Experiencing the Holidays in New York City
TWO DAY ITINERARY
With two whirlwind days in the Big Apple you can see and do a lot of the festive things that the city puts on each year. From skating at Rockefeller Center to catching the Rockettes at Radio City Music Hall to seeing the holiday decor around the city, it will be jam-packed with holiday fun. With this itinerary, you will experience the top things to do during the holidays that fit neatly into a two-day itinerary.
NEW YORK CITY DURING THE HOLIDAYS
New York City is one of the most popular places to visit during the holidays with how the city goes all out to celebrate. Almost 7 million visitors descend on the Big Apple in the weeks between Thanksgiving and Christmas, making it extremely busy. Although it is busy, with proper planning and implementing the tips shared throughout this guide, you can have a great visit during this busy and festive season.
Where we stayed
The New York Marriott Marquis – Times Square. We have stayed here a few times when traveling as a family. The rooms are spacious for NYC hotels, the lounge and restaurants on site are convenient, and the location can’t be beat.
When we went
We visited New York City the third week of December, back home on December 21st. We had two nights (and 2 1/2 days) in the city, which was perfect. Having been to NYC many times before, this was just a trip to experience the holiday season. Crowds were increasing each day that we were there and on departure day things really seemed to pick up. Our hotel was chaos as we checked out and traffic was heavy as we left midtown Manhattan. We recommend a weekday visit and earlier in December, as the weekend right before Christmas seemed to really pick up in terms of crowd levels!
About This Itinerary
We arrived into New York City at 8:30 a.m. on December 19, which allowed us a full day on arrival day. It was a busy day with a very early start but it worked out great to have the full day. On departure day, December 21, we had a 3:50 p.m. flight back home. This allowed time in the morning to fit in a few more things. Spending just two nights in the city eliminated an extra hotel night. If you want to fit in more sites or spread things out over more days, this is of course an option. For us, visiting all the holiday must-sees were pretty much the only things on our agenda as we had been to New York City many times before. So, spending just two nights with two and a half days in the city worked out great.
This is a “what we did” itinerary, which makes it easy for you to follow along or tweak and adjust based on number of days you have or your specific interests. For more in-depth information check out our guide on the Top Things to do In New York City at Christmastime. We go into more detail on specific places and also share lots of planning info and tips.
DAY 1
On Today’s Agenda:
- Shops at Columbus Circle
- Columbus Circle Holiday Market
- Central Park
- Lunch: The Smith – Lincoln Center
- Grand Central Station
- Summit One Vanderbilt
- Lotte New York Palace Christmas Tree
- Dinner: La Grand Boucherie
- Shopping along 5th Avenue
We arrived into LaGuardia Airport (LGA) in New York City on a direct flight from Louisville at 8:30 a.m. After collecting our luggage and grabbing some coffee to go, we took an Uber to our hotel located in midtown Manhattan, arriving around 9:45 a.m. We were luckily able to check in and get into our rooms early. If this is not an option, your hotel can most likely hold your luggage for you until check in time.
From our hotel, we walked to the Shops at Columbus Circle, as they opened at 10:00 a.m. We shopped a bit while checking out the pretty holiday decor.
The Columbus Circle Holiday Market as seen from the Shops at Columbus Circle
Across the street, the Columbus Circle Holiday Market opened at 11:00 a.m. so we made our way there about 15 minutes before they opened. With arriving early, we had minimal crowds, took some pics, and perused the shops to see what they would be selling.
The booths each sold different things such as specialty foods, glühwein (mulled wine, a staple in German Christmas markets), souvenirs, crafts, and more.
Lots of tasty food and drinks at the Holiday Market
We enjoyed this Christmasy shopping experience while sipping on a tasty hot drink. Getting here at opening time (or just before) makes for a great experience.
The Columbus Circle Holiday Market is located at the very southern end of Central Park. After checking out the holiday market, we made our way into Central Park, as it is such a pretty respite from the hustle and bustle of the city.
Central Park is so pretty in all seasons. A day after this photo was taken, it snowed!
From here, it was a five minute walk to our lunch reservation at The Smith – Lincoln Center. We had a lovely lunch of soups and salads, perfect on this cold winter day. The restaurant was lively at this time, setting the tone for the trip full of happy people enjoying the holidays in New York City!
After lunch, we walked back to the hotel, resting a bit as we had been going strong since the early hours this morning. (This is a good time, if you don’t want a rest break, to fit in a site before the evening events). After a bit of rest and a nice afternoon coffee break, we walked to Grand Central Station, checking out the beautiful interior with ornate architecture and the famous clock.
Grand Central Station
People watching is a lot of fun here, too, as people scurry throughout the station catching their trains. To reach Summit One Vanderbilt, it is a short jaunt outside across Vanderbilt Avenue on the west side of Grand Central Station.
Summit One Vanderbilt is a multi-level observation deck at the top of One Vanderbilt, a skyscraper in midtown Manhattan. Located right next to Grand Central Station, you can easily combine a visit to Summit One Vanderbilt with the iconic train station.
A visit to Summit One Vanderbilt is an experience. First, the elevator whisks you up 91 stories in a matter of seconds. When the elevator doors open, you are transported into this part art-installation part-observation deck, a very unique way to view the city.
The views up here are incredible. Facing the Chrysler building to the east…
the Empire State building to the south…
Hudson Yards to the west…
and Central Park to the north. You get to see all of New York’s best from one observation deck!
PRO TRAVEL TIP: Book your Summit One Vanderbilt time slot 90 minutes before sunset. You will get to experience the immersive rooms during the daylight and then watch as the sky slowly turns shades of varying colors before finally turning to night with the city lights shining bright. Ending the visit with a drink from Apres’, the bar at the top, while taking in the views of the city turning to night is the “apple” on top of a great day in the city 😉
This evening, we had a 6:30 p.m. dinner reservation at La Grand Boucherie. It took us about 15 minutes to walk there from Summit One Vanderbilt, which was a great walk, taking in all the holiday decor along the way. We had a few extra minutes so we took a quick detour to the Lotte New York Palace Hotel, located just behind St. Patrick’s Cathedral. The hotel has a beautiful tree in its courtyard and wreaths decorating its gates.
The hotel allows people to check out the tree in the courtyard and even has a booth set up in the corner selling food and drinks, but be mindful that this is a working hotel with guests coming and going. We walked around the courtyard checking out the massive beautiful tree, glowing so beautifully against the night sky.
Dinner at La Grand Boucherie was wonderful. The restaurant was jam-packed so a reservation is a must! The Christmas decor really set the ambiance and we enjoyed our delicious meal in this festive atmosphere.
After dinner, we walked down Fifth Avenue for some of the best lights and window displays in the city.
Saks Fifth Avenue
We shopped a bit and enjoyed the lights and displays…and saw the crowded Rockefeller Christmas tree from across the street!
Crowds at the tree in the evening
What a great first day!
PRO TRAVEL TIP: Early morning or late at night are the best times to view the Rockefeller Christmas Tree with minimal crowds. Our visit was between 8:00-9:00 a.m. and we were able to get close to the tree and take photos. The morning light is also great for photography. In the evening, crowds are heavy until about 10-11:00 p.m.
DAY 2
On Today’s Agenda:
- Skating at the Rink at Rockefeller Center
- Winter Village at Bryant Park
- Lunch: Industry Kitchen
- Brooklyn Bridge
- Hudson Yards
- Macy’s Herald Square
- Radio City Rockettes and/or Dyker Heights lights in Brooklyn
- Broadway Lounge at the Marriott Marquis Times Square
Our morning began with coffee and breakfast at our hotel. We headed out at 7:30 a.m. for a quick walk to Rockefeller Center.
The Rockefeller Christmas Tree
Skating at the Rink at Rockefeller Center is a bucket list experience and one not to be missed during your visit to New York City in the winter. The skating rink is quite small, but so iconic, especially under the glow of the massive Christmas tree. By arriving before 8:00 a.m., there were just a few people around so it is a great time to visit the Rockefeller Center Christmas Tree.
The Rink and Christmas Tree at Rockefeller Center
For an extra special experience, consider getting up very early as the city turns the lights on the tree at 5:00 a.m.!
Our Experience: We booked an 8:00 a.m. time slot for the Rink, which meant that we had from 8-9 a.m. to skate. We arrived at about 8:10 a.m. and this ended up working out perfectly. Our 8:00 a.m. group was already on the ice skating and a line had formed for the 8:20 a.m group. By arriving at this time, we missed the line for our 8:00 a.m. group as they were already on the rink, were able to get our tickets scanned right away, and had no line to get our skate rentals. And 45 minutes ended up being more than enough skating time! There are lockers on site and you will have to lock up any bags, including purses, as no baggage is allowed on the rink.
Can you take photos? Mike was the one in our group who didn’t skate so he took some photos from up above.
Skating here was fun!
People do stop on the ice to take photos, selfies and even ask others to take pics, especially under the Rockefeller Christmas tree. So having a phone or small camera in your jacket pocket works well to take photos while skating. But don’t forget to enjoy the experience!
Is it worth it? Absolutely, yes! It is one of the most iconic ice skating rinks in the world and ice skating is a fun activity for the whole family. While the Rink at Rockefeller is smaller than other rinks in the city, such as the rink at Bryant Park and the Wollman Rink in Central Park, I much preferred the intimate experience at the Rockefeller Rink. Yes it is small but it sufficed for our purpose of enjoying a leisurely skate. Less people on the rink made for an enjoyable experience and being able to take a photo under the glow of the Rockefeller Christmas tree made it especially unforgettable!
Ava and me by the Rockefeller Tree while skating
After skating, we ducked into Ole & Steen, across the street from Bryant Park. We enjoyed coffee and a mid-morning snack and getting out of the cold for a bit! The Winter Village at Bryant Park opened at 11:00 a.m., so at about 10:30 we headed out to check it out. By arriving early, before the booths opened, we were able to visit the beautiful Christmas tree and check out the booths before the crowds arrived.
The Winter Village at Bryant Park was our favorite of the holiday markets in the city
Again, Christmas market staples were for sale such as glühwein and hot chocolate, although this market had speciality foods and drinks for sale.
The booth selling raclette already had a long line early right when they opened as did the gourmet hot chocolate, available with and without alcohol. This open air market had such a cozy atmosphere, complete with a large ice skating rink in the center. It ended up being our favorite holiday market.
The skating rink at Bryant Park
From here, we took an Uber down to the southern end of Manhattan for lunch. We walked through Stone Street, a pedestrian-only historical area in the financial district and continued on to Industry Kitchen, our lunch spot.
Stone Street, part of a historical area of lower Manhattan
During the winter months at Industry Kitchen, the outdoor seating area is converted into these cozy huts that you can reserve for dining al fresco no matter the weather!
Dining al fresco, even in the winter
Industry Kitchen is a usual stop for us when in New York City, as Braden claims they have the best margarita pizza!
After lunch, take a stroll along the promenade for great views of the Brooklyn Bridge.
Great views of the Brooklyn Bridge are just a short walk from Industry Kitchen
From here, we took an Uber to Hudson Yards. The Shops at Hudson Yards is a great shopping venue with typical mall shops such as Mango and Lululemon as well as high-end stores like Tiffany’s and Louis Vuitton. The decor inside is beautiful!
The Shops at Hudson Yards is decorated so beautifully for the holidays
If you go out the back door of the shopping complex you will see the massive Vessel, a honeycomb structure with stairs taking visitors up 16 stories for unique views.
The Vessel is located just outside the Shops at Hudson Yards
After visiting Hudson Yards, it is less than one mile to visit the iconic Macy’s – Herald Square. If you want to visit Santa, be sure to book your time slot ahead of time as reservations are required. In 2024, reservations to visit Santa opened five days before. Bookmark this site so you can access it for your holiday planning.
Tonight, we split up as we had different things we wanted to do. Ava and I had a tour of Radio City Music Hall followed by the Radio City Rockettes Christmas Spectacular. Mike and Braden went on this tour through Get Your Guide, which took them down to Brooklyn via bus and then on a walking tour of Brooklyn’s most decorated neighborhood, Dyker Heights. Skylar went to see Hadestown, a Broadway Musical. It worked well to see things that piqued our individual interests, however if your kids are younger or you all want to see the Christmas Spectacular, Broadway shows, or Dyker Heights lights, you can add those on individually with more days in the city.
Radio City Music Hall, so festive!
The backstage tour was interesting as we toured areas normally off limits to the public, learned a lot about the history of Radio City Music Hall and the Rockettes, and ended the tour with meeting a Rockette.
Tour of Radio City Music Hall, before the Christmas Spectacular
The Christmas Spectacular was an incredible show! Ninety minutes of high kicks, singing and dancing Santa Claus, and holiday stories. This is a must for the ultimate Christmas in New York experience.
The end of the Rockettes Christmas Spectacular
Mike and Braden really enjoyed their tour of the Dyker Heights neighborhood to see the over-the-top Christmas lights and decor.
The Dyker Heights neighborhood in Brooklyn has become famous for its over-the-top Christmas light displays. Tourists fill the sidewalks and tours guide people through the history of this tradition while viewing these extraordinary displays.
Colorful lights, snow machines, animatronics, 25 foot tall Mr. and Mrs. Claus, and so much more adorned the exteriors of the homes. Some of the residents had vendor booths set up raising money for various charities by selling goods such as gingerbread men, hot chocolate, and Christmas cookies.
For more guided holiday light tour options for Dyker Heights:
After our evening events, we met back up at our hotel and enjoyed a late dinner and drinks at Broadway Lounge, one of our favorite places to dine with its aerial views of Times Square. There are outdoor terraces that you can access for crowd free views of one of the most heavily touristed areas in the world!
Our preferred view of Times Square – from up above at the Broadway Lounge
DAY 3
On Today’s Agenda:
- Brunch at a beautifully decorated restaurant, such as Papillon or Tavern on the Green.
- Travel day home!
We slept in this morning as we had had early mornings on the prior two days. Adding in anything else you want to see or do before your late afternoon or evening flight home is doable.
A leisurely brunch is a great way to end your holiday time in NYC. Both Papillon and Tavern on the Green popped up on numerous lists of restaurants with great food and festive holiday decor. You definitely need to book reservations far in advance for these, though!
With More Time
If you extend your visit an extra day, so three nights, you can see the Radio City Rockettes Christmas Spectacular one night and the Dyker Heights Christmas lights on the other.
If this is your first visit to New York City, there is so much to see and do. In fact, we created an article, Twenty Five Great Things to do in NYC with Kids & Teens, to cover some of the best things to do in the city, from the famous landmarks to lesser known sites. Peruse the article to add any of these on to your Christmas in New York itinerary.
Read More!
Below are more guides on travel to New York City:
Top Things to do in New York City at Christmastime
Top Things to do in New York City at Christmastime TOP THINGS TO DO & HELPFUL TIPS It is no secret that New York City
How to Organize Your Time in New York City
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