The young leader arrived at the Marina Bay Sands at around 10pm, ferried from the St. Regis Hotel where he is staying via armoured car and a sea of body guards.
Kim smiled as he walked and waved towards the crowd of tourists, families and media.
Shortly afterwards, the same army of black suited body guards escorted him from the building to take in the evening air.
Bizarre scenes ensued as the crowd of a round 50 escorts walked Kim and his sister, Kim Yo Jong, along the waterfront, crossing the Jubilee Bridge.
Kim has been indulging in a fair bit of sight-seeing, as one is inclined to after leaving North Korea. He has already been to see the Gardens by the Bay with Singapore's foreign minister, Vivian Balakrishnan.
However, aside from the many diplomatic engagements it would appear the 34-year-old leader is in Singapore not just for business but also pleasure.
Yet having a night out is easier said than done when your every movement is closely watched. However, Kim had the element of surprise on his side.
The shock news that Kim was "heading out" meant that reporters scrambled to follow the secretive North Korean leader's very public movements.
Like many other reporters Kirsty Needham of the Sydney Morning Herald had to abandon dinner plans to follow Kim, who had mostly "remained out of sight in the St Regis."
Kim will be attending the summit with Trump at the Capella Hotel today at 9am local time, though many details still remain to be ironed out by their seconds and advisors.
We hope the dear leader of the DPRK is feeling refreshed after his evening jaunt and ready for the day's peace talks.