Christmas in New York City: Top Picks for a Holiday Weekend in the Big Apple

Top picks for Christmas in New York City

It’s December, which means one thing if you live or are visiting New York City — it is crazy busy! But I love all the energy and think it’s one of the best times to visit. A few months back, Kevin and his cousins concocted a fun idea: to hit up NYC for the first-ever “Cousin’s Weekend.” Which made me immediately want to channel my favorite Bridesmaid moment…

Okay, maybe we’re not that wild…. But we certainly packed in a full weekend! Here’s a fun-filled rundown of our favorite moments if you’re going solo or planning a family outing!

Day 1: Saturday morning

Kevin is excited to be in NYC for the holidays!

Kevin and I flew in on the red eye from Los Angeles, and I got ZERO sleep. I mean zilch. Our room wasn’t ready so we hit up a coffee shop where we quickly fell  asleep. I half expected to wake up covered in change and with sandwiches piled on top of me! We have no shame.

Ground Central Coffee shop in midtown is a great place to relax and unwind (or look homeless in our case!)

After the quick catnap, we met the cousins at TKTS in South Street Seaport to buy discounted Broadway tickets. The real secret about this location is that it’s significantly less crowded than the Times Square booth AND it sells Sunday matinee tickets. Double score! From there, it’s a 20 minute walk to Joe’s Shanghai in Chinatown.

The gang’s all here – chowing down on soup dumplings and Chinese at Joe’s Shanghai.

Joe’s Shanghai is perfect for groups and is on every itinerary I put together for New York City. A few things to note: there is always a wait, the staff is pushy, the health grade fluctuates (and not in a good way!). And the bathrooms? Don’t even get me started. If you can, hold it. It’s that scary. But the food here is amazing. And over 10 years of eating here, I haven’t gotten sick once (knock on wood!).

Afternoon: It’s shopping time!

Kevin loves a deal! Checking out the signs at the trendy shops starting in Little Italy to Soho

We got a lot of walking in! We planned a route that allows for plenty of breaks along the way. Oh, and the first of MANY dessert stops. Honestly, I haven’t had this much sugar in months. But it helped keep me awake after pretty much going non-stop.

Holy cannoli! The desserts at Ferrara La Dolce Vita in Little Italy are legendary.

It felt a little strange to order a brownie from the Little Cupcake Bakeshop in Soho. But easily a top 5 brownie of all time. A must stop!

We recommend starting the walking tour at the corner of Mulberry Street and Canal, heading North on Mulberry through Little Italy to Prince Street in Soho, which is lined with plenty of shops and cafes. Some of our favorites stops included McNally Jackson Store (which sold nothing but pens… only in New York), the MOMA Design Store (with this hypnotic clock we were obsessed by…until we saw the price tag of $7,000) and Studio Manhattan Art & Design (with unique nick knacks that make perfect stocking stuffers). Plus no trip could be complete for Kevin and the cousins without a good bookstore (also called McNally Jackson if it isn’t confusing enough!).

Pens galore at McNally Jackson! I clearly couldn’t hold back and bought one of the cheapest one for $2 (which seemed like a steal at the time but probably cost 50 cents in reality).

The cousins let everyone know we were here!

This pillow would be perfect for LA. Checking out the goods at Studio Manhattan in Little Italy.

I see you Kevin…. Seriously, you don’t need any more books!

Evening: Broadway!

Broadway bound, on the train up to the theater district in midtown

After plenty of walking, we grabbed a quick bite at Bare Burger (another good spot for groups), then headed up to the big evening event: seeing the musical Waitress on Broadway. I was shocked how quickly we all came to agreement on seeing this show. After all, 2 of the people in the group were on Broadway (seeing many shows) and the rest of us have seen a mixture of productions. Waitress was a crowd pleaser and starred pop singer Jason Mraz. Kevin had no idea who he was, but after several unsuccessful attempts of belting out his most popular song, I gave up. Clearly, Kevin was not a fan of the hit single “I’m Yours.” It couldn’t have been my singing… just saying.

Standing out front of the Brooks Atkinson theater where we saw Waitress

And finally, what better way to wrap off day 1 than more dessert!?  Yes, please. Cookies galore at Schmackary’s just blocks away from the theater.

The cookie monsters — Mmmm, give me cookie!

Day 2: Sunday Morning

Kevin and I got a quick morning workout in doing SLT Pilates (no rest!). Then hopped in an Uber to the Lower East Side to join the cousins for my first escape room experience at Mission Escape Games. So this was pretty intense and I’m pretty sure I was clueless a good 98% of the time. Though I did find a hidden key (you’re welcome everyone). This was clearly not the first escape room for the cousins as they flew through the room at breakneck speed. Most people don’t even escape.  If they do, it’s with mere minutes on the clock.  Not us! But my favorite moment was when cousin Claire jokingly cracked, “I think we should go professional guys.” And the guy working at the escape room replied, “I really think you have potential.” Who knew that was a thing?

We did it! My first escape room experience.

Sunday Early Afternoon: More snacking and walking!

It’s been nearly 12 hours since we had dessert, so we seemed overdue for something. We hit up Doughnut Plant located just a few blocks away. I’ve said it before, but I’m really not a doughnut fan. But these doughnuts were no joke. In particular, the tres leches doughnut is worth a trip here from midtown alone. I sampled the others, and while they were all good, the tres leches knocked my socks off.

A doughnut in the shape of a flower

Just two doors down is a shop I’ve wanted to visit for years called The Pickle Guys. Most of the cousins didn’t jump on board with this. I guess pickles and doughnuts don’t really go together. It’s a little overwhelming at first — with all the workers inside wearing hoodies scooping out all things pickled from the plastic tubs that line one end of the room to the other. I basically just wanted a pickle. So I asked the guy to pick out his favorites.

Woo hoo, pickle picture! Okay, I went a little overboard on buying the pickles

From here, we got in some more walking.  Just 16 minutes away is the Canal Street Market. This is a new, trendy market with food stalls and a connecting shopping area. There is also a comfy lounge area in the back where we mostly hung out and caught up (while some of us perused the many stalls with very expensive items you definitely do NOT need but still wanted to buy anyway).

Food hall at Canal Street Market

Broadway Bound: Matinee time

You know it’s New York theater when the seats are so tight you’re almost on each other’s laps!

Our Sunday matinee started at 3 PM and rather than a musical this time, we saw “The Play That Goes Wrong.” I really enjoyed this show. It was so different from Waitress, but was pretty much 2 hours of non-stop laughs. I never heard of this show before. But once again, another good pick from the cousins.

Sunday night: Chelsea Market and High Line

Kevin digs into some tacos from the hip Chelsea Market

After the show, we took the subway to Chelsea Market, a massive dining hall with plenty of options to please anyone in the group. We all scattered where Kevin got Mexican and I got a Cambodian rice bowl (and again, I had no idea this was a thing and I’ve been to Cambodia).  There are sit-down restaurants and food stalls. So it’s a great choice for a group with varying degrees of hunger. After dining, we headed into the basement — following the NYC cousins to a hidden bar called The Tippler. It’s quiet — at least on a Sunday night. I always appreciate a bar where you don’t leave with laryngitis from shouting the conversation all night.

The Tippler, a speak easy basement bar at Chelsea Market

We couldn’t believe that cousin’s weekend was coming to an end. Kevin never visited the High Line, a 1.45-mile-long elevated park created on a former New York Central Railroad track on the west side. So we decided to check it out. The High Line is blocks away from the Chelsea Market so we bundled up in our winter coats and gloves and went for a chilly walk. At least we had a few drinks in us that warmed us up (kind of!).

We headed back North where we eventually made our way across Manhattan, stopping to check out the store front displays at Macy’s and their big set up for the Macy’s Day Parade (which I never miss!).

And while the night was still early (well, for New York) we all had to go our separate ways. Until our next holiday cousins weekend! And no matter where that might be, I’m sure there will be plenty of dessert! At least we got a lot of walking in.

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Christmas in New York City: Top Picks for a Holiday Weekend in the Big Apple
Article Name
Christmas in New York City: Top Picks for a Holiday Weekend in the Big Apple
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Christmas and the holidays are the best time to visit NYC! Check out our itinerary for a perfect weekend in NYC with the best bakeries, shops and Broadway.

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