The last time an American president embarked on a tour of Asia this long, it ended with George H W Bush collapsing during a state banquet, and vomiting on the Japanese prime minister.
Donald Trump's team will be hoping this goes better.
The President himself has been assuring reporters that the 12-day, five-nation trip, which was apparently originally envisaged as two separate visits, will not be a problem for him.
Speaking on board Air Force One, en route to Japan, he said, "It's gruelling, they tell me, but fortunately that's historically not been a problem for me.
"One thing people will say, that's not been a problem."
He also used the time during the flight to defend his handling of North Korea, claiming there had been "Twenty-five years of total weakness", so we are taking "a very much different approach".
And then he took the opportunity to defend himself.
Asked about the newly-empowered leaders of Japan and China he will be meeting, who have both recently consolidated domestic power, he replied, "Excuse me, so am I."
As evidence, Mr Trump pointed to the US stock market's record high, remarking, "I've always been great with money, I've always been great with jobs."
On the ground in Japan, he has so far cut a more restrained figure.
Despite sharing the stage inside an aircraft hanger at Yokota Air Base with a fighter jet, his speech to US troops avoided his usual taunting references to Kim Jong Un as "little Rocket Man".
But there can be little doubt who he was referring to when he warned any dictators against underestimating American resolve.
And then he was off, on board Marine One, to a country club for lunch and nine holes of golf with the Japanese prime minister Shinzo Abe and golf pro Hideki Matsuyama, who has said he will try his best not to lose to Mr Trump.
The course will be one of the venues for the 2020 Olympic Games.
Mr Trump calls Mr Abe a "very good friend", and the Japanese prime minister has been quick to present himself as the President's best friend in Asia, travelling to Trump Tower to meet then President-elect Trump last year, and sharing 16 phone calls during his term in office so far.
Over a working lunch of hamburgers and ketchup at the clubhouse, the two friends signed white caps with the slogan, "Donald And Shinzo Make Alliance Even Greater".
This may be a slightly corny way of expressing it, but that is what this leg of the trip is all about – signalling the United States commitment to its alliance with Japan, and these two men's unity on North Korea.
From here, the trip will get tougher.
Mr Trump and Mr Abe do agree on North Korea, the united front on this is real, but the same cannot be said for the leaders of South Korea and China, where the President's tour will take him next.
South Korea's President Moon has repeatedly stressed that military action on the Korean peninsula is not an option, and he will never allow another Korean war, while President Trump threatens fire and fury.
In Beijing he will meet a newly emboldened Xi Jinping, fresh from a Communist Party Congress that has enshrined his political thought into the party constitution, an honour previously reserved for Mao Zedong.
Mr Xi has proclaimed his country is at an "historic juncture" and moving closer to "centre-stage".
Mr Trump can expect to be greeted with extravagant ceremony, and no shortage of spectacle, but he is likely to find a leader unwilling to compromise on issues of substance.
There are other potential difficulties ahead.
Mr Trump signalled on the flight that he expects to meet his Russian couterpart Vladimir Putin during the APEC Forum in Vietnam, ostensibly to push him for help with North Korea.
But the optics may not help a president trying to leave behind his domestic political troubles and the federal investigation into Russian meddling in the US election.
And that's before he gets to Manila to meet Rodrigo Duterte, arguably the world's second most outspoken and unpredictable president.
This could be a very long 12 days.