Young Trump and Obama in New York with Local Private Guide

Experience the Personal Journeys of Trump and Obama in New York City

If you’re curious about the paths that led Donald Trump and Barack Obama to the White House, this private tour offers a rare glimpse into their formative years in New York. For $199 per person, you get a 3-hour guided walk through some of the city’s most iconic neighborhoods—starting at Trump Tower and ending at Columbia University—with a local guide who knows the city and these stories intimately.

What we love about this experience is how it combines personal stories with historic sites, creating a narrative that’s both educational and engaging. The opportunity to walk through neighborhoods where they grew up, work, and first made their mark makes this tour feel authentic and intimate. Plus, the inclusion of a subway ride adds a layer of genuine New York City immersion.

One potential drawback is that the tour covers quite a bit in a short time, which might leave some feeling rushed—especially if you’re a slow walker or want to linger longer at certain spots. Nevertheless, it’s a perfect fit for history buffs, political enthusiasts, or anyone wanting a local, personalized perspective on NYC’s role in shaping two of America’s most famous presidents.

This tour suits travelers who appreciate detailed storytelling, are interested in personal histories behind public figures, and are comfortable walking and using the subway. It’s also ideal for those who enjoy small, private groups that can be tailored to your interests.

Key Points

• Authentic Personal History: Focuses on the childhood and early careers of Trump and Obama, offering a behind-the-scenes look at their beginnings.
• Iconic NYC Sites: Visits places like Trump Tower, Columbia University, and Grand Central, blending personal stories with city landmarks.
• Private, Customizable Experience: A private tour with your own guide, allowing for flexibility and personal attention.
• Walking and Subway: Combines walking with subway rides—an efficient way to see the city like a local.
• Focus on History and Architecture: Highlights important buildings like the Chrysler and Lever House, giving context to NYC’s development.
• Great for Enthusiasts: Ideal for travelers interested in political history, New York’s architecture, or personal stories of famous figures.

A Deep Dive into the Tour Experience

Starting Point: Trump Tower

Your journey begins outside Trump Tower at the iconic 725 5th Ave, where your guide will point out the spot where Donald Trump announced his 2015 presidential bid. You’ll see the three-floor atrium of pink and white veined marble and the 60-foot waterfall—a spectacle that’s as much about branding as architecture. Learning that the building architect was Der Scutt and the construction manager Barbara Res (the city’s first female in that role) adds a layer of NYC history to the site.

You’ll get a chance to peek inside the Trump Café if you wish, and your guide will share fun tidbits: that the upper floors house 278 apartments with former residents like Steven Spielberg and Sofia Loren, with prices ranging from $800K to $10 million. Trump’s private penthouse on the top three floors, where his children grew up, is a highlight. This stop sets the stage for understanding Trump’s rise from a Manhattan real estate figure to a presidential contender.

Exploring Obama’s Roots in Midtown and Queens

Next, the tour takes you to Lexington Avenue at East 51st Street, where a young Obama, just 22, commuted to work as a corporate journalist. You’ll see the walkup apartment where he lived in the early 1980s—a stark contrast now surrounded by upscale doorman buildings. Nearby, the tour passes the Smith and Wollensky steakhouse, a classic NYC eatery, and the towering Lever House (1951), which revolutionized office building design with its glass facade.

A short walk then leads to Dag Hammarskjöld Plaza, where Obama’s first job outside college was at Business International Corporation. His writing about economic issues paints a picture of a young man just beginning to understand the world’s complexities. Your guide will share stories of his early career and how his experiences in New York laid the groundwork for his future leadership.

Trump’s Manhattan Residences

Back in Trump’s realm, the tour visits Trump Tower Plaza at 47th and 1st. This 72-floor residential skyscraper (completed in 2001) was the tallest residential building in the world for two years. Former tenants like Derek Jeter, Bill Gates, and Harrison Ford underscore the building’s prestige. Your guide will point out details like the $1 million+ apartments and mention Trump’s own penthouse where his children grew up.

The United Nations and Historic Sites

Moving closer to international affairs, the tour stops briefly at the UN headquarters at 42nd and 1st. Here, you’ll see the Raoul Wallenberg monument, learn about the UN’s founding in 1945, and appreciate how New York became a hub for global diplomacy. The guide will share insights about the UN’s evolution from fuel storage to an essential part of world politics.

The Daily News Building and Iconic Architecture

Next, you’ll explore the Daily News Building at 42nd and 2nd, where both Obama and Trump discovered their talents as young men. The building’s famous globe lobby and floor arrows pointing around the world are visual reminders of NYC’s role as a media and business hub. It’s a fascinating stop that combines media history with the city’s architectural grandeur.

Close to here is the Chrysler Building, once the world’s tallest building in 1930, and Grand Central Terminal—a true NYC landmark. Your guide will point out the “whispering gallery”, where a simple whisper can be heard on the opposite side, a fun architectural quirk that captures the spirit of NYC’s design innovation.

The Rebirth of the Commodore Hotel and Obama’s First NYC Home

The tour’s historical highlights include the Hyatt Grand Central, which was originally the Commodore Hotel built by Cornelius Vanderbilt in 1919. In the 1970s, Donald Trump convinced his father to buy and rebuild the hotel, a bold move at the time. Today, the area is thriving again, illustrating how Trump’s early investments reshaped parts of NYC.

Finally, the tour takes you to Frederick Douglass Circle in Central Park, where Obama first lived as an undergraduate. You’ll see the alley where he stayed the night when he couldn’t get into his walkup, and learn how rent prices have skyrocketed from $360 in 1981 to $3,000 today. Nearby, Columbia University is where Obama earned his BA in Political Science in 1983. You’ll see the historic campus, including the Low Library, where he and his roommate studied and where the Manhattan Project was launched during WWII.

Ending at Columbia University

The tour concludes at Columbia, a school with roots dating back to 1754. Your guide will give you insights into its various schools—from Law to Journalism—and its connection to major historical moments, like Einstein’s work on the Manhattan Project. This spot encapsulates Obama’s academic journey and the intellectual roots of NYC.

Bonus: Passing Through Central Park

As you walk through Central Park, your guide’s knowledge of the city’s film and TV scenes will add extra flavor. You’ll recognize spots from Seinfeld, Breakfast at Tiffany’s, and other classics—all while soaking in the park’s calming green escape amidst the city’s hustle.

What You Can Expect

Throughout the tour, your guide will share engaging stories, highlight architectural details, and capture photos of your group at key sites. The small, private group setup ensures personalized attention and makes it easier to ask questions or tweak the route.

Since the tour includes public transportation—specifically, a subway ticket within a $10 budget—you’ll experience an authentic way of getting around NYC. The walks are moderate, but comfortable shoes are recommended, given the amount of ground covered in about three hours.

Value and Practical Considerations

The tour’s price of $199 reflects a personalized experience with a knowledgeable guide and customized itinerary. The inclusion of all taxes, local tips, and expert advice for exploring NYC afterward adds value. Keep in mind that food and drinks are not included, so plan your meals accordingly. Also, as this is a private tour, it’s ideal for families, couples, or small groups seeking a tailored NYC experience.

Who Will Love This Tour?

If you enjoy political history, city architecture, or personal stories of influential Americans, this tour is perfect. It offers a blend of history, architecture, and personal anecdotes that illuminate how NYC shaped two of America’s most recognizable leaders. Travelers who prefer small, private groups and flexibility will appreciate the personalized touch.

This tour is less suited for those who want a luxury ride or heavy tourist crowds, as it emphasizes walking and subway travel, but it offers a more authentic and intimate experience of New York life and history.

Frequently Asked Questions

How long is the tour?
The tour lasts approximately 3 hours, covering multiple sites across NYC, combining walking and subway travel.

What is the price?
It costs $199 per person, which includes all taxes, a private guide, and subway tickets costing up to $10.

Is this a private tour?
Yes, it is private, meaning only your group will participate, allowing for personalized attention and flexibility.

Where does the tour start and end?
It begins outside Trump Tower at 725 5th Ave and can finish at any location you prefer, including Columbia University.

Are food and drinks included?
No, food and drinks are not included, but your guide can recommend spots along the route.

Is this suitable for all fitness levels?
The tour involves walking and subway rides; travelers should have moderate physical fitness.

What sites will I see?
You will visit historic sites related to Trump and Obama’s early lives, NYC architecture like the Chrysler Building, and iconic locations like Grand Central.

Can I customize the itinerary?
Yes, the guide offers a customizable experience based on your interests and preferences.

Is there a cancellation policy?
Yes, you can cancel free of charge up to 24 hours in advance for a full refund.

To sum it up, this Young Trump and Obama in New York tour offers a compelling mix of personal stories, historic sites, and city architecture. It’s ideal for travelers keen on understanding the early influences that shaped two very different American presidents, all within the vibrant backdrop of Manhattan. With its private guide, flexible route, and authentic NYC experiences, it provides a thoughtful, engaging way to explore the city’s role in their journeys—and in history itself. If you’re looking for a personalized, story-driven tour that combines political intrigue with urban charm, this one deserves a spot on your NYC itinerary.