His 107-day absence, friends say, is the longest stretch he has spent outside of New York since he was born in Queens in 1946.
Yet the President isn't returning for long. He is scheduled to meet Australian Prime Minister Malcolm Turnbull, who will join Trump at the 75th Anniversary of the Battle of the Coral Sea aboard the USS Intrepid, the aircraft carrier-turned-museum parked along Manhattan's West Side.
Friends close to Trump and former campaign advisers tell CNN the homecoming could be clarifying for the President, a one-time New York standard whose name is plastered around Manhattan -- usually in gold. Some acknowledged his loneliness and longing for New York.
"Donald Trump has lived, eaten and breathed New York City for 70 years," said Michael Caputo, a former campaign aide who lives and works in New York. "And for him to be away from what really makes him tick for so many years, it's a sacrifice for him."
Trump, though, won't be doing New York his (old) way this week. After speaking on the Intrepid, the President is expected to forgo a trip to the eponymous Trump Tower and instead will head to Trump National Golf Club in Bedminster, New Jersey, where he will likely spend the weekend.
Of course, Bedminister is home to Trump, too. It is where his daughter was married and where the then President-elect interviewed job prospects for his new government after winning November's election. Trump also wants to be buried on the property.
A White House official declined to discuss the President's travel plans, saying only that Trump was eager to return to the city.
A city that shaped him
The lack of time in New York is significant, given the way the city shaped Trump. His personal story is intertwined with the constantly changing history of the metropolis.
As President, he has regaled reporters with stories about riding in between the subway cars (something that is illegal), joked about how he was a mainstay on the New York tabloids and told friends that he misses the slice of New York he had become accustomed to. His aides, sensing that longing, have tried to bring aspects of New York to the White House.
Growing up the son of a prominent developer in Queens, Trump longed to move to Manhattan early in his life. He and his friends, without their parents' approval, would ride the subway into Manhattan and marvel at the circus-like atmosphere that seemed to teem from Times Square and other areas in New York, friends say.
As soon as he could, Trump moved to New York and built his real estate empire into a springboard for his national rise to fame. Trump was a mainstay at New York events, on radio stations and local television. He plastered his name on anything he owned, seemingly marking his territory in the city he once longed to frequent.
While his boisterous ventures eventually begat his presidential campaign and all of it was centered around New York, the people who make up New York haven't always loved Trump back.
Trump Tower has been beset by protests for months and the people of New York have largely rejected his presidency. Every borough of New York City -- except Staten Island -- voted against Trump in 2016.
One Trump friend, who requested anonymity to speak freely, said it was not insignificant that Trump's first trip to New York was coming after his first 100 days in office.
"He is going to have just great clarity," the friend said. "He is going to be able to look back on what he did wrong, what he did right. I think it is going to be refreshing experience."
As Trump's first 100 days in the White House came to an end, the President has seemed reflective about the job, his expectations and his old life that he bluntly conceded he missed.
"I loved my previous life. I had so many things going," Trump said in an interview with Reuters last month. "This is more work than my previous life. I thought it would be easier."
He later added: "I do miss my old life. I like to work. But this is actually more work."
But Trump has yet to try to capture that old New York life with frequent visits. He acknowledged to Fox News in April that was because it was "very expensive for the country" and inconvenient for New Yorkers because the New York Police Department and Secret Service have to largely close the streets around Trump Tower.
Trump Tower has been fortified for his protection, particularly because first lady Melania Trump and 11-year-old son, Barron, have been living there full-time. A new government spending bill the President is set to sign this week includes about $23 million to help cover the costs of strengthening security at Trump Tower. It's part of about $120 million in additional funding to help cover the costs of protecting the Trump family.
"I always feel a little bit guilty when I go there," Trump told Fox News late last month, speaking of his penthouse apartment inside Trump Tower where he holed up for much of his transition. "I feel guilty when I go back to here, because I hate to see the New Yorkers with the streets closed."
The bipartisan spending deal includes $60 million to help reimburse money that local governments are spending on protection in Palm Beach, Florida, New York and New Jersey. Trump has made Florida visits to his private club, Mar-a-Lago, as president.
"Although the federal government does not otherwise reimburse costs of state or local law enforcement for activities in support of the United States Secret Service protection mission," the legislation reads, "these funds are being provided in recognition of the extraordinary costs borne by a small number of jurisdictions in which a residence of the President is located."
New York has born the biggest financial burden, with the city's police department spending $300,000 a day protecting Trump Tower between Election Day and his inauguration on January 20, and $127,000 to $145,000 per day since then.
"We are getting what we are owed," New York Mayor Bill de Blasio said in a statement praising the state's congressional delegation for helping win the reimbursement money. "That's good news for our city and the hardworking police officers faced with this unprecedented security challenge."