What to do in NYC at Christmas Time | Cashmere & Jeans (2024)

My mom and I just got back from NYC last week and we had the best trip ever! We’ve basically been planning for this our entire lives. Ever since I can remember, we have always talked about going to NYC together on a girls trip during the holidays, but we just never planned it. And out of the blue, one day, I had a thought. My mom will be turning 60 in January and what better way to celebrate than in New York this year. Something that we had always dreamed of doing together! Here is my complete guide on what to do in NYC at Christmas time- what we did, ate, saw and what to wear.

Side note-I’ve been to NYC a few times over the years. I use to have a job that was headquartered right in Herald Square that I use to travel to at least once a year. And then Kurt and I decided to go there to celebrate our first wedding anniversary. And I’ve never really been that big of a fan. I obviously kept going back, but the city is always so dirty and smelly and while I have a ton of fun, I’m always excited to get back to Chicago. Well, being there during the holidays has completely changed my mind about the city! They KNOW how to do Christmas! And everyone is so festive and cheerful and now I want to go back every year during the holidays!

What To Do in NYC During Christmas

• Rockefeller Plaza is an absolute must see! We went there every day, multiple times of the day. It was our favorite thing to do while there. There is this awesome energy that comes thru and it’s so infectious. You can only help but smile. While down there, you can’t miss the massive tree in all of it’s glory. One morning we grabbed a coffee from Ralph’s Coffee which is this adorable food truck and walked around. There is also ice skating down there which we decided not to do because it was a little chilly. If you do plan on ice skating, I recommend going early and during the week. The line can get pretty long.

one of the windows at Bergdorf’s. I sent this one to Kurt because he LOVES chocolate!

the Cartier building wrapped up like a bow!

• Shop down 5th Avenue: My mom and I both love to shop so naturally the first thing we did after we landed and got some food in our bellies was head to 5th Avenue to do some shopping! Just strolling down the street is so fun in itself too because all of the storefronts decorate and go all out for the holidays. I’ve never seen anything prettier than the decorations inside of Bergdorf Goodman’s. It was on a whole other level! And it wasn’t your typical holiday decor either. It was like a winter wonderland. Some of my other favorites to see were Sak’s, the Cartier building (they wrap their building up in a huge red bow), and Tommy Hilfiger.

the tree at the Palace Hotel

the tree at the Peninsula hotel

the Plaza Hotel Christmas tree

• See the Christmas decorations at the upscale hotels: The Peninsula had beautiful decorations and had this beautiful staircase that lead up to the tree. The decorations were to die for. But my favorite of all was at the Palace Hotel. They had this enormous tree outside in their courtyard that was unlike anything I had ever seen. It was so so pretty and you just stood there in awe taking it all in! If I was going to splurge on a hotel, this is where I would stay! And we got to go inside The Plaza too, which I will talk a little more under where to eat. You are only able to enter thru the lobby if you have reservations or are staying there or else no on else is allowed inside. Their tree was stunning! And matched their opulent ceilings and decor. It was unreal! Everything inside is very ornate and just simply stunning.

• Sak’s Light Show:The Sak’s decorations are so over the top, I don’t even know how to describe them! And every night at around 5 pm they have a light show where they play music and do different light changes on the front of the building. It is a must see! But do not go on the weekends! We had no idea what was going on, but Saturday when we were out shopping, we walked out of Sak’s around 4pm and was met by this huge cluster of people. I’m not even sure how we got thru the crowds because we were shoulder to shoulder and could barley move. We had to fight and push our way thru and were were laughing the whole time because we just couldn’t believe all of the people! People were already lining up to get a good spot for the light show. We were down there every night around this time too and Saturday night was by far the worst! Stay away!!! Monday was the best day because you could actually manage to walk around and see the lights. Try and go during the week if you can.

• St. Patrick’s Cathedral:This is one of the most beautiful churches I’ve ever seen. I was in awe! It is kind of sad how much of a tourist attraction is it, but regardless it is jaw dropping. We lit a few candles and said some prayers and sat down to take in all of the beauty. It was breath taking and also a really great place to relax for a bit if you need to get off your feet.

the tree at the New York Public Library!

• New York Public Library:We decided to walk to dinner our first night and stumbled upon the New York Public Library and I was so glad we got to see this because it wasn’t originally on my list! The library is breathtaking- truly gorgeous! The entire library is covered in marble, even the staircase leading up to the entrance is all marble. That night, they were getting ready for a wedding in the back and we peaked our heads in and it looked like it was going to be a stunning wedding!

• Grand Central Station:I’ve never seen this before so it was an attraction I really wanted to see. It was beautiful and so old school looking. We walked up onto the balcony and you were able to see the whole station.

• Walk around Central Park:We headed here after we had lunch at the plaza because it is right across the street. It’s so crazy to see all of these huge buildings and then out of no where there is this HUGE park right in the middle of them. We didn’t stay long because it was chilly and windy.

• Ralph Lauren Store:This was on my must see list because I had saw on Instagram how gorgeous it was! And it was even prettier in person. After we browsed in the store for a bit we ended up walking around in the neighborhood for a bit. It was all super high end stores, so it was fun to do some window shopping.
• Macy’s inHeraldSquare:I told you we were all about the shopping. We headed here because my mom was on the hunt for a pair of boots. I’ve never seen a store bigger than this one. I mean it just kept going and going and going. We spent a good thirty minutes alone on the women’s shoe floor. It was insane and everywhere we looked there was another section to look at.

• Top of the Rock:Kurt’s mom actually bought my mom and I tickets to Top of the Rock to celebrate my mom’s birthday which was the sweetest and most thoughtful gift ever! We decided we wanted to go at night to see all of the lights of the city. An elevator takes you up to the 67th floor of the building and the top of the elevator is glass so you see the elevator moving. Kind of scary and exhilarating all at the same time! There are three floors that you can go out onto and the top two floors are open to the sky, so it’s defiantly a little chilly and a little scary! But the views were unreal! And it was such a fun night. You don’t really realize how big the city actually is until you see if from that viewpoint.

• 9/11 Memorial Museum:We both really wanted to see this museum and we ended up going on our last day. You can buy tickets in advance and pick a specific time which makes it super convenient. I have actually been before when Kurt and I visited, but this is such a neat museum that I wanted to experience it again. It’s just crazy because I can actually relate to everything because I lived thru it all. And I remember seeing the news stories. We spent a couple of hours here but you can spend an entire day here if you really wanted to.

• See the Radio City Rockettes Perform:We didn’t originally plan on seeing this show, but our last afternoon we didn’t have anything planned so we decided to buy tickets. We bought tickets the same day so you get a little better price. And I’m so glad that we ended up seeing this show! When I was researching what to do at Christmas time this always came up. And I can see why. It was one of the most Christmas-y things we did on our entire trip! The show was amazing! I mean truly amazing. I can’t even begin to think how much practicing they do because everything was so uniform and perfect. And all of their costumes were just do die for and all of the music just put you in the Christmas spirit. We left with huge smiles on our faces!

• Times Square:Times Square is only a couple of blocks from Rockefeller Center and Radio City Music Hall (where we saw the Rockettes), so after the show we walked over there. It was just starting to get dark out and at one point I looked at my mom and said- it feels like they just turned the lights out on us. And then the sky lite up! I mean talk about lights!! They were flashing all over the place, people were everywhere and there were cabs driving all over.

• FAO Swartz:I am SO excited that we actually got a chance to go into the store!! It is located in Rockefeller Center and since we spent so much of our time there, every chance we got we would peak at the line to get in. Yes, there was a huge, wrap around line for blocks usually, just to even get into the store! Monday night at around 5pm the line didn’t look too bad so we decided to hop into line. And we only waited about five minutes. It was most likely short at that point because the Sak’s light show had just started and maybe also because it was a Monday night and around dinner time? We couldn’t figure it out, but I would suggest going around this time if you can! The store was awesome inside and I found so many cute things that I just had to have. I collect the holiday Barbie’s from every year. My mom buys they every year for me still to this day! So, we ended up buying it this year in FAO Swartz, which is such a cool experience.

Where We Stayed In NYC

We stayed at the Freehand Hotel in Gramercy Park and it was perfect. The location was only a short cab ride away from everything we wanted to do. The staff were all so pleasant and super nice. And while the rooms were super small, they were cozy, well kept and very clean. And when I mean small, I really mean small haha. We were glad we packed light because there wasn’t much room for anything. But we were hardly in our room at all and by the time we got back at the end of the night we were exhausted, so we fell right to sleep.

What We Ate In NYC

• We landed around 11 on a Saturday and by the time we got into the city and checked into our room, we were starving. So we went to the restaurant attached to our hotel, called Simon & the Whale and it was so delicious. They were still serving brunch so we split the breakfast sandwich and some yogurt with fruit and granola and it was out of this world delicious!

• Our first night we made reservations at The Smith, mainly because the food sounded amazing and because Smith is my maiden name! So we thought it was kind of funny! The place is an upscale bar type of restaurant and casual, yet still on the dressier side. We started with the potato chips covered in blue cheese dressing that are making my mouth water right now. And we split the short rib pasta which was out of this world good! Highly recommend this restaurant if you are looking for good food that won’t break the bank.

• We had high tea at The Plaza Hotel one day for lunch and it was quite the experience! I’ve never had high tea before so I was in my glory. All of the food was amazing! And it all looked so gorgeous you almost didn’t want to eat it. I tried a bite of everything they gave us! It was truly a once in a lifetime experience and I’m so glad we got a chance to experience it. If you plan on going, I would suggest making a reservation well in advance. And be prepared to pay a ton because it’s super expensive! I told my mom this is the most I’ve ever spent on food where I wasn’t drinking and it wasn’t a steak dinner! But in the end it was well worth it.

• My mom is a huge corn beef sandwich fan so we googled the best and ended up at Katz’s Delicatessen one night for dinner. The experience was very raw New York and I felt like a local that night. You ordered your food at the front and then sat down to dine. And let me tell you, it was an amazing sandwich. The corned beef was so thick and juicy and tender. So, so good! Luckily there wasn’t a line when we went, but I could bet money that this place gets super packed on the weekends for lunch.
• In the basem*nt of Rockefeller Center there are all kinds of quick restaurants and shops. We ate at one of the pizza shops one afternoon because we needed something fast and quick or else we would be late for the Rockette’s show! It was really good too and they have tables you can sit at around that overlook the ice skating rink, so it’s kind of cool to see. Another great place if you are in need of a quick place to eat is the basem*nt of the Plaza Hotel. It was filled with restaurants that all looked really good. We didn’t end up eating here, but we walked thru it and it’s another really great option if you don’t want to go to a sit down restaurant.

• Rolf’sis an absolute must if you are headed to NYC during the holidays. As soon as I booked our tickets and we knew what dates we were going to be there, I called and made a reservation for dinner. The entire ceiling of the restaurant is completely covered in Christmas decor. And I mean over the top light, ornaments, icicles, etc. It was very gaudy! I wasn’t expecting the food to be good after reading reviews, but we were pleasantly surprised! It is a German restaurant and we even had a German waiter with an accent! My mom ordered sausage and I had chicken schnitzel and we ate as much as we could (the portions were huge). We were defiantly a little annoyed considering we had a reservation and had to wait outside for a good thirty minutes before our table was even ready. But I will admit, once we were inside, it was all worth it! And if you end up staying at the Freehand where we stayed, Rolf’s is only three blocks away. We ended up walking home from dinner that night.

What to Wear in NYC in December

Jacket: J.Crew | Scarf: J.Crew | Hat: Amazon | Jeans: Rag & Bone | Shoes: J.Crew | Bag: Senreve

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I was not expecting it to be as cold as it actually was! When I looked at the weather, it was going to be high 30s and sunny. And in Chicago, that usually feels like a heat wave, especially when the sun is out. I didn’t expect it to be as windy as it was there either. So make sure you dress in layers- lots of layers!

I ended up wearing a lighter winter coat, but would have preferred my warm Canada Goose jacket, especially in the morning hours when it was still super chilly. By the afternoon it always warmed up and was more bearable. And you will defiantly need a scarf, hat and gloves to bundle up in. As well as warm, comfy shoes because you will do lots of walking. I look like I wore the same outfit every day haha, but I swear I showered and changed every morning! It’s just because we were always bundled up in our jackets.

I really can’t wait to go back, especially during the holidays. This trip might be my new favorite tradition that I just started!

xoxox Amanda

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