Trump’s
New York
36 HOURS IN
NORTHEAST
A Gilded Itinerary Through Donald Trump’s Favorite New York City Places
By Eric Barton | May 12, 2025
AUTHOR BIO: Eric Barton is editor of The Adventurist. He has reviewed restaurants for more than two decades and has written for publications including Food & Wine, Outside, and Men’s Health. Email him here.
I wouldn’t call this a political trip. Nobody’s chanting. Nobody’s storming anything. This is a tour for the curious: the gawkers, the irony chasers, the dinner-party historians. If you’ve ever wondered what it’s like to stand inside the marble-and-mirrors mausoleum that is Trump Tower, or sip a $45 cocktail named after the 45th president while contemplating your life choices—this one’s for you.
You’ll eat at his favorite spots, sleep in his branded hotel, and walk the blocks where he went from Manhattan dealmaker to reality TV star to, well, you know. It’s not exactly the High Line. But it’s a New York story all the same.
FRIDAY
3 p.m. Check in, high above the fray
At Columbus Circle, the Trump International Hotel & Tower looms above Central Park like a giant monogrammed luggage tag. The rooms are plush in a 2006 sort of way—leather headboards, granite counters, remote controls with buttons that still click. If the skyline view doesn’t impress you, the sheer commitment to branding will.
3:30 p.m. Visit the Tower That Built the Myth
Step into Trump Tower on Fifth Avenue and you immediately understand the concept of maximalism. This is the origin point of the Trump aesthetic: gold, mirrors, security guards, escalators that would be a fine place to announce a presidential run. The public atrium still feels like 1980s Manhattan, right down to the smell of shoe leather from the Gucci store. Downstairs you’ll find Trump Pizza—yes, that’s a real thing now—serving pepperoni slices and MAGA merch in equal measure.
4:00 p.m. Stroll by Trump Park Avenue
A few blocks north sits Trump Park Avenue, a rebranded hotel-turned-condo tower that once hosted The Beatles back when it was still the Hotel Delmonico. Trump slapped his name on it in the early 2000s and turned the place into a quiet stronghold of old-money aspiration.
5 p.m. Glimpse Trump Palace
Keep walking to Trump Palace on East 69th, once the tallest residential tower on the Upper East Side. It’s got all the usual Trump design tics: dramatic height, shiny façade, minimal charm. Still, it looms in that very particular way Trump buildings do, like it’s both trying to impress you and steal your parking space.
7 p.m. Steak and nostalgia at the Grill
Back at Trump Tower, the Trump Grill still serves dry-aged porterhouse with a side of time travel. The décor is pure power-lunch nostalgia: gold trim, padded booths, and enough white tablecloth to start your own Senate hearing. It’s not the best steak in the city, but it’s definitely the only one that once came with a taco bowl endorsement.
Trump International
SATURDAY
9:00 a.m. Power breakfast with Central Park views
Head downstairs to Nougatine, Jean-Georges Vongerichten’s more relaxed cousin to his namesake fine-dining spot next door. This is where the day-traders and hedge-funders come to butter their toast like they mean it. The soft-scrambled eggs are excellent. The room feels rich without trying too hard—which is to say, not very Trump at all.
11:00 a.m. Take a walk through old Trump territory
Cut through Central Park to Wollman Rink. For years, this was one of Trump’s favorite talking points: “I fixed the ice rink,” Trump has said. It’s no longer run by the Trump Organization, but the frozen fingerprints remain. He didn’t build it. He just took credit for it. In Trump terms, that makes it his.
1:00 p.m. Balthazar, with a side of beef and history
Head downtown to SoHo for lunch at Balthazar, where restaurateur Keith McNally swears Trump was a regular in the late ’90s. Today the crowd leans more influencer than investment banker, but you can still imagine him buttering a baguette with one hand and flipping through Page Six with the other. Order the steak frites and feel mildly superior.
3:00 p.m. The old Trump SoHo
Just west is the Dominick Hotel, formerly Trump SoHo until the lawsuits and plummeting bookings prompted a quiet de-Trumpification. The building still looks like a flash drive someone jammed into the Hudson skyline. If you like your scandals with turndown service, it’s worth a photo stop.
4:30 p.m. Visit Trump World Tower
Swing by the shadowy hulk of Trump World Tower across from the United Nations. At 72 stories, it was once the tallest residential tower on Earth, housing everyone from foreign dignitaries to people who definitely don’t want their names on the mailbox. It’s dark glass and quiet security. If the Upper East Side is Trump’s face, this is his poker face.
7:30 p.m. Dinner at Jean-Georges
Back at the Trump International, Jean-Georges delivers the kind of evening Trump himself might call “tremendous.” Two Michelin stars, precision service, and dishes so photogenic you’ll forget you’re technically still inside a Trump-branded property. The tuna ribbons and the signature foie gras are still worth the splurge, assuming your conscience allows.
40 Wall Street
SUNDAY
9:30 a.m. Pastry diplomacy at Trump Sweets
Back to the atrium at Trump Tower, where Trump Sweets sells cookies, coffee, and edible souvenirs to people who think dessert tastes better if it comes in a gold wrapper. You’re not here for the quality. You’re here because it’s absurd. Buy the cookie. Take the selfie. Embrace the performance.
11:00 a.m. Take the Tour D’Trump
Wrap up the weekend with the unofficial “Tour D’Trump,” a self-guided tour through the man’s New York landmarks. Stops may include the Trump Building at 40 Wall Street and the Trump Plaza building that went up with help from the mob. Finally, make the trip out to Queens for Trump’s childhood home, at 85-15 Wareham Place in Jamaica Estates, which until recently was overrun with feral cats. Like the entire weekend, the tour is not an endorsement or a protest—it’s just America, reflected in gold foil.
1 pm A final lunch as grand as the man
Finally, end the weekend at the New York City chain with a Western theme, Jackson Hole Burgers. This is the home of Trump’s favorite burger—yes, even more than the one from the golden arches. Slathered in guac and blanketed in bacon is how many of the burgers here arrive. But no matter how you top yours, every burger here is thick, stacked high and towering, just like the buildings in New York with Trump’s name on them. Yes, this burger is analogous of the man, a ground beef symbol of the mark Donald Trump left on the city. Take a bite and imagine he’s sitting next to you, probably selecting YMCA on the mini jukebox.
