The White House has been quick to note that this is a "working" vacation. The president won't be leaving the duties of office totally behind.
It's fair to say, however, that Mr Trump will spend more than a little bit of time on the fairways. The White House is coy about how much the president has played golf so far during his time in office, but given that he's visited his golf properties at least 43 times so far, he almost certainly has teed up more at this point in his administration than any past president.
So while he's lining up his shots over the next two weeks, will memories of his past six months in office break his concentration? Will an ill-timed twinge of concern turn what would have been a solid drive into a wayward slice or cause a sure-thing birdie putt to lip out of the hole?
How many of his apparently unlimited supply of mulligans will he have to use to soothe a troubled mind?
The president may comfort himself with thoughts of low unemployment or a booming stock market. He may smile when he recalls the cheering crowds at recent campaign-style rallies or the unexpected coup of the Democratic West Virginia governor joining the Republican Party.
But as any vacationing piker knows, when a holiday ends there's twice as much work and a load of problems that have piled up in the meantime. Even if the president sails through his vacation without a care, there are plenty of troubles brewing back in Washington. Here's a look at some of them.
Perhaps the single biggest legislative accomplishment of the Trump presidency so far is the law imposing new sanctions on Iran and North Korea and strengthening existing ones on Russia. Given that the president signed the measure with extreme reservations, it's safe to say things aren't going according to plan.
Efforts to repeal and replace Barack Obama's signature healthcare reforms were dramatically dynamited by a handful of Republicans and a united Democratic Party in the Senate. An overhaul of the tax law is currently barely a glimmer in legislators' eyes. The proposed modifications to the legal immigration system recently unveiled at the White House have been deemed dead on arrival in Congress, while any kind of infrastructure spending package is going nowhere fast.
When the politicians return to Congress in September they will have their hands full with more pressing matters. Hardliners may attempt to prevent the treasury from issuing new government debt - raising the "debt ceiling" - without extracting spending cuts. New appropriations bills must be passed to avoid a government shutdown.
All this leaves little time for big new legislative efforts to reach fruition before the calendar flips to 2018 and legislators start thinking about their re-election campaigns.
View from the tee: The president faces a treacherous par four, with water on both sides and sand around the green.
If Mr Trump's domestic agenda creates headaches, the international outlook has the makings of a splitting migraine.
North Korea continues to press ahead with its nuclear and ballistic missile programmes, despite harsh presidential tweets and steely gazes from the vice-president. The administration has warned of grave consequences, but what's his next step?
Mr Trump has called on China to do more - while at the same time threatening to take punitive trade measures against that nation for intellectual property theft. While Mr Trump and Chinese President Xi Jinping had a cordial summit in Mar-a-Lago in April, Sino-American relations could be heading toward treacherous ground.
The president also has some hard choices to make when it comes to Afghanistan, where his generals are calling for an increase in troop numbers to break a strategic stalemate with Taliban insurgents. While Mr Trump often has said he will defer to the Pentagon on military matters, some of his civilian advisers view an increased commitment as counter to candidate Trump's America-first foreign policy promises.
As if that weren't enough, Iran could also become a political flashpoint if the president follows through with his reported desire not to certify that the nation is complying with the multi-party nuclear agreement when it next comes up for review in October. It's another area where various presidential aides are giving diametrically opposed advice - and the president will have to be the decider.
View from the tee: A high-risk, high-reward scenario where almost everyone will be relieved if the president decides to play it safe.
At a Thursday evening rally in West Virginia, Mr Trump attempted to paint the ongoing investigation into possible links between his campaign and Russian attempts to influence the 2016 presidential election as an us-against-them situation.
"They're trying to cheat you out of the leadership that you want with a fake story," he said.
The president's speech came on the heels of news that special counsel Robert Mueller has convened a grand jury to assist in his investigation - giving him new powers to subpoena documents, solicit sworn testimony and, with sufficient evidence, bring criminal indictments.
Over the past weeks reports have circulated that Mr Mueller is casting a wide net in his probe, looking at the controversial June 2016 meeting between senior members of the Trump campaign and Russian advocates, as well as the business dealings of Mr Trump and those close to him.
Then there are the ongoing congressional committee investigations. Presidential son-in-law Jared Kushner and former campaign manager Paul Manafort have already spoken with investigators behind closed doors. They - or Donald Trump Jr - could be called for public testimony at some point in the months ahead, which would make for a national political spectacle.
The concurrent investigations could all end up duds - or set off explosions that shake the very foundations of the Trump presidency. The answer lies somewhere on the other side of August.
View from the tee: In the words of Bill Murray's Carl Spackler in Caddyshack, 'The heavy stuff isn't going to come down for quite a while'.
Just over two weeks ago Mr Trump had a chief of staff, a press secretary and no communications director. As he heads to New Jersey he has a new chief of staff, a new press secretary and a recently fired communications director.
He has an attorney general who says the president's swipes at him over the past few weeks were "kind of hurtful" and who just held a press event that seemed primarily designed to convince Mr Trump that, yes, he's trying really hard to fight leaks, just like he asked.
His national security adviser, HR McMaster, is systematically removing aides brought in before he took over from Michael Flynn - individuals who were more in step with White House adviser Steve Bannon's fiercely nationalistic worldview.
As a result Mr McMaster himself has become the target of a concerted attempt by some on the right to force him from his job. A website called McMasterLeaks featured a cartoon of the retired general as a puppet being controlled by liberal billionaire (and conservative bogeyman) George Soros, who himself was puppeteered by "the Rothschilds". (The website has since changed "Rothschilds" to "Saudis" after accusations of anti-Semitism.)
The long knives have come out over the past two weeks, forcing Republican establishment figures like Reince Priebus and Sean Spicer from their senior White House jobs.
Mr Kelly, another former general, is supposed to be bringing new discipline to the West Wing, but the verdict on his efforts won't come until long after Mr Trump has returned to the Oval Office.
View from the tee: A golf course can't operate when the caddies are at war with each other.
The president has a lot to worry about as he rides around the links in his golf cart, but the real moment of reckoning may not come until he's back in the clubhouse, freshening up after his round.
As he checks his hair in the bathroom mirror, he may come face to face with the biggest aid - or obstacle - to his long-term presidential success. Himself.
Time and time again over the past six-plus months Mr Trump has undermined his agenda with ill-timed tweets or off-message comments, needlessly complicating what is already the hardest job in the nation.
He managed to alienate several Republican senators - Lisa Murkowski of Alaska and John McCain of Arizona - who were instrumental in sinking his healthcare reform legislation.
Just last week he took multiple swipes at Congress, including the leadership of his own party, saying they "look like fools" for not doing away with the legislative filibuster and laying the current poor state of US-Russia relations at their feet.
Given that the president needs Congress's help in the days ahead, such antics seem of questionable wisdom.
Already one Republican Senator, Jeff Flake of Arizona, has made a very visible break with the president. The media are buzzing with reports that others may be plotting to go their own way.
Congress has tied the president's hands on Russian sanctions. Legislation is being drafted that would limit his ability to dismiss special counsel Robert Mueller. The Senate is staying in session just to keep the president from using a procedural trick to replace Mr Sessions without their consent. Despite the president's urging, there are now bipartisan efforts to come up with ways to modify Obamacare and not repeal it.
View from the tee: Golfing legend Ben Hogan once said "the most important shot in golf is the next one". President Trump's most important decisions are the ones he makes next.
On Friday Donald Trump jetted off to his resort golf club in Bedminster, New Jersey, for a 17-day vacation.