There, Singapore's Foreign Minister, Vivian Balakrishnan, took a selfie with Kim and Education Minister Ong Ye Kung in front of a wall of flowers.
Kim, in the middle, was smiling and looking directly into the camera. "Jalanjalan," Balakrishnan wrote on Twitter, using the Malay term for going for a walk.
Then the group crossed over Jubilee Bridge, an architecturally impressive pedestrian walkway over the Singapore River, to Marina Bay Sands, a breathtaking building comprising three towers with an enormous boat-shaped structure on the top.
The hotel and casino complex is owned by Las Vegas Sands, the company run by Sheldon Adelson, one of Trump's biggest donors.
Kim smiled and waved at the crowd gathered at the entrance to Marina Bay Sands, some of whom cheered and clapped for him.
The North Korean leader was accompanied by his sister and close aide, Kim Yo Jong, as well as cameramen for North Korea's state television channel, suggesting that his city tour will be featured on North Korea's news broadcasts.
Guests at the Cé La Vi bar on the Marina Bay Sands' tiered 57th floor realised something was up soon after 8 pm, when the deck on the level below was cleared and the area secured. Around 9.30 pm, in swept about 50 bodyguards, according to staff, with Kim in the middle.
He stood on the 56th floor's rooftop "Sky Park" looking over the city, with its skyscrapers topped by illuminated Citibank and HSBC signs.
Kim was there for about 10 minutes, according to staff and patrons.
"I wondered why he was here. Doesn't he have a meeting in the morning?" asked a British businessman drinking beer on the edge of the roof deck, the perfect spot to watch Kim on his tour.
The staff weren't told who was coming to the bar, but they guessed. It was "scary," said one.
After Kim and his entourage left, cleaners wiped away fingerprints from the glass barriers, according to local reports.
Singapore is a comfortable place for North Koreans. It is in Asia, and it has been ruled by one family for almost 60 years. It has strict rules, although nowhere near as strict as North Korea's.
And its astonishing economic transformation offers a model for a strong developing state.
Because the island nation is so relatable, the Singaporean nongovernmental organisation Choson Exchange has brought more than 100 North Koreans here over the past nine years, teaching them about finance and market economics and development.
"Bringing North Koreans to Singapore is about telling them that if they take the right steps, someday they will be a prosperous global city, too," said Geoffrey See, the Singaporean who started Choson Exchange.
"And this economic story is reflected in the infrastructure in the bay area, with the skyscrapers lining the business district, the Marina Bay Sands hotel crowning the skyline and the Esplanade flanking the bay."
In fact, See has taken his North Korean groups on almost exactly the same city tour that Kim undertook, although - unlike Kim - the other North Koreans stopped for a drink beside the infinity pool atop the Marina Bay Sands boat.
Singapore's Government appeared to be sending a signal to Kim about the possibilities for his own future, See said.
"I would not be surprised that part of the message the U.S. has for North Korea in bringing them here is to say, 'If you take the right steps tomorrow, this could be the global prosperous city or country you can be in a generation,' " he said.
