• Flatiron Building - The tour begins with a comprehensive overview of history and the city’s expansion uptown. Photographs illustrate the transformation of the area from farmland to a chic city center.

The history of the Astors is explored, including the creation of the first Waldorf=Astoria and their social interactions with families like the Vanderbilts, who represented the new industrial wealth.

• Madison Square - Photographs enhance a brief walk and discussion around Madison Square, covering the histories of Met Life and the original Madison Square Gardens during the peak of the Gilded Age.
• Broadway - The tour navigates the remnants of the long-forgotten city, from a time when telephones and electricity were new and uncommon in households. It was the era of department stores, apartment buildings, and office towers, introducing new lifestyles for a growing middle class. Each thoroughfare intersecting at Madison Square offered different class-based attractions, including a red-light district above 23rd Street and west of Broadway.

The tour highlights the carriage trade shops of upper-class wealth along Broadway, featuring the old Lord & Taylor and Arnold Constable & Co buildings, among others.

• Fifth Avenue - Below 23rd Street, Fifth Avenue has a unique development history unlike any other in the city. Here, the Garment District was “diverted” from Midtown, creating a distinct built environment.
• Sixth Avenue (Avenue of the Americas) - Sixth Avenue was the middle-class shopping district and still showcases its impressive array of buildings as the city transitioned from cast iron to steel frame construction. Notable buildings include: Seigel-Cooper, B. Altmans, Hugh O’Neill’s, and Adams Dry Goods Store.
• Broadway - Above 23rd Street, history takes a dramatic turn as a few steps lead into the old Tenderloin, an area of concert-saloons, brothels, and gambling halls from a time when home entertainment centered around the piano.
• Flatiron District - The tour crosses back to Fifth Avenue, entering a realm of significant architecture. Featured building types include early experimental ventures into multi-family housing: apartment-hotels, French flats, bachelor flats, and early co-ops. Notable buildings include: the Wilbraham, Holland House, Seville, and the Martha Washington.
• Madison Square Park - The tour concludes in Madison Square Park with intriguing histories, including the Worth Monument, Delmonico’s, and the old Brunswick Club.

• Expert guide

• Gratuities

Visitors will gain an understanding of how compact the Gilded Age city of New York was. Shopping and theater districts for the upper and middle classes were located just a block or so apart. Additionally, the apartment building, department store, and office tower were all new innovations, reaching their social peaks around Madison Square, coinciding with the advent of telephones and electricity.

The most intriguing aspect is the close proximity of these venues, from the upscale shops and residences of families like the Roosevelts, Astors, and Schermerhorns, to the blocks of illicit, often lively nightlife activities in the old Tenderloin, just a few blocks away.

This tour is a remarkable exploration of the Gilded Age city of New York around Madison Square.

For a full refund, cancel at least 24 hours before the scheduled departure time.