It’s The Most Wonderful Time Of The Year… A NYC Holiday.

F71B2BB3-D2EE-466D-A7E8-623424555892When is the best time to visit New York City you ask? The “Big Apple”, the “City That Never Sleeps”, or whatever you want to call it is a great destination to visit in December. Why you wonder?

Many Hollywood films have used New York City as the backdrop for holiday films such as in “Home Alone 2”, “Elf” and the iconic “Miracle on 34th St”. If you haven’t visited NYC during the holiday season, you may think this ‘tis the season’ spirit found in Hollywood films could be a false depiction but I can personally testify that this city really does look and feel the way Hollywood movies depict it in their films.

While I have been to this truly magical city multiple times and during different times of the year, my favorite time to visit has become during the month of December when this city truly brings the holiday spirit to life better than any other city I have visited including my hometown, Chicago. (Sorry Chicago but NYC wins this one.) The holiday window displays, music, shopping, Santa’s in almost every corner, holiday decor and the various holiday activities happening throughout the city can make even a scrooge have a change of heart.

It’s very easy to be infected by the spirit of the city and feel like the only medicine to get you into the holidays when December starts creeping around is a couple days in New York City. And so, it’s no surprise that I found myself wanting to return again last year to get into said “holiday spirit” as I did back in 2014.

Want to get infected with the NYC holiday spirit? You need as little as 3 days. This guide is based off my trip which lasted 3.5 days.

Getting Around

Flights – New York City is one of the major international airport hubs of the world, making it easy to get here from any corner of the world. Flights tend to also be quite reasonable in terms of costs if you are traveling from abroad or even within the United States. I for example have found round trip (aka return trips) to NYC from Chicago for only $75 USD which is very reasonable when you compare the cost of visiting other destinations in the USA from Chicago.

Cabs – The iconic yellow cabs are everywhere so start practicing how to hail one like a boss as this can be a fine art during peak times, busy areas, etc.

Uber – Uber does operate in the city of New York allowing for easy travel around the city including the various airports which is always useful.

Need to download UBER? Use my $5 promo code for a free ride on your first trip: “r83uv”. Download the app HERE and enter the promo code to redeem.

Subway – The subway system in New York can get you anywhere in the city. Sure, it can be overwhelming at first and you may find yourself going in the opposite direction as I have in the past but this helps with building that tough New Yorker skin just waiting to emerge even as a tourist. Leverage google maps for the best travel options as these are very up to date.

Walk – I can’t stress enough walking when visiting a city and New York is especially one I recommend getting around by foot. Not only will this give you a taste of how eclectic this city is but it’s also very easy to navigate and depending on where you are going, much faster than using a car or the subway system.


English is the main language spoken in the “Big Apple” but given the diversity of people living here and the various neighborhoods like Little Italy, Bronx and Chinatown you may find yourself hearing other languages throughout the city. Embrace it, it’s what makes this city so great.

NYC Holiday Spirit Must Do’s

  • Rockefeller Center – See the Christmas tree, the legendary skating rink and all things holiday happening here.
  • 5th Ave Window Displays – Bergdorf Goodman, Macy’s windows on 34th Street are the famous window displays from the film, ‘Miracle on 34th, Lord & Taylor, Henri Bendel, Saks Fifth Avenue, Barneys, Bloomingdales, FAO Shwarts. They are all in the same area of the city and easily walk-able. (Google walking tours HERE to find an array of maps.)
  • Central Park – Stroll through the iconic park, go ice skating or watch people ice skate if you can’t be bothered waiting in long queues and enjoy all the city holiday feels.
  • Bryant Park Christmas Market – Great market to visit for unique and homemade gifts.
  • Rolf’s – Restaurant bar that is decked out in Christmas stuff. This is the most famous one but there is usually a ton of pop up bars that come every year too so do some research.
  • Radio City Music Hall – It’s the most wonderful time of the year after all so why wouldn’t you see the most ‘tis the season’ show, The Radio City Rockettes.


Where Else To Visit While Here – It doesn’t all have to be holiday related. Make sure to see some of the must-see icons below if you have extra time.

  • The MET – Beautiful building with beautiful art to match and yes, this is where “camp” comes to life every year at the MET gala.
  • World Trade Center Visit the site of the 911 terrorist attacks and see how the city is reclaiming this area by honoring the past while moving forward toward the future.
  • Empire State Building – I personally cannot speak for the view since I’ve never been drawn to go inside or to the top but it’s hard not to miss this iconic building when walking in Manhattan.
  • Statue of Liberty – The history, the stories this lady could tell. It’s certainly up there on things to see while visiting.
  • Brooklyn Bridge – Another iconic symbol of NYC seen in many films.
  • MoMA – My favorite museum in the city so I highly recommend this one if you like modern art. The balcony cafe inside the museum that overlooks the garden is certainly a great place to grab a drink and slow down for a bit.
  • Times Square – Yes, it will be super touristy but yes, it’s kind of a must while here.


Where & What To Eat

  • Nom Wah Tea Parlor – Oldest tea parlor in NYC and possibly the U.S. serving delicious dim sum in China Town.
  • Black Tap – Known for their epic shakes. Come on an empty stomach and share either the shake or entree as their portions are massive. Try the ‘Cake Shake’ even if it’s not your birthday.
  • La Mela – One of my favorite places to eat authentic Italian food in little Italy. Big family style portions with all the Italian feels from decor to their Italian American staff.
  • Absolute Bagels – There are ton of places for bagels in NYC and locals will all have their favorite spot but when you get taken to a place that has a line that doesn’t seem to end and then confirm the taste for yourself, you know you’ve been taken to a place worth writing about.
  • Apotheke – Trendy concept style bar with delicious mixologist created cocktails. (TIP: It’s next to Nom Wah Tea Parlor so a perfect place for post dinner drinks.)
  • Serendipity 3 – Another location used as the backdrop for the 2001 film, “Serendipity”. This legendary NYC restaurant is known for their desserts; including the most expensive sundae in the world; the “Golden Opulance Sundae” at a price of $1000 USD (You heard it here; I will have this before I die.) and their iconic “Frozen Hot Chocolate” which I highly recommend and way more affordable then the first dessert mentioned. If I can’t sway you maybe mentioning that the likes of celebrities such as Marilyn Monroe, Andy Warhol and Beyoncé have frequented here may seal the deal and have you visit.
  • Cafeteria – Upscale diner with creative fusion items on the menu including their ‘mac and cheese spring rolls’.


Where To Stay

If you aren’t as fortunate as I am to have a good circle of friends in NYC who I can crash with when I visit then keep in mind that accommodations in the city can be quite pricey. Consider staying in an Airbnb if you would like more homey accommodations such as a kitchen and staying in Brooklyn and Hoboken which are a short subway or ferry ride away from Manhattan.

Tip: Have you tried Airbnb? Sign up with my link here and you will receive up to $55 USD off your first trip.

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