Private Walking Tours of New York City


Chicago may justly claim to be the birthplace of the skyscraper, but the tall building came of age in New York. There is no place like Manhattan to see the multifaceted forms, functions, and fashions of skyscraper architecture, from the days when a 10-story building was considered daring to the Postmodernist plans for the architectural redevelopment of the World Trade Center complex.

Ten of the buildings that have claimed the title of “tallest in the world” have been in New York and six of them are still extant. We will see all six of these buildings along with sites of those that are gone (such as the demolished Singer Building—see postcard at left—and Ground Zero).

Participants on this tour will visit five neighborhoods (the Civic Center, Financial District, Greenwich Village, Flatiron District, and Midtown), transporting between stops on the subway. The tour lasts between 3 and 4 hours (depending on how long the subway rides take), but this is certainly not all walking. Also, in order to understand skyscraper development in the context of the growth of city as a whole, we will probably buildings that are not skyscrapers, such as the Brooklyn Bridge, City Hall, the Alexander Hamilton US Custom House, the Arch in Washington Square Park, and the main branch of the New York Public Library.

This tour is specially priced—please see below for full details.

A few of the many skyscrapers seen on this tour include:

The Park Row Building

The Woolworth Building

The Marine Midland Bank (now Brown Brothers Harriman)

One Liberty Plaza (originally the US Steel Building)

40 Wall Street (originally the Manhattan Company)

The Bayard-Condict Building

One Fifth Avenue

The Flatiron Building

Lever House

The Seagram Building

Rockefeller Center

The Chrysler Building

4 Times Square (Condé Nast headquarters)

The Empire State Building

This heavily illustrated tour uses historical photographs from the mid-19th century onward to show how New York City went—in the space of just of few decades—from a city of eight-story buildings to having skyscraper upon skyscraper clamoring to be the tallest in the world.


Because of post-9/11 security concerns, most of the buildings visited on the tour—including the Woolworth, Chrysler, and Seagram Buildings—do not allow interior visitation. The tour can arrange to end at either the Empire State Building or Rockefeller Center for those who wish to see those buildings on their own.


This tour lasts approximately four hours and costs a flat fee of $200 for groups of 1-4 people. For parties larger than 4 people, the cost is $50 per person. Please inquire about discounts for student groups or parties larger than 10 people. This price does not include subway fare and we suggest that all tour participants have MetroCards before the tour begins.

To contact us about booking this tour please use our
online booking form (preferred) or call (toll-free) 1-877-572-9719