Young Trump and Obama in New York with Local Private Guide
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September 2026
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Quick answer
Is Young Trump and Obama in New York with Local Private Guide worth booking?
Young Trump and Obama in New York with Local Private Guide is a 3-hour experience in New York, United States, from $59 per person. It scores 53 out of 100 on the Outty Ranking, which we label “Worth a Look”. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 53 / 100
- Rating
- Not yet rated
- Duration
- 3 hours
- From
- $59 per person
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 Mi
What you get
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.
What's included
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
Not included
- Food and drinks
- Gratuities (optional)
What you'll see and do
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 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.
15 minutes here
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 here
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 here
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 here
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 here
Chrysler Building
The Chrysler building was the World’s tallest in 1930 for 11 months. Then the Empire State.
20 minutes here
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 here
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 here
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 here
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 here
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 here
Where it starts and ends
Meeting point
New York
Meet your private guide outside at the clock
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
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
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Friendly Local Guides
Know before you go
- 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
Photos
Good to know
- Duration
- 3 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $59 to $299
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 53
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Young Trump and Obama in New York with Local Private Guide: questions travelers ask
Practical detail on this experience, plus the wider planning questions for New York.
How much does Young Trump and Obama in New York with Local Private Guide cost?
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Prices start at $59 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in New York usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Young Trump and Obama in New York with Local Private Guide take?
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Plan for about 3 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in New York is not rushed.
Is Young Trump and Obama in New York with Local Private Guide worth it?
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It holds an Outty Ranking of 53 out of 100, which we label "Worth a Look". That score blends traveler sentiment (0/5 across 0 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in New York, and how flexible the cancellation terms are.
Can I cancel or reschedule Young Trump and Obama in New York with Local Private Guide?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Young Trump and Obama in New York with Local Private Guide suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 3-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Young Trump and Obama in New York with Local Private Guide?
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Around 0 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in New York can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in New York and add a light layer if any part of the 3-hour experience runs outdoors or after sunset.
Where does Young Trump and Obama in New York with Local Private Guide start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central New York within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in New York?
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New York has more bookable experiences than any other city on Outty, and the quality spread is brutal. Observation decks are commoditised, so we score them on timed-entry reliability and sunset slots. Food tours and borough walks are where the ranking really separates operators, and the top scores in the city all come from small-group guides. On Outty we rank every New York experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Grand Canyon VIP Helicopter Tour, Half-Day Bus Tour of NYC Top Highlights, NYC Bus Tour of Brooklyn, Bronx, Queens: Art, Food & Sports. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit New York?
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September to early November, and late April through June. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in New York?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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