How to Spend Three Days in New York City
I’m lucky enough to have been to New York City on a couple of different occasions prior to this trip. My first experience with the city was when I turned 13 years old. At the time, we had extended family living in the city. For my 13th birthday, my mom and I spent a long weekend in New York and stayed with our relatives. My second experience with the city was three years later when I travelled to New York with my high school orchestra. These were two very different trips that allowed me to see different parts of the city and experience it in two different ways: with family and then with friends and peers.
As you can imagine, I was so excited to return to the Big Apple for a third time – this time as an adult and with my boyfriend, Will, as my travel companion. Despite both of us having visited the city before, we were able to enjoy new experiences and discover parts of the city that were unfamiliar to us which in a way made it feel like we were experiencing the city for the first time all over again.
We both booked Thursday and Friday off of work so we could make the trip into a proper long weekend before returning to Canada on the Sunday. We flew with Porter Airlines from the Billy Bishop Airport in downtown Toronto and landed at Newark Liberty International Airport in New Jersey, opting for an early morning flight so we would have practically the entire day in the city to explore.
Where We Stayed
We were extremely lucky with our accommodations for this trip. Will’s aunt and uncle have an apartment in the city that we were able to use for the duration of our trip. The apartment is located in Tribeca, a neighbourhood in Lower Manhattan. There were lots of great restaurants and shops in this area and the rest of the city is easily accessible by subway.
Getting Around New York City
One of the many amazing things about New York City is how easy it is to get around. Between the extensive subway system, taxis, ferries, and ride shares, it is possible to get anywhere in a pretty timely manner. Learning how to navigate the New York City subway can be a bit daunting – especially if you come from a city like Toronto where there are only three subway lines. That being said, taking the time to learn the nuances for New York’s subway will make travelling around the city so much faster.
Will and I made the most of the New York subway. We opted to each purchase a 7-day unlimited MetroCard, which are $32 USD. After doing the math we figured that this would be the cheapest option as opposed to doing the pay-per-ride model. MetroCards can be purchased at machines at any subway station in the city.
Another fun way to get around certain parts of the city is by ferry. We took the East River ferry from Wall Street/Pier 11 to DUMBO in Brooklyn and then from DUMBO to Williamsburg. In this case, the ferry was much faster than taking the subway and it gave us incredible views of the Brooklyn and Manhattan Bridges, Brooklyn, and the New York City skyline. Fares are only $4USD and the ferries run frequently throughout the day.
Day One
Our first day in New York City was jam packed. Our morning started with our alarm going off at 3:50am to get us up for our 6:45am flight. I would like to note that this was far too early. We arrived at the Billy Bishop Airport in Toronto at 4:40am to discover that the airport doesn’t even open until 5am and that security doesn’t open until 5:30am. Lesson learned!
After the quick flight to New York, we made our way from Newark, New Jersey into the city via train to check in to our place. We found a nice spot in Tribeca to sit down for brunch and then explored the neighborhood a bit before picking up our keys at 11am. Once we were settled, we had a brief period of rest before heading out into the city for the afternoon and evening’s events.
What We Did
Explored Central Park
After resting up a bit we hopped on the subway and headed uptown to explore Central Park. Did you know that Central Park is 843 acres? Will and I both grossly underestimated its size – I don’t even want to say by how much because it is honestly embarrassing. At least we were on the same page!
There are so many things to see in Central Park including:
- Bethesda Terrace and Fountain
- Strawberry Fields (The John Lennon memorial, not an actual field of strawberries)
- Loeb Boathouse
- Belvedere Castle
- Bow Bridge
These are only a few of the many things to see in Central Park. It would be easy to spend a whole day in the park due to its vastness, but we only had a couple of hours.
Saw a Broadway Show
The Book of Mormon is the Broadway show that Will and I went to see. Will had seen it before and thought it was hilarious, so he suggested that we go see it during our trip. I didn’t really know anything about the show before going to see it, beyond the fact that it was written by the creator of South Park. It was hilarious! I would definitely recommend it for anyone looking for a good laugh.
Visited Times Square
After the show we made our way to Times Square to look around before heading home. I’d never been to Times Square after dark before, so it was a whole new experience for me. It was really cool to see everything lit up at night like that.
What We Ate
When we arrived in New York after a long morning of travelling we were tired and hungry and had a bit of time to kill until we could pick up our keys for the apartment we stayed in. Will did some research and found Two Hands Tribeca. We sat in here for a delicious brunch and a much needed rest after the events of the morning. I had the açai bowl and it was 10/10.
For dinner we ate at the iconic Central Park restaurant, Tavern on the Green. We made our dinner reservation in advance to insure we would get a table. Eating here worked out perfectly because we were able to explore Central Park beforehand and the show we were seeing on Broadway after dinner was a short walk away. The food was delicious and there is a lovely patio where you can eat in the warmer months.
Day Two
Our second day in New York was arguably more jam packed than our first. We started the morning with a delicious brunch in Tribeca, then spent the majority of our day exploring Brooklyn and making the most of the warm, sunny weather. We did a ton of walking on day two and my feet were feeling it after a poor choice in footwear the previous day.
What We Did
Explored DUMBO
DUMBO – an acronym for Down Under the Manhattan Bridge Overpass – is a neighbourhood in Brooklyn. To get to DUMBO we took the East River Ferry from Wall Street/Pier 11. I mentioned this above, but the ferry is a great option for getting to Brooklyn from Manhattan because it’s cheap ($4USD), it’s fast, and you get stunning views of the city from the water.
After arriving in DUMBBO, we walked around the Brooklyn Bridge Park, went to Washington Street to get a picture-perfect view of the Manhattan Bridge, and walked around the neighborhood. Brooklyn Bridge Park has one of the best views of the Manhattan Skyline and the Brooklyn Bridge. You may recognize the iconic picture spot seen in the image above with the blue bridge, more formally known as the Manhattan Bridge. In fact, this picture spot is so iconic it has its own name on Google Maps! Visit the DUMBO – Manhattan Bridge View to take your own iconic pictures of or with the Manhattan Bridge.
Explored Williamsburg
Williamsburg is another Brooklyn neighbourhood bustling with trendy cafes, interesting street art and repurposed factories. We took the East River Ferry from DUMBO to North Williamsburg. This option was way faster than walking or taking the subway and gave us more excellent views of the Manhattan skyline!
In Williamsburg we grabbed a couple slices of iconic New York City pizza for lunch and then explored Bedford Ave. Bedford Ave is the longest street in Brooklyn and is home to a host of independent shops, trendy restaurants and cafes, and some seriously great people watching.
Walked Across the Brooklyn Bridge
To get back to Manhattan, we walked across the Brooklyn Bridge. This is a staple thing to do in New York City. If walking isn’t your thing, there are city bikes all over the place that you can rent to ride across. The Brooklyn Bridge has a walking trail for pedestrians that’s completely separate from the cars so you can enjoy the views and the bridge’s architecture without having to worry about traffic.
Visited Washington Square Park
Back in Manhattan we made the trip to Washington Square Park, which you may recognize by its iconic archway and fountain. We were only in the park briefly before heading home to rest before an evening of more activity, but you could easily pass an hour or two sitting in the park reading or just people watching.
Saw a Show at the Comedy Cellar
The Comedy Cellar is a famous comedy club in Manhattan where many big names in comedy have been known to perform. We missed the initial booking, so ended up attending the midnight show. It was pretty fun to go to the late show, so I didn’t mind at all.
Before the show, you line up outside to check in and be assigned a table. Phones, smart watches, and cameras have to be sealed inside an envelope that is provided when you check in so no recording or photography happens during the show. By some luck Will and I ended up at table number two, which was pushed up directly against the stage. This meant that we not only had front row seats to a hilarious night of comedy, but that we also got roasted consistently throughout the night.
There were six comedians who each did a set throughout the night and a host to keep the evening flowing and the energy up. It was a lot of fun and definitely something I would do again.
What We Ate
Our day started with a delicious brunch at Bubby’s in Tribeca. This was a recommendation Will received from one of his family members before we left, so we had made a reservation in advance. Making a reservation in advance was definitely a good idea because Bubby’s is a popular spot! We walked by the following day and there was a line down the block to get in for brunch.
You can’t go to New York City without trying the pizza. For lunch we each ordered a slice at Krispy Krust Pizza in Brooklyn and then split another slice at Joe’s Pizza. Both were delicious.
Before heading back to Manhattan we stopped at the Brooklyn Ice Cream Factory in DUMBO for a cone. The ice cream was good, but it was honestly a bit overpriced in my opinion.
We had a later dinner at Wagamama before heading to the Comedy Cellar for the midnight show. Wagamama serves Asian-inspired dishes with a variety of sharable plates, noodles, and rice dishes to choose from. Will and I picked a couple of sharables and a main to split between the two of us. The service wasn’t phenomenal, but the food was delicious and the atmosphere was very cool.
Day Three
What We Did
Unfortunately, our final day in New York City was an incredibly rainy one. In addition to seeing Fifth Ave and Chelsea Market we had intended to walk the High Line, but we decided against this due to the rain. It really was not very pleasant to be outside.
Walk Fifth Ave
We took the subway to the edge of Central Park where the Plaza Hotel is located and then walked down in the direction of Lower Manhattan. Fifth Ave is lined with luxury and big-box stores such as the famous Tiffany & Co featured in Breakfast at Tiffany’s. We personally did not go into any of the stores, but we admired them from the sidewalk.
Our walk ended at Rockefeller Center where we stopped to view the famous plaza and Prometheus statue. We didn’t stay here too long as the rain was really pouring down at this point.
Visit the Chelsea Market
Being inside Chelsea Market was a welcome change from the rainy sidewalks of Fifth Ave. Chelsea Market has a great food hall and unique shops that make it easy to pass an afternoon there. Will and I grabbed some lunch and did a bit of browsing in the shops before heading back to Tribeca.
What We Ate
We had a late start to the morning after a late night the day before. Tribeca Bagels was near our apartment and hit the spot for a quick and easy breakfast before taking on the day.
Day three’s lunch was at the Chelsea Market. I grabbed a delicious slice of pizza from Filaga in the market’s food hall. There were tons of tasty looking option to choose from and I went with the Dolce Inferno. Will treated himself to a burger from Creamline, which also looked very good.
Our last dinner in the city was probably my favourite. On a recommendation from Will’s family, we made a reservation at Tamarind, an Indian restaurant in Tribeca. We shared a couple of appetizers as well as two mains between us and that was the perfect amount of food. Indian food is one of my favourite types of food, so I was thrilled to be eating here. A standout menu item for us was the Amritzari Seekh which is marinated paneer cheese, grilled peppers, and tomato sauce. We both loved this dish.
Travel Takeaways for New York City
Make a Splitwise to Track Shared Expenses
Splitting travel costs with other people – especially if you’re travelling with a larger group – can get confusing. To keep track of who owed who what, Will created a Splitwise to log all the costs from our trip and who paid for each item. Splitwise makes it easy to keep track of shared expenses, which makes settling up at the end of a trip headache-free.
Familiarize Yourself with the NYC Subway Before Your Trip
The New York City subway can be incredibly confusing and overwhelming if you aren’t familiar with its nuances. Before your trip, take the time to familiarize yourself with the subway system. We found this video to be incredibly helpful.
Keep Snacks on Hand
I’m the type of person who gets angry when I’m hungry – hangry, if you will – so keeping snacks on hand is important for me on long travel days or days with little down time. I personally love these Gomacro granola bars for carrying while travelling. I brought them to Europe with me, New York, and I’ve got some packed for my upcoming trip to Newfoundland.
Wear Sensible Footwear
This seems like a no-brainer and yet I’ve made the mistake of breaking in a new pair of shoes on not one, but two of my New York trips. Needless to say, my feet paid the price. Don’t be like me, wear sensible, tried and true shoes, your feet will thank you.
The 9-9-9-9-9 Zip Code Trick
This is a great hack for travelling anywhere in the States. If you’ve ever tried to make a purchase with a Canadian credit card in the States you may have been asked to enter your zip code and been at a total loss. This happened to me in LA when I was trying to buy gas and I ended up having to go to a different gas station… A trick to get around this is to enter 9-9-9-9-9, that’s five consecutive number nines, when prompted for your zip code. We used this trick to pay for our MetroCards and it worked like a charm!
Other City Guides
If you enjoyed reading through this guide, be sure to check out my other city guides:
A (Self-Proclaimed) Local’s Guide to Vancouver
Barcelona on a Budget: A Three-Day Itinerary
I hope you have enjoyed following along with my New York City adventure and that the tips shared here will help you plan your own NYC trip! As always, any feedback is greatly appreciated, so feel free to leave a comment!
xx
Ashley
What a great guide! Loved reading all about your trip and I appreciate all the details you provided. Not sure when I’ll return to NYC but will definitely be referencing this when I do!
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