Travel | Travel Tips

How to Spend a Holiday Weekend in New York City

March 3, 2019

Spending the holiday season in New York City is an unforgettable experience! Christmas in New York City is just magical. If you’ve dreamed of visiting during the holidays, this guide shares information for planning a successful trip. I’m sharing what I did, where I ate/drank and even tips for your next Christmas trip to New York City!


Where I Stayed

Fairfield Inn & Suites Manhattan/Central Park – New York City is expensive, particularly during the holidays. I found a great deal at the Fairfield Inn and Suites Manhattan/Central Park and booked about 6 months in advance. The rooms are modern, clean and on the smaller side. We didn’t mind the size so much since we didn’t spend much time in the room. The location is a 10 minute walk from Columbus Circle and in a great position to get to Central Park. Times Square is about a mile walk, which is nice to be away from the touristy chaos.

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Things to Do

Christmas Display Windows

No one does holiday windows like New York City. You can spend hours walking up 5th avenue admiring the display windows. The hardest part is looking without wanting to buy everything!

On the front of the building is an extravagant timed light display which is what everyone attempts to see in the evening. The light display is on every 10 minutes and runs for about 4-5 minutes.Bergdorf Goodman is another popular one for Christmas displays.

Stroll along 5th Avenue and look at the famous windows of Macy’s, Saks, Bergdorf Goodman, Barney’s and more. Don’t forget to stop to see the famous Christmas Tree at Rockefeller Center.


Rolf’s Bar and Restuarant

Many people recommended Rolf’s Bar and Restaurant as a place to eat at Christmas due to its elaborate Christmas decoration and light display. I personally would recommend going for a cocktail. Be aware that it gets very crowded during the holidays; so if you’re planning to have dinner here then make a reservation. In order to get in for a cocktail, I suggest arriving before they open and lining up outside. Know that you’ll be standing shoulder to shoulder at the bar once you get in.


Visit Christmas Markets

Around NYC you’ll find popular Christmas markets and small pop-up shops. You can find anything from local goods, to food, to drinks, to art, to clothing, and so much more! It is really amazing to see, even if you don’t buy anything. One of my favorites is the Union Square Holiday Market, an internationally renowned Holiday Market located at the heart of New York City, in Union Square Park. This is a great market for unique gifts created by local craftsmen and artists.


Rockefeller Christmas Tree

The ambiance around Rockefeller Center is spectacular during the holidays. One of the most popular things to do in New York at Christmas is to see the Christmas tree. If there’s one thing you have to do during Christmas in NYC, it’s visit the Rockefeller Tree.


Ice Skating

Ice skating in NYC during the holidays is just as iconic as anything else in the city. There are multiple places around the city to enjoy this activity, depending on how much you want to spend.

Some popular options include:

  • The Rink at Rockefeller Center ($32/ ticket + $12 skate rental)
  • Wollman Rink at Central Park ($11.25/ticket + $8 skate rental + $11 lock rental— cash only!). Ticket prices will vary depending on peak seasons and if you have children or seniors with you.

Visit the Plaza Hotel

The Champagne Bar began as the Champagne Porch, which was introduced with the hotel’s opening in 1907. Today’s Champagne Bar was beautifully renovated in 2014 and is located adjacent to The Plaza’s lobby and Fifth Avenue foyer. Click here for menu. Not interested in Champagne? Enjoy a stroll throughout this magnificent hotel.


See a Show

A holiday visit to New York isn’t complete without catching a spectacular show. There are so many options in the Big Apple, so just find one that fits your liking and budget! The most famous show is probably the Christmas Spectacular featuring the Rockettes at Radio City, but there are also multiple renditions of the Nutcracker, Christmas themed musicals, and more.


Top of the Rock

Ascend 70 floors up to 360 degree views from three different indoor and outdoor observatory decks. My favorite part of the whole experience was seeing all of the different views. Depending on where you were on the observation deck, the views include the vast greenery of Central Park and the stunning views of the Empire State building. Tickets prices range from 30 – 85 USD. I recommend picking a time slot before 9 am if you want pictures without other people in them. Going for the sunset is also beautiful, however it is a popular time.


Day Trip to Brooklyn Bridge, Brooklyn Heights and DUMBO

Free 3-hour walking tour that begins with a walk over the Brooklyn Bridge, an icon of New York City for over 125 years, with spectacular views of Manhattan and Brooklyn. The tour then moves on to a stroll of Brooklyn Heights, America’s and New York City’s first suburb. The tour then explores the neighborhood DUMBO. Dumbo stands for Down Under the Manhattan Bridge Overpass and is a neighborhood in the New York City borough of Brooklyn. It encompasses two sections: one located between the Manhattan and Brooklyn Bridges, which connect Brooklyn to Manhattan across the East River, and another that continues east from the Manhattan Bridge to the Vinegar Hill area.


Dyker Heights, Brooklyn Light Displays

If you are feeling adventurous, hop on the train and head to Dyker Heights, Brooklyn for some of the most unbelievable Christmas light displays you will ever see! House after house of families who go above and beyond the usual outdoor twinkle lights and a reindeer or two.  The pictures don’t even do it justice.  It’s truly a sight to see in person!


Where to Eat + Drink

  • Rubirosa – 5 star pizza located in Nolita with family style group dining and a cozy bar. Gluten free pizza and pasta options.


  • The Lodge at Gallow Green – Located in Chelsea, during the colder months, a cabin-themed watering hole temporarily takes over the rooftop of the McKittrick Hotel. The Lodge at Gallow Green is designed to resemble a cozy alpine retreat and offers the same level of detail as the set of Sleep No More (which takes place just a few floors below). Though there are plenty of cozy bars and restaurants in the city, the Lodge takes its theme to a new level—Visitors can snuggle on bunk beds, peruse books and specimens displayed on wooden shelves or sit at a desk covered in pinecones and rolled parchment. An outdoor fire pit surrounded by a small forest of evergreens give the sense of a true mountain getaway.


  • Serra by Birreria – Located in the Flatiron District and on the rooftop of Eataly, journey north for the winter as La Birreria transforms its rooftop for the season. The Italian countryside restaurant on the roof will be transformed into SERRA ALPINA by Birreria. Complete with a new cozy look, the greenhouse “pop-up” will be changing with the season, featuring Alpine dishes created by our chefs and creative mountain-infused cocktails. Enjoy an amazing brunch and cocktails.


  • Cecconi’s – Stunning waterfront view with pastas, wood-fired pizza, weekend brunch and great cocktails.


  • Locanda Verde – ‘Locanda’ in Italian is a local place to eat and drink. Directly translated, Locanda Verde means “green inn serving a seasonal, urban Italian menu of Antipasti, house made Pastas and much more.


  • The Chelsea Market – an enclosed urban food court, shopping mall, office building and television production facility located in the Chelsea neighborhood.


  • Jack’s Wife Freda – Cozy West Village cafe serves affordable Middle Eastern-inspired sandwiches, salads, and egg dishes that are tasty, but not too heavy.
  • Butter – The American restaurant is helmed by Food Network star and Executive Chef Alex Guarnaschelli, who uses greenmarket offerings to create a seasonal menu. Located in Midtown.
  • Stanton Social – located in the LES with a swanky vibe and signature cocktails. The food is amazing and so are the drinks!
  • Mr. Purple – located in LES and part of the Hotel Indigo’s 26-floor expansion on the Lower East Side, this cocktail den sprawls across two outdoor terraces with a swimming pool and soaring views of the Manhattan skyline.
  • Beauty and Essex – located in the LES with a pawn shop upon entrance and even a champagne bar in the restrooms.
  • 230 5th Rooftop – You’re probably thinking why would I visit a rooftop in the Winter? Well, this particular spot has adorable rooftop igloos! Not only are they festive but they hold up to 12 people and keep you warm. These igloos fill up very quickly so be prepared to wait in line! Once inside, you get a complimentary red blanket and a selection of seasonally-appropriate cocktails. If you come earlier in the day they even have a brunch menu!
  • Toloache – Mexican restaurant located between Broadway and 8th avenue. The food is authentic and SO delicious. Definitely a place for dinner if you’re craving Mexican.
  • Secret Speakeasy – Please Don’t Tell Call 212 614 0386 THE DAY OF to see if you can get in.


Tips:

  • I recommend arriving VERY early to the main touristy sites to see them when they are less crowded.
  • Prepare for the crowds and lines because everyone else also wants to spend Christmas in New York.
  • Dress warmly! December in New York can be really cold with a crazy windchill
  • Christmas tree at Rockefeller Center closes at 11:30 PM, so get there before then.
  • Give yourself more time for everything. With so many people, everything takes longer. Avoid taking a taxi at all, if you can, but especially in the area of midtown. Expect traffic gridlock.
    Whenever possible travel by subway. I found taking the subway was the fastest option.
  • If you’re hoping to take photos without the crowds then go at the crack of dawn.
  • Whether you want to eat or drink at holiday favorite restaurants, make reservations well in advance.

Planning to visit New York City? Book your trip on Kayak.com through my affiliate link. Kayak offers the best prices by scanning hundreds of travel sites in seconds and gathering flight deals from across the web and putting them in one place, at no extra cost to you!




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