The best tours of off-the-beaten-path neighborhoods in NYC

Sugar Hill got its name during the Harlem Renaissance, as “life was sweet” for the wealthy African Americans who lived in the district. Thurgood Marshall, Langston Hughes and Duke Ellington all spent time in the row houses here. Peep the stunning Queen Anne–style architecture and immerse yourself in the vibrant community on this walking tour of the area.

Alexander Hamilton moved uptown to a country estate in what is now Harlem in the last two years of his life. Today, his home, now known as Hamilton Grange, still stands in the same neighborhood, though it was moved to St. Nicholas Park in 2011. Turn-of-the-century architecture seems to lie around every corner in this lush, tree-lined neighborhood. See why this historic area makes such an appealing escape from lower Manhattan on this two-hour walking tour.

On the hunt for some gorgeous, glamorous Gilded Age architecture? Well, you won’t find many better places for it in New York than the area around Mount Morris Park in central Harlem. Unlike elsewhere in Manhattan, the nineteenth century streets have been kept largely unaltered. This three-hour tour will take you all the way through the neighborhood’s history, from the earliest Native American settlers to the Revolutionary War.

Few visitors know anything about Roosevelt Island, a secluded residential community that feels worlds apart from the rest of the city. Once used for insane asylums and hospitals, Roosevelt Island is now home to a thriving population of about 14,000 residents. But, if you have the stomach for it, revisit the island's troubled past on the 'Island of Lost Souls' tour. Pass eerie sites, like the neo-Gothic ruins of the smallpox hospital, the first pathological and bacteriological research lab and the NYC Lunatic Asylum, opened in 1841. After you learn about the island’s history, board the aerial tram for a sky-high trip over the East River into Manhattan.

Once an industrial hub, Long Island City has turned empty warehouses to desirable condos and apartments in the last several years. You can see both the old infrastructure—train tracks, bridges and forgotten factories—and the new Queens springing up. Experience the neighborhood that’s slowly becoming an attractive option for city dwellers looking to escape sky-high rents in the tastiest way available: via its eateries. Try a 100-year-old burger (well, the recipe anyhow), French pastries, traditional Neapolitan cuisine and much more.

Flatbush is one of the oldest neighborhoods in NYC – and, as you’d expect, it’s totally packed with fascinating stuff to see and learn about. Here you’ll find the city’s oldest high school and a church which dates all the way back to 1654. Originally called Midwood, Flatbush features Victorian, colonial revival and neo-Tudor homes. All of which you’ll learn loads about over the course of this two-hour tour.

Not one for the fainthearted, this. Lasting five to seven hours, you'll be driven from the home of soul, Harlem in Upper Manhattan, all the way down to Coney Island for one of Nathan's world famous dogs. Along the way you'll learn about the birth of hip hop in the Bronx, visit the home of the the New York Mets (Flushing Meadows Park, and pass through the Jewish neighborhood of Crown Heights. 

Residents of the other four boroughs like to poke fun at Staten Island: “You have to take a boat to get there! Never date someone from Staten Island!” and so on. What they don’t know is that the community southwest of Manhattan offers plenty of tempting attractions, like the Snug Harbor Cultural Center, art galleries and museums. Give it a chance on this three-hour private tour of the underappreciated borough. 

Yes, the Bronx is home to Yankee Stadium, but that’s not all this borough should be known for. It’s also the birthplace of hip-hop and the one-time residence of Edgar Allen Poe, and offers tourist attractions like the Bronx Zoo and several Depression-era murals funded by the Works Progress Administration. Explore a side of the Bronx that few tourists ever see on this walking tour.

Hoboken isn’t technically a part of New York City, but since it lies just across the Hudson River, why not check it out? You’ll catch a few stunning views of the Manhattan skyline as you take a ferry across the river. Once you’ve set foot in New Jersey, you’ll see the street where the first game of baseball was played and scope out Frank Sinatra’s birthplace. There’s even time to grab a cannoli from Carlo’s Bakery (of Cake Boss fame) before heading back into the Big Apple.