As he tries to calm allies anxious about his "America First" message, he'll be followed by fallout from his firing of FBI Director James Comey and the appointment of a special counsel to probe the president's campaign ties with Russian Federation.
In Saudi Arabia, where Mr Trump's repeated denunciations of Iran have been welcomed, United States flags lined roads along with pictures of Mr Trump and King Salman and the message "Together we prevail".
US President Donald Trump takes questions from reporters during a joint news conference with Colombian President Juan Manuel Santos at the White House May 18, 2017 in Washington, DC.
This will be his "debut" trip, where he'll have to manage a politically complex itinerary, which will test his - already proven - diplomatic inexperience.
Both are topics Miller has spoken out against throughout his career on Capitol Hill and in the White House.
The Trump administration is also expected to announce $110 billion in advanced arms and training to Saudi Arabia during his visit to Riyadh on Saturday, US officials familiar with the deal told the Associated Press.
Just this year, Donald Trump Jr opened the Trump International Golf Course in the same city, built with Nakheel's archrival Damac Properties.
His travel ban, in the name of protecting the U.S. against terrorism, also specifically targeted all Muslim-majority countries, a move that was derided by Muslims everywhere, including in the Middle East.
Immigrant arrests soar under Trump, fewer deported
The national unemployment rate is at 4.4 percent, awfully close to full employment. That's an 18.2 percent increase from a year ago during the same period.
"Speeches would normally be worked on for four to six weeks in advance, but this is an understaffed White House that has been focused on a fusillade of bad news". "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. Trump's powerful senior adviser, his son-in-law Jared Kushner, led a West Wing team to craft the agenda, laden with religious symbolism.
Shortly thereafter, Secretary of State Rex Tillerson said: "Iran is the world's leading state sponsor of terrorism and is responsible for intensifying multiple conflicts and undermining U.S. interests".
No sitting United States 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. "Does he invest in the relationship with the Atlantic partners in the same way that every president has done since Pearl Harbor?" he says.
The kingdom has arranged a dizzying schedule of events for the two days Trump will be in town - inviting figures as varied as Sudanese President Omar Al Bashir, Bret Baier, a host on the Fox News Channel that is popular with Trump and his supporters, and American country singer Toby Keith, who is to perform for a male-only crowd in capital, Riyadh.
The president was already under attack for firing Mr Comey in the midst of an Federal Bureau of Investigation probe into Russia's role in the 2016 election and possible collusion with Mr Trump campaign members.
In his recent meeting with Palestine Authority (PA) leader Mahmoud Abbas, Trump assured him: "We will get it done".
And in Sicily, the president will meet with the other leaders of the G7, a gathering of Western economic powers. "And their - the goodness of people of all faiths will prevail over this evil".
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. I faced great pressure because of Russian Federation. Trump's first trip is much farther from home.