As far as we know, his despot father only traveled out of the country by train, and rarely at that, because of fears of assassination.
Trump and Kim are due to meet in Singapore on Tuesday.
Not only is there a lot at stake politically, for lawyer Mr Kim, it's also personal.
There's wild speculation about how Kim will perform on the world stage: Will he bring, for instance, his armored limousine and his dozen well-armed, well-muscled bodyguards to march alongside his rolling fortress in a half-sprint?
Trump said Saturday that once they met, he would know for how long to continue talks and whether it would amount to a waste of time to go forward.
Meanwhile, Reuters reported on Sunday that an IL-76 cargo plane had appeared on tracking data flying from Pyongyang to Guangzhou in southern China, where it refueled to fly onwards to Singapore.
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At best, a framework will be agreed upon in which North Korea agrees to completely and verifiably denuclearise, and the rogue state actually follows through on its commitment. How can such rallies take place there?
There was heightened security at the St. Regis hotel in central Singapore, one of the hotels where the leaders were expected to stay.
Why's he taking the risk?
Beijing wants the summit, says Yun Sun, director of the China program at the Stimson Centre, relieved for any de-escalation in tension.
He also said that the "mainstream, corrupt, destroy-Trump media" was sent into a hysterical fit after the president's actions.
Agreeing to a troop withdrawal from South Korea would be the worst possible outcome for the summit, said Christopher Hill, a former USA ambassador who ran negotiations with North Korea in the George W. Bush administration. In 1999, United States inspectors found no evidence of violations of the Agreed Framework and talks on a high-level North Korean visit to the USA began.
"You know, President Trump has talked about a Nobel Peace Prize, he certainly isn't going to get it. Kim Jong-un isn't going to get it. Moon Jae-in, who knows?", Kristof shrugs.
What is clear is that it was only once China threw its weight behind economic sanctions that North Korea started talking. I'm sure the North Koreans would sign up for that. Their only issue is how much they have to give up.
"I'd like to accomplish more than that", Trump said.
Trump "likes it when "experts" are on CNN freaking out", the source said. In 2003, Libya agreed to give up its nuclear, chemical, biological and missile programs to restore its standing in the worldwide community and get sanctions relief. While the Trump administration has called for complete, verifiable denuclearization on a swift timetable, Pyongyang has signaled it expects a more incremental approach in which it receives reciprocal benefits along the way.