A focused, three‑hour walking tour that traces addresses and landmarks tied to Barack Obama and Donald Trump across Midtown and the Upper West Side. Expect city sidewalks, one subway ride and grounded historical context delivered with an objective tone.
More ways to explore the area's outdoor wonders
Stand beneath the ornate clock at Grand Central Terminal and the city seems to compress — commuters flowing like a river, overhead the painted constellations watch silently. From here a three‑hour walk threads Midtown and the Upper West Side, following addresses, buildings and neighborhoods where two future presidents spent formative years.
Difficulty
moderate
Duration
3 hours
Fitness Level
Moderate — comfortable walking fitness with occasional stairs for subway access
Wildlife
History
The tour links sites where mid‑20th century urban development met postwar growth; Columbia University and Midtown offices shaped careers and civic life in the 1980s.
Conservation
High foot traffic in historic areas can stress street trees and plazas; use public transit, avoid littering and respect private property to limit impact.
Reserve your spot on the Private Tour in Presidents Obama and Trump's Success in NYC today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Carry an OMNY/MetroCard
You’ll use one subway ride—load a contactless fare or MetroCard in advance to keep the group moving.
Wear supportive walking shoes
Sidewalks are mostly even but you’ll be on your feet for three hours with short standing stops.
Start in the morning
Begin early to avoid peak commuter flows and summer heat, improving views and photo ops.
Respect private residences
This is an exterior tour; avoid trespassing or loud behavior near doorman buildings and apartments.
Supportive walking shoes
Good traction and cushioning make three hours of pavement far more comfortable.
Refillable water bottle
Staying hydrated is important, especially on warm days when shade is limited.
summer
Light, layered jacket
Urban winds and river breezes can be brisk; layers let you adjust on the move.
fall
Contactless fare (OMNY) or MetroCard
Needed for the single subway ride and any short transfers during the tour.