We just came back from a few days in New York. I’ve always wanted to go during the holidays and I feel like I planned a trip that was just perfect for us. I put a lot of thought into what would make this trip memorable and I’m really glad we chose experiences over shopping and saw the best parts of NYC in December. Here is our itinerary along with what I’d see, what I’d skip, and why.

Day 1 Rockettes/ Midtown:

I woke up before the kids and ordered Modern Bread and Bagel so we could eat while we were getting ready and get going. It’s a famous gluten free restaurant with the best bagels and breakfast food. If your family isn’t GF, just do Essa Bagel which you can stop in or have delivered. Just make sure to order right when you wake up to give it some time.

Then we walked over to Rockefeller and peeked in the Today Show window. I didn’t realize you’d be able to see right in and watch them film a segment. We got started around 9:00 and our first day was a Thursday so crowds were minimal. We went right over to FAO Schwartz because my girls HAD to see Jellycat Diner, which is their only US location. As we waited I line, were told by the family in front of us that you needed reservations. I quickly looked on their website that stated you do not need a reservation, but the family just saw it posted on Jellycat’s Instagram days prior. The family had teen girls who decided in line that they were too old for the experience and very nicely gave us their reservation. You can purchase their adorable stuffed animals without a reservation, but the diner food stuffies are specific to the experience that you apparently need a reservation for. When it’s your turn, you can choose from the diner menu (pancakes, waffles, hot dog, burger) and then they make your food come to life. They ‘cook’ them over a toy grill in a pan, pretend to salt and pepper them, and add ketchup and so on. It sounds strange, but the whole production was done with so much heart (thank you Shy!) that my girls felt connected to their little stuffies and were beaming at the end. There is a premium though with each toy being $50, but you’re paying for the experience and since we didn’t get a lot of souvenirs I thought it was worth it.

We then looked around FAO which was pretty chaotic but still worth a peek. It was a lot smaller than I thought it would be, and there was a line to get in that wrapped around the store down the street when we left so plan to get there early.

After that we headed to Dig for a quick lunch, then to our 2:00 Rockettes show. I loved having this show during the day so our nights we free. I really liked the fun of the show, it features singing and other performances that aren’t just the Rockettes. It is a 90 minute show that should probably be 60. There were acts that I’m sure have been in place for many years that just aren’t exciting anymore. I could hear the audience get restless and people get up to go to the bathrooms. I would also say because of this, I wouldn’t have kids younger than 8 or 9 attend. My 11 and 9 year olds who see shows all the time were a little bored during parts but liked it overall. All of this to say I did really like it and I would recommend it to others to see. It felt so Christmasy and the projections on the walls make it so magical, just know that there are slower parts to it and see the matinee to free up your night.

After the show we walked just across the street where Radio City, Rockefeller Plaza, FAO, and even the Jimmy Fallon show are so there is a ton of foot traffic, street vendors, and music happening. There was a band playing Christmas music with people all around just enjoying the scene. We danced by the fountain, took photos, and for the first time had a minute to take in being in NYC! It’s this little unplanned moments of enjoying the city that we just loved.

We had some time before our dinner res so we walked a few blocks to St. Patricks Cathedral. I’d been here years ago but didn’t fully remember how majestic and beautiful this church is. The sheer size of the building is incredible and you can spend hours just looking around. You can pay for different lengths of tours, but we just hit the gift shop and looked around for a good hour. We made stops around the church lighting candles and admiring the life sized nativity. It was somewhat crowded but completely manageable and turned out to be my favorite stop of the trip. I didn’t know how interesting it would be for the kids, but they really enjoyed looking at everything too. It was also a nice break from the cold.

I had made a reservation that evening at Wild in the West Village. It was a little bit of a haul but it’s an entirely GF menu with lots of veggie options and the food was seriously outstanding. It was really small, like 10 tables and most of them full. It was dimly lit with Christmas music in the background and such cute decorations. It was like a movie and such a perfect Christmas vibe that I didn’t want to leave. I’m so glad we took the Uber 20 minutes in traffic, it was totally worth it.

After dinner we went back to the hotel and watched A Christmas Story which just happened to be on TV. We all showered and with the time change everyone was ready for bed and an early start to the next day.

Day 2 SoHo/ Little Italy:

Little Italy was what I was most excited to see the whole trip so I planned a whole day on that side of town. I had brunch years ago at Balthazar in SoHo and made a reservation for us a month prior. The only time I could get was 9:00 and my girls were still fast asleep at 8:00 so I canceled the reservation and let them sleep knowing they’d be doing a lot of walking. I’ll make it back someday!

We walked to Fresh & CO around the corner for bagel sandwiches and smoothies. They did a great job with food allergies and preferences and the food was decently priced. Then we got an Uber to the Urban Outfitters in SoHo for a place I saw online that my girls were dying to see, Brooklyn Charm. They were doing a pop up there thankfully because we weren’t going to be in Brooklyn or at their other location at Chelsea Pier. We had so much fun designing our own necklaces and I even made a little Christmas bracelet too. The girls working there were sweet and made it such a fun experience. It was also affordable with the charms being $6 and the necklaces being $20-$50 depending on which you choose.

We then walked a few blocks to Little Italy where a miracle took place. I had read and watched everything pertaining to Rubirosa, one of the busiest restaurants in Little Italy with tons of press about their tie dye pizza that features marinara, vodka sauce, and pesto. They also make all of their own pasta daily along with gluten free pasta. I tried to get a reservation the second I could at midnight 7 days in advance but could only score 2 two tops that wouldn’t seat the 5 of us. I took them not knowing how that would work out but hoping for the best. We walked by Rubirosa as they had just opened and went in explaining to them that we had a reservation that wouldn’t work for us. They told us we could have a 5 top at 2:15. I was completely overjoyed and our lunch was outstanding. It’s a long, narrow place that feels quaint and very old New York. It was decorated beautifully for Christmas and had holiday and other fun songs playing. The crowd was cheerful and roaring with conversation and the whole place was warm and smelled like fresh garlic simmering with olive oil and sauce. This was another place that was worth seeking out. The tie dye pizza was delicious and it even came in a GF version as did a pasta that was as good as any we’d ever had. If you can’t get a reservation, pop in when they open and see what happens.

Before our reservation though, we walked the streets of Little Italy stopping in places I wanted to see. DiPalo’s Fine Foods, Ferrara’s Bakery for gelato and some Italian treats. And of course the Christmas in New York store which is 2 giant floors of Christmas collectables and ornaments. It’s overwhelming and beautiful and fun to get an ornament or 2 which is what we do every trip we take so our tree is mostly ornaments from places we’ve been. We were able to go to the end of Little Italy to get a photo with the iconic sign before turning around and heading back up for Rubirosa which is at the northern end.

At around 3:30 we knew we had to scoot back up to Rockefeller for our ice skating and tree photo reservation. They do have lockers if you need them, so you don’t have to stop back at your hotel like we did cutting it way too close. We took our tree photo first since the line was short before heading to the chaotic waiting/ get your skates area. It’s tight and crowded and filled with people putting on skates without enough benches to sit down. Then they allow people out in groups based on your time. You get an hour on the ice which feels like an eternity. I didn’t want to skate too late when it would be really cold. The rink is small and you can go right up to Prometheus, the gold Rockefeller statue with the tree right behind it. The crowds of people on the streets are behind a barrier and can’t get close to the rink, you can see them taking photos of everyone skating. This was the most magical part of the trip. Try for a dusk reservation so you can skate during the day and then by the lit up tree and the city lights. 4:00-5:00 works but I looked up when sunset was to make sure we got both parts of the day and also earlier in the night so it wouldn’t be too cold. Once the lights sparkle there’s no other experience that feels more like Christmas. This is one not to miss.

After this I wanted to walk around and see the department store lights (more on that below), but it ended up being so crowded and not worth the walk. So we went to grab a quick bite and then back to the hotel where Home Alone 2 was playing which was so perfect since it’s in New York and the next day we were going to Central Park.

Day 3 Central Park/ Times Square:

This was our last full day and I had a hard time coming up with what to do. I wasn’t sure if Central Park was going to be interesting enough but when I saw that it was going to be 40 and sunny most of the day so I decided to go for it. I had planned out a walking route with the landmarks I wanted to see along the way that was an hour-ish going into the park via the upper west side where we had brunch. We saw the Belvedere Castle, Bow Bridge, The Mall, Wollman Rink, Gapstow Bridge, and then exited by the Plaza Hotel where we caught our cab and just barely made our last stop. What I didn’t expect about the day was that we’d all be completely dazzled by the majesty and vastness of the park. One minute we’re inside a castle, and the next we’re dancing to live music and watching street performances. There is just so much diversity about the area that the term ‘park’ doesn’t even begin to cover. We turned an hour walk into several hours with plenty of stops along the way even chatting with bird watchers who were very excited to talk with my littlest about the hawk they were photographing in a tree. We ended up walking over 8 miles that day and the park was something I can’t believe I’d always skipped on my previous trips. It completely exceeded my expectations. It was such a nice change of pace from the city, and something we could experience that wasn’t centered around shopping. A tip I would give is to visit the park on what would be the busiest day of your trip to avoid the crowds as much as you can. I was happy we did this on Saturday because the whole midtown area was SO much busier Saturday than it was Thursday or even Friday.

From there we managed to barely make our reservation at the absolutely incredible SUMMIT One Vanderbilt. You take an elevator 91 floors up where you visit 3 floors of mirror and floor to ceiling glass to experience expansive views of NYC above the skyline. It’s a sensory experience that gives you a perspective on just how vast NY really is. We loved this so much and spent hours here. We weren’t sure what to expect but sitting near a window looking out and spotting places we’ve visited was a lot of fun. For the risk-adverse, know that the elevator feels like you’re barely moving it’s so well built and takes only 40 seconds to ascend. They also make sure the elevator isn’t too full so you don’t feel like you’re crammed in too tightly. The line for security to get up is the worst part and takes a while, you also stop to put covers over your shoes and stilettos aren’t allowed so keep that in mind as well. It’s more of a process getting to the elevator going up than anything else. Once we were up it was great and the crowds were very manageable. Even the long line to come back down was managed well and took about 5 minutes. It’s hard to describe how we felt in that space but it was an experience I’m so happy we did as a family and it felt amazing. I also read online to book just before sunset (more on that below) which is a must.

From here we ate a quick but delicious diner at Le Botaniste then had a choice to make; either pop into Macy’s which was close by, or go to Times Square. We decided that Times Square would be the most unique experience and walked the long, cold walk over. I really wanted to do the New Year’s Eve Wishing Wall which is a free kiosk where you write your wish for the new year on a square piece of tissue paper that they collect and drop with the rest of the confetti in Times Square for the ball drop on New Year’s Eve. We all LOVED this idea and were so happy to do it. The line was short, about 10 minutes and we watched the performers and goings on around us to kill time so it seemed a lot shorter. I was reminded, having been in Times Square in the past, that it’s a place to visit at night to see the lights, and it isn’t a place you want to be for very long.

After we signed our confetti, we walked around a little bit and saw all of the things which included a group of teens making TikTok’s doing little dances, a 360 cam where you could take a video of your family with Jay Z’s New York blasting in the background, and the scammers all dressed up like second rate Minnie, Mickey and Spiderman. They jump in your photos and then demand a tip. This didn’t happen to us but we were ready having seen it online. There was a Grinch wandering around asking for photos with people, but the girl with him did specify that it would cost them. We didn’t stop in the M&M or Hershey stores as that didn’t seem interesting to us and there was a line to get into both, so we walked around getting the full vibe of the city, and walked back to our hotel unable to get a cab or Uber. Keep that in mind for Saturday because we didn’t have this problem Thursday or Friday at all.

This was a huge walking day as we got back to our hotel after 8:00 in time to pack and Postmates cookies from Levain Bakery which also has a GF cookie which was the best cookie I’ve ever had. Full stop. This one is worth the hype, I wish we could’ve gone into the bakery but once you see how hard it is to get from one place to another that isn’t right in your area, you really want to stay put. Delivery came quickly via bike as did the delivery from a local diner where I got some food for the morning since we’d be up at 5:00 for our flight and I didn’t know if the airport would have anything open for us to eat once we were there. Love that about NY, anything you want anytime you want it.

And just like that our 3 days were over. There were only restaurants I’d wished we had more time for, but not really anything else. We saw exactly what we wanted to see. Here is some info I picked up along the way to share for your holiday trip to NYC.

DO:

Plan your outfits knowing you won’t really see a single one in photos. I spent hours looking up New York Street Wear on Pinterest which is a joke because all of our photos are just with my heavy coat and scarf which is what all locals wear anyway. Oh, and earmuffs to keep you warm without messing up your hair. I appreciated that tip. It’s just so cold and windy that we have coats on the whole time. I did see that some locals wear long underwear under their lighter or fashion coats and outfits just to be warm and pull them off. I brought long underwear and a cute coat but neither saw any time out of my suitcase. I wisely dressed in my warmest wear and I’m thankful I did.

Research your reservations. For example, I read that mezzanine seats were best for The Rockettes and boy were they right. All of the front rows were available while mezzanine was largely picked over. It’s because the curved interior walls have constant projections on them which are part of the show. You could see people in the front of the house looking back not being able to see a magical part of the show that tied it all together. I also read about getting tickets to SUMMIT One Vanderbilt around sunset so you could see the skyline during the day, the sunset, and the city lights. This tip made that entire outing so much more enjoyable and we stayed for hours seeing it all unfold.

Get reservations for restaurants and have some fast casual places earmarked near where you’re going. I’m so happy I did this. I knew there were a few places I wanted to eat where I needed a res, but I also didn’t want to be chained to restaurants at times when our plans were more fluid. I also had to research places where my daughter with Celiac could safely eat without being sick on the trip. I looked at reviews, menus, and called them to see how much they understood food allergies and it paid off. Midtown, Times Square, and Midtown East are all extremely crowded this time of year since everything is in that same area so try and eat during off times if you can. I also looked up fast casual spots like Dig, Fresh & CO, Vanderbilt Market (we didn’t end up eating here but I had it as an option), and we LOVED Le Botaniste which was vegan and 100% gluten free near SUMMIT. I also marked Pizzarte which had Gluten free pizza, OBAO, Totto Ramen, and others in areas where we’d be so we wouldn’t feel stuck if someplace was too busy. You don’t want to be on your phone looking up restaurants in the middle of a crowded street when your kids are starving. It’s good to be prepared.

Get the Rockefeller tree photo as well if you’re skating. Or even if your’e not. I saw this as an option when I booked our skating experience and almost didn’t do it. It got us skating before our scheduled time since we were already let in by the rink, and the photos were so beautiful! They took a ton of pictures and we loved them all. This is one you don’t want to miss even if skating isn’t your thing. Get the tree photo, you won’t regret it.

Plan a combo of indoor and outdoor things. Since it will be cold and likely windy you’ll want to have something that you can see that’s indoors just in case the weather or snow is too much. Instead of Central Park, I had the American Museum of Natural History lined up and ready to go just in case the weather took a turn.

Figure out how you’re getting around. We took Ubers the first few days and they were $45-$60 per (short) trip because of surge pricing. They also took forever to get to us, so it wasn’t idea. When we did catch cabs they were filthy and sketchy. One guy looked at Reels on IG the entire time even while driving, narrowly avoiding a few accidents. He also was taking the longer route as I could see on my phone while Ubers don’t charge per minute and they often looked to see where they could take shortcuts around traffic. Download the Citymapper app and take the subway. This tells you exactly which subway to take from where you are to where you’re going which is easier and less frustrating. I did download it but ended up in Ubers and cabs the whole time but next time I’ll get on the subways for longer journeys.

Skip

Don’t waste your time seeing things you can see at home. For us, this was an easy call and I was so happy I was able to trim the fat on a few things we can see right here in Colorado. This included Broadway shows. We’ve seen Hamilton (twice!), Lion King, Wicked, and everything we’d all enjoy as a family. I wanted to experience holiday specific things and not sit in a theater for a few hours for anything other than the Rockettes. Any other time we’d visit NYC, I’d grab tickets but this wasn’t first on our list for the holiday.

I also felt this way about the Macy’s Santa Experience. It’s where you can enter a ticketed only area in Macy’s and at the end have a professional photo taken with Santa. I feel like if you’ve seen one department store Santa, you’ve seen them all. I also read on their site that even though you have a reservation, you might wait 30-90 minutes anyway. If it’s something you’re dying to do, read up on when the reservations become available because they’re a few weeks out and go quickly.

Outdoor markets. Union Square, Bryant Park and Columbus Circle all have outdoor holiday markets with vendors selling the same things; ornaments, hot chocolate, trinkets, etc.. We have a market here in Denver that we adore and visit yearly so I wanted to skip the crowds (which I read were awful) and see other NY sights.

Although it pained me, I ultimately skipped the Dyker Heights displays. It’s an area in Brooklyn with brownstones that feature over the top lights and displays. There are bus tours and walking tours all with a charge. I had to dig through lots of info to learn that you can walk around on your own as well but there aren’t restrooms and cabs can be scarce. We do drive around and see lights here in our area which aren’t all together on the same block or nearly as magical but the distance of an hour long drive each way would’ve meant axing a few things that I really wanted to see for something that could potentially be a logistics nightmare. It just wasn’t worth the drive this trip. Maybe if we had more to do in Brooklyn it would have made sense, I’d love to go one day and then check out Lioni’s afterward for a sandwich.

Another thing I thought would be top of my list that we ended up skipping were the window displays outside of department stores. I had a whole route planned out to walk down 5th starting at the Plaza hotel (which also doesn’t let people in unless you have a reservation or are a guest there) just to look at lights. Night one we drove past a few and they were very pretty but not worth an hour of walking just to see them. It’s honestly not as dazzling as I hoped, not to mention the extremely crowded streets make it impossible for littler kids to see anything. My 9 year old said she mostly saw backs and butts when we were walking around. I hadn’t thought about her specific view point as I loved seeing all of the New York sidewalk sights. We finally put her on my husbands shoulders so she could see, but even my 11 year old didn’t see as much as my 12 year old did since she’s not quite adult height yet.

Rolf’s. It’s overpriced German food. Yes it’s decorated beautifully, but so is Lillie’s Victorian so go for tea there instead if you can get a reservation.

I actually brought a large carry on duffle bag for things bought and didn’t come close to filling it. Outside of a a few ornaments and little things for family and gifts, we didn’t get a ton of things for ourselves which is exactly what I wanted. When the girls are older I’ll take them to NY during the summer and we’ll shop and explore more restaurants, the 911 Memorial, Statue of Liberty, and some of the other places they’d love. This trip was all about the holidays and we captured exactly that over the weekend. Hope your trip is as magical as ours! Happy Holidays.