Young Trump and Obama in New York with Local Private Guide
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Young Trump and Obama in New York with Local Private Guide

Active
3h
For a full refund, cancel at least 24 hours before the scheduled departure time.
Instant confirmation
Mobile or paper ticket accepted

About this experience

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.

Available options

Young Trump and Obama in New York with Local Private Guide

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
Friendly local guide
Customizable itinerary based on your preferences

Detailed itinerary

1
Stop 1

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.

2
Stop 2

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.

3
Stop 3

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.

4
Stop 4

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.

5
Stop 5

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.

6
Stop 6

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.

7
Stop 7

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

8
Stop 8

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

9
Stop 9

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
Stop 10

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.

11
Stop 11

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.

12
Stop 12

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).

What's not included

Food and drinks
Gratuities (optional)

Available languages

Guide guide
EN

Important information

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

Meeting point

Meet your private guide outside at the clock

About New York City

New York City, often referred to as the cultural capital of the world, is a sprawling metropolis that never sleeps. With its iconic skyline, world-class museums, Broadway shows, and diverse neighborhoods, NYC offers an unparalleled urban experience that blends the historic with the modern.

Top Attractions

Statue of Liberty

A symbol of freedom and democracy, the Statue of Liberty is a must-visit. Take a ferry to Liberty Island for close-up views and a visit to the museum.

Historical 3-4 hours $18.50 (grounds access), $21.70 (pedestal access), $24.10 (crown access)

Central Park

A vast urban park offering a green escape in the heart of the city. Enjoy walking paths, boat rentals, and various attractions.

Nature 2-4 hours Free (some attractions have fees)

Times Square

The bustling heart of NYC, known for its bright lights, Broadway theaters, and vibrant atmosphere.

Entertainment 1-2 hours Free (shows and shopping have separate costs)

Empire State Building

An iconic Art Deco skyscraper offering panoramic views of the city from its observation decks.

Architecture 1-2 hours $44 (Main Deck), $74 (Top Deck)

Metropolitan Museum of Art

One of the world's largest and finest art museums, housing over 2 million works of art.

Museum 3-5 hours $25 (suggested admission)

Brooklyn Bridge

An iconic suspension bridge offering stunning views of the Manhattan skyline and East River.

Architecture 1-2 hours Free

Must-Try Local Dishes

New York-style Pizza

Thin-crust pizza with a wide, foldable slice. Toppings vary but often include pepperoni, mushrooms, and sausage.

Dinner Can be made vegetarian or vegan.

Bagel with Lox

A classic NYC breakfast consisting of a toasted bagel topped with smoked salmon, cream cheese, and often capers or red onion.

Breakfast Contains dairy and fish.

Cheesecake

Creamy, rich cheesecake, often served with fruit toppings or chocolate sauce.

Dessert Contains dairy.

Pastrami on Rye

Thinly sliced pastrami piled high on rye bread, often served with mustard.

Lunch Contains meat.

Popular Activities

Hiking in Central Park Kayaking in the Hudson River Rock climbing in the Bronx Spas and wellness centers Yoga and meditation classes Strolling through botanical gardens Museum visits Broadway shows

Best Time to Visit

May to September

This period offers warm weather, outdoor festivals, and all attractions in full swing. However, it's also the busiest and most expensive time to visit.

15°C to 30°C 59°F to 86°F

Practical Information

Language

  • Official: English
  • Widely spoken: Spanish, Chinese (Cantonese and Mandarin), Russian, Hindi
  • English: Widely spoken

Currency

US Dollar (USD)

Time Zone

EST (GMT-5) / EDT (GMT-4) (Daylight Saving Time)

Electricity

120VV, 60HzHz

Safety Information

Overall Safety Rating: Generally safe

NYC is generally safe, but like any major city, it's important to be aware of your surroundings and take precautions.

Important Precautions:
  • • Be aware of your surroundings, especially at night
  • • Keep valuables secure and out of sight
  • • Use common sense and trust your instincts

Getting there

By air
  • John F. Kennedy International Airport • 24 km (15 miles) from downtown
  • LaGuardia Airport • 13 km (8 miles) from downtown
By train

Penn Station, Grand Central Terminal

By bus

Port Authority Bus Terminal, Greyhound Terminal

Getting around

Public transport

The subway is the most efficient way to get around NYC. It operates 24/7 but can be crowded during peak hours.

Taxis

Available • Apps: Uber, Lyft

Rentals

Car, Bike, Scooter

Neighborhoods

Manhattan Brooklyn Queens Bronx Staten Island

Day trips

Niagara Falls
650 km (400 miles) • Overnight

A breathtaking natural wonder featuring three waterfalls: Horseshoe Falls, American Falls, and Bridal Veil Falls.

Washington D.C.
370 km (230 miles) • Full day

The capital of the United States, offering iconic landmarks, museums, and government buildings.

Philadelphia
150 km (93 miles) • Full day

A historic city known for its role in the American Revolution and its vibrant cultural scene.

Festivals

New Year's Eve in Times Square • December 31 Macy's Thanksgiving Day Parade • Fourth Thursday in November NYC Pride • Late June

Pro tips

  • Use a MetroCard for easy and discounted subway and bus rides
  • Walk as much as possible to explore the city and its neighborhoods
  • Try street food for a quick and delicious meal on the go
  • Visit popular attractions early in the morning or late in the afternoon to avoid crowds
  • Use apps like Google Maps or Citymapper for real-time navigation and transit information
From $25 per person

Price varies by option

Adults
Age 18-99
1
Childs
Age 0-17
0
Booking requirements:
  • Min travelers: 1
  • Max travelers: 15
  • Adult required for booking
Secure booking
Free cancellation available
Instant confirmation

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