How to Spend 48 Hours in New York City

How to Spend 48 Hours in New York City

Whether you travel by car, train, or plane, NYC is a hop, skip, and a jump from Boston and for some reason, I have never been until now.

It’s insanity, I know. 

At the beginning of 2019, one of my goals was to visit New York City for the first time and I’m so glad I finally got to visit with Chris. Since we were only in the city for 48-hours I tried to prioritize the “important” things one would do on their first visit to NYC and I’m pretty impressed with how much we squeezed in without losing our sanity. If you’re planning a trip to NYC, I hope this post gives you a few ideas of things to do during your visit!

How to Spend 48 Hours in New York City

How to Get There

Since we were only going to be in the city for a short period of time, we opted to fly from Boston to maximize our time for activities. On our flight there, we flew into LaGuardia and Ubered into the city, and on our flight back, we flew out of Newark. Instead of Ubering to Newark (it was something ridiculous like $98 and would take 55 minutes), we ended up taking the train for a grand total of $12 for the same amount of time. It was also super easy.

Where to Stay

During our stay, we stayed at The Gregory Hotel, which we book through Hotel Tonight (aka my favorite way to save money while traveling!). The hotel doesn’t have very many amenities, but the room was big, the bed was comfy, and it was just one block up from the Macy’s flagship store and was easy to get to, no matter what we had planned during the day.

I, unfortunately, didn’t snap very many pictures of the hotel, but I did get these of the bathroom in our room and the hallway – SO cute!

the gregory bathroom
The Gregory Hotel Hallway

How to Get Around

Other than Ubering from the airport on the first night, we only took an Uber two other times during our trip – Once in the morning to the Top of the Rock and once to dinner to meet up with friends, and that was only because I was wearing heels and my feet were exhausted.

We walked about 10-12 miles on Saturday after visiting the Top of the Rock – Yes, to the Upper East Side, through Central Park, down to Hudson Yards, and back to our hotel. On Sunday, we gave the Metro a try, which was super easy! If you’re overwhelmed by the idea of taking public transportation in a new city, Google Maps is so, so helpful and tells you exactly where to go, what line to take, etc.

What To Do

As I mentioned, we squeezed a lot of stuff into the two days we had in NYC. There were some things I wanted to do during our trip but we didn’t have a chance to tackle them, especially with the cold rainy weather on Sunday.

Top of the Rock – The first thing I planned (and one of the only things I planned) for the trip, was going to the Top of the Rock. We purchased tickets ahead of time (thanks for the tip, Allie!) and went first thing in the morning to avoid the crowds. There were still a lot of people there, but it wasn’t too bad.

top of the rock new york
top of the rock
central park

Rockefeller Center – After Top of the Rock, we headed downstairs and visited Rockefeller Center! I was honestly expecting it to be much larger than it was, but hey, TV makes everything look bigger 😉 The skating rink was already up and people were skating, even though it was a chilly morning.

st patricks cathedral
st patricks cathedral ceiling

St. Patrick’s Cathedral – Since we were in the area, we popped into the St. Patrick’s Cathedral and I have one word: WOW. I honestly didn’t even know there was a cathedral in NYC until my dad sent me a picture of him walking by it a few weeks ago on a work trip. We spent some time inside enjoying the people, space, and history before continuing with our day!

Central Park – I am a huge fan of parks in the middle of cities and how hard everyone works to allow us to enjoy a little slice of heaven in the middle of chaos. Chris and I spent an hour or so walking through starting up near the Upper East Side until we hit 59th Street. So magical ✨

The Vessel & Hudson Yards – Chris and I have been eyeing the Vessel on Instagram since it’s completion in March and I know that it’s a tourist trap, but we just had to visit. The architecture of the piece is absolutely amazing. The line to walk up it was super long, so we opted to view it from afar before we headed inside to walk around in Hudson Yards.

the vessel new york

The High Line – After walking through Hudson Yards and grabbing a bite to eat, we walked along The High Line and took the city views in from above. I love that they turned the old train tracks into something everyone can enjoy instead of (let’s face it..) being a giant eyesore and wasted space!

East Village & Soho – On Sunday we headed to East Village and Soho to walk around and adventure a bit. It was raining and a little chilly so we didn’t spend too much time in the neighborhoods but it was nice to fit it in! We popped into stores, grabbed a bite to eat, and tried to stay dry!


9/11 Memorial – One of the saddest parts of our trip, visiting the 9/11 Memorial left the both of us completely breathless.

The Oculus – What’s a trip to NYC without visiting the Oculus? We popped into a few stores and walked around the building, admiring the architecture.

world trade center

Where to Eat

The Penrose – Breakfast at The Penrose on Saturday morning was my absolute favorite meal of our entire trip. The food was so freakin’ good. The space was cozy, the food was delicious, and the coffee. SO good.

What we ordered: French toast sticks, fried chicken and waffle, bacon egg and cheese deluxe, coffee, bloody mary

Queensyard – While visiting Hudson Yards, we popped into Queensyard to relax and grab a quick drink. The interior reminded me a lot of Earls but a little bit more elevated. The views of the Vessel were amazing!

What we ordered: Cold brew martini (I highly recommend!), espresso martini, rosé cider

queensyard martini

Lillie’s Victorian Establishment – One of Chris’ really good friends from college lives in New York and we met her and her boyfriend for drinks and a bite to eat on Saturday night at Lillie’s Victorian Establishment. It was decked out for Halloween, the tall ceilings were gorgeous, and the food was really good! Definitely more of a tourist-y place since it’s essentially in Times Square but I loved the vibe and would 10/10 go back.

What we ordered: Roasted garlic hummus, pretzels, empanadas, curry fries

Brendan’s Bar and Grille – Attached to our hotel, we stsalopped into Brendan’s for a nightcap on Saturday night (the mozzarella sticks are so good!!!) and to watch a bit of playoff baseball.

Bluestone Lane – I first tried Bluestone Lane on my trip to DC over the summer and was absolutely obsessed so I had to visit while we were in NYC!

What we ordered: Cold brew, salmon toast, prosciutto toastie

Tompkins Square Bagels – The bagel shops in NYC do not mess around! We ended up at Tompkins Square Bagels on Sunday while visiting East Village and it was delicious! Note to self: don’t wait until 12:30 PM to get a bagel – the line will be ridiculous.

What I ordered: Asiago bagel with plain cream cheese

tompkins square bagels

Leave a Reply


  1. 11.12.19
    Lizzie said:

    Wow you did a ton in a short amount of time! New York is amazing! I’ve been several times for fashion week, but I’d really love to go back with my husband and just be a tourist for a few days 🙂


    • 11.12.19
      Rachel said:

      Your trip for fashion week this past season looked absolutely incredible!

  2. 11.12.19
    Makaela said:

    Man, I just went to NYC for a pharmacy conference, which was already jammed pack with things to do. I wish I would’ve ventured out more to do more things. Definitely saving this list for later when my fiancé and I can make a quick trip to NYC.

    • 11.12.19
      Rachel said:

      Ah, so fun! There’s always next time 😉 Let me know what you end up doing!

  3. 11.12.19

    Yes to all of this! The Vessel was one of my favorites last time I visited NYC.

    • 11.12.19
      Rachel said:

      The architecture is so cool! I definitely need to read more about the creative process.

  4. 11.12.19
    Mariah said:

    Aw Chris on the blog! Love it! Looks like such a great trip.

    • 11.12.19
      Rachel said:

      It was a blast!

  5. 11.12.19
    Katie said:

    What a fun trip to NYC! I went a few years ago and loved it- hope to visit again soon!


    • 11.12.19
      Rachel said:

      I’m itching to go back in the spring!

  6. 11.12.19
    Megan said:

    New York is amazing! I’m so glad you guys had a great time. There’s always so much to do there.

    • 11.12.19
      Rachel said:

      I can’t wait to go back in the spring!

  7. 11.12.19
    Candace said:

    NYC in only 48 hours?! What a whirlwind! Props to you for making the most of your visit. Central Park is absolutely beautiful this time of year!

    • 11.12.19
      Rachel said:

      It was a quick trip but so much fun!

  8. 11.12.19
    Stephanie said:

    I am SO jealous right now. New York is about a 6 hour drive from Richmond and yet I’ve never once gone as an adult. And the only times I’ve ever been at all were when my family was on a road trip to the North and we were just passing through. I know I had a slice of pizza, ran into the Macy’s on 34th street, and “saw” Times Square. One day I’ll certainly be back for more!

    • 11.13.19
      Rachel said:

      We drove through Times Square and I was SO overwhelmed so I opted to avoid it on foot 😉 I can’t wait to go back again (maybe in the spring???) – Maybe we can have a little girls date!!

  9. 11.12.19
    Lee said:

    oo The Gregory looks really nice! also this post is making me crave a trip back to NY!!

    • 11.13.19
      Rachel said:

      It was SO cute!

  10. 11.12.19

    I live in NY and will never not be amazed by all this city has to offer!! Sounds like you had such a nice time xoxo sarah

    • 11.15.19
      Rachel said:

      There’s so much to do!

  11. 11.13.19
    Kileen said:

    It looks like you guys had an awesome trip in NYC! This post makes me wanna go back to NYC so bad!

    cute & little

    • 11.15.19
      Rachel said:

      It was so fun! I can’t wait to get back in the spring!

  12. 11.13.19
    Annie said:

    I love NYC! It’s such a fun, vibrant city, and there’s so much for everyone to enjoy there, regardless of what you enjoy! Looks like you had some delicious food too – yum!

    • 11.15.19
      Rachel said:

      I can’t wait to go back in the spring for more adventures!

  13. 11.13.19
    Marlene said:

    You packed a lot into 2 days! I haven’t been to NYC in years and this totally makes me want to go back. Such an amazing city

    • 11.15.19
      Rachel said:

      It as exhausting! I can’t wait to head back in the spring to do even more!

  14. 11.14.19
    Laura Leigh said:

    Girl you took so many great snaps! And y’all did A LOT in 48 hrs – super impressed. Also, can we talk about that hallway at your hotel – gorgeous!

    xo Laura Leigh

    • 11.15.19
      Rachel said:

      Isn’t it so cute!? The hotel was in the perfect spot, making it easy to get everywhere in the city fairly quickly!

  15. 11.15.19

    I love NYC!! You got to see and do so much and now you’re making me want to go back! I hope you enjoyed your trip!

    • 11.15.19
      Rachel said:

      It was so fun! I can’t wait to go back!