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!
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.
- Broadway Theatre
- Times Square
- Central Park
- Metropolitan Museum of Art
- The High Line
- Statue of Liberty
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.
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
Afterwards, we wandered a bit around the Times Square area to see all the holiday and Christmas displays.
LOCATION: Manhattan, New York, NY | Website
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.
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
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
Day 3: Chelsea
The next day was dedicated to hitting up one of the more ~hip~ parts of New York City, Chelsea.
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
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 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.
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.
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.
It was absolutely adorable and super photo-worthy!
LOCATION: 960 Lexington Ave, New York, NY | Website
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.
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!
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