The unpredictable president arrives having already upturned expectations when it comes to the decades-old Middle East conflict, giving Palestinians more hope than they may have anticipated and disappointing right-wing Israelis who heralded his election.
He has spoken of reaching "the toughest deal to make", one that has long bedeviled US presidents, vowing "we will get it done".
But he is also contending with a raft of problems back home, including a special counsel investigating whether his associates colluded with Russia.
Any leader would face an enormous challenge in seeking to bring the Israelis and Palestinians together for meaningful talks, and Trump's inexperience and domestic political struggles will only add to it.
Beyond that, Trump has faced criticism from Israelis in recent days related to the White House's approach to the ultra-sensitive status of Jerusalem.
Concerns have also been raised over Trump's sharing of intelligence with Russia said to have originally come from Israel.
"I think the trip's in a lot of jeopardy being able to be productive because of all the chaos and controversy that's going on in Washington," Dan Shapiro, US ambassador to Israel under Barack Obama and now a senior fellow at Tel Aviv's Institute for National Security Studies think tank, told AFP.
- 'Palestinians are cautious' -
Trump arrives in Israel on Monday afternoon following his visit to Saudi Arabia, where Washington announced a huge $110-billion arms deal with Riyadh, and will hold talks with Prime Minister Benjamin Netanyahu later in the day in Jerusalem.
He is expected to become the first sitting US president to visit the Western Wall, the holiest site where Jews can pray and located in east Jerusalem, which Israel occupied in 1967 and later annexed.
Israel sees all of Jerusalem as its undivided capital, while the Palestinians view east Jerusalem as the capital of their future state.
On Tuesday, he visits Bethlehem in the occupied West Bank for talks with Palestinian president Mahmud Abbas.
After a visit later Tuesday to the Yad Vashem Holocaust memorial in Jerusalem, he is due to give a speech at the Israel Museum.
Trump has sent mixed signals about how he will approach the Israeli-Palestinian conflict.
He cast uncertainty over years of international efforts to foster a two-state solution when he met Netanyahu at the White House in February.
At that meeting, he said he would support a single state if it led to peace, delighting Israeli right-wingers who want to see their country annex most of the West Bank.
At the same time, he urged Israel to hold back on settlement building in the West Bank, a longstanding concern of Palestinians and much of the world.
He also held face-to-face talks in Washington with Abbas earlier this month, confidently predicting that a peace agreement was within grasp.
Trump advocated during his campaign breaking with decades of precedent and moving the American embassy from Tel Aviv to Jerusalem, a prospect deeply alarming to Palestinians.
He has since backed away, saying the move was still being looked at.
Trump's seeming openness to at least some of Abbas's concerns has given Palestinians more reason for hope than many may have expected, but still reason to remain wary, some analysts say.
"The Palestinians are cautious since Trump's position is not clear and seems to be still developing," said Palestinian political scientist Ghassan Khatib.
"Trump's early days led to worry, so now with the help of other Arab countries they want to balance Trump's position on the Israeli-Palestinian conflict."
- 'Blame game' -
On the Israeli side, Netanyahu heads what is seen as the most right-wing government in the country's history, and members of his coalition were elated with Trump's election.
Some even called for an end to the idea of Palestinian state.
Trump's actions since have left them disappointed, with the embassy remaining in Tel Aviv -- at least for now -- and the White House seeking to restart peace efforts.
Even if Trump can see beyond his domestic political troubles and focus on moving peace efforts forward, he will have to overcome the constraints of both Netanyahu and Abbas.
The 82-year-old Palestinian leader has grown unpopular, while Netanyahu will have difficulty making significant concessions that his right-wing base will accept, many analysts say.
"Neither side wants to be in the position of saying no to him, and that does give him some leverage," Shapiro said.
"But it's still an uphill effort for an administration that is still new to these issues, relatively inexperienced and with parties who are very well-practised in positioning for the blame game rather than trying to work toward a common goal."
(This story has not been edited by NDTV staff and is auto-generated from a syndicated feed.)