5 Boroughs of NYC: 5-Day Itinerary


New York City is comprised of five boroughs: Manhattan, Queens, the Bronx, Brooklyn and Staten Island. While most tourists spend the majority of their time in Manhattan, the other boroughs offer a more authentic glimpse into the lives of ‘real’ New Yorkers. This five-day local itinerary takes you through the five boroughs of NYC and to some of the most iconic sites in the city.

What Are the 5 Boroughs of NYC?

New York City is comprised of five boroughs (or municipalities). Each used to be its own city (well, the Bronx was actually a family farm) and became a part of the Greater New York City Area in 1892. 

Today, everyone considers themselves New Yorkers. But many residents consider themselves Americans first, of their boroughs second and New Yorkers third. Each borough also has its own unique flavor and vibes — and feels like mini-cities within a much larger city. 

Day One: Manhattan

Stop 1: Upper West Side

The Upper West Side is predominantly a residential neighborhood, but it’s a great way to get a glimpse into city life. 

We recommend wandering the streets north of Lincoln Center just to soak in the upper-class vibes. One site you can’t miss? The Cathedral of St. John of the Divine, the largest cathedral in the world. Head here around 9 a.m. to make it up to Harlem just in time for breakfast. 

Stop 2: Harlem

Harlem is one of the most historic neighborhoods in the city. It was where the Civil Rights Movement took shape and where many African American musicians, artists and writers once lived. For an off-the-beaten-path activity, head up to the Schomburg Center for Black Research to learn about the area’s history.

On your way to Greenwich Village, we recommend walking through Central Park by entering at W. 72nd St. and exiting at the southeast corner of the park.

Stop 5: Greenwich Village/East Village 

Greenwich Village and the East Village are two bohemian neighborhoods. Greenwich Village was once home to famous Beat Generation poets and the East Village was the birthplace of punk music in the U.S. We recommend wandering down Bleecker Street, grabbing a falafel at Mamoun’s and eating on a bench in Washington Square Park. Walk along St. Mark’s Place in the East Village to catch some of those punk rock vibes.

Stop 6: Chinatown

New York City’s Chinatown is the largest Chinatown in the U.S. Walk along Canal Street to get a glimpse of the famous food stores that supply the restaurants in the city. Stroll down Mott Street between Canal and Bowery to see the historic area. Columbus Park is where locals meet for mahjong and tai chi. 

We also recommend stopping by the Museum of Chinese America (MoCA) to get a better understanding of why Chinatown is so important to NYC’s history.

Stop 7: Walk Across the Brooklyn Bridge 

End your day with a stroll across the Brooklyn Bridge. At the end of the bridge, you’ll reach Brooklyn Bridge Park, which offers one of the best views of the city’s skyline at night.

Day 2: Manhattan – Part 2

Stop 1: UES

Start your day on the Upper East Side, a residential neighborhood. One of the best the less-traveled activities is taking the tram to Roosevelt Island — a quiet oasis within the city. Walk around the island to the old smallpox hospital before heading back to the tram or the subway.

Stop 2: Rockefeller Center

Top of the Rock is one of the most visited observation decks (you can even see another famous observation deck, the Empire State Building, from here!). We recommend skipping TOTR in lieu of Bar SixtyFive, a bar that’s only one floor below the observation deck. 

It offers great views but it’s less crowded and admission is only the cost of a drink. 

Stop 3: Little Italy

Little Italy is (as the name suggests) quite a small neighborhood. This eight-block area is home to some beautiful streets and one of the biggest festivals in the city, the Feast of San Gennaro. We recommend strolling along Mott and Mulberry Streets and stopping at the Italian American Museum.

Day 3: The Bronx and Staten Island 

The Bronx is one of the city’s boroughs that’s not well-traveled by tourists. Yet, there’s so much to see and do here. We recommend spending the lion’s share of your visit to the Bronx on Arthur Avenue, NYC’s ‘real’ Little Italy.

After your time in the Bronx, take MetroNorth (the commuter train) to Grand Central Terminal and switch to the 4 or 5 trains to Bowling Green to catch the Staten Island Ferry.

On your trip to Staten Island, you’ll Today, pass by the Verrazano Narrows Bridge and the Statue of Liberty. 

Very few visitors disembark the ferry to spend time on Staten Island. This is the most residential borough of NYC. We recommend heading to Lakruwana for some of the best Sri Lankan food in the city. 

Day 4: Brooklyn

Brooklyn has a population of almost 3 million residents. If it were its own city, it would be the third-largest in the U.S.! While you probably already know all about Coney Island and the Brooklyn Bridge, we recommend simply getting to know the flavor of each neighborhood.

Brooklyn Neighborhoods

  • Flatbush/Lefferts Gardens (great for Caribbean food — just east of Prospect Park)
  • Redhook and Gowanus (factory vibes with great restaurants and views)
  • Park Slope and Carroll Gardens (neighborhoods just east of Prospect Park with tons of restaurants and shopping)
  • Brooklyn Heights and DUMBO (two upscale neighborhoods on the Brooklyn-side of the Brooklyn Bridge with tons of restaurants)
  • Williamsburg and Greenpoint (two hipster neighborhoods with restaurants, shopping and great views)

Day 5: Queens

Queens is another residential borough. It’s so large that most visitors (or locals for that matter) ever visit every inch of it. To save precious travel time, we recommend heading to Astoria for breakfast before taking the train out to Flushing Meadows Corona Park to visit the Museum of the City of New York.

Stick around Flushing for lunch (head to the Food Hall at Queen’s Court Crossing for authentic Chinese fare) or take the train to Jackson Heights for Nepalese food. We recommend Lhasa Fast Food (a great momo shop in the back of an electronics store).

Spend your afternoon at the Museum of the Moving Image, an homage to the movies and TV shows that were filmed at Kaufman Astoria Studios, the largest movie and TV studio in NYC. 

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