Presidents Trump and Obama's Life Private Tour Expert Guide
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September 2026
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Quick answer
Is Presidents Trump and Obama's Life Private Tour Expert Guide worth booking?
Presidents Trump and Obama's Life Private Tour Expert Guide is a 3-hour experience in New York, United States, from $79 per person. It scores 51 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
- 51 / 100
- Rating
- Not yet rated
- Duration
- 3 hours
- From
- $79 per person
Take a unique perspective on New York City while exploring its political scene on our tour. Stroll around the city to capture the iconic locations linked with Mr. Trump and Obama, who lived four miles apart for four year
What you get
About this experience
Take a unique perspective on New York City while exploring its political scene on our tour. Stroll around the city to capture the iconic locations linked with Mr. Trump and Obama, who lived four miles apart for four years (1981–85) before anyone knew them. See where both young men with big dreams worked, lived, and caught the subway in the Big Apple. Explore the city’s places that may have inspired politicians in their careers and discover other presidential locations along the way. The tour includes Grand Central, the Plaza Hotel, Central Park, and Columbia University. Learn more about Nixon, Grant, Eisenhower, Clinton, Teddy and Franklin Roosevelt. • Explore the crucial places linked with the politicians on our 3-hour walk through NYC • Enjoy the private experience and undivided attention of your guide • Take another perspective on the Big Apple and get an insider’s look at the city’s landmarks • Follow in the footsteps of ex-presidents and learn new facts from their biographies.
What's included
Included
- Must see and off the beaten path
- Learn the life story of American presidents - Nixon, Grant, Eisenhower, Clinton, Roosevelt
- Unique historic and cultural experience in NYC
- Private tour with expert historian
- Customizable itinerary depending on your preferences
- All Fees and Taxes
- Friendly local guide
Not included
- Food and drinks
- Gratuities (optional)
What you'll see and do
Grand Central Terminal
Start your informative walking tour at Grand Central Terminal, a beautiful station constructed in 1913 and preserved by the residents of NYC from destruction. The iconic beaux-arts building is one of the world’s ten most-visited tourist attractions, with 21.6 million visitors in 2018, excluding train and subway passengers. Learn some facts about Donald Trump and how he rebuilt the aging Commodore Hotel into the Hyatt Regency in 1975 at the age of 29.
20 minutes here
Dag-Hammarskjold Plaza Greenmarket
At 47th and 2nd Avenue (885 2nd Ave.), Barack Obama, 23, wrote reports for the Business International Corporation, which subcontracted for the UN nearby. See the UN down the block and collect more facts about the ex-president. Apart from that, get a chance to take a look at a nice market and get a little rest from the buzz and excitement of Midtown New York while strolling through.
20 minutes here
Upper East Side
Head on to the Upper East Side, a luxurious residential neighborhood that is famous for its restaurants, designer shops, and splendid houses. Meet classical dark-red brick houses and elite skyscrapers. Both Trump and Obama’s histories lead you here. Admire the building of the Hotel Delmonico on Park Avenue, which was built in 1929 and which Trump bought in 2001 for $115 million and renamed it The Trump Park Avenue. Today it's 120 condos and 8 penthouses. The hotel was the location where The Beatles were staying when Bob Dylan came to visit them on Friday, August 28, 1964. The Beatles were, at the time, in the middle of their first U.S. tour. Obama's 2nd apartment is a mile from here, too.
20 minutes here
Trump Tower
Get up close and personal with Trump Tower on the 5th Avenue and take in a magnificent view from that point. The building was constructed in 1983, headed by the first female construction manager, Barbara Res. The tower was designed to stand out from the “boxy” style of the highrises, so the architect Der Scott made a 28-faced edifice with an inverted pyramid of cubes at the base.
10 minutes here
Central Park
Take a walk to the Central Park area, a famous New York oasis. Trump owned three buildings along Central Park South, starting with the Plaza Hotel. Trump Parc and Trump Parc East are condominium and apartment buildings that opened in 1930 and 1917, respectively. Learn more about the park as you walk by the famous Zoo and the Pond, where Obama once posed for a photo. Get on Subway at Columbus Circle.
30 minutes here
Columbus Circle
Constructed in the late 1960s, the Gulf and Western Building, designed by Thomas E. Stanley, is now the Trump International Hotel. Take a picture with the monument to Christopher Columbus constructed in 1892 to celebrate the 400th anniversary of the Discovery of the Americas. Get a chance to know more about illustrious buildings you’ve seen in movies as well as some architectural peculiarities of the place, like the Hears Building.
40 minutes here
Visit Tom’s Restaurant of Seinfeld at 112th Street, where Obama and his roommate Phil Boehner had breakfast at $2 each. Enjoy great service and good food in a friendly atmosphere.
20 minutes here
622 West 114th Street was Obama’s last apartment before moving to Chicago in 1985. He jogged along Riverside Park Drive. Take a stroll down the Riverside neighborhood and get to General Grant’s Tomb a few blocks north. Discover the Riverside Church with one of the most copied paintings in the world, "Jesus at Gethsemane."
10 minutes here
Columbia University
Get to Columbia University, 1754, where Obama spent most of his four years in NYC. He had his first apartment on West 109th Street in 1981. He was a Junior at Columbia, and he slept in an alley near Amsterdam Ave. for the 1st night. Walk through the Columbia campus, which opened in 1896. Obama said he studied at the Low Library because it was heated. Learn about other places on campus connected with the ex-president.
10 minutes here
Where it starts and ends
Meeting point
New York
Meet your guide at the info booth clock in the middle of the station
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Finish the tour at Columbia University and hear how Columbia University is associated with 86 Nobel Prize winners
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
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- 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
- $79 to $170
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 51
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Presidents Trump and Obama's Life Private Tour Expert Guide: questions travelers ask
Practical detail on this experience, plus the wider planning questions for New York.
How much does Presidents Trump and Obama's Life Private Tour Expert Guide cost?
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Prices start at $79 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 Presidents Trump and Obama's Life Private Tour Expert 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 Presidents Trump and Obama's Life Private Tour Expert Guide worth it?
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It holds an Outty Ranking of 51 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 Presidents Trump and Obama's Life Private Tour Expert 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 Presidents Trump and Obama's Life Private Tour Expert 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 Presidents Trump and Obama's Life Private Tour Expert 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 Presidents Trump and Obama's Life Private Tour Expert 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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