The do’s and don’ts of a winter trip to New York: Flatiron District/SoHo/Greenwich Village/West Village/Chelsea/Upper East Side/Upper West Side/Central Park

Hey there Upper East Siders! Just kidding, you probably aren’t reading this from the Upper East Side; that’s why I’m recapping the do’s and don’ts for you! I am super excited about this post because if I could only live in one place for the rest of my life, it would most definitely be SoHo. From downtown to uptown, I have a lot to cover in this post, but these neighborhoods truly are my favorites in the city. While Midtown is great, and it is definitely a do, it can just be very touristy and congested. In the midst of all the hustle and bustle, it’s easy to forget that there are parts of the city that may be a little less crowded. So my first do is simply this: do explore areas outside of Midtown, especially the ones that I’ll list below.

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Do make a quick stop in the Flatiron District, even if it’s only to see the iconic building. While on  the surface it may seem that this area is mostly for native New Yorkers, I love walking around here because it makes me feel like less of a tourist. There are a bunch of cute little coffee shops and bakeries in this area, you kind of just need to wander around for a little bit. Also, the shopping is great here, and stopping by Madison Square Park is always a good idea, although I could imagine it would be even better to visit in the spring or summer.

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Of all the do’s that you’ll see on this list, here is the one that I want to emphasize the most: do go to SoHo. As I’ve mentioned, this is where I could spend the rest of my life and be perfectly content. Of all the areas in New York City, SoHo is my favorite because of the shopping and the aesthetic; simple as that, it’s a fabulous area. It’s home to all sorts of trendy stores, ranging from designer boutiques to specialty stores, and classics like Madewell and Topshop. Even though some of the stores in SoHo might also be found further uptown on 5th Avenue, the vibe just isn’t the same. The cobblestone streets and fire escape adorned buildings give SoHo such a unique feeling and style, and walking around here is honestly therapeutic for me (sorry, but there is such a thing as retail therapy). In addition to the amazing shopping, do check out the great restaurants in this area, especially the original Black Tap (no further details right now, look for an upcoming blog post). All in all, my only don’t here is don’t skip over SoHo.

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After shopping in SoHo, you’ll certainly want to eat; do head over to Greenwich Village and the West Village to fulfill all of your culinary desires. Honestly, it gets to the point where there are so many options that you don’t know what to choose, but you really can’t go wrong here. While it might just be the name, by Chloe. is somewhere that I would definitely recommend. It’s a vegan restaurant with lots of yummy options, plus they even have Sweets by Chloe. right next door, so you’re all set for dessert. While food might be your primary concern, another do in Greenwich Village and especially West Village is do walk around the area. The walk ups in this area are so beautiful, and are honestly just #housegoals. Wandering around here is so peaceful, especially because you really won’t encounter all that many people on the different side streets. Between the shopping, the food, and the architecture, the trifecta of SoHo, Greenwich Village and the West Village have my heart, so please make sure they are on your do see list.

Other things that you do want to see downtown include Chelsea Market and the High Line in Chelsea; although if the weather is too cold, you might want to save the High Line for another day. Chelsea Market is a huge indoor space with different shops, boutiques, and lots of restaurant options. It’s a super fun place to just walk around and shop while getting out of the cold for a while. The High Line is a park that is built on top of an elevated rail line; while the views are still cool in the winter, the pictures I’ve seen of it when the weather is warmer just makes me want to go back again. There are also lots of other sights to see downtown, including the 9/11 Memorial, Wall Street, Battery Park, and the Statue of Liberty. While I think that seeing these should fall on any general do see list, I would say don’t feel like you have to go in the winter; I feel like you get the most out of these places when the weather is warmer and you can actually walk around without being frozen the whole time.

Heading back uptown, you definitely do want to explore the Upper East and West Sides, especially if you’re a fan of Gossip Girl. These areas are also fun to walk around in because they are less congested, and the buildings are super nice to look at (hello old money). In comparison to other areas, there is less to do in these neighborhoods simply because they are more residential, however, you will find good bakeries and coffee shops here. The places you really do want to make sure you see are right in between the two upper sides: The Metropolitan Museum of Art and Central Park.

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I will be completely honest with you; you do need to see The Met, however, don’t think you will be able to see all of it. I was completely overwhelmed when I went to The Met for this first time. There were so many different wings with so much art, and as beautiful as it was, I felt very lost. I would say that if you do make a game plan of what you want to see, you will go in feeling a lot more prepared. For me, there were a couple of things that I knew I needed to see; one was the infamous staircase that all of the celebrities are photographed on during the Met Gala (still waiting on my invitation, btw), another was the Anna Wintour Costume Collection gallery, and the last was the 19th and 20th Century Paintings Wing  featuring paintings like Degas’ ballerinas and Monet’s water lilies. One pro-tip about The Met is that their admission price is simply a suggested donation amount; basically, you can pay what you wish; so don’t feel like you have to pay the full $25 if you will only be looking at one exhibit. Also, if you happen to be a fan of Gossip Girl, do make sure to take a picture on the steps of The Met; it’s the Blair thing to do.

Whether you explore the Upper East and West Sides or not, you definitely do need to visit Central Park. I don’t care if it’s 10 degrees outside; bundle up and walk through the park, you won’t regret it. I’ll admit that while it may be more enjoyable when the weather is warmer, it still has so much charm in the winter. One of my favorite sites is the Boat House, partially because of the movie 27 Dresses. Finding iconic movie or tv show backdrops is part of the charm of Central Park, and on a warmer day, it’s a fun place to just kind of get lost. If you are a fan of Eloise, you’ll also want to make sure that while you’re in the Central Park area, you do stop by The Plaza Hotel; this was one of my must do’s while I was in the area.

Clearly, there are many, many things to make sure you do in New York City during a winter trip. While the weather might be chilly in the winter, you shouldn’t let that deter you from visiting then. Especially around the holidays, there are so many festive decorations that make the city even prettier than normal. New York City is in a class of its own in my mind, so I really believe that you can’t go wrong visiting at any time of the year. As I make plans for a trip back, I’ve begun having withdrawals; this means that I’ll probably make New York City the center of many of my upcoming posts. Make sure you look out for upcoming blog posts on specific restaurants and *donut shops* that I stopped at in NYC during my trip. If there’s any last piece of advice I can give, it would be don’t be afraid to let yourself fall madly in love with the city; there truly isn’t anything else like it in the world.

XOXO, Chloe

Stylish and Starving at Twenty Something