How to Spend 5 Days in New York City- Itinerary for First Time Visitors

New York City is a place I felt like I knew even before I’d ever visited. A backdrop to countless movies and television shows, New York City has been making appearances in my living room for as long as I can remember.

Planning a 5 day trip to New York City felt like making plans to meet a pen pal I’ve grown to know so much about, but never met in person. I was curious to experience this city of icons, bringing to life the Empire State Building, Brooklyn Bridge, Central Park, and Statue of Liberty.

Upon arrival, we were met with endless possibilities of things to see and do in New York City. It was simultaneously energizing and exhausting, especially for first time visitors.

With no shortage of ideas for how to spend 5 days in New York City, we set out to explore this beloved metropolis. Here’s how our first trip to New York City turned out and a day-by-day look at our New York itinerary.

Our 5 Day Trip to New York City- Visiting NYC in January

We decided to visit New York City in January and it turned out to be a great choice for someone like myself who isn’t a big “city person”.

Being there in January was nice because not once did we have to wait in line at any of New York City’s popular tourist sites, even though they were set up to manage large crowds (it must be madness in summer). Fewer people also made it easier to get standby tickets to tapings of the late night talk shows. Plus, there were a lot of good deals on hotels, Broadway shows, and city sightseeing cards like the New York CityPASS and New York Pass.

We even got lucky with some unusually mild weather and were able to leave the winter gear at home. Although, I was kind of hoping to see Central Park covered in snow!

How to Spend 5 Days in New York City- Itinerary for First Time Visitors

For our first trip to New York City, we definitely wanted to have the quintessential New York experience. We admired famous landmarks, attended shows, ate cheap pizza, and even had a museum day.

Five days was the perfect amount of time for a first trip to New York City. We didn’t feel rushed and were able to visit all the main tourist attractions in New York City that were of interest to us. Even though we accomplished a lot on this trip, there are still so many things to do in New York City that we’d have no trouble finding ways to spend a future trip.

Here’s a look at how we spent 5 days in New York City. We hope our NYC itinerary gives you some ideas of things to do on your first trip to New York City!

Day 1- Lower Manhattan, Brooklyn, Saturday Night Live

After a very early morning waiting in line for Saturday Night Live standby tickets, we headed down to Lower Manhattan where we took a walk down Wall Street, rode the Staten Island Ferry, visited the September 11 Memorial, and walked across the Brooklyn Bridge. The day ended on a high note by actually getting in to see Saturday Night Live!

Wall Street & the Charging Bull

On our way to the Staten Island Ferry we took a quick walk around the Wall Street area, home to New York’s Financial District. Some highlights include the New York Stock Exchange, Federal Hall (site of George Washington’s inauguration), and Trinity Church (where Alexander Hamilton, one of the Founding Fathers of the United States, is buried).

South of Trinity Church, at Bowling Green, we saw the famous Charging Bull. Also known as the Wall Street Bull, this bronze sculpture gained notoriety in 1989 after the artist, Arturo Di Modica, dropped it off unannounced in front of the New York Stock Exchange.

The Charging Bull was intended as a gift of encouragement to New York after the stock market crash of 1986, but officials at the NYSE weren’t impressed. Police hauled the sculpture away, but it was later given a permanent home at Bowling Green where it stands as a symbol of prosperity and the “power of the American people”, just as the artist intended.

Staten Island Ferry & Statue of Liberty

The Statue of Liberty is a must see on a first trip to New York City. To save money, we opted to take the free Staten Island Ferry, which sails past the Statue of Liberty, instead of paying for the ferry that takes passengers directly to Liberty Island.

While the Staten Island Ferry doesn’t sail as close to the Statue of Liberty as the sightseeing boat cruises do, it got close enough to give us an appreciation of the emblematic statue. We felt satisfied seeing it from the water and didn’t feel like we missed out by not going to the park.

Once at Staten Island, we disembarked the boat and immediately re-boarded for the return trip back to Manhattan. The city views were wonderful!

National September 11 Memorial

After our ferry ride, we walked towards the towering One World Trade Centre to see the National September 11 Memorial.

The memorial honours those individuals who died in the terrorist attacks of September 11, 2001. Their names are engraved on bronze panels surrounding two pools of water embedded in the footprints of the fallen Twin Towers. Water cascades down the edges of the memorial before disappearing into a hole in the centre of the pool.

It was a solemn place to visit and brought back memories of watching that shocking event unfold on television. While most people were there quietly paying respects, unfortunately there were also many people taking smiling selfies in front of the memorial. So inappropriate.

Brooklyn Bridge & DUMBO

From the memorial, we walked through City Hall Park and then onto the Brooklyn Bridge, one of New York City’s most recognizable landmarks.

It was a sunny Saturday, so the bridge was bustling with people strolling across the East River. We took our time walking across the Brooklyn Bridge, stopping to take photos, read plaques, and admire views of both Manhattan and Brooklyn.

Once we reached Brooklyn, we wandered down to the trendy DUMBO (Down Under the Manhattan Bridge Overpass) neighbourhood for a pizza lunch. DUMBO’s converted warehouse buildings are home to independent shops, galleries, performance spaces, cafes, and restaurants.

We spent most of our time along the waterfront at Brooklyn Bridge Park, people watching and enjoying views of lower Manhattan, and the Manhattan and Brooklyn bridges. There’s even a carousel from the 1920’s!

We originally planned to walk the Brooklyn Bridge back to Manhattan, but our feet were too tired so we ended up taking the subway.

Saturday Night Live

Most people who visit New York City won’t get to see Saturday Night Live because tickets are hard to come by, but if you’re one of the lucky ones it’s an interesting experience.

To get free standby tickets for Saturday Night Live, we lined up outside of 30 Rockefeller Plaza (48^th street side) at 5:15 am Saturday morning. The line was long, since many people had slept on the sidewalk overnight, but not too crazy so we decided to try our luck. At 7:00 am the staff came out and distributed numbered tickets for the dress rehearsal and the live show (you have to choose one and show some ID). Even though we got a standby ticket for the live show, it was not guaranteed we would get in.

Later that night we had to return to the NBC studios with our tickets and line up in the same order as before. Once people with guaranteed tickets were seated (you have to enter a lottery for those), staff started letting a few people in at a time until all the seats were filled. We were the last group of 10 to be let in so it was pretty exciting!

As for the show itself, we both thought it was a little anticlimactic. The studio was a lot smaller than expected, with lights and cameras interfering with visibility. Also, the way the sets were positioned meant we couldn’t see some of the sketches at all.

The highlight wasn’t necessarily the show, but rather getting to see behind the scenes of how the live broadcast is put together. It’s amazing what they can do with such little space and time!

Day 2- Central Park, Comedy Show

After only one day in the big city, I was craving some time in nature so we spent nearly the entire day exploring Central Park. We ended our evening by taking in a comedy show.

Central Park

Central Park was easily my favourite place in New York City. Even though there wasn’t the snowy scenery I was hoping to see in January, it still was a lovely place to spend the day.

Central Park is full of bridges, archways, lakes, meadows, wooded areas, gardens, sports fields, and miles of paths- 58 miles, to be exact. The variety of activities and scenery (each area had its own look and feel), meant we had no trouble spending a whole day here. I feel like you could go to Central Park over and over again and still discover something new.

A few of our favourite spots in Central Park were Belvedere Castle, Bow Bridge and the Lake, Gapstow Bridge, and the winding, forested paths of The Ramble.

The area we spent the most time at was Strawberry Fields, a 2.5 acre parcel dedicated to John Lennon who lived, and was sadly gunned down, at the Dakota apartment building directly across from here. At the Imagine mosaic there was a musician playing the music of John Lennon and the Beatles, so it was a relaxing place to sit and contemplate.

One thing we didn’t do that was at the top of my New York City wish list, was go skating at Wollman Rink. There’s no way our feet could handle it after walking ¾ the length of the park!

Read my full post about our Central Park self-guided walking tour.

Comedy Show

New York City is home to some of the best comedians in the world, so taking in a comedy show was a great way to spend an evening. There are a lot of clubs you can visit but we just spontaneously bought tickets from a guy selling in Times Square.

Day 3- Midtown Manhattan, Taping of the Daily Show

Day 3 of our trip to New York City was spent in Midtown Manhattan. We went up the Empire State Building, visited the Intrepid Sea, Air and Space Museum, then scored tickets to a taping of the Daily Show with Trevor Noah.

Empire State Building

Another icon of New York City, the Empire State Building soared to fame as the world’s tallest building from 1931-1970. The Art Deco skyscraper stands 443.2 m (1,454 ft) tall and boasts 2 million square feet of office space.

After clearing security, we headed up to the 80^th floor where the Dare to Dream Exhibit is located. The exhibit chronicles the building’s history through photographs, architectural sketches, and construction notes.

Following the exhibit, we took the elevator up to the 86^th Floor Observatory, the highest open-air observatory in New York. The deck wraps completely around the building, allowing for 360-degree views of New York City.

Unfortunately, the day we went up the Empire State Building the air was hazy and filled with brown smog, hampering the view. We kept hanging around hoping the air would clear, but it never did. I was disappointed at first, but later in the trip realized that the Top of the Rock observation deck offers far better views of New York City than the Empire State Building anyways (more on that later).

Buy: Empire State Building Skip the Line Ticket

Intrepid Sea, Air and Space Museum

The Intrepid Sea, Air and Space Museum is not your typical New York City tourist attraction. In fact, it’s not something we expected to see in New York at all.

Docked at Pier 86 on the Hudson River, is a 266 m (872 ft) aircraft carrier called the Intrepid. After serving in World War II, the Cold War, the Vietnam War, and working as a NASA recovery vessel, the Intrepid was decommissioned in 1974, later becoming the centerpiece of the Intrepid Sea, Air and Space Museum.

We spent probably 2 hours or more exploring the Intrepid and still didn’t see everything there was to see. We spent most of our time on the Flight Deck viewing the aircraft collection and wandering through the Navigation and Flag Bridges.

While the Intrepid and its aircrafts are the main focus of the museum, you can also see Space Shuttle Enterprise and go inside the submarine Growler, the world’s oldest existing nuclear submarine. As we went through the tight quarters of the sub, I kept thinking how tough it must have been to live and work there, not seeing daylight for up to 3 months at a time!

If you go to the Intrepid, we recommend taking one of the guided tours (there are many different topics to choose from). We learned so much on the Intrepid 101 tour and even got to test out the aircraft elevator!

Buy: Intrepid Sea, Air & Space Museum Priority Access Tickets

The Daily Show with Trevor Noah

The Daily Show with Trevor Noah films only a few blocks away from the Intrepid, so was a convenient next stop.

Getting standby tickets to The Daily Show was a little bit different than for Saturday Night Live because you have to book a reservation just to wait in line. I made our reservation a few weeks in advance, so now we just had to line up outside the studio and hope we arrived early enough to get in, since its first come first served, until all seats are filled. We arrived around 4:30 pm, even though check-in wasn’t until 5:00 pm, and got into the show.

While it was a completely different experience than SNL, I enjoyed attending a taping of The Daily Show more. The studio was large and every seat in the house had a good view. It also was more interactive because Trevor would talk to the audience during breaks, even sharing his honest opinion about his guest after the interview.

Later that night it was fun watching the broadcast to see how the interview was edited and if we could hear ourselves cheering!

Day 4- Midtown Manhattan

Today was a much slower paced day as we only visited the American Museum of Natural History, Times Square, and went to a Broadway show.

American Museum of Natural History

The American Museum of Natural History is one of the largest museums in the world, so it’s no wonder we spent so much time here. With 45 permanent exhibition halls, I was overwhelmed by how much there is to see.

We started our visit by watching a 3D film about the flight of birds, then began making our way through the exhibition halls. We saw displays about human origins, climate change, dinosaurs, meteorites, ocean life, and mammals.

As a travel lover, my favourite exhibitions were the Cultural Halls. I enjoyed seeing artifacts from different regions of the world and learning about the cultures that originated there. As we stared up at a reproduction of a moai from Easter Island, we commented that a museum, no matter how great the exhibits, doesn’t compete with experiencing a place first hand.

An area that Mike really enjoyed was the Hall of North American Forests, since he works in forestry. A highlight was seeing the tree cookies, especially one from a 1,400-year-old giant sequoia. Although, it made me really mad to know that lumberjacks had cut down such an old tree!

The American Museum of Natural History is so comprehensive that I feel like anything you want to know about the world you can learn here.

Broadway Show

Attending a Broadway show is a must for first time visitors to New York City. There are almost 40-venues offering Broadway and off-Broadway shows, but we opted for a timeless classic- The Phantom of the Opera.

Since it was NYC Broadway Week, we got 2-for-1 tickets for the show. We even managed to get 4^th row centre seats just two days before the performance.

Times Square

After the Broadway show we took a walk through Times Square. A tourist mecca, Times Square is surrounded by shops, television studios, Broadway theatres, restaurants, hotels, and some of the largest digital billboards we’ve ever seen.

A popular gathering place is the large red staircase above the TKTS booth. Here you can bask in the glow of Times Square, looking down the video screen lined street towards One Times Square and the famous New Year’s Eve Ball.

It doesn’t matter what time of day you visit Times Square, there’s always a pulsing energy. Frank Sinatra was right- New York truly is a city that never sleeps!

Day 5- Midtown, Lower Manhattan, Jersey City

On our last day in New York City we went to Rockefeller Center, walked the High Line in Lower Manhattan, then went on a sightseeing boat cruise. We ended our night with a trip across the Hudson River to Jersey City where we enjoyed the night-lights of the New York City skyline.

Rockefeller Center and Top of the Rock

Rockefeller Center is a massive complex of commercial buildings but its main tourist attractions are Radio City Music Hall, the NBC Studios and Top of the Rock Observation Deck at 30 Rockefeller Plaza, and the ice skating rink.

You can do tours of Rockefeller Center but we were only interested in visiting Top of the Rock. With 3 levels of indoor and outdoor viewing decks, Top of the Rock offers fantastic views of New York City.

The best part was having the Empire State Building in the cityscape, which you obviously don’t get at the observatory on the Empire State Building. We could even see Central Park, although a new building going up will soon obstruct the best view.

Rockefeller Center is also known for its artwork, with a number of statues, friezes, and murals gracing the property. Notable statues at Rockefeller Center include the bronze gilded Prometheus bringing fire to mankind (at the western end of the sunken plaza, overlooking the skating rink in winter), and Atlas carrying the celestial vault on his shoulders (in the International Building’s courtyard, facing St. Patrick’s Cathedral).

Buy: Top of the Rock Flexible Date Ticket

The High Line

Walking the High Line was a great way to escape the bustle of New York without leaving behind the big city ambience.

This linear public park on Manhattan’s west side used to be an elevated railway track that transported freight into Lower Manhattan. It’s been repurposed into a pedestrian pathway lined with benches, plants, and art installations.

The High Line runs from Gansevoort Street in the Meatpacking District, passing through Chelsea before terminating at West 34^th Street.

There are numerous access points for the High Line, but we decided to walk the entire park. It took us about half an hour to walk the High Line, including a few short stops to admire the sights.

Sightseeing Boat Cruise

Aside from walking in Central Park, one of my favourite things we did during our 5 days in New York City was go on a sightseeing boat cruise around Manhattan.

Starting at Pier 83 on the Hudson River, our 1.5 hour boat cruise sailed along the west side of Manhattan, past Ellis Island and up-close to the Statue of Liberty. We then continued up the East River, passing under the Brooklyn, Manhattan, and Williamsburg bridges, before turning around and continuing back to Pier 83.

The cruise was narrated live and the guide shared insightful information about New York City’s landmarks. Since we did the cruise later in the afternoon, the city was bathed in warm, golden light as the sun began to set. It was a beautiful time to enjoy the New York City skyline!

Buy: 90 minute Landmark and Harbour Cruise

Exchange Place Waterfront, Jersey City

Still enamoured with the skyline views of New York City we saw during the boat cruise, I wanted to head across to Jersey City and photograph Manhattan at night.

We took the PATH train to Exchange Place, which is right on the waterfront and steps away from J. Owen Grundy Park. The park’s promenade offers exquisite views of Lower Manhattan, particularly of One World Trade Centre, and is a quiet, uncrowded place to photograph New York City at night.

Viewing Manhattan at night, under a clear, starry sky was a romantic way to end our first trip to New York City!

Final Thoughts About Our 5 Days in New York City

I wasn’t sure I would enjoy a trip to New York City, since I prefer outdoor adventures and smaller towns, but I’m happy to report that wasn’t the case.

I’ll admit, I went to New York half-expecting not to like it. Everything I’d heard about the city being expensive, crowded, and filthy was true (the subway is disgusting). But one reputation the city didn’t live up to concerned the people.

I’d always heard that New Yorkers were rude and impatient, but in our experience that wasn’t the case. People were far more friendly and helpful than we expected, especially when it came to directions. They would go out of their way to ask if we needed help finding somewhere, telling us what subway line to take and what station to get off or transfer at.

Looking back, what I appreciated most about the city was its architecture. I love how the older buildings have been preserved, as their artistic architectural details are not common in modern constructions. New York City is a wonderful example of how the past and present, old and new, can coexist in a harmonious way.

Sure, New York City isn’t perfect, but there’s something about it that even a skeptic like myself can’t help but be drawn into!