And the White House's approach to the ultra-sensitive status of the city came under intense scrutiny after a senior USA official reportedly snapped that the Western Wall is "not your territory" and is "part of the West Bank" while discussing details of the president's visit with Israeli counterparts.
However, a major highlight of his trip would be his address to the Muslim world.
In another "Nixonian" gesture, President Trump has organized a small global tour, recalling former President Richard Nixon's famous trip to the Middle East and Europe in June 1974, weeks before resigning from his post as president.
Trump generated controversy as a presidential candidate with a call for a temporary ban on Muslims entering the United States, which he called a national security plan to prevent Islamist militant attacks. His administration's proposal to limit travel from several Muslim-majority countries is tied up in court. His first worldwide destination as president, Saudi Arabia, is where he reportedly registered eight companies during his campaign.
"It's nearly always true that when a president goes on a big foreign trip, especially one that has some important summits. that dominates the news and knocks most other stuff out", said Republican strategist Charlie Black.
In his sermon, the imam urged those attending the summit to work towards "constructive dialogue, cooperation and tolerance".
No sitting U.S. president has ever visited the Western Wall, the holiest site in Judaism, since American policy maintains that the final status of Jerusalem has yet to be determined. Comey demurred, Trump insisted and then, at a ceremony to honor law enforcement officials that worked the inauguration, the following event occurred., emphasis ours. Peace talks with Israel will top the agenda and Mr Trump is expected to express his support for Palestinian "self-determination".
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Trump will also have to demonstrate during his tour through Belgium and Italy, the arguments behind his isolationist policies and the prospects he might have with regard to the European Community and North Atlantic Treaty Organisation, whom he would have attacked during his electoral speech. Then he heads to Israel, followed by a meeting with Pope Francis at the Vatican.
Bremmer said he'd find it to be a successful trip if "Trump can just get through the meetings".
This will be closely watched after Mr Trump's conflicting pronouncements on the alliance.
"The Middle East leaders, particularly in the Gulf and Jordan, were not pleased with the way Obama handled Middle East policy from their point of view and, as a outcome, just because they have a different president leading foreign policy, that is welcomed", Shibley Telhami, a professor and pollster at the University of Maryland, told Al Jazeera.
Correspondents say the other G7 leaders are eager to hear Mr Trump's thoughts on trade and other issues at first hand.
"This is the single greatest witch hunt of a politician in American history!"
Trump and his wife Melania left aboard Air Force One on what will be an ambitious six-stop trip that takes in Saudi Arabia, Israel, the Palestinian territories, the Vatican, Brussels and Sicily.
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