Air Force One touched down earlier Saturday at the King Khalid airport in Riyadh, where Trump was greeted on a red carpet-bedecked tarmac by Saudi King Salman bin Abdulaziz Al Saud and other high-level Saudi officials.
The grand welcome - which featured a military brass band and a fighter jet flyover - demonstrated just how highly anticipated Mr Trump's arrival was to this Middle Eastern kingdom.
It also seemed designed to flatter a President famous for a gilt lifestyle. In Riyadh, a five-storey image of Trump's face was projected on the exterior of the Ritz Carlton hotel where he stayed, and large billboards of Trump and King Salman lined the highway from the airport.
But things only got weirder from there with the president's faux pas and theatrics in the Middle East attracting considerable attention on social media.
'Curtsy' to king of Saudi Arabia
The first awkward moment came as Trump accepted a prestigious award from King Salman bin on Saturday.
As he bowed his head to receive the Collar of Abdulaziz Al Saud, the country's highest civilian honour, Trump appeared to curtsy.
His actions provoked a fierce back and forth on Twitter between his supporters and critics. His critics were quick to point out how Trump had savaged then-president Barack Obama for bowing to King Abdullah in 2009.
Others said it showed how Trump is kowtowing to the Saudis.
His supporters, meanwhile, claimed that he was merely bowing down so that the elderly Saudi king could place the medal around his neck.
Trump's sword dance
Trump along with other White House officials participated in a ceremonial sword dance in Saudi Arabia outside the Murabba Palace on Saturday.
The president was joined by his staff for the ceremonial dance and Twitter users delighted at how awkward they all looked.
Video of the dance shows Secretary of State Rex Tillerson and Commerce Secretary Wilbur Ross dancing with swords perched on their shoulders as part of a line of men in traditional Saudi garb ahead of a state dinner.
Trump, surrounded by Saudi officials, bopped back and forth with a smile on his face, while White House chief strategist Steve Bannon, chief of staff Reince Priebus and chief economic adviser Gary Cohn busted out more demure moves.
The traditional men's sword dance is known as the 'ardah'.
Other world leaders including Prine Charles and former US president George Bush have previously taken part in the ardah.
Trump's speech "unconvincing"
Trump's Sunday speech, the centrepiece of his two-day visit to Saudi Arabia, addressed the leaders of 50 Muslim-majority countries to cast the challenge of extremism as a "battle between good and evil" and urge Arab leaders to "drive out the terrorists from your places of worship".
The speech came amid a renewed courtship of the United States' Arab allies as Trump held individual meetings with leaders of several nations, including Egypt and Qatar, before participating in a roundtable with the Gulf Cooperation Council and joining Saudi King Salman in opening Riyadh's new anti-terrorism centre.
During the 2016 U.S. campaign, Trump mused about his belief that "Islam hates us."
And only a week after taking office, he signed an executive order to ban immigrants from seven countries - Iraq, Iran, Syria, Sudan, Libya, Somalia, and Yemen - from entering the United States, a decision that sparked widespread protests at the nation's airports and demonstrations outside the White House.
That ban was blocked by the courts. A second order, which dropped Iraq from the list, is tied up in federal court and the federal government is appealing.
But on Sunday, standing before dozens of regional leaders, he said Islam was "one of the world's great faiths."
US President Donald Trump poses for photos with King Salman and others at the Arab Islamic American Summit in Riyadh, Saudi Arabia. Photo/AP
The speech was met with scepticism and frustration in the Muslim world.
Several experts in the Middle East described his sudden shift in tone on Islam as unconvincing.
Trump's an "exhausted guy"
While running for presidency, Trump heartily criticised then President Barack Obama for not using the term "radical Islamic extremism" and said that refusal indicated that Obama did not understand America's enemy.
But on Sunday, Trump condemned "Islamic extremism," "Islamists," and "Islamic terror," but not once uttered the precise phrase he pressed Obama on.
A White House official later said that was not intended and attributed it to the president being "an exhausted guy."
Trump made no mention of the disputed travel ban, signed days after he took office, that temporarily banned immigration to the U.S. from seven majority Muslim countries: Iraq, Iran, Syria, Sudan, Libya, Somalia, and Yemen.
Both the original order and a second directive that dropped Iraq from the banned list have been blocked by the courts.
"Boy, those shoes"
Before the speech, Trump held individual meetings with leaders of several nations, including Egypt and Qatar.
Trump's meeting with Egyptian President Abdel-Fattah el-Sissi underscored their burgeoning kinship.
Trump praised el-Sissi for the April release of Egyptian- American charity worker Aya Hijazi, detained in the country for nearly three years.
El-Sissi invited Trump to visit him in Egypt, adding, "You are a unique personality that is capable of doing the impossible." As the participants laughed, Trump responded: "I agree." The president then complimented el-Sissi's choice of footwear: "Love your shoes.
Boy, those shoes" after their brief remarks to the media.
Trump cut short his program in Saudi Arabia, abruptly skipping an event aimed at highlighting how social media can be used to combat extremism. He sent his daughter, Ivanka, instead.
Trump's next stop as part of his Middle East visit is Israel.
