10 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 like the babka at Breads Bakery and have plenty of opportunities to snap photos. $50

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 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. $35

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. $25

Photograph: Courtesy CC/Flickr/Troy Trolley

The oldest neighborhood in Manhattan is also the furthest south: the Financial District. Here, you’ll find taverns frequented by George Washington and other Revolutionary War soldiers, the neoclassical facade of the New York Stock Exchange, the wobbly cobblestones of Stone Street and other remnants of the 18th century. After all, if you want to see how far New York has come, you have to trace history all the way back to the beginning. $35

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 90-minute tour. You’ll feel like an amateur archaeologist as you look for clues hidden in plain sight. $35

Not many tourists venture north of Central Park, but those looking for interesting architecture ought to. Harlem’s Mount Morris Park Historic District covers 16 blocks of Gilded Age buildings, from splendid homes to gorgeous churches. Get acquainted with the area on a three-hour walking tour of the neighborhood, capped off with lunch at a local restaurant. $65.35

These three-hour tours are all led by urban planners, architects or historians who happen to also be lifelong New Yorkers—city experts twice over. Your guide will cover the evolution of Gotham’s architecture, from the late 19th century through today. Expect to see a wide variety of styles including the Beaux Arts facade of Grand Central Terminal and the ornamental exterior of Tudor City. $86

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 on a two-hour walking tour to get a feel for the western part of the borough. $24

Photograph: Courtesy CC/Flickr/Jay Woodworth

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 on this private half-day tour. You’ll 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. $200

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. $78

Photograph: Courtesy CC/Flickr/Andrea Schaffer