit All About?
The ultimate aim is to end a nuclear stand-off on the Korean peninsula - no easy feat.
US Secretary of State Mike Pompeo said the preparatory talks were moving quite rapidly "and we anticipate that they will come to their logical conclusion even more quickly than we anticipated", reports Reuters.
But that doesn't mean the talks themselves will go as swiftly.
Pompeo played down the possibility of a quick breakthrough and said the summit should set the framework for "the hard work that will follow", insisting that North Korea had to move toward complete, verifiable and irreversible denuclearisation.
Get that nailed down and he said the summit provides "an unprecedented opportunity to change the trajectory of our relationship and bring peace and prosperity".
When Does It Kick Off?
What Does Trump Think About It All?
The President elaborated slightly on Sunday, saying: "We've got a very interesting meeting ... tomorrow, and I just think it's going to work out very nicely."
But then he says that about pretty much everything.
What Do The Experts Think?
Many experts on North Korea, one of the most insular and unpredictable countries in the world, remain sceptical Kim will ever completely abandon nuclear weapons.
They believe Kim's latest engagement is aimed at getting the United States to ease the crippling sanctions that have squeezed the impoverished country.
The road to the summit has been a rocky one and has already been called off once. In the lead-up, North Korea rejected any unilateral nuclear disarmament and wants the United States to remove its "nuclear umbrella" protecting South Korea and Japan.
The relationship between the two countries got off to a bad start under Trump, who last year derided Kim as a "maniac", referred to him as "little rocket man" and threatened in a speech to "totally destroy" North Korea - a country of 26 million people - if it attacked the United States or one of its allies.
Kim responded by calling Trump a "mentally deranged US dotard".
What About Kim?
The famously secretive Kim has been, well, famously secretive, but commenting for the first time on the summit, North Korea's state-run KCNA news agency earlier said the two sides would exchange "wide-ranging and profound views" to reset relations. It heralded the summit as part of a "changed era".
Discussions would focus on "the issue of building a permanent and durable peace-keeping mechanism on the Korean peninsula, the issue of realising the denuclearisation of the Korean peninsula and other issues of mutual concern," KCNA said.
What's On The Menu?
Lobster bisque, beef tenderloin and ice cream were on the lunch menu on Sunday.
Well, funny you should ask, as there's also a birthday cake for Trump, who turns 72 on Thursday.
What Do The Locals Think?
Some people were grumbling in the wealthy city-state because of travel delays caused by the summit and the price of hosting two leaders with massive security needs. Singapore's prime minister, Lee Hsien Loong, has said it will cost the country about S$20 million ($15 million), more than half of which will go on security.
"Thanks PM Lee for spending $20 million of taxpayers money, which can ... help a lot of needy families in Singapore to survive," posted one Facebook user.
Others complained about the traffic jams in downtown Singapore.
Will It Work?
It could go either way – a Trump administration official, speaking on condition of anonymity, said the US side was entering the talks with a sense of optimism and an equal dose of scepticism, given North Korea's long history of developing nuclear weapons.
"We will not be surprised by any scenario," said the official.