Whether the 12-day journey to Asia offers a welcome diversion -- or whether his preoccupation with Russia becomes a dangerous distraction -- is a question that will be answered along the way as he leaves Washington on Friday.
A premium has been placed on avoiding snags that would bring the President outside his comfort zone -- including, according to one official involved, a mandate that familiar food be available during Trump's meals.
"No whole fish with the heads still on, nothing too spicy," is how one person involved in the trip's planning characterized the instructions for Trump.
The Asia trip has stirred anxiety among some aides in the White House, largely because developments in the Russia investigation have created a distraction during a critical time of preparation. Some briefings were delayed. Other meetings were cut short.
But once Air Force One lifts off on Friday, a senior adviser said, the trip would change the subject and the surroundings for the President.
"This trip will do what we often can't do: keep the President focused on the matter at hand," said a senior administration adviser who is involved in planning the trip.
For a President who often is difficult to pull away from the television or the phone, the sweeping change in time zones and the busy schedule will present a diversion.
Trump's aides worry a poorly timed tweet in a region rife with nuclear tensions could derail sensitive talks with leaders in Japan, South Korea, China, Vietnam and the Philippines. Distractions over the Russia investigation could prove damaging in Trump's high-stakes talks.
The ambitious foreign trip presents an opportunity to create distance, literal and figurative, between the President and a scandal-obsessed Washington. Trump himself sought to demonstrate confidence on Wednesday, telling The New York Times
that he is not "angry at anybody" over the Russia probe and that he was looking forward to the Asia trip.
But pitfalls abound, and Trump himself has expressed concerns at how the recent swell of Russia-related news could impact his negotiations with Asian leaders.
Trump has fumed at the actions taken by Mueller, which he fears make him appear politically weak. He's suggested to some aides that his ability to negotiate with leaders -- who themselves are enjoying new political muscle -- could be hampered.
"These are leaders who know what's going on back home," said one senior White House official, noting Trump himself was aware of the dynamic he's flying into.
On Trump's first stops in Asia, he'll encounter leaders recently emboldened. Japanese Prime Minister Shinzo Abe saw his ruling party win big in snap elections last month. South Korea President Moon Jae-in was elevated to the office in May.
And President Xi Jinping exited China's communist party congress this fall having consolidated power in historic fashion -- a position that analysts said would provide him a boost in his talks with Trump.
"Obviously, he's in a very strong position with no visible or other domestic opposition, as compared to what best can be described, I think, as a challenged President Trump, whether it's Russia issues, tax reform challenges, things of this nature. So that certainly gives Xi Jinping a bit of a leg up," said Christopher K. Johnson, a senior adviser at the Center for Strategic and International Studies in Washington.
Trump is anticipating intense talks with his counterparts on security and trade issues, but is concerned that the timing of this week's criminal charges in the Russia probe will hurt his standing, according to senior White House officials.
"He worries about his ability to negotiate with various entities and how much he's hamstrung by this," a second senior White House official said.
International trips, for any new president, present a steep learning curve.
But Trump embarks on this five-country tour of Asia with relationships already blossoming with leaders across the region. The White House says the trip has two leading objectives: the rising nuclear threat from North Korea and trade.
On Wednesday, Trump appeared cognizant of the sensitivities surrounding the trip. Bemoaning the US trade deficit with China ahead of a Cabinet meeting, Trump withheld insults directed at those responsible.
"I don't want to embarrass anybody four days before I land in China, but it's horrible," he said.
The President will be accompanied by a smaller contingent of advisers compared to his earlier foreign trips.
After a brief stop in Japan, daughter and senior adviser Ivanka Trump is heading back to the United States to help push tax reform. Jared Kushner, a senior adviser and the President's son-in-law, is only scheduled to go on part of the trip. Treasury Secretary Steven Mnuchin and the President's chief economic adviser, Gary Cohn, are also staying behind to press the tax reform issue.
First lady Melania Trump is also only scheduled to be alongside the President for the first portion of the trip.
Commerce Secretary Wilbur Ross, Secretary of State Rex Tillerson and national security adviser H.R. McMaster will be on the trip throughout, an official said, but none of the advisers are as close to Trump as some of those who are not accompanying the President. White House chief of staff John Kelly is also aboard, and has told other aides it is incumbent on all staffers to help keep the President focused.
The White House has worked to mitigate Trump's fatigue on this trip by building in a night in Hawaii on the way to Asia, and ensuring stretches of down time while he's in each country, according to a senior administration official. But the official privately acknowledged that any trip to Asia -- much less a 12-day slog -- is going to be "exhausting for any president."
The schedule for the trip has been overseen by McMaster with input from Kelly, both of whom have been keeping an eye both toward keeping Trump occupied on the road, but not overly loaded with intense bilateral talks.
Trump's aides and former business colleagues have described the President as largely averse to extensive foreign travel, preferring instead to sleep in his own bed and negotiate with leaders on his on turf.
The person involved in the trip's planning said officials in each country on the trip have been warned that Trump is not comfortable with new cuisines and prefers familiar foods, like well-done steak and ice cream. Previous presidents' aides have similarly asked their foreign hosts to accommodate the tastes of the commander in chief.
In Japan, Abe has commissioned a pop singer to perform at dinner (the singer, Piko Taro, is behind the hit song called "Pen-Pineapple-Apple-Pen" that the President's granddaughter, Arabella Trump, performed in a viral video last year). Trump's first hours in both Japan and China will be spent in more informal settings instead of in serious negotiations. He'll play golf with Abe shortly after landing in Tokyo, and will tour the Forbidden City with Xi upon arrival in Beijing.
In the week before he departs, Trump has scheduled a series of short briefings, including one-on-one meetings with Tillerson and Defense Secretary James Mattis, both of whom traveled to Asia in the past months. Trump has also spoken to lawmakers about his visit to Asia.
Like his past foreign trips, Trump's officials have prepared briefing materials with an eye toward brevity -- ideally one page -- with maps and charts and photos. That includes materials preparing Trump for some of his higher-stakes meetings with leaders, including with the Philippine strongman Rodrigo Duterte, who he's never met.
Amid the raft of news about Russia, however, Trump's aides have acknowledged that Mueller's probe have proven sidetracking.
"It is very distracting to the President, as it would be to any citizen, to be investigated for something, while at the same time trying to carry the weight of what being President of the United States means on his shoulder," chief of staff Kelly said during an interview on Fox News this week.
"He and I have, as you might imagine, multiple conversations a day, generally in the morning when we first talk, it'll be about these kind of things; just general conversation before we get down to business. But it is very distracting for him," he added.
CORRECTION: This story has been updated to reflect that unlike previous foreign trips, Trump has not discussed this trip with Sen. Bob Corker.