{Trip Report} Winter in New York City

Cheers to Friday, friends! Thanks for all your fun and kind comments on this week’s posts…they really helped get me back in the swing after our Spring Break. Although, I can’t think of a time I was more ready for the weekend…or rather, ready to sleep in a bit! I love the later light, but adjusting to Daylight Saving’s Time is no joke!

I’ve started organizing our pictures from last week’s trip to Montana and Wyoming, and can’t wait to show you…but first wanted to share the quick trip to New York Mr. SP and I took last month. We’ve both been to NYC several times on our own (I was there three times just last year!), but never once have we been together. I always have a great time there, but was especially excited to experience the city with him, and during Winter.

Hi Sugarplum | Winter in NYC

We were there over Valentine’s weekend, which also ended up being the coldest weather on record for the city. Or something like that. #exaggerator Listen, when it dips below 40-degrees, it might as well be the North Pole because it all feels frigid to me! #texasweenie

I’m not going to lie, I was a little nervous about just how cold it would be, and unsure of what and how to pack! I even called my favorite cold-weather dweller for advice and a pep talk. Sure it was cold, but it didn’t stop us from having a ball…we just spent more time in coffee shops, cafes, and cabs than we might normally would. Not a bad thing, right!?

Hi Sugarplum | Winter in NYC

During our four days, we got a little bit of everything Mother Nature had to offer…snow, rain, sun, and both freezing and mild temperatures. It was glorious to see the city in each condition, and sometimes it felt as if we had the place to ourselves. 
Since it was both Valentine’s Day and our first trip there together, we went all-out with as many quintessential New York experiences as we could squeeze in a long weekend. Well, except the ones that required long stretches of time spent outside (I’m looking at you, Staten Island Ferry). 

Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC
Hi Sugarplum | Winter in NYC

Style Tip: Turns out fur lined hoods are not only cute, but seriously block the wind and snow. Stylish and functional = winning!

Hi Sugarplum | Winter in NYC

Fun Fact: There are 15,000 of these red fire call boxes around the city, some dating back to the late 1800s, and most still fully operational. In fact, during the mayhem of September 11, 2001, they were one of the only communication methods still working that day. Funny I’d never noticed them before, but now that they’ve been pointed out, I saw them everywhere!

Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC
Hi Sugarplum | Winter in NYC
Style Tip: To stay warm, but still relatively stylish, I started with fleece tights and silk thermals under my jeans and shirts, then layered on striped turtlenecks and wool turtleneck sweaters. Then add wool socks, hat, weather-resistant boots, and a sturdy, but fitted coat. And when the cold finally creeps through, stop for hot chocolate!
Hi Sugarplum | Winter in NYC
Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC

Mr. SP had never seen a Broadway musical, and kind of poo-pooed the idea. So we first saw, Blackbird, featuring Jeff Daniels and Michelle Williams…a very serious two-man play about a very uncomfortable subject. Essentially, they’d carried on an affair when he was 40 and she was 12. And the play is their confrontation 15 years or so later. I avoided eye-contact with the sweet little lady sitting next to me when it was over. And pretty much everyone else in the theatre. But the acting was mind-blowing.

Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC
Hi Sugarplum | Winter in NYC

Travel Tip: The cheapest way to experience some of the swankiest, moodiest bars in town is to pop in mid-afternoon for just the price of a cocoa or coffee. The cold gave us a great excuse to try this out several times! I especially loved The Bowery.

Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC
Plaid Scarf | Sweater (on super sale) | Jeans | Faux-Fur Parka | Similar Boots | Sunglasses

I even layered multiple pairs of tights so I could wear my fun dresses to the theatre at night…topped with a colorful coat for more style and warmth. 

Hi Sugarplum | Winter in NYC

I got my musical fix with Something Rotten…a hilarious rip on musical theatre with over-the-top costumes, singing, and dancing. Even Mr. SP was cheering and whistling at the end. We love, love, loved it!
Travel Tip: If you see better seats available, try to move down during intermission. Many ushers don’t mind since they’d rather have the seats closer to the stage filled.

Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC
Striped TeePlaid Scarf | Sweater (on super sale) | Jeans | Faux-Fur Parka | Sunglasses
Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC
Plaid Scarf | Sweater (on super sale) | Jeans | Faux-Fur Parka | Similar Boots | Sunglasses
Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC

Travel Tip: I’m a big fan of Uber, but we fell victim to massive surge-pricing on several occasions while there (I’m talking $47 to go 10 blocks!), so started using regular yellow cabs instead. They never have surge pricing and all cars accept credit cards now!

Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC
{Where We Stayed}
This is most-definitely my favorite hotel I’ve stayed in New York thus far, and easily in 
my Top 5 of all hotels we’ve stayed worldwide. It’s the perfect blend of cool & cozy, 
with impeccable service, friendly staff, & tons of extra touches that made our stay seamless. 
The location is two blocks from Central Park, cabs were plentiful, & the rooms a great escape 
from the loud, busy streets of the city. Not to mention, reasonably priced for NYC! 
Seriously, I wouldn’t hesitate to recommend this spot to anyone!
Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC

{What We Loved}
*Foods of New York Tours ~ I did the food tour of Greenwich Village last Spring & couldn’t wait to do the Nolita Tour with Mr. SP! We are not organized tours kind of people, but these are amazing & we had a blast. It’s typically a small group of 12 food-loving people (so you know they’re fun!), led by a laid-back, knowledgable guide. They walk you through your chosen neighborhood, pointing out fun facts & history, all the while stopping in the best food spots for 20-30 minutes at a time. Each restaurant has a table prepared & immediate food service just for your group, so it feels very VIP. It’s the absolute best way to learn about & explore your favorite neighborhoods, not to mention, discover amazing restaurants. We always end up going back to one or two of them at a later time.
*911 Memorial ~ An incredibly emotional experience, and one you won’t regret. I wasn’t exactly looking forward to reliving 9/11, but also felt spending a few hours of my time here was the least I could do to honor all those lost loved ones. I recommend starting with the short movie in the theatre…it’s a really well-made documentary that brings back the emotion of that day & helps set the tone for everything you’ll see in the museum. It also saved time by making reservations.
*Broadway Shows ~ I’ve never seen a bad Broadway show, but I’m an easy critic. I used both Broadway Box & Theater Mania to book discounted tickets prior to our visit.
*The High Line ~ The city converted an old freight rail line into a lovely park that is elevated above the street level, and runs for many blocks. It’s also got great views of the harbor.
*Walk the Brooklyn Bridge & explore Brooklyn Heights neighborhood (then take a cab or subway back because it’s far!)

*The Plaza Food Hall ~ The lower level of the swanky hotel is open to the public & full of fun, inexpensive food counters.
*Museum of Modern Art Rooftop Bar ~ Easily one of the loveliest views of the city, and it’s free!
Hi Sugarplum | Winter in NYC

Hi Sugarplum | Winter in NYC

And of course, food was a huge part of the weekend for us…so much so, that I’m working on a separate NYC Eats post. You can find some of my favorite restaurants, along with more fun New York experiences, and additional hotel reviews in my NYC Street Style + Guide. And since it’s almost Spring, this Packing for NYC in Spring post might come in handy, too.

What’s your favorite New York City experience or memory? I know I’ll never forget this visit with my Valentine, and hope it’s only the first of many! Happy weekend, lovebugs!

{Weekend sales worth checking out}


Nordstrom // Tons of end-of-season markdowns!
World Market // Up to 50% off all Dining Furniture
GAP // Save 40% off with code MY40 (including my fave new striped popover top!)
Old Navy // Save 30% off $75 with code ENJOY
Pottery Barn // Up to 60% off all Easter
Loft // Save 40% off all sale styles
J.Crew // Extra 30% off spring styles with code SPRINGSTYLE

Leave a Comment

35 Comments

  1. Meghan wrote:

    My husband works in NYC and while we've been so many times, I still love doing the touristy thing! I definitely want to do a food tour now! And I love that you dressed up for the theater, but honestly did you feel overdressed? The theater has become so casual lately!

    Posted 3.18.16 Reply
    • We saw a little of everything…but since they were evening shows, it did lean a little dressier. But you're right, you could definitely go either way. I like to err on the side of overdressed most times, and honestly, loved an excuse to get really dressed up!! Made the night so special! Especially since you spend a small fortune on show tickets!! 😉 xo

      Posted 3.18.16 Reply
  2. How I love New York City! We went the first time two years ago for our 25th anniversary and last year for our daughter's high school grad trip. It was so wonderful seeing your photos. I hope we can go back again soon!

    Posted 3.18.16 Reply
  3. Ive always wanted to visit NYC! looks like you guys had a really fun trip!

    FYI- i just want to let you know that Eskimo is not the proper word for the Inuit people. It is seen as derogatory…

    Posted 3.18.16 Reply
    • Oh yikes, I had no idea! Thank you for telling me!

      Posted 3.18.16 Reply
  4. That was the coldest weekend!! Brrrr!!! I love going to Bway shows, I've only been to musicals, no plays yet. That one sounded intense but amazing. Love these style posts. NYC is so much fun–any time of year!

    Posted 3.18.16 Reply
    • I also forgot to add that my favorite things to do are explore Central Park and Bryant Park is really nice too!! Walking is the best as I do not like the cabs, they make me carsick and scared for my life. I prefer the subway but always go with people who know how to navigate them!! Chelsea Market, Brooklyn Flea and Schmogasberg in Brooklyn is fabulous!! Taking the boat tour is a great way to see the sights. We still haven't done Staten Island Ferry either! Broadway show then strolling through crazy Times Square…the food everywhere!

      Posted 3.18.16 Reply
    • I've done several of these and loved them too…the rest I've added to my list for next visit!! xo

      Posted 3.18.16 Reply
  5. I was there in December for a work conference (brought husband with me and then stayed a few days extra since it was also my bday weekend) and the weather was warmer than it was here in Dallas. Stayed in Times Square the first night as that's where the conference was, but then when it was on our own dime, we moved over to the East Village and rented an apartment through Home Away/AirB&B. I highly suggest this as my #1 travel tip. You get a very authentic feel for the city, and the prices can't be beat ($160/night for a precious East Village apartment). Plus, I always say the EV is my favorite place in NYC due to its easy-going vibe and funky little cafes, pubs and shops. 🙂 And from there, you really can walk the entire island – weather permitting (as we did – from EV to Central Park down to Battery Park and back up through China Town and Little Italy). We only take cabs to and from the airport and get lots of steps in when we visit. I really love NYC and think it would so awesome to live there, but I'd miss Texas too much. The struggle is real… haha

    Posted 3.18.16 Reply
    • Love the Air B&B idea…will def have to look into that next time! We typically walk everywhere when we travel too, but it was just too cold to walk long distances this trip!!

      Posted 3.18.16 Reply
    • Jennifer Swanson wrote:

      Cassie, great recommendations! I kept this post on file for more than two years, in anticipation for my two trips to NY in 2020. The first – girls trip! My mom, sister, niece and I enjoyed dinner at Otto tonight. Delicious!
      Please update your link to the rooftop bar (referenced as the best site of the city, and free!). After a long walk yesterday to the MOMA, we learned that what you likely referred to was the rooftop at the Metropolitan Museum of Modern Art, not the MOMA. The MOMA has only a 6th level cafe, which requires a ticket. What a disappointment!
      I’d like to recommend Room Service as a delicious, reasonable Thai restaurant. Beautiful decor.
      Thanks for the other great recommendations!

      Posted 1.18.20 Reply
  6. I really love your travel posts! It's so great to see others food favs and unique places to stay from other travel lovers. The only time I've stayed to visit NYC was back when my family went to Bermuda for Christmas and we had a day long layover in NYC so we did a van tour as a family. I think I was 11 years old? This is a sad thing too because I live in Boston! I should be able to get my tush back down there and I haven't yet!

    Posted 3.18.16 Reply
  7. Kristen wrote:

    Looks like a great trip! I always enjoy your trip reports. We went to NYC a few years ago around Thanksgiving and I'm wanting to go back for a visit in the Spring or Summer. I feel like the seasons change the city so much!

    Posted 3.18.16 Reply
  8. The Tenement Museum is really interesting and then you have to get cookies from Ferrara Bakery in Little Italy!

    Posted 3.18.16 Reply
  9. How does the faux fur jacket run?

    Posted 3.19.16 Reply
    • It runs true to size for me…I'm wearing an XS and had plenty of room for sweaters under! xo

      Posted 3.21.16 Reply
  10. Love this! Have you been to Chicago? I have a girls' trip in June and I want an inside scoop. 😉

    Posted 3.19.16 Reply
    • Dana Ivy wrote:

      I'm from Chicago!!!! Maybe I'll write a post for what you can do on a girls trip on my blog! Best city in the world!! Xox Dana Ivy // http://www.iadorewhatilove.com

      Posted 3.19.16 Reply
    • I went to Chicago about 10 years ago and LOVED it! I think I might be due for a repeat trip!! Would love to see some posts about it! xo

      Posted 3.21.16 Reply
    • Yes! Please do!

      Posted 3.21.16 Reply
  11. Dana Ivy wrote:

    Love New York anytime of year!!!!! No matter when I go I always get that giddy and excited feeling inside!!

    Xox Dana Ivy // http://www.iadorewhatilove.com

    Posted 3.19.16 Reply
  12. I have never been to New York but your tour really made me feel like I have been now. btw…I featured your blog on my shout out saturday post today as one of my favorite fashion blogs. Have a great and warm weekend.

    Posted 3.19.16 Reply
  13. Susie wrote:

    Cassie, You rocked NYC Susie

    Posted 3.19.16 Reply
  14. Winter in the NYC is nice but summer is awesome and this post makes me miss it even more!

    Posted 3.19.16 Reply
  15. Hope it was as fun as you've made it look. You really captured the essence of New York in your pics.

    Posted 3.20.16 Reply
  16. Lisa B wrote:

    Hi Cassie- love your blog! I also check your instagram too…but I do not have insta myself. Do you have to have instagram to use liketoknowit? Can you explain here for those of us who do not "get it"?! Thanks. xo

    Posted 3.22.16 Reply
  17. I think I could go over and over and never have the same experience! So loving all this info.

    Posted 3.22.16 Reply
  18. Erin wrote:

    OH my gosh. Your layering is cracking me up. I would have just worn jeans, a sweater, a winter cost and hat she gloves walking around at that time. #chicagonative :0)

    Posted 3.25.16 Reply
  19. New York is one of our favourite places in the world. We r from the UK so it's a big expense but we have now travelled as a couple (pre-kids) and with a 11 and 8 year old. We were determined to share our love of the city with our children as soon as we felt they were old enough to appreciate it. The children were blown away by the place and we are all desperate to find an opportunity to go back again. I blogged about doing NYC with kids at http://homeheartharmony.com/2014/09/27/our-new-york-adventure/ Loved hearing your tips, the food tour definitely sounds like one to put on the list for a future trip and we will definitely be booking a Broadway show too. Thanks for sharing xx

    Posted 3.27.16 Reply
    • Loved your post!!! Thanks so much for sharing, Sue!

      Posted 3.27.16 Reply
  20. I really appreciate your post and sharing your beautiful moments with us. I love NYC its all time favorite place. And I’ll love to read your next post too.

    Kim | http://www.condorny.com

    Posted 3.29.16 Reply
  21. I was really surprised that one of my favorite places there was the Highline Park. I could have stayed there all day! Glad you had such a wonderful trip!

    Posted 3.31.16 Reply
  22. We went to NYC last summer, it was very hot and humid but we still enjoyed our trip. We’ll definitely consider going to NYC in winter. New York City may be known as the most expensive city in USA, but there’s also no shortage of free things to do. I already visited some museums, Time Square and Statue of Liberty. We also went to a lot of diners and clubs and I watched free concerts at Central Park after checking out the NYC Parks website. By the way, I found a website listing free events in New York which is great because I didn’t have much of a budget. I think FreeEventFinder.com might be useful to people also visiting New York who are looking for free things to do.

    Posted 5.24.16 Reply
  23. Tania Edwards wrote:

    I loved your post. As someone from Australia, who will be going to NY in winter this has really helped. Are you able to link what your hubby wore ie:shoes, tops etc or even ideas. Thank you

    Posted 4.28.17 Reply
    • Cassie wrote:

      Check my posts from our recent trip to National Parks…he packed similar stuff to that!! xo

      Posted 4.29.17 Reply