New York's Most Fascinating Walking Tours

The Tenement Museum’s walking tours take you on a journey through the Lower East Side, a neighborhood shaped by a convergence of immigrant cultures. This tour stops at seemingly insignificant places to reveal hidden stories, helping attendees understand the neighborhood’s history while engaging with its present. Make sure you explore the museum’s two tenement buildings at 97 and 103 Orchard Street to get a deeper perspective of their past residents and what it was like to live there all those years ago.

Join the self-described “pre-eminent drunken gurus of Village lore” on a bookish tour of Greenwich Village. The Literary Pub Crawl visits the previous homes and favorite watering holes of America’s most celebrated writers, including Dylan Thomas, Allen Ginsburg, Emma Lazarus, Edna St. Vincent Millay, Jack Kerouac, Edgar Allen Poe and Mark Twain. The success of the company’s flagship tour of the Village, which started in 1998, has spawned similar offerings in Brooklyn, Times Square and on the High Line.

On this two-hour tour, get insight into the organized crime syndicates who controlled New York from the start of the 20th century. There are three tours to choose from: The Rise and Fall of the American Mafia, which takes you on an after-dark trip through Little Italy and the East Village; the Little Italy and Chinatown Gangsters Walking Tour, which covers the gangs of Mulberry Street from the 1840s through the 1920s; and Jewish Gangsters of the Lower East Side Tour, which tells the tale of the tenement gangsters known as “Kosher Nostra.”

When you book a PhotoTrek tour, you get a guide and a personal photographer in one. Explore the city, picking up local recommendations for things to see and dishes to eat along the way, while your guide directs impromptu photo shoots of your group. You’ll finish up the day with plenty of Instagram content and the stories attached to New York’s most recognizable landmarks. The guides will also teach you how to master the subway, so you can navigate the city like a local.

The New York Adventure Club unlocks little-known attractions across the city. While many of its offerings are confined to one location (think a matcha ceremony in a secret Japanese tea garden or a lesson with an urban beekeeper), many of the unusual itineraries involve plenty of walking. You can explore the abandoned Ellis Island hospital complex, take in the sights of City Island, the Bronx (aka the “Cape Cod of New York”), or soak up elevated views of Manhattan from the secret rooftop farms and wineries at Brooklyn Navy Yards.

The Brooklyn Food and Fashion Tour is perfect for those who want to return home with apparel that’s a little more unique that an ‘I heart NY’ T-shirt. It’s hosted by a fashion and textile designer who’s also trained as a personal shopper (hello, industry discounts!). The tour stops at boutique clothing stores in Williamsburg, one of Brooklyn’s trendiest neighborhoods, as well as a handful of food spots to keep you fueled for the four-hour shopping spree.