Trump left the Shangri-La Hotel in the city-state of Singapore at around 8 a.m. local time (0000 GMT) for the Capella Hotel on Singapore's resort island of Sentosa, where he is meeting with the DPRK leader.
About 10 minutes after the departure of Trump's motorcade, Kim's motorcade was seen leaving the St. Regis hotel, which is just hundreds of meters away from where Trump stays.
On the way to the venue, no bystanders were seen as Singapore's government has tightened security around the largest offshore island of Singapore. Singapore's Navy has also strengthened maritime patrols near Sentosa island.
A black limousine, believed to be carrying Kim with two DPRK national flags fluttering on the hood, was escorted by black vehicles and police squad cars.
Trump arrived at the Capella Hotel at about 8:14 a.m. (0014 GMT). Some 10 minutes later, Kim came to the venue.
The two leaders planned to meet one-on-one for up to an hour with only their translators at their sides. The tete-a-tete was scheduled to kick off at 9 a.m. (0100 GMT).
It would be followed by a larger meeting and working lunch, attended by their entourages.