🎄Christmas in the Big Apple 🎄

Trip Date - December 19-23, 2025

Number of Days - 5

Who went - Jenn (51), Terry (52), Olivia (22) & Boone (15) Here is the exact itinerary See next year's plan - 2026 Christmas in the Windy City!

We love New York City (see other trip highlights here), and there is no better time to experience it than during the holidays. We took both kids to NYC the weekend before Christmas and had an amazing time! We stayed in a small apartment near Bryant Park with 2 bedrooms. It wasn't fancy but the location was ideal and it worked for the time that we spent there (which was really just to sleep!) Friday, December 19 After checking into the hotel, we took the train to Union Square Holiday Market for some leisurely shopping and snacks. This is a smaller version of the Bryant Park market - much less crowded. Terry and I tried some delicious chicken-on-a-stick while the kids went for the viral pasta made in a Parmesan wheel.

Dinner was at Lillie's Victorian - with it's over-the-top holiday decorations, it did not disappoint! We enjoyed holiday cocktails and dinner before heading to see some holiday lights. Reservations required! (My first choice, Rolf's, was fully booked by the time we made reservations. Self-proclaimed "the most festive restaurant in NYC," reservations open around Labor Day. Plan ahead!)

Festive decor at Lillie's

Festive drinks at Lillie's

We knew we wanted to see the Dyker Heights Christmas Lights, so we jumped on the subway and headed to Brooklyn. Lots of people book a guided tour to do this, but we didn't find it necessary. Doing it on our own was cheaper and provided way more flexibility - and the logistics were simple. There is a ton of information online about the best way to see the lights, I used this guide.

Cold... but worth it!

After the lights, we jumped back on the train to Rockefeller Center for our first look at the Christmas Tree.

Tip - stick Channel Gardens in your Google Maps for the perfect place to watch the Saks Fifth Avenue Holiday Light Show (every 10 minutes from 5-11P). Definitely worth the stop (we did it twice while we were there!)

Saturday, December 20 We were up bright and early to tackle some NYC sight-seeing. We started with a delicious breakfast at George's before jumping in line for the Statue of Liberty cruise. We had 830A security check-in tickets - we ended waiting about 30 minutes for a Ferry. We had secured Pedestal tickets, which we thought were totally worth it for a really unique view of Lady Liberty. (By the time we planned our trip, tickets to the Crown were sold out - next time! Plan ahead!).

Having Pedestal tickets afforded us some great views without the crowds!

Lunch was at Bill's Bar & Burger, a great casual spot next to the 9/11 Memorial & Museum which was our next stop. It was a sobering afternoon, but everyone agreed that it was a great stop.

We spent the afternoon at the Bryant Park Christmas Market (tip - if you want to ice skate, book ahead! You cannot buy tickets at the park) before meeting family for a delicious dinner at Serafina Always 61st. We were able to fit in a quick stop at FAO Schwartz. The line was about 30 minutes but the kids really wanted to experience the magic!

Family in NYC!

Sunday, December 21 We started our day at Grand Central with delicious donuts from Doughnut Plant.

This was a great way to fuel us to the top of Summit One Vanderbilt. Both kids declared this their favorite part of the trip, and it was truly an unforgettable experience. We booked the Summit Ascent (which included an extra climb in a glass elevator) - it was cool - but I don't think it was worth the extra cost. The main experience was the highlight.

A couple of tips for SummitOV - book the first ticket in the morning (8A). By the time we got there at 930, it was crowded and we had to be strategic to get good pictures. I imagine going up first would allow you to avoid the bulk of the crowds.

I would also suggest buying the photo packet when you buy your tickets online - you only need one per party. This allows you to download all the pictures they take - and provides access to professional photographers throughout the exhibit. The cost was minimal and it was definitely worth it!

After soaring to new heights, we were hungry and had delicious pizza by the slice at Artichoke Basille's (highly recommend) before hitting the line for Santaland at Macy's.

Yes, our kids are grown, but they were still excited while we waited about an hour to see the big man himself. The photos were great and the experience was a blast. (Tickets go onsale 6 days ahead of time at 630A and my experience was they sold out in seconds - definitely plan ahead!)

Our next stop was Radio City Music Hall, because no trip to NYC at Christmas is complete without seeing the Radio City Rockettes Christmas Spectacular (my absolute favorite thing in NYC during the holidays!). Our tickets to see Santa were at 1P and our Rockettes show was at 4P - this was perfect timing. We were able to explore Macy's before heading to the show.

We love Ellen's Stardust Diner and stop there every time we are in the city. This was the kids first time and they loved the singing servers. IMO, this is a must stop at any age! The wait was about an hour and totally worth it. We ended the evening wandering around Times Square before heading back to the hotel.

Monday, December 22 We started with bagels at H&H (Columbus Ave) before heading to the American Museum of Natural History. We had tickets at 10A (when they opened) and spent about 2 hours reenacting the Night at the Museum.

Lunch was amazing pastrami sandwiches at Pastrami Queen on 72nd before heading over to Central Park.

We booked a Central Park Pedicab Tour and the entire family enjoyed it. Our drivers stopped multiple times for photos and had told great stories about the park.

After our ride through the park, we strolled down 5th avenue to see the Christmas window displays for our sunset visit to the Empire State Building.

A few notes about this - after doing Summit One Vanderbilt, the Empire State Building was a little underwhelming. It is iconic, and the kids enjoyed it - but I'm not sure I would book it again. One summit (especially the one we saw) was enough. We did purchase skip-the-line tickets - which was great. However, we also bypassed some exhibits about the building, so if that's important - wait in line! We had an Italian dinner at Trattoria Trecolori. The location was great and the food was decent. We wouldn't seek it out in the future, but it worked for us before heading to see & Juliet at the Stephen Sondheim Theatre.

Everybody loved the show - highly recommend!

After the show, we quickly made our way to Rockefeller Center, where we had a prebooked 950P time slot for a photo with the tree (this was the latest time possible, and it was a tight fit).

I'm so glad we did it, we got some fantastic pictures with the tree with no crowds and no waiting! Definitely worth the rush and the $45! Sunday, December 23 We had flights around noon, which gave us just enough time to for last-minute bagels (our best of the trip) and a final stroll around the Grand Central Holiday Fair. We will remember this festive trip for years to come!