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A Perfect New York Itinerary for 5 Days

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
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
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
Zach &Zoe Raw Honey shop in the Chelsea Market
Zach & Zoe Raw Honey shop in the Chelsea Market
The High Line Park in New York City
The High Line Park in New York City
Westfield World Trade Center Oculus
Westfield World Trade Center Oculus
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 4 Comments

  1. Jodie

    Wendy, this is great information!

    1. Wendy

      So glad you found it helpful Jodie!

  2. Carole Carlson

    I loved your commentary on New York. It is one of my favorite places and you included some things to see that I never thought of.

    1. Wendy

      Thanks, so glad you enjoyed it!

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