On Wednesday, he will be in Saudi Arabia to meet King Abdullah. On Thursday, he will be in Egypt to deliver his much-anticipated address to Muslims.
He has already taken four mini-jabs at the subject – in his inaugural address; his Jan. 27 interview with Al-Arabiya TV; his March 19 video address to Iran; and his April 6 speech to the Turkish parliament.
This has drawn mixed reviews:
He wouldn't be addressing the Christian world, or the Jewish, Hindu or Buddhist worlds. Why the exception for Muslims?
By framing terrorism in religious terms, he's treading the same turf as militant Islamists, on the one hand, and Bush, on the other.
He has no choice but to fix the shattered relationship between the U.S. and the Muslim world.
What are his challenges? Four experts I spoke to outlined them:
Where's the beef? Juan Cole, author of Engaging the Muslim World (Palgrave Macmillan), said Obama has done well to ditch Bush's formulation that tackling Muslim militants was "like taking on the Axis powers in World War II, and the way to do it was through conquest, occupation and a transformation of the Muslim world.
"That was a huge conceptual error, doomed to failure."
Jihadists are not the old Soviet Union nor Nazi Germany. Non-state actors are best dealt with as the criminals they are.
However, Obama has a challenge of his own. "Beyond denying the Bush paradigm, he must develop his own positive paradigm. I haven't heard that articulated," said Cole, professor of history at the University of Michigan.
John Esposito, co-author of Who Speaks for Islam? What a Billion Muslims Really Think (Gallup Press), also feels Obama is running out of time. "The window is beginning to close on him."
Egypt: "There's a real irony in the leader of the free world delivering a major speech to Muslims in one of the most repressive parts of the world," said Nader Hashemi, author of Islam, Secularism and Liberal Democracy (Oxford).
Hosni Mubarak is an oppressive dictator, "one of the most despised, in part due to his close alliance with the U.S. and collusion with Israel in maintaining the siege on Gaza."
A better platform would have been Indonesia, the largest Muslim nation, or Pakistan, Turkey or Bangladesh, all evolving democracies.
Israel-Palestine: It's the No. 1 issue for Muslims, said Esposito, director of the Center for Muslim-Christian Understanding at Georgetown University in Washington.
Hashemi, a native of Toronto now teaching Middle East and Islamic politics at the University of Denver, recalled Obama's words in Sderot last year that if his daughters were subject to daily rocket fire, as Israelis were from Hamas, he'd do everything in his power to stop it.
"This begged the question: if the president's daughters were refugees who could not return home, stuck in one of the most densely populated areas of the globe, and subject to an ongoing siege, would Obama also do everything in his power to alleviate their suffering?
"Failure to speak in moral terms about the plight of the Palestinians will be a massive setback for his Muslim outreach initiative."
Iraq: If Obama's pullout plans work out, he'll have neutralized the second biggest source of anger.
Embracing dictators: Polls show that Muslims are as desirous of democracy as any other people. And they resent the Western hypocrisy of promoting democracy and human rights but cavorting with Arab dictators and monarchs.
"Without naming Egypt, I think Obama will say that the U.S. will no longer be supportive of autocrats, who deprive their people the right to freedom," said Shuja Nawaz of the Atlantic Council, a Washington think-tank on international affairs.
But that's what Condoleezza Rice said in Cairo in 2005, and nothing came of it. Nawaz: "Frankly, that's his biggest challenge – how to deal with the Islamic autocrats."
Iran: Cole said Obama is sending mixed signals. "He wants face-to-face talks with Iran but has named Dennis Ross as the point person. He's a well-known hawk on Iran. The Iranians are upset and have made it clear they're not going to sit down across the table from Ross.
"Also, Obama is using the Bush rhetoric about not allowing Iran to have a nuclear weapon. But American intelligence agencies do not see an Iranian nuclear program."
Esposito noted that Obama is not threatening to go to war with North Korea, despite its nuclear blasts. It is, thus, important to "indicate that he is not going to be stampeded into a military action against Iran."
Afghanistan/Pakistan: Nawaz, author of Crossed Swords: Pakistan, its Army, and the Wars Within (Oxford), said Obama's economic package for Pakistan's tribal areas has been well-received by Pakistanis. They are also behind the military initiative against the Taliban, being undertaken under U.S. pressure.
"The public is fed up with the Taliban but the anger can quite easily turn against the government and the U.S, given the dire situation of the internally displaced people."
Is all this doable? Cole, for one, thinks so. "Give Obama eight years, and things will look different."