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How To Spend 48 Hours In NYC

How To Spend 48 Hours In NYC

Steal my itinerary, here's how I spent 48 hours with my high school bestie in NYC.

Jessica @anindigoday's avatar
Jessica @anindigoday
Apr 29, 2025
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How To Spend 48 Hours In NYC
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14 years ago I started a blog while I hated my day job. That same year, my high school best friend and I decided to take a weekend trip to NYC. She had a client who had a studio in FiDi that they let us stay at, which was such a treat for two 24 year olds just starting out in our careers.

That same friend came to visit me this weekend and we reminisced about that trip. I had totally forgotten about drinks at the Gansevoort and the Broadway show we saw, Priscilla, Queen Of The Desert. But I do remember trying to switch trains and not knowing we had to go to a different platform to get said new train. And then once we left the station to just find a cab, we learned that cabs turn over at 4pm and it was impossible to find our way back. With no Uber on our phones, I really don’t remember how we navigated the city and trains. But apparently, we figured it out.

I remember wanting to see Times Square and took a photo in front of all the billboards like the ultimate tourists that we were. My friend Alex wanted to see The Plaza because she grew up loving Eloise.

It was fun to see how our lives have evolved and unfolded in those 14 years since we last did a weekend in NYC. I wonder what 24 year old me would think of my NYC apartment and the fact that the little blog she was writing in that studio, sharing my “outfit du jour” in the morning with a blurry iPhone photo before we started our day, is now her full-time time job and she lives in the city she always dreamed of calling home.

This trip was so nice and we got super lucky with the weather. Perfect 70-degree days and just a few essential plans on our itinerary. We walked through some of my favorite neighborhoods, tried three new to me restaurants and saw a great show. Here’s everything we did in our 48 hours in NYC. Not too much that your days felt overwhelmed, but also note to self, take more time to sit and enjoy. Oh and always wear the good sneakers, your feet will thank you.

How I Spent 48 Hours With My Bestie In NYC

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