Winter break in New York City

I have visited New York City a few times, but there’s always something new to discover in this world class city. In 2017, Mr. Chuckles and I spent about a week there in early December. We found this to be a nice time to visit, as you get to experience the hustle and bustle of the city as it prepares for Christmas. New York City is always crowded, so there isn’t really much of a low season, except perhaps in February during the post-holiday period, when it’s depressing and cold all across the eastern seaboard. Weather-wise, early December was tolerable for us with temperatures hovering around 10 degrees Celsius. Thanks, global warming!

Getting there

We flew on a 1.5 hour flight from Toronto via Porter Airlines and stayed at the Holiday Inn Times Square, which we booked through Hotwire. As expected, even with the travel ‘deal’, accommodations in New York are expensive so we still ended up with a bill of about $300 CAD per night since we were staying in the centre of Manhattan.

The hotel was very centrally located and probably a good option for first time visitors, but in future I think I would like to stay outside of Midtown to get a more relaxed and authentic New York experience. We ended up really liking the neighbourhoods in lower Manhattan, so will probably look around there for our next trip.

Day 1

Exploring around Midtown

We arrived in early afternoon so stopped for lunch at a pizza place around the corner of the hotel. Our first $1 New York slice! Mr. Chuckles became obsessed with these over the course of the trip. We’ve since found ‘New York style’ pizza in other cities, like Las Vegas, but they are never really quite the same.

Then we did some wandering around Midtown. We checked out St. Patrick’s Cathedral, passed by Central Park, edged through a crowd to catch a glimpse of the tree in Rockefeller Square, and walked through Times Square where we found buff Santa.

For dinner, we had the best pasta at Marea, a Michelin star Italian restaurant on E 59th Street.

Jazz in Greenwich Village

Afterward, we headed south for a glimpse of Greenwich Village. As a Friends aficionado, I had to check out the Friends’ apartment building located on Bedford Street. Unfortunately, photography conditions were poor so I only have this one shoddy photo.

Friends apartment New York City

Then we went over to Smalls to enjoy an evening of jazz. This small club located on the basement level of a building on West 10th Street has developed a reputation as a hotbed for New York jazz talent, and often features lesser known musicians.

Smalls Jazz Club New York City

Day 2

Visiting the financial district

We headed to Wall Street for our second morning in NYC, and then to One World Trade Center where we did the requisite tourist thing and went up to the observatory for views overlooking Manhattan.

A walk around Chelsea

In the afternoon, we headed west and took a walk down the Chelsea Highline, a 1.45 mile elevated linear park that runs along a former New York Central Railroad spur and features some creepy looking art installations.

An evening of comedy

For dinner, we went to Eleven Madison Park, which is currently number 4 in the world’s 50 best restaurants. We capped off the night at Comedy Cellar, which I’ve been to a couple times and always love. This is the place where several notable comedians have performed, including Louis CK and Dave Chappelle. You get a super entertaining, laugh out loud show for only about $15 USD.

Day 3

Morning at the museum

Most of the museums in NYC are pay-what-you-can, so we made a visit to the American Museum of Natural History for a low cost excursion. Ooh, dinosaurs.

Lunch in Harlem

At lunchtime, we headed up to Harlem. If you base your perception of NYC on Hollywood movies, you may associate this neighbourhood with being a sketchy place. Although it still has a relatively high crime rate compared to the remainder of the city, several parts of it have rapidly gentrified and have become quite trendy. I actually stayed here in an Airbnb during my trip a couple years earlier.

Harlem is a top spot to visit jazz clubs, eat soul food, and is full of history as a focal point of African-American heritage. We ventured here for the food, specifically fried chicken and waffles at Amy Ruth’s, a down-home restaurant serving southern comfort food, popularized by its feature in a number of travel guides.

An evening with the Rockettes

In the evening, I procured tickets to the classic Christmas Spectacular starring the Rockettes, at Radio City Music Hall. The show is pretty entertaining and glitzy. We were bewildered when they actually brought out a live camel for one of the scenes and still wonder where they keep it backstage.

Day 4

Down to Lower Manhattan

On this day, we decided to go way downtown. We headed toward the Lower East Side and stopped at Russ & Daughters for their famous bagels with smoked salmon and cream cheese. This was followed by a walk through Chinatown and across (part of) the Brooklyn Bridge.

Chinatown New York City
Brooklyn Bridge New York City

An afternoon of art

Then we headed back up island to visit the Museum of Modern Art. There were lots of great pieces to see here, although I would have liked to also make a stop at the Guggenheim for their contemporary collection. Maybe next time.

For dinner, we went to Momofuku Ko, chef David Chang’s 2 Michelin star outpost in the Bowery which serves an ‘Asian accented’ tasting menu. I actually preferred this place over Eleven Madison Park even though it isn’t rated as highly.

Day 5

The last hoorah

My photo taking energy must have dwindled on the last couple days of the trip, as I don’t have many in my album.

We did spend some time checking out Grand Central Station, and also visited The Metropolitan Museum of Art (The Met). Again, admission was pay-what-you-can and we were able to occupy a couple hours admiring some more fine art. The museum was beautifully done up for Christmas as well.

Grand Central Station New York City
Met Christmas tree New York City

More good food

Food-wise, we had one more fancy meal when we went for lunch at Le Bernadin, the elite French seafood restaurant helmed by chef Eric Ripert. It is one of only five 3-Michelin star restaurants in New York City.

Sometime around here was also when we went for dinner at Tonoshi Sushi, the best omakase place Mr. Chuckles and I have ever been to. Seriously, we still talk about it. This small, appearingly no-frills spot in the Upper East Side has only three seatings per night with about 12 seats each. It’s totally worth it to make the effort to get a reservation, and we will probably try to have a meal there again the next time we’re in the city.

Day 6

Final farewell

For our grand finale in NYC, I recall eating some more pizza, making a stop at Shake Shack, and catching one last view of Times Square before we headed home.

Times Square New York City

See ya next time, New York!

Original post 09/03/2019 | Updated 12/11/2019

11 responses to “Winter break in New York City”

  1. […] We started our second day at St-Viateur for classic Montréal bagels. We’ve found these bagels at our local grocer in Toronto but wanted to try them fresh from the source. Unfortunately it turned out a bit disappointing, as they were not served toasted or with any toppings (we purchased a single serve portion of Philly cream cheese from their fridge). We much preferred our fresh bagel experiences in New York City. […]


  2. […] No photos from this day. We had a mega portion of breakfast at a pancake place near our hotel and then lunch at Portillo’s for the classic Chicago hot dog. In the evening we enjoyed the most delicious ribs at Twin Anchors, before catching a show at Second City MainStage. The Second City show was highly recommended, but I didn’t find it particularly memorable or entertaining. I think I much prefer stand-up to sketch comedy and would much prefer a night at Comedy Cellar in New York City. […]


  3. jasonlikestotravel Avatar

    Such a great city, sounds like you had another fun trip! The live camel thing sounds so weird though, I’m surprised they’re able to do that.
    Agree on the accommodation being crazy, we ended up staying in a hostel in Brooklyn on our visit. Kept it slightly cheaper and a a nice part of the city to stay in too 🙂

    Liked by 1 person

    1. Yes I think I’ll keep Brooklyn in mind for the next trip out there! We didn’t make it out to any of the other boroughs.

      Liked by 1 person

  4. […] and meatballs is a classic Italian-American dish, introduced by Italian immigrants in New York City sometime in the early 20th century. This dish differed significantly from the meatballs prepared […]


  5. […] visited around the world, I do have to admit that it is relatively humble. It is certainly no New York City or Tokyo. However, I am happy to live here, in a city that has a low crime rate, that is clean, and […]


  6. […] was one of our first stops on a food-intensive winter trip to New York City. This one Michelin star restaurant is situated just south of Central Park, and is known for its […]


  7. […] place that produced the famed cronut which attracted hordes of foodies to its flagship location in New York City. We had the opportunity to try the Japanese inspired hojicha cronut along with a kouign-amann. My […]


  8. […] in New York City is a magical time. If it weren’t for the pandemic, I would have loved to make another trip […]


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