Skipping a low-key stop in the United States' low-key northerly neighbor -- a traditional dry run on foreign travel for a new president -- Trump will instead touch down in the capitals of three major world religions, a dramatic in-person entry into the fraught intersection of faith, politics and national security.
The trip to Saudi Arabia, Israel and the Vatican is a splashy debut for a president who has, until now, largely avoided major trips outside of Washington.
He's spent most of his time away from the White House at his private estate in Florida. When he arrives in the Middle East toward the end of May, he'll be traveling abroad later in his presidency than any commander in chief since Lyndon B. Johnson, who waited more than 10 months after President John F. Kennedy was killed to travel abroad.
After the Vatican, Trump will make stops in Brussels and Sicily for NATO and G-7 meetings. Those stops were announced earlier this year.
Effort to counter radicalism
According to Trump's aides, the trip is designed as a symbolic show of resolve to top US allies, whom the Trump administration hopes will renew their efforts to combat radicalism and intolerance around the world.
But people familiar with the trip's planning said it's also meant to demonstrate a new era of American foreign policy in high-octane fashion. Revealing the trip during a Rose Garden ceremony Thursday for the National Day of Prayer, Trump deemed it a "major and historic announcement."
"Someone clearly saw the Vatican, Israel and Saudi Arabia as a broad stage where the President could demonstrate a certain degree of unity and ecumenism and go to places where he could be guaranteed a high degree of symbolism when it came to his first presidential trip," said Aaron David Miller, a senior fellow at the Woodrow Wilson International Center for Scholars.
"The trip provides a dramatic stage on which to act out his presidential role," Miller added.
The first stop in Saudi Arabia was designed specifically to rebut perceptions that Trump is anti-Muslim, according to a person who helped plan the stop.
The Islamic world has been rattled by some of Trump's actions, including signing an executive order barring entry to citizens of certain Muslim-majority nations and vowing during the campaign to end all Muslim immigration into the US.
"We thought that was very important because obviously people have tried to portray the President in a certain way," said a senior administration official. "But I think that what he wants to do is solve the same problem that a lot of the leaders in the Islamic world want to do."
Speaking Thursday, Saudi Foreign Minister Adel al-Jubeir said he believed the trip will help rebut impressions that Trump is anti-Islam.
"It's a clear and powerful message that the US harbors no ill will toward the Arab and Muslim world," he said. "It also lays to rest the notion that America is anti-Muslim."
Trump's stops in Riyadh, Jerusalem, Rome, Brussels and Sicily are not set to be long -- in some cases, he expects to spend only a night, according to officials who are planning the trip. But at each stop, Trump is hoping to demonstrate his faith in traditional US allies that his administration claims were slighted by the previous administration.
Contrast with Obama
President Barack Obama skipped a visit to Israel during his first trip to the Middle East in 2009, an opening slight in what became a sour relationship during his tenure in office. Saudi Arabia, along with other Arab Gulf nations, then felt neglected when Obama brokered a deal with Iran over its nuclear weapons, leading to fears the US was realigning its interests in the region.
"All the conversations we've had with all the leaders around the world show that there is a lot of frustration with how things have been done to date, and I think he's driven by common sense, and he's driven by a real practical approach to try to get things done," said a senior administration official.
President Barack Obama's first stop abroad was in Canada, and every US president since Jimmy Carter has made that or Mexico his inaugural foreign destination. The stops reaffirmed what have traditionally been close cross-border ties in North America -- relationships that have grown tense under Trump amid trade disagreements and a dispute over his proposed border wall with Mexico.
Canadian Prime Minister Justin Trudeau invited Trump to visit during a phone conversation soon after Trump was elected in November. Trump, at this stage, hasn't accepted, though a person close to Trudeau said he doesn't feel snubbed.
People who helped plan past presidents' foreign trips said a jaunt across the border also provided new White House aides a relatively easy trip to work out the logistical kinks of moving a president into a foreign country.
Trump's approach is markedly different, and could present pitfalls. Trump has not yet named a chief of protocol -- an ambassador-level position that assists in working out detailing plans with a foreign government before a President travels abroad.
In countries like Saudi Arabia and Israel -- each with distinct religious and political sensitivities -- matters of protocol can become essential in how a trip is perceived. Even if Trump's hosts are eager to execute a gaffe-free visit, Trump himself will need at least some preparation to avoid a cultural miscue.
"I don't think there are any traps that will be set," Miller said. "The question is whether he generates them on his own. And gets out of his own way. And there's no way to predict that. As carefully orchestrated and choreographed as these trips may be, there's always the possibility of a stumble or an inappropriate remark."
Past presidents have found that dealings with the tradition-bound Saudis can sometimes prove awkward. Photos of President George W. Bush holding hands with then-Crown Prince Abdullah in 2005 led to accusations he was too close to the oil-rich kingdom. Obama faced claims he was overly deferential after he appeared to bow to Abdullah -- who by then was King -- during a summit meeting in London in 2009.
Trump's maiden voyage overseas will look different than Obama's international forays for other reasons as well. They aren't likely to feature the types of sweeping addresses that Obama delivered regularly abroad. Nor are they expected to feature the types of cultural stops that Obama relished during his foreign swings.
Short stays in each place
The in-and-out itinerary hews closely with Trump's preferred style of travel as chief executive of his real estate business, when he would fly his private jet abroad for business meetings but rarely linger for long.
A person who traveled with Trump during his tenure atop the Trump Organization in the 1990s described a businessman not particularly enthralled with foreign travel: He did not easily adjust to time-zone changes and was regularly jetlagged, the official said. He steered clear of local cuisine. And the customs of foreign businessmen -- particularly in Asia, where deals are regularly sealed over a night of drinking -- sometimes irked the teetotaler Trump.
For a president and his aides, foreign travel can be a particularly grueling slog. Meetings regularly begin as soon as Air Force One touches down in a far-flung time zone, leaving little time for a commander in chief to adjust to a new setting, or clock. Visits in foreign capitals often involve state dinners that extend late into the evening followed by early talks the next day.
Trump's ambitious itinerary for his first trip -- five stops in a little more than a week -- is also bound to be taxing. But in the minds of White House officials, the grind is worth it in order to properly introduce Trump to a world that's still largely skeptical of his presidency.