New York City Weekend Trip | NYC Things to Do | First Time in New York

March 21, 2022

New York City is surprisingly one of those places I've always wanted to go to but never got around to making plans. When my high school friends, Komal and Carigan, reached out about a trip, I could not say no! Everything was booked in about a month in advanced to give you some reference to our plans and how carefree they really were.

We flew up in the early hours of a Thursday morning and flew home late Sunday evening. This way, we were able to get the most time possible in New York. Both of them went on a trip a few years prior and have been back since. This being my first time, we tried to do a few traditional tourist activities, but we did skip out on a few of the tourist go-to's. 

I break down each of our days to show you how we spent a long weekend in New York City (and didn't really spend too much money). If you are looking for suggestions on restaurants or things to do, skip to the bottom! I've included recommendations from local friends, things we've done, or things we researched to do and didn't get around to.

The Basics:

Hotel: Holiday Inn Manhattan on 6th Ave - mediocre, but moderately priced hotel where we were met with friendly front desk receptionists. The reviews on google have it at a 3.6/5 and I would have given it a 3/5. It was fine and affordable, but the room was beat to sh*t and really cramped for 3 people. 

Transportation: We prearranged a van to take us from the Airport to the Hotel. We reserved it from Carmel, so we didn't have to worry about lugging our bags through the subway. This cost the three of us $40 each round trip (excluding tip). 

While in the city, we Ubered ONCE the entire time we were in New York. We purchased a 7 day metro card for $33 and took the subway everywhere. Since we were in a group of three, we always felt comfortable riding it at night but never rode past 11:00 PM. 

  • Google and Apple maps have come a long way and actually provide insight on which train to get on for your desired location, how many stops, and where to go after exiting the subway. This made it really easy for us to map out where we wanted to go and find the nearest stations to us.

What We Did:

  • Coffee and chilled by the Giant Red Ornaments (in the fountain plaza at 1251 Avenue of the Americas - Sixth Avenue)
  • Walked around 5th Ave, did some light shopping
  • Visited Times Square during the day 
  • Ain't Too Proud - We planned on seeing this Broadway show on this evening, but it was cancelled twice due to COVID
  • Visited Rolf's - See more below

Woman holding Drink at Rolf's in New York City (NYC)
Taken at Rolf's

Where We Ate:

Blank Slate - Quick and easy bite to eat! We sat outside and the food was overall pretty good.
  • Rustic Chicken Sandwich with GF bread. 
Rolf's - This was a fun visit. I've heard mixed experiences about their food, but it is worth the trip for the decor and their themed drinks. Definitely make reservations for the Bar (or restaurant)  beforehand. It gets pretty packed and you don't want to have to wait in a long line!!
  • Christmas Smoothie and Burnt Toasted Almond drinks. Both were creamy and delicious!
Thep - Probably one of the best Thai restaurants I've ever had. That says a lot because I eat a lot of Thai food. See below for what we ordered.
  • Park Mor (Pictured Purple Dumplings)
  • Golden Sachet
  • Crispy Calamari (Pictured)
  • Pork Belly Clay Pot (Pictured)
  • Duck Pad Thai

What We Did:

Taken in Bryant Park

Where We Ate:

The Heart & Soul of Greenwich was a food tour in Greenwich that was recommended to me by a friend. It was SO GOOD. It lasted about 3 hours and left us really full. There were about 5-6 stops and 3 of them were hearty servings. I liked that it provided a history tour as well.

Serra by Birreria - I did not love the food, but the decor was on point. If you are looking for an instagram-able spot, this is it. They decorate their rooftop according to the season, and it is so beautiful! If you want authentic or above average Italian food, please go somewhere else.

  • Brussel Sprouts
  • Prosciutto Ravioli 

What We Did:

  • Casual Vintage/Consignment Shopping
  • Union Square Holiday Market
  • 5th Ave shopping
  • Ain't Too Proud - We planned on rescheduling from Thursday to this evening, but it was cancelled again due to COVID

Where We Ate:

Gregory's Coffee - This was near the hotel and I stopped in for a quick, early breakfast. It's a larger family run business in NY, NJ, and D.C. Good & quick!
  • Matcha Latte
  • Avocado Toast
Tompkins Square Bagels - low maintenance, to-go bagel shop we stopped at in Greenwich Village.It was very good but I wish I did a regular bagel and dealt with the stomach pain instead.
  • GF bagel with lox, red onion, and Scallion w bacon cream cheese
New York Pizza Suprema - Decent pizza place that delivered to the hotel. We wanted something easy/quick for the hotel and this worked great. There are definitely better places to go but this wasn't bad!
  • Cheese Pizza
PhD Terrace - really cool rooftop spot. They had it enclosed for the winter and it was gorgeous! Great drinks and ambiance. Do me a favor and get the mac n cheese balls - they were SO good.
  • Crispy Mac & Cheese Balls
  • Pretzel bites

What We Did:

  • Shopping in Greenwich Village
    • Boutiques and Vintage stores
    • Porto Rico Importing Company (great for gifts)
  • Central Park
  • Levain Bakery

Where We Ate:

Levain Bakery - I got an Oatmeal Cookie and scarfed it down it was so good.

Root & Bone - probably the top 2 meal of the trip. My expectations were high as a Southerner and it did not disappoint!
  • Deviled Eggs - WOW so good. A great combination of tangy and salty.
  • Fried Green Tomatoes
  • Chicken & Waffles - The brine was amazing! The waffle was fine, but not up to the chicken's standards!


Brunch Options: 

Lunch Places to eat:


* These are activities we actually did