Young Trump and Obama in New York with Local Private Guide

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3 hours (approx.)

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Overview

Step into the footsteps of two of America's most influential figures—Barack Obama and Donald Trump—on a guided tour through New York City that traces their paths from humble beginnings to the White House.

We start in Midtown Manhattan, where Mr. Obama once worked as a corporate journalist, before heading out to Queens, where Mr. Trump learned the ropes of the family construction business. Along the way, your guide will weave fascinating stories about their childhoods, their teenage years, and the families that shaped them.
The tour begins at the site of Trump's 2015 presidential announcement and ends at the iconic Columbia University. Each stop is a milestone in their careers, offering a unique glimpse into their journeys to the White House.

Your guide will take photos of you along the way, capturing memories of this unforgettable experience. Political affiliations aside, this tour offers a fascinating look at New York City’s rich history and the lives of two of its most famous sons.

What's Included

See the historic places that the leaders of the USA visited
Multiple start times available
Authentic local New York experience with an expert
Private walking tour with the use of subway
Expert advice where to go and what to do after the tour
Subway ticket is within $10
All taxes
Customizable itinerary based on your preferences
Friendly local guide

Food and drinks
Gratuities (optional)

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Meeting Location

Meeting point

5th Avenue
New York, NY 10022, USA

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Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

116th and Broadway
New York, NY 10027, USA

Your guide can finish the tour at any place you prefer, feel free to discuss your preference with the guide at the beginning of the tour

What To Expect

Trump Tower

Meet outside at the clock. See the escalator landing where in 2015 he announced his presidential run. The architect of the 57-floor horizontal setback tower is Der Scutt from Pennsylvania. The construction manager, Barbara Res, was NYC’s first female of that field. The atrium is three floors of pink, white veined marble. It has a 60-foot waterfall. The lower half of the building is office space. The upper half are 278 apartments. Former residents there were Johnny Carson, Steven Spielberg and Sofia Loren. Cost = $800K to $10 Million. Mr. Trump’s New York residence is the 3-floor penthouse. His five children grew up there. You may eat at the Trump Café, Trump Grill and Trump Ice Cream parlor. The studio for The Apprentice studio is on the 5th floor (no visitors). A Trump souvenir shop is downstairs. Nearby are Tiffany’s, Bergdorf Goodman, the Plaza Hotel and the World’s biggest Mac/iPhone store. The iconic Danish scene from Breakfast at Tiffany’s was here.

15 minutes • Admission Ticket Free

Lexington Avenue & East 51st Street

A 22-year-old Mr. Obama’s first commute was at the Lexington Avenue subway at 51st Street. He would also take the M15 bus. In 1983, he lived in another walkup in a rundown part of the Upper East Side; the area is now doorman buildings. Walk Smith and Wollensky at 3rd and 49th Street. An iconic steakhouse since 1977. Also see the Waldorff Astoria and Citi Tower. Look down the corporate canyon of Park Avenue to the Helmsley Tower and Met Life Building (Pan Am). The first ‘glass tower’ Lever House is here (1951). Hear how Seagram’s Building (1956) shaped office construction for the next 20 years.

15 minutes • Admission Ticket Free

Dag Hammarskjöld Plaza

Dag Hammarskjold Plaza (47th and 2nd) is where Barak Obama got his first job after college. He was a corporate journalist for a UN contractor: Business International Corporation. He wrote reports on economic standing in developed and undeveloped nations.

20 minutes • Admission Ticket Free

Trump Tower

Trump Tower Plaza at 47th and 1st is a 72-floor apartment building completed in 2001. At 861 feet, it was the tallest residential tower in the World for 2 years. Tenants were Yankee star Derek Jeter. Other former tenants were Bill Gates, Harrison Ford and Sofia Loren. Cost = $1 to 10 million.

10 minutes • Admission Ticket Free

Raoul Wallenberg Monument

The UN at 42nd and 1st. Mr. Obamas 1st job required his proximity here. Also pass the Raoul Wallenberg monument, US mission, the General Assembly and the iconic 1953 tower itself. The UN began in April 1945 with all nations invited. This excluded Axis powers and recently surrendered Axis such as Italy. The UN was a former site for fuel storage and slaughterhouses, which moved to New Jersey and Queens.

10 minutes • Admission Ticket Free

Daily News Building

SE Corner of 42nd and 2nd is the only spot on earth to see where both Mr. Obama and Mr. Trump discovered their talents as two young men in their 20s. Also see the famous Geography lobby of the Daily News Building, the Chrysler building and Grand Central Terminal. In the Daily News Building (1930) see the Globe with floor arrows pointing around the World. Clark Kent in 1978 ran by here.

10 minutes • Admission Ticket Free

Chrysler Building

The Chrysler building was the World’s tallest in 1930 for 11 months. Then the Empire State.

20 minutes • Admission Ticket Free

Grand Central Terminal

Grand Central Terminal (1913) has the biggest mistake in NYC. Get there and find out. Do the ‘whisper arch’ too.

30 minutes • Admission Ticket Free

Hyatt Grand Central New York

The owner of the New York Central Railroad, Conelius “Commodore” Vanderbilt, built the Commodore Hotel in 1919. In 1975, the Commodore hit hard times. Half empty and broken toilets. A 29-years old Donald Trump convinced his father Frederick Trump Sr., to buy it for rebuilding. Father thought this was a bad idea. NYC was bankrupt. The area was rundown. Now the Grand Center Terminal Area is booming.

10 minutes • Admission Ticket Free

Frederick Douglass Circle

Frederick Douglas Circle (2010) at the NW corner of Central Park is where undergraduate student Obama first lived. See the alleyway where he slept is first night when he couldn’t get into his 1905 walkup building. Also see the ‘Seinfeld’ restaurant where Mr. Obama and his roommate had breakfast for $2. In 1981, apartment #3E, 142 West 109th Street rented for $360. Today it’s $3,000.

20 minutes • Admission Ticket Free

Columbia University

In 1983, Mr. Obama earned a BA in Political Science. He and his roommate studied often in the heated Low’s Library. Their old radiator often broke. Columbia started as King’s College in Lower Manhattan in 1754. It moved to its present location in 1896 and renamed Columbia. The Pulitzer Prize is run by the School of Journalism, which is the World’s leading school of news writing. Columbia also has the Schools of Law, Engineering, Architecture, Nursing, Teaching, Sciences, History and Medicine. In 1941, the nuclear fusion ‘Manhattan Project’ under Enrico Fermi and Albert Einstein began here in secret. Both Teddy and Franklin Roosevelt’s attended Law School here. Other assorted alumni are Frank Sutton (Gomer Pyle), Peter Buck (Subway Sandwich), Madeline Albright, Art Garfunkel and 87 Nobel Peace prize winners.

10 minutes • Admission Ticket Free

Central Park

As a bonus, your guide is also an expert on other major NYC landmarks, including the United Nations, the Chrysler Building, Grand Central Terminal, Central Park, and Columbia University. Along the route, you'll pass by locations made famous in iconic movies and TV shows like Sex and the City, Catch Me If You Can, Breakfast at Tiffany’s, Seinfeld, The Devil Wears Prada, and Superman (1978).

10 minutes • Admission Ticket Free

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Additional Info

Confirmation is instant and will be received at time of booking
Wheelchair accessible
Service animals allowed

Public transportation options are available nearby
Travelers should have at least a moderate level of physical fitness
Infants and small children can ride in a pram or stroller

Frequently Asked Questions

(6)

Q: What is the cancellation policy for the Young Trump and Obama in New York with Local Private Guide?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (EDT). Read more Apr 2025