
*2020 Disclaimer: These photos were popping up in my memories, so I thought it’d be fun to recap this trip from 2016. So, don’t be alarmed by these photos with the crowds and no masks in sight! They are from years ago! Carry on…*
There is truly nothing like New York at Christmas! My first trip to New York City was during December and it will forever be one of my favorite trips! Thanks to about ten million viewings of the movie ELF, our kids were also enamored with New York…or as my oldest son called it at the time…”Yew Nork”. (swoon)
When we had kids and started traveling with them, we intended to make sure we took them to the “big” places when they could remember them. But, there’s something magical about taking your kids places when they are small – seeing it through their eyes and watching their reactions is a gift for you as a parent that is truly unmatched!
So, in 2016, we decided to take the boys to New York for a quick, 4 day dose of Christmas magic. For reference, my boys were 5 and 3 at the time of this trip. Since I had been to New York at Christmas before, I made a quick list of things I wanted to do with them.
Generally, when planning a trip, here’s my basic planning method. (I’ll dig into this further in a future post, so consider this a preview!)

- Make a list of “must-dos” for your trip.
- Map the things you want to do, then group activities by location.
- Search for restaurants near the attractions and save in your map.
- Schedule tickets or reservations as needed. Days on your trip with ticketed events will have more firm schedules, then you can fill in those days with activities near the ticketed locations based on the weather or how you’re feeling during the trip.
- Make a loose schedule of the grouped activities and restaurants by day.
Here was my list of “Must Dos” in New York with Kids:
- Big Stuff
- Go Ice Skating in Central Park
- See the Rockefeller Christmas Tree
- Visit Santa at Macy’s on 34th Street
- Attend Christmas Spectacular Starring the Radio City Rockettes
- Visit Times Square at night
- Play in Central Park
- See the Empire State Building
- See the Statue of Liberty
- Smaller Experiences (These are things we didn’t really schedule, but made mental notes that we wanted to make sure they did on their first trip to New York…most of which are food related!)
- Ride in a taxi
- Ride the subway
- Eat a bagel with cream cheese
- Eat at Ellen’s Stardust Diner
- Eat New York Cheesecake
- Eat a hot dog from a street vendor
- Eat sugar spice pecans from street cart
- Eat New York pizza
Day 1
After landing in New York, we rode a taxi (check!) into the city and got settled at our hotel. It was around lunch time when we arrived, so we started with a meal at Ellen’s Stardust Diner. This restaurant is the home of the world-famous singing waitstaff. While you’re served diner-style food, Broadway hopefuls sing to you! It’s such a fun experience for the kids and a diner is ALWAYS a good choice when eating with kids in a city.
Since it was raining on this day, we chose to explore the indoor American Museum of Natural History (think: Night at the Museum). At this point, our kids hadn’t seen the movies yet – they were too young to enjoy them. But, it was still a fun, indoor activity to enjoy on a rainy day. We rode the subway (check!) from the diner to the 81st street stop for the Museum. The boys loved the dinosaur skeletons and solar system exhibit most. With littles, the museum trip doesn’t last long! We saw the big exhibits then headed back to the Times Square area near our hotel. It REALLY started raining then, so we ducked into M&M World and The Disney Store to let the boys look around. The Times Square stores, while VERY touristy and typically over-crowded are SO much fun for little kids. It was good timing to explore the stores – as it was a week day in the pouring rain, so it wasn’t crowded at all. We ended the first day with a slice of New York cheesecake and went to bed!
Day 2:
We stayed at the Row Hotel, mostly for it’s convenient location to Times Square. As an added bonus, it had a modern food court inside with decent food options. When traveling with kids, its SO important to have some close food options to your hotel. We started the second day with breakfast at the hotel food court, then headed toward mid-town to the Empire State Building and Macy’s. We didn’t go to the top of the Empire State Building – mostly because the boys didn’t really care to go. But, they enjoyed seeing it from the outside and seeing the fancy lobby where “Buddy’s Dad works!”
Then, we went to THE Macy’s on 34th street to see Santa! Man – what an operation! We reserved a time to see Santa and it was a REALLY wonderful (and FREE) experience! The costumes of the elves and the decorations were really well done and the reservation option made the wait time really short. After the boys told Santa ALL their wishes, we snagged a snack then went outside Macy’s to enjoy their interactive window displays.
The weather was perfect, so it was a great time to enjoy some play time in Central Park! My boys STILL talk about climbing rocks in Central Park. They had so much fun! On a family vacation, especially one in a big city, it is IMPERATIVE to let your kids have some free play time outside. If you keep them too scheduled and drag them from one activity to another, they will turn quickly into monsters. So, don’t over do it! Let them enjoy and explore the nature around them! I promise – it will provide some of your best memories as a family! Climbing rocks, seeing some memorable Home Alone 2 sites, hot dog cart lunch and enjoying the beautiful Manhattan skyline, made for a great afternoon!
We had a big evening planned, so we went back to the hotel to take a nap. Listen, when you’re in a big city, you can feel tempted to squeeze as much as you can into your day. But, when traveling with little kids, just like making time for play, you MUST allow time for rest. Otherwise, your kids will do what they do at home when they are over-tired – throw an absolute fit and then everyone will be miserable. So, don’t over do it!
After our rest, we headed to Rockefeller Center for The Radio City Rockettes Christmas Spectacular! This was my first time seeing the show and I am SO GLAD I saw it with my kids! It was such a fun, kid-friendly, family Broadway-type experience. It was so well done and the kids were engaged the entire time! Live theater is a must in New York and this is a MUST-DO at Christmas time. They do a great job at making the experience great – no matter your seat!
After the show, we grabbed dinner then went to see the Rockefeller Center Christmas Tree! Obviously, the tree is a must see in New York and the boys enjoyed watching the ice skaters and look at all the beautiful lights and displays in the the 30 Rock area too. A great way to end a wonderful day!
Day 3
We decided it was time for a New York bagel on Day 3. The boys loved reading New York, Baby! – a book I had gotten for them on a previous business trip to New York. The character gets a bagel and cream cheese, so the boys had to follow suit.

The weather was great on this day, so it was a perfect time to do some more activities in Central Park. As we made our way into the park, the boys were intrigued by the horse drawn carriages offering rides around the park. So, we decided to go for it and take a ride. They loved feeding the horses and clip-clopping around Central Park and along the busy streets in Manhattan. The boys waved at everyone they saw like they were in a parade! So cute!
After the carriage ride, we went ice skating at the Wollman Rink. While ice skating at Rockefeller Center is certainly iconic…you’ll spend most of your day waiting in line for it! With a 5 year old and 3 year old…it’s just not worth it. And, honestly, I like the views in Central Park better! My oldest did NOT enjoy ice skating. He had a complete melt down. I think he was a bit overwhelmed by trying something new in a big crowd. But, my youngest LOVED it!
After ice skating, we snagged some New York Cheesecake at Juniors then went back to the hotel to rest.
Since the weather was nice, we decided it’d be a perfect night to see Times Square. So, after a fun meal of soup dumplings and hand-pulled noodles at Kung Fu Kitchen, we headed to see the lights in Times Square.
There is really nothing like watching your kids see something as BIG as Times Square when they are young. It was mesmerizing for them! We made note of where the “ball” would drop on New Year’s Eve and enjoyed seeing ads of movies and things they recognized. There was a singing group singing Christmas carols – so beautiful and a great Christmasy evening.
Day 4 – Last Day in the City
Our last day in the City – we decided to go get a closer look at Lady Liberty…but when we arrived, it was SO blisteringly cold, we decided to just look at her from the dock. I regret not braving the cold to see her up close, but oh well. We have something to do next time we visit! While in Lower Manhattan, we took a peek at Freedom Tower, got coffee and hot cocoa in The East Village and found the setting of my favorite sitcom – Friends. The East Village is SO pretty, y’all. We really enjoyed walking around that part of the city. The next time we visit the city, I’d like to stay in this area for a different take on Manhattan.
We have some family that lives in New York, so we spent the afternoon visiting them to end our trip! We had an evening flight out and I think these photos sum it up nicely! They were exhausted!
Real Talk
Listen – this trip was really great and full of fun memories. BUT. Our youngest was 3 years old and while we took taxis and subways a lot, his little legs got tired really quickly. So, my husband spent a lot of this trip with Andy on his shoulders. It was pretty exhausting. So, those breaks we took during the day were partly for my husband too! Just keep that in mind when visiting a big city with littles. I’ve heard of people getting strollers – which seems odd for a 3 year old – but might have been worth it. Hard to say!

But I have no regrets about this trip! It was such fun to experience these things with the kids at the ages they were. And honestly, for me…travel is always worth it.
-Cheers!