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How to Spend 5 Days in New York City

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How to Spend 5 Days in New York City

Shay and I decided to go on a girls’ trip to New York City for 5 days over the winter break.

It was my first time flying anywhere, and I was pretty nervous but excited at the same time.

The flight was shorter than expected, which was great because it wasn’t a very comfortable flight!

We spent 5 days exploring and eating our way through the city, and it was a lot of fun.

Here’s our how to spend 5 days in New York City during the winter!

Christmas in New York City

Our 5 day New York City itinerary

Since we were staying with Shay’s family, our schedule wasn’t jam-packed with activities.

We enjoyed just taking our time to explore NYC during our 5 day itinerary!

Here’s our day-by-day itinerary.

Day 1

  • Broadway Theatre
  • Times Square

Day 2

  • Central Park
  • Metropolitan Museum of Art

Day 3

  • The High Line
  • Chelsea

Day 4

  • Statue of Liberty
  • SoHo

Day 5

  • Manhattan

Day 1: Toronto to New York City

We flew from Toronto to New York City in the afternoon.

Right after landing, we had lunch at an Iranian restaurant with Shay’s family.

We then spent some time settling in at Shay’s aunt’s apartment before heading out to see a Broadway show.

Broadway Theatre

We saw Finding Neverland at the Broadway Theatre.

Although I did fall asleep for a bit during the middle, we really enjoyed it!

LOCATION: 1681 Broadway, New York, NY | Website

What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog
Seeing Finding Neverland at the Broadway.
Broadway theatre in New York City

Times Square

Afterwards, we wandered a bit around the Times Square area to see all the holiday and Christmas displays.

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LOCATION: Manhattan, New York, NY | Website

What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog
What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog
What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog
What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog
Times Square in New York City
Disney characters at Times Square in New York City
We ran into these Disney characters who tried to charge us after offering to take photos with us lol.

Holey Cream

Our last stop of the night was Holey Cream, where we had donut ice cream sandwiches.

It’s only around a 10 minute walk from Times Square, but it was kind of a sketchy area for two young tourists to walk in alone at night.

LOCATION: 791 9th Ave, New York, NY 10019, United States


Day 2: Central Park & The Met

We spent our first full day of our 5 day New York City trip exploring Central Park and the Metropolitan Museum of Art.

At night, we had plans to eat at an Italian restaurant with Shay’s family in Manhattan.

Central Park

Although all the trees were dead, it was still really nice exploring Central Park during the winter.

We spent most of our time trying to find the Friends fountain, which we managed to find in the end!

It was also fun checking out the view of Central Park from Belvedere Castle (a literal castle in the middle of the park).

LOCATION: Central Park, New York, NY | Website

What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog
Central Park in New York City
The Friends fountain in Central Park, New York City
We managed to find the Friends fountain.
What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog
John Lennon Memorial in Central Park, New York City
The John Lennon memorial in Central Park.

Metropolitan Museum of Art

Since the Met was pay-what-you-can, we figured we’d check it out.

The museum was huge, and there was a lot of beautiful art and unique works to see!

LOCATION: 1000 5th Avenue, New York, NY | Website

The Metropolitan Museum of Art in New York City
I never watched Gossip Girl, but Shay wanted a photo in front of the Met steps.
What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog
The Metropolitan Museum of Art in New York City
The Metropolitan Museum of Art in New York City
What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog

Day 3: Chelsea

The next day was dedicated to hitting up one of the more ~hip~ parts of New York City, Chelsea.

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We started off by walking along the High Line!

The High Line

We visited the High Line, which was such a nice little walk.

Definitely one of our favourite areas of New York City!

LOCATION: The High Line, New York, NY | Website

What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog
The High Line in New York City
What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog
What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog
Art gallery at the High Line in New York City
We checked out an art gallery in Chelsea.
What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog

Day 4: Statue of Liberty & SoHo

Our next day was dedicated to seeing the Statue of Liberty and exploring the SoHo neighbourhood.

We didn’t really take any photos, but we had a lot of fun exploring.

Statue of Liberty

We took a roundtrip ferry to Staten Island so we could see the Statue of Liberty.

As we tried to find where the ferry was, scalpers kept aggressively trying to sell us tickets even though it’s a free ferry!


SoHo

SoHo is a chic neighbourhood in New York City, known for their high-end shops, restaurants, and art galleries.

We spent some time wandering around the area and ate at an amazing Spanish tapas restaurant called Boqueria.


Sprinkles

We stopped by Sprinkles for some cupcakes – they were so delicious!

If you don’t know what Sprinkles is, they’re a cupcake bakery known for their ATMs where you can order cupcakes through a machine.

What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog

Day 5: Manhattan

Our last day in New York City was more of a chill day.

We stopped by a cute little bakery for breakfast, had lunch at a vegan restaurant, and spent the rest of the day taking our time packing.

Corrado Bread & Pastry

We had breakfast at this European-inspired café in the Upper East Side.

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It was absolutely adorable and super photo-worthy!

LOCATION: 960 Lexington Ave, New York, NY | Website

Corrado Bread & Pastry in New York City

We ate our last lunch in New York at this vegan restaurant I forgot the name of and had a pizza with cashew cheese on top.

What to do in New York City | best things to do in NYC | top activities in New York | girls' weekend in New York City, USA | Diary of a Toronto Girl, a Canadian lifestyle blog

New York flights & accommodations

Looking to book your flights and accommodations for New York City?

I love booking all of my flights and hotels on Expedia and collecting points towards free rewards.

I use Airbnb when I’m traveling on a budget, and I have a separate blog post all about how to find the best Airbnbs.


Check out my NYC vlog to see more of our trip!

We had a lot of fun spending 5 days in New York City, and I can’t wait to go back again.

Have you been to New York City? What are your favourite things to do in NYC? I’d love to know in the comments!

P.S. if you liked this post, you might like this post on how I spent 24 hours in New York City, or any of my other posts on traveling in the USA.

Be sure to keep up with me on InstagramTwitter, Facebook, and Pinterest if you aren’t already!

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Jessica Lam | Toronto lifestyle, fashion, beauty, and travel blogger | Diary of a Toronto Girl, a Canadian lifestyle blog

Looking to spend 5 days in New York City? Here are the best things to do and all the top places you need to eat at during your NYC trip!
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