A Perfect New York Itinerary for 5 Days

A Perfect New York Itinerary for 5 Days

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The City That Never Sleeps

I thought five days in New York would be perfect.  We could visit the most popular sites, dine at the best restaurants, see a Broadway show and go home satisfied.  

Boy, oh boy, was I wrong!

This city needs weeks, maybe even months to do it justice.  My list of what to do during our next trip is getting longer by the day. However, this is also an expensive city, so for most people, staying much beyond five days isn’t realistic.  So I’ll share our New York itinerary for 5 days which covers the essential sites while not breaking the bank.

Jason viewing the 9/11 Memorial
Jason viewing the 9/11 Memorial

Day One--9/11 Museum & Memorial, and a show on Broadway

Since we selected a hotel in the Financial District it was easy to start with the 9/11 Museum and Memorial on our first full day in the city.  I’ve been to New York City several times in my life, but this was the first trip since 9/11. Living on the West Coast, it’s easy to forget about the ongoing impact of this horrific day in American history.  However, the families and friends of the 2,996 people who lost their lives are rarely allowed to forget. To make it even worse, people continue to die due to lingering respiratory illnesses and cancer.

Remaining steel beam from the World Trade Center displayed in the 9/11 Museum
Remaining steel beam from the World Trade Center displayed in the 9/11 Museum

The memorial is comprised of two waterfalls and reflecting pools.  They are both expansive and sobering, appropriately reflecting the enormity of the devastation.  The names of everyone who died on that day is cut into metal panels around the pools. We visited the memorial about three times during our stay, eventually walking all the way around both pools, frequently touching the names of men and women. 

Opened just four years ago, the 9/11 Museum thoroughly recounts the story of that fateful day as well as the long and painstaking recovery process.  The number and variety of artifacts retrieved helps visitors understand the big picture while also appreciating the loss of individual lives. There’s a giant metal beam melted by the intense heat, and small pieces of uniforms from rescue workers that lost their lives--all of it is sobering.    

We visited in September, so lines for the museum were manageable.  However, during the peak summer season its worth purchasing your tickets in advance online.  If you really want to avoid lines consider purchasing a "skip-the-line" ticket through Get Your Guide.

Memorial Stairs in the 9/11 Museum--used by some survirors to escape the World Trade Center
Memorial Stairs in the 9/11 Museum--used by some survirors to escape the World Trade Center

I didn’t plan it, but the Broadway show I selected for that evening tied in with the theme of 9/11, but from a completely different perspective.  The award winning show, Come From Away, recounts the story of 38 flights diverted from U.S. airports on Sept. 11, 2001, to Newfoundland, Canada where they would remain for several days. The flight diversions were ordered by the U.S. government while it tried to understand what had just happened and minimize the possibility of any more attacks.   The citizens of Newfoundland cared and provided for all of these passengers, crew, and even their pets. Their kindness and generosity were in stark contrast to the evil of the terrorist attack.  Lifelong friendships and even marriages developed from this collection of diverted flights.

Come From Away uses just twelve actors to play the thousands of town folk and passengers.  Its creatively staged and brilliantly performed. I will definitely see this show again when it travels in 2019 to Los Angeles.

Wendy and Jason enjoying dinner at Tony Di Napoli's in New York City
Wendy and Jason enjoying dinner at Tony Di Napoli's in New York City

On our way to Broadway we stopped in Time Square for dinner at Tony Di Napoli’s.  I had read great reviews of this classic Italian restaurant, and we were not disappointed.  It’s a popular restaurant so reservations are highly recommended. The seafood pasta dish we had was excellent, as was the service.  The combination of Tony Di Napoli’s and a Broadway show made for the perfect New York night.

Zach &Zoe Raw Honey shop in the Chelsea Market
Zach & Zoe Raw Honey shop in the Chelsea Market

Day Two--Chelsea Market Food Tour, Westfield World Trade Center & Eataly Downtown NYC

I’ve frequently written about the food tours we’ve taken (most recently in Quebec and Barcelona) since they are a great way to explore a city.  The Chelsea Market Food Tour offered through Foods of NY was great! We enjoyed exploring the market, learning about its history and sampled many tasty treats, most notably deep fried Oreos.  

After the tour we spent some time strolling the High Line, the famous New York park developed on old elevated railroad tracks that opened in 2009. The total length of the park is 1.45 miles, so it could easily provide a few hours of enjoyment.  There are lovely gardens, plenty of seating, food vendors, and a dozen large artworks. My next trip to New York will definitely include more time here.

Want to explore more of the city on foot? Try walking the Manhattan Bridge.

The High Line Park in New York City
The High Line Park in New York City

Finally, we ended our day at the Westfield World Trade Center which is across the street from the 9/11 Museum.  What defines this building is the “Oculus”, the highly unique external structure of this building as designed by Santiago Calatrava.  The Oculus houses both a transportation hub and a large shopping center. The cost of this building was extraordinary, and not without controversy, but I for one really enjoyed viewing it from many different angles.

Westfield World Trade Center Oculus
Westfield World Trade Center Oculus

After exploring the Westfield World Trade Center a bit, we decided to have dinner at Eataly Downtown NYC.  There are three restaurants in this giant Italian market and after some deliberation we selected La Pizza and La Pasta.  We sat next to the wall of windows and enjoyed a lovely view of the 9/11 Memorial at sunset. This is the third city in which we’ve eaten at Eataly, and they are all excellent.  

View of Ellis Island and Manhattan from Liberty Island
View of Ellis Island and Manhattan from Liberty Island

Day Three–Statue of Liberty, Ellis Island, and Wall Street

Jason, Ryan and I really enjoyed this day of our trip, despite the 90 degree heat and humidity.  It’s a bit of work to finally see Lady Liberty and Ellis Island, but completely worth it.

First, it’s highly recommended that tickets be booked in advance through Statue Cruises for those hoping to get into the crown or pedestal of the Statue of Liberty. I bought our tickets online two months prior to our trip and was disappointed to learn that the crown tickets were already sold out. So I booked the first available time for the pedestal which was 11 a.m.

Jason and Ryan on the ferry to Liberty Island
Jason and Ryan on the ferry to Liberty Island

When we arrived at Battery Park to board the ferry we waited about 15 minutes to go through security and then board the boat.  In the city that experienced 9/11, security for this activity is taken very seriously, comparable to that of an airport. The ferry ride takes about 30 minutes--and is not air-conditioned--but is an excellent opportunity to take photos or videos of the statue.  

When we finally arrived on Liberty Island we went straight inside the statue, took the elevator up to the pedestal and enjoyed the air-conditioned museum for about an hour.  The museum documents how the statue was conceived, financed and built. I was surprised to learn that Gustave Eiffel (architect of the Eiffel Tower) played a critical role in the Statue of Liberty’s creation by designing the internal steel structure to secure it.

Taking a tour with Ranger Anthony of the Ellis Island Museum
Taking a tour with Ranger Anthony of the Ellis Island Museum

After leaving the statue, we boarded the ferry for a quick ride to Ellis Island.  Here we had lunch, watched a 30 minute video and took a short ranger led tour of the museum.  The Ellis Island Museum is quite large, and really deserves a few hours to explore, but we were getting tired and decided to head back to our hotel for a nap.  The return ferry ride to Battery Park takes about 20 minutes.

Battery Park Sea Glass Carousel
Battery Park Sea Glass Carousel

In the evening Jason and I strolled past Wall Street and the New York Stock Exchange, checked-out the Charging Bull and Fearless Girl statues and then enjoyed some time in Battery Park.  This is a quiet park mostly known as the place to board the Liberty Ferries. However, it has lovely views of the bay, a few memorials, and even a sea-themed carousel. We had already had dinner, but there are a couple of nice restaurants here offering bay views.  

Free Tours by Foot New York, a street in Soho
Streets of Soho in New York City

Day Four–Free Tours by Foot New York and Joe’s Pizza

We love free walking tours, and New York is now the fifth city in which we’ve taken one.  If you’ve never taken one of these tours, I highly recommend it. Technically the tour is free, but guests are encouraged to tip their guides at the end.  

NYC is a large city so there are several tour options offered by Free Tours by Foot New York,  but we decided to explore Soho, Little Italy and Chinatown. (In Chicago, we also enjoyed using Free Tours by Foot.) The tour was scheduled for 3 hours, but actually lasted a bit longer, so come prepared for plenty of exercise.

On our way to the tour meeting spot, we were all hungry, and fortunately we walked right past Joe’s Pizza in Greenwich Village. This famous pizza joint was opened in 1975 and still has lines out the door on a daily basis. We ordered a few slices and they did not disappoint.  Don’t let the lines deter you, this place is highly efficient at taking and delivering your order quickly.

Architectural detail on a building in Soho in New York City
Architectural detail on a building in Soho

We met our guide, Renee, and began our tour in Soho.  Renee did an excellent job of detailing the history and architecture of Soho--there are many lovely buildings in this part of New York.  However, I was disappointed to see how gentrified this neighborhood has become.  After a dozen high end stores like Ralph Lauren and Louis Vuitton open shop, the result is a neighborhood that could be anywhere in the U.S. or even the world.  Rents are now crazy high and celebrities are buying coops in the area.

Free Tours by Foot New York, The famous Mulberry Street in Little Italy
The famous Mulberry Street in Little Italy

What I enjoyed more on our free walking tour was visiting Little Italy and Chinatown. These parts of the city have far fewer chain stores and still maintain much of their original charm.  There aren’t many Italians left in Little Italy, but there are many traditional restaurants, coffee shops and bakeries. Chinatown has actually become a mix of Chinese, Taiwanese and Southeast Asians residents. Once again, our guide did a good job of sharing the history these two neighborhoods, helping us see these parts of the city as so much more than just a collection of shops and restaurants.

Despite our earlier pizza stop, we were starving by the end of the tour which fortunately was in Chinatown.  We decided to do a split dinner, part in Chinatown and part in Little Italy because it was just too tough to decide between these two cuisines. 

African Mammal Hall at American Museum of Natural History--photo courtesy of AMNH
African Mammal Hall at American Museum of Natural History--photo courtesy of AMNH

Day Five–Central Park and American Museum of Natural History

Ryan has long wanted to visit the American Museum of Natural History since its where portions of the movie, Night at the Museum, were filmed. This is a very large museum, with many additional attractions for purchase. I recommend doing some research in advance to focus your visit on your areas of interest.  

Our favorite amongst the permanent exhibits was the Hall of Ornithischian Dinosaurs. No matter how many times I visit a dinosaur exhibit, I always learn something new.  And if you’re a fan of the Night at the Museum movies you’ll also want to visit the Mammal Halls. No matter your age, or the ages of your traveling partners, there is something at this museum for you!

Wendy enjoying Central Park
Wendy enjoying Central Park

Since the museum is across the street from Central Park, it’s ideal to combine these two sites.  At 840 acres, Central Park cannot be seen in one day. Instead, it’s wise to take a look at the park’s website in advance to see what interests you and then head to that section.  

We did not have the time to take advantage of the Central Park Conservancy’s tours, but I definitely want to do this in the future.  They offer about fifteen options--both free and paid--including a few specifically for families. Instead of a tour, we strolled the Southern portion of the park and just enjoyed a peaceful place in the midst of a hectic city.  

Trinity Church in the Financial District
Trinity Church in the Financial District

Tips for a Successful Trip to New York City

We moved around the city through a combination of the subway, Uber and walking.  The New York City subway is extensive, but it can be very frustrating to navigate.  Not all stations offer the machines to purchase tickets, so visitors just arriving should ask for guidance about this from hotel staff or AirBnB hosts.  And when you do find a machine, go ahead and purchase what you’ll need for the length of your stay. Finally, this is a subway experiencing frequent construction which alters routes daily.  Check in with the subway staff when possible to get some guidance.

New Yorker’s may not have a reputation for being friendly and “smiley,” but when asked for help, they always deliver.  From the construction worker to the convenience store counter clerk to the random person on the subway platform, every single person we asked for help delivered.  So my advice to future visitor’s, don’t be afraid to ask for help because New Yorker’s want you to enjoy their city.

Outside the Chelsea Market
Outside the Chelsea Market

It’s estimated that 61 million people visited New York City in 2017--a record number!  Needless to say, visitors will experience crowds, even off season. My strong recommendation is to book your tickets, tours and restaurant reservations in advance.  Often this allows you to skip at least one line, and be sure you’ll actually see what interests you.

Finally, enjoy New York City for all of its grit and glory.  Its crowded, noisy, smelly, congested, and there is construction everywhere.  But it’s also one of the world’s financial hotspots, home to the best shops, museums, restaurants, and theaters in the world.  I had forgotten how great this city is, so I’ll be back soon.

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New York Itinerary 5 days
New York itinerary 5 days
New York itinerary 5 days

This Post Has 2 Comments

  1. Wendy, this is great information!

    1. So glad you found it helpful Jodie!

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