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Several months ago, my sister pitched the idea to me to go on a sister trip to New York in December, to experience Christmas in the city. We had been together before, but it was 14 years prior and during Thanksgiving. Experiencing the Macy’s Thanksgiving Day Parade in and of it self is a bucket list item, but I had heard Christmas in NYC was just as magical (if not more so) and jumped at the chance. I was able to find a pretty cheap flight from LA and that was that. We started planning! We spent 5 days there and I could have added 2-3 more days easily to experience everything the city has to offer during this time… one of those being a rest / spa day. Trekking around New York City is not for the faint, that is for sure!

Keep reading to see what we did, where we ate, and what I would want to do next time! If you want to see the quick travel recap video I did, click here.

Central Park

As I mentioned, I went with my sister to New York, but it wasn’t just with her. Her best friend and one of her sisters joined us as well. Emma B. (Maggie, my sister’s bestie’s sister) travels to New York a lot, so Emma P. (my sister) told she wanted her to take her. I talked a lot with Maggie over the last couple of years because of my sister’s engagement, so the joke is that the Emmas let us tag along. We all came together from different cities (Los Angeles, Dallas, Houston, Austin) and made the trip work.

5th Avenue

Times Square

OUR ITINERARY

Here’s what we did! Emma B. started the itinerary for us on a shared group note on our iPhones and we filled in from there with random things we wanted to do and places we wanted to eat. If you are stumped on where to start, try focusing areas you’d like to visit (ie Brooklyn) and planning out what you want to do in each spot. Note that we had already done things like The Statue of Liberty, Ellis Island, etc so we didn’t use our time to experience those things. My suggestion is to not focus on those things in December if you go, as you can do those any time. There are certain things you can only do during Christmastime, so I would prioritize those if you travel there in December.

I’ll share what we did in paragraph form, but I’ll make a bulleted list at the very bottom if you prefer a brief synopsis or want a good reference.

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Lillie’s Victorian Establishment

THURSDAY

I took a redeye flight from Los Angeles to Newark on Thursday evening. The original thought was to take meetings / work from NYC while I was waiting for everyone else to get there. I did do some work, but I was also really tired… I’m still glad I got there early, but I would lower my expectations around my productivity after a redeye in the future. I will say that we got to check in early because I arrived so early / before the rush. I was able to get us on a list before anyone else, as you can’t always get ahold of the front desk to request that morning. This is also a great workaround to not paying for early check in, as you are physically the first one there to get a room.

FRIDAY

I suppose I could have found somewhere cool to work and explore, but I decided to go straight to the hotel to. make the best of traffic from Newark. I know that I could have done the bus and the subway, but I was tired and just forked over the money for a Lyft. We stayed at Crowne Plaza Times Square. We actually initially booked The Row Hotel in Times Square, but they cancelled on us without explanation less than 2 weeks before our event. I had to stay on them and call / email frequently, but I was finally able to have them rebook us at The Crowne Plaza. Times Square isn’t my favorite location, but it was a centrally located spot. It was hard to find a hotel that had two beds and allowed 4 people, so our options were limited. My first choice was The Mondrian on Park Avenue, but we decided to go with the one that was a little bit more budget friendly. I walked to Toribrow Ramen for lunch (I got the Toribrow special) and by the time I made it back, my room was ready for early check-in. This was around 1 :00 pm. Also note that they said they would call me when the room was ready, but never did. I just went back to the hotel and got inline to speak to someone. When I got to the front of the line, they said it was ready and gave me my keycard no problem.

Once my sister arrived, we grabbed a snack (lol mozzarella sticks) at The Playwright Celtic Pub near the hotel, then went to Chinatown for an event. Initially we were going to go see the 9/11 Memorial Pools because sister hadn’t seen them before, but we went the wrong way on the train (don’t worry, we caught it pretty early) and decided we didn’t really have enough time to do it and be back for our 9:00 pm reservation.

Finally, the rest of the group arrived and we walked over to Lillie’s Victorian Establishment. It is super cute and I’m glad we went, but it was a little disappointing, because they weren’t decorated for Christmas yet and that is one of the reasons we went there. We went December 2nd, so you would think it would be up, but only the Union Square location was decorated for Christmas at that point. The Times Square location was decorated by December 9th. Keep that in mind if you want to go when it is all Christmasy! We split the chicken sandwich, fries, and some brussels sprouts. Everything was good, but the brussels were our favorite. We grabbed another drink at a nearby bar that I do not recommend, and then got some late night Joe’s pizza to really get in the spirit of NYC.

The Music Man with Hugh Jackman and Sutton Foster

SATURDAY

We hit the pavement running with an early brunch reservation at The Waverly Inn. Make sure to request to sit inside in the courtyard. They consider it inside, not outside. It’s super cute and homey. Get the breakfast sandwich. It comes with chips and they were yummy, but I the fries looked so good, I think I would want to swap for those when I go again.

Next we walked to Chelsea Market. If you have ever been to the Dairy Mart in Denver it is a similar feel to that, but much bigger. It is this array of shops and restaurants inside where the Oreo cookie was created. Even if it isn’t Christmastime, it is a fun place to browse. They let you walk around with drinks (yes even alcohol), so grab a beverage and go for a stroll. We bought the most at the Pearl River Mart - it was a fun, Chinese market that has been around since the 70’s. We all split a bowl from Very Fresh Noodles and it was fantastic. Very much worth the wait if there is a line. If we were hungrier we would have tried Miznon as well.

It was rainy this day which actually worked out in our favor since most of what we did was indoors; however, it let up by the evening. We took advantage of this and walked to Washington Square Park and rested for a bit on a bench there. We decided to get a pre-dinner drink at The Garret next. It’s a speak easy above a Five Guys and is always busy, but fun. Even when I went back in 2017, it was hopping. It made me happy to see it so busy post-covid! We quickly walked to Olio e Piu from there for dinner and was seated at the prime spot by the Christmas tree. Not to mention it was cozy and the Bolognese was delicious. For dessert we went to Van Leeuwen Ice Cream. I can actually get this in LA, but it is made in Brooklyn, so I didn’t mind double dipping. I typically liked to visit places I can only get there.

Summit One Vanderbilt

SUNDAY

This morning we went to Black Fox for coffee which was wonderful. I bought a bag of beans to bring home to Nick! It is more of a craft coffee place than a specialty place (meaning they focus on coffee quality than pizzazz), but hey do offer cappuccinos, seasonal lattes, etc.They also had food, which looked pretty yummy, though we did not partake. We left a little late this morning and did not have enough time to stand in line at Essa Bagel. We went and stood in line for a second, but because we had morning reservations where the time slot was important, we didn’t want to risk. it. We grabbed bagels at Zucker’s Bagels instead which was the right decision, because we barely made it to next location on time.

We spent the early afternoon at Summit One Vanderbilt. As someone who had experienced The Empire State Building and One World Trade Center, it was still worth it and arguably has a better view. You need to buy tickets for this ahead of time and you should aim to get there on time if not early. It took a while to stand in line and get through the madness, even with tickets so plan your time wisely. Our slot was at 11:00 am, but we didn’t get in until closer to 12:00 pm. Grand Central Station is nearby, so we walked around it for a bit, because it feels even more special during Christmas.

We rushed from Summit to go see our respective Broadway shows. My sister and I saw The Music Man with Hugh Jackman and Sutton Foster at the Winter Garden Theater. We loved it! Our friends saw Funny Girl with Lea Michele. They said it was amazing.

We spent that evening in Brooklyn. We rode the subway from Manhattan and got a drink at Bohemian Bar in Brooklyn. I wouldn’t recommend how we structured our night / it is just how it worked out with our reservation. It was great, it just involved a lot of back and forth. We caught a ride from Cobble Hill to go to Williamsburg for dinner at Bonnie’s and it was delicious. If you want a cocktail get the lychee fizz and ask for a shot of gin. Our favorite dish was the pepper steak with crunchy noodles. This is hard to get a reservation to get which is why we had a 9:00 pm slot - another option we considered was Antidote. We then went back to the Cobble Hill area and had a drink at Elsa bar. We tried to get late night pizza at Lucali, but they ended up closing early. We wanted to see the Christmas lights in Dkyer Heights, but at the end of the night we were too tired and further away from them than we meant to be. We also were being mindful of the subway times and getting home.

Rockefeller // Prince Street Pizza

MONDAY

We began the day with brunch at Sarabeth’s. I love the quiche! After that we strolled around Central Park, which I can never spend enough time doing, especially during this time of year. We did stop and look at Wollman’s rink, but we didn’t skate there. We walked to Alice’s Tea Cup (Chapter 1) for lunch and it was so cute and fun. It was one of those places I have had on my list for a while and finally went. I had the Merry Unbirthday Tea and Emma P. and I split a curried egg salad sandwich. I was disappointed they didn’t serve chips with the sandos, but omg do not sleep on their salad because it is DELICIOUS. It has a peanut vinaigrette of sorts which sounds interesting, perhaps a bit out of place at a tea room, but honestly it was the star of the show.

Alice’s is a short walk to Levain Bakery, so we grabbed their famous cookies (get the double chocolate peppermint if you’re there in December) and made our way over to Rockefeller Center to ice skate. Make sure to buy your tickets in advance and arrive on time to make the most out of your time slot. It’s iconic and so fun. Since we were so close, we used this time to check out the beautiful decorations on all the stores on 5th Avenue. Chanel was probably my favorite, but Cartier was gorgeous too and you can’t beat the Saks light show. FAO Shwarz is nearby if you want to drop by the famous toy store as well.

We had a little break and used this time to catch the subway to the 9/11 Memorial Pools since by sister hadn’t seen them before. We didn’t have time for the museum, but I’d like to do that in the future.

From there we caught the subway to Union Square and shopped their Holiday Market. One booth we stopped at was Rubyzaar Baked for the viral Smores Hot Chocolate. Prince Street Pizza was on our list of to-do’s and was our favorite pizza of the trip. It is walkable from Union Square. The spicy pepperoni was our favorite, but the spicy vodka was a close second. They have a location in Los Angeles, that I plan on taking Nick to. We had that as a pre-dinner snack, because we had plans to have drinks at Attaboy before dinner. They don’t take reservations and it is pretty small, so we got there as close to open as possible. WORTH IT. Amazing cocktails and service. They were $25 a piece which I admit is high, but for the quality of ingredients and their custom way of doing it, I would even pay $27 - $30 per. Or maybe that’s just LA prices rubbing off on me ;)

For dinner we went to a cozy little stop on Bond Street called Il Bucco and ended the night with Gelateria Gentile. They have another gelato location in Brooklyn if you find yourself over there.

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Aritzia

TUESDAY

Our last day!! We made sure to book later flights, so we could still enjoy most of our time. We grabbed coffee and tea (I had quiche too) at Maman, which is a darling coffee shop. Next we had bagels at Baz Bagels where they make really pretty (and yummy), tye-dyed bagels. It’s not their OG Brooklyn location, but there is a Catbird next door to the bagel place and I got another permanent bracelet added to my wrist.

We could have taken the subway, but we ended up just walking to Chinatown and browsing shops along the way. Coming Soon and Sweet Pickle Books to name a few. We had lunch at Nom Wah Tea Parlor. You need reservations! It was all good, but there was a beef noodle dish that was our favorite. We walked to Soho next just to enjoy the shops and sights. Honestly we were so tired at this point that we went to the top floor of Aritzia to grab a free coffee / hot chocolate and relax for a minute.

After that, I split off from the group, because I had to make my way to Newark to fly out. I took the subway by myself to get back to the hotel to pick up my bags (the bellmen held it for me), but got off one stop early. I just had to see Macy’s Herald Square to glance at the window displays and all of the lights and I’m so glad I did. It was the perfect cap on my trip.

Macy’s Herald Square

As promised, here’s a bulleted list of our travels:

WHERE WE STAYED

Crown Plaza Times Square

WHERE WE ATE

Toribrow Ramen (Times Square)
Playwright Celtic Pub (Times Square)
Lillie’s Victorian Establishment (Times Square, also has a Union Station location)
Joe’s Pizza (Broadway, has other locations)
Waverly Inn (West Village)
Very Fresh Noodles (Meatpacking District, Chelsea Market)
The Garret (Greenwich Village)
Olio e Piu (Greenwich Village)
Van Leeuwen Ice Cream (West Village, has other locations)
Black Fox Coffee (Midtown West, has other locations)
Ess-a-Bagel (Midtown East, has other locations)
Zucker’s Bagels (Garment District, has other locations)
Bohemian Bar (Cobble Hill)
Bonnie’s (Williamsburg)
Elsa Bar (Cobble Hill)
Lucali Pizza (Cobble Hill)
Sarabeth’s (Central Park, has other locations, make sure it has food / not just bakery if that is what you’re looking for)
Alice’s Tea Cup (Chapter 1, Upper West Side, has other locations)
Lavain Bakery (Upper West Side, has other locations)
Prince Street Pizza (Between Soho / Bowery / Lower Manhattan, Little Italy, 1 NYC location, also has 1 in LA)
Attaboy bar (Near Little Italy)
Il Bucco (Bond Street / Bowery)
Gelateria Gentile (Nolita, has other locations)
Maman Coffee (Little Paris, multiple locations)
Baz Bagels (between Lower Manhattan and Chinatown)
Nom Wah Tea Parlor (Chinatown, multiple locations)

WHAT WE DID

Chelsea Market
Washington Square Park
Summit One Vanderbilt
Grand Central Station
Broadway Show
Central Park
Rockefeller Center / Ice Rink
5th Avenue Shops
9/11 Memorial Pools
Union Square Holiday Market
Catbird
Coming Soon
Sweet Pickle Books
Soho Shops
Macy’s

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Bohemian Bar

WHAT I WOULD DO DIFFERENTLY

We had a great itinerary, but I would make sure we have enough time to wait in lines / transport / make sure shops are open better in the future. There’s also a balance of planning things out and leaving on time while not feeling rushed or overwhelmed that I’d like to achieve too.

WHAT I WANT TO SEE / DO THE NEXT TIME I’M THERE DURING CHRISTMAS

Rockette’s Show
Dyker Heights Christmas Lights (Brooklyn)
Rolf’s (Christmas bar, no reservations)
The Mark Hotel (decorates splendidly for Christmas)
Tavern on the Green (would like to go regardless, but especially at Christmas)
Ride the special Christmas subway car (we saw it, but didn’t ride it - it’s a pretty red train and is decorated for the season and only runs certain times.)

WHAT I WANT TO EXPERIENCE THE NEXT TIME I’M THERE REGARDLESS OF SEASON

Ess-a-Bagel
Lucali Pizza
More Museums (I’ve done them before, but always love them)
Tea at The Plaza
Carbones
More time at Central Park
Family Meal (Nick and I ate here under the Blue Hill name. We’d love to go back and try it rebranded.)
9/11 Museum
Polo Bar
Loeb Boathouse (I’ve seen it, walked past it, but never dined. It’s currently under construction.)

Grand Central Station // Chelsea Market

TIPS

Trains and walking will get you further faster than any cab or rideshare can at peak times
You can use apple pay for train instead of loading a metro card/its the same price $2.75 per ride
Watch the weather closely. It actually wasn’t really cold when we were there. In fact, the year we went for Thanksgiving was colder than it was this trip. It all just depends!
Pack light - hotel rooms are small. We didn’t go back to the hotel at all during the day to make the most of our time, so I dressed appropriately for the entire day and only brought one outfit per day. I carried on a hard suitcase and a weekender bag as my personal item.
Even when packing light bring at least two pairs of shoes so you can alternate every other day. When you walk a lot, your feet get sore in even the most comfortable pair of shoes. I brought my docs and these waterpoof boots.
Include a rest day if you can or at least a partial rest day. A massage, or something along those lines would have worked wonders. We were so sore by the end.
Assume you need reservations / tickets for everything. A lot of reservations are on RESY. If you have an Amex platinum or above, create your account with it and you’ll get better reservation slots.
Split food! Yes we ate a lot, but most meals we split by 2 and sometimes even 4 ways depending on how hungry we were / if we just wanted to try something.
Check out the local guides. I should have looked more at this beforehand. I love following A Guy Named Patrick and trust all his recommendations. It wasn’t until after I got back that I remembered that I follow Yu of @FishsFlourish and she has tons of NYC travel posts, especially during Christmas.

Honestly I was tired from just writing this. Looking back I can’t believe we accomplished all that we did! If I had to pick a favorite day, I think Monday was it. Sunday is a close second. There are things I would do differently, but all in all it was a great trip and I’m so glad we went. I hope to get in another NYC Christmas trip sometime soon because it is oh so fun. Bon voyage!!