9 fascinating architecture tours in NYC

Perhaps no building in New York City stands out more than the Flatiron Building, the triangular landmark sandwiched between Fifth Avenue and Broadway. Get an up-close-and-personal look at the iconic piece of architecture on this three-hour tour of the neighborhood. You’ll also learn a bit of Union Square history, sample local bites at institutions like the award-winning bakery Breads Bakery and Italian food hall Eataly. You'll also have plenty of opportunities to snap photos in two of New York's most picturesque neighbourhoods.

Budget range? Worth it for the thorough commentary and heavy flow of food. 

The Chrysler Building, Grand Central Station, Tudor City, Times Square: So many of the city’s best-known buildings are clustered around Midtown. Join this three-hour private walking tour to peer up at the skyscraper spires and even step inside a few of the buildings’ lobbies. You’ll walk away with a comprehensive understanding of the Midtown’s history. 

Budget range? More spenny than a group tour, for sure. 

The name “Victorian Flatbush” is a bit of a misnomer, as the neighborhood actually includes stately Queen Anne, colonial, Tudor and neo-Revival homes. Tour the area to spot countless examples of stunning architecture, a church that Peter Stuyvesant founded in 1654 and the city’s oldest high school. This walk also offers a glimpse at the process of gentrification—a controversial topic in this neck of the woods. 

Photograph: Courtesy CC/Flickr/Troy Trolley

Budget range? Quite expensive, but you're paying for a great guide and the unique setting.

Grimy modern-day Penn Station doesn’t exactly seem like an architectural landmark, what with its filthy waiting areas and leaking sewage. Still, the transit hub serving more than 650,000 commuters a day is a crucial part of the fabric of this city and has been since the original building was completed in 1910. Though the first structure was demolished in 1963, you can still find a few vestiges from the past if you know where to look. Uncover some of the station’s artifacts and plenty of its history on this 2+ hour tour led by accredited urban planner. 

Budget range? Reasonable for a private tour of a secret, lesser-explored location. 

There are a number of Harlem tours in operation, with knowledgable guides giving you an insight into the vibrant culture of the area. Some even include live gospel music in New York’s Mount Morris District and a fine dining brunch. 

Budget range? Varies, but the cheapest is very affordable.

These tours cover a variety of lesser-known treasures and famous landmarks, many of which you would have spotted in TV and film. Your guide will explain the evolution of Gotham’s architecture, from the late 19th century to modern day. Expect to see a wide range of styles including the Beaux-Arts facade of Grand Central Terminal and the ornamental exterior of Tudor City. 

Budget range? The group tours won't cost you much, or you could splash out on a private tour that's tailored to your interests and pace. 

Though DUMBO is just east of Brooklyn Heights, the two neighborhoods could not have more different architectural styles. Brooklyn Heights is full of brownstone townhouses built in the 1800s, an area known as America’s first suburb. The cobblestone streets of DUMBO, on the other hand, run between trendy lofts, galleries and boutiques built inside repurposed factories and warehouses. Explore both areas at your own pace with this self-guided tour via the Action Tour Group app.

Photograph: Courtesy CC/Flickr/Jay Woodworth

Bugdet range? Cheap, even for a self-guided tour. 

European settlers first came to the Bronx in the 1600s—in fact, the borough’s name comes from Jonas Bronck, the Scandinavian immigrant who first settled in Mott Haven in 1639. Trace the history of the Bronx through its architecture and visit the Grecian-style Bartow-Pell Mansion built in 1842, cross the Art Deco–influenced Triborough Bridge and even explore the quaint nautical scene on City Island. 

Budget range? All pretty affordable.

New York City’s vast network of subways, streets, bridges and tunnels is nothing short of an urban wonder, when you stop to think about it. Devote a few hours to understanding the city’s bridges as you pass under each of them on a boat tour up the East River. The tour is accredited by the American Institute of Architects and led by professors from Parsons and FIT, so come prepared for a scholarly dive into city infrastructure. 

Photograph: Courtesy CC/Flickr/Andrea Schaffer

Budget range? A pricer option, but includes a ride on a yacht...