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.

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.

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.

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.

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.

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.

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

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

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.

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.

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.

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).