How to Spend Two Days in NYC

New York City is an awesome city with infinite possibilities of things to do or see. We had a weekend to spend there in June and wanted to make the most of our time there. Since we live in Chicago, just being in a city doesn’t do much from us (walking around Manhattan doesn’t feel too different than walking around the loop), so we wanted to experience things that stood out as things that make NYC special. If you’re planning a weekend here and need some ideas of how to spend your time, then this post is for you!

Day 1:

Start the day off with a rooftop brunch or lunch. New York has so many fun rooftop restaurants to choose from with beautiful views and delicious food. We chose Serra by Birreria which is located in the Flatiron Eataly location.



After your rooftop meal, treat yourself to some shopping! There are endless amounts of shopping in New York. If you’re like us and can’t afford the luxury shopping, try some chain stores that you can’t find in most US cities, like my personal favorite, & Other Stories. 

Next, visit some iconic sites such as Grand Central Terminal, Empire State Building, St. Patrick’s Cathedral and Rockefeller Center. If you want to visit the top of the Empire State or Rockefeller Center for the best views of the city, it will cost about $40 per person. We chose not to do this, but have heard it is worth the cost if you are looking for a good view point.

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Grand Central Terminal

Once you’ve seen some iconic sites, it’s time to get out of the hustle and bustle of the city and take a walk in Central Park. Central Park is hands down our FAVORITE part of the city. There are so many beautiful views, it is surprising quiet and is bigger than we ever imagined. We started off our walk in the ramble and the lake section. It felt like we were on a hike in the woods in some parts! Then we made our way down to the southeast corner where there is a hill with a wonderful view of the city.

central park 2

central park

central park 3

Once you’ve had a long walk in the park, it is time for dinner. It isn’t a visit to New York without having some pizza slices. Joe’s Pizza is a great option but honestly, most pizza by the slice places we have tried are all delicious (and cheap!).


After dinner (and after the sun goes down), walk through Time’s Square. This is something everyone says NOT to do, however, it is something that is so unique to New York and in our opinion, a must see at night. It is crowded and loud and not somewhere you probably want to hang around for too long, so we chose just to walk through it in passing.


When you finish a walk through Time’s Square, head down to Greenwich Village and enjoy a late night comedy show! The infamous Comedy Cellar is located here. This was a must do for us while visiting NYC since we absolutely love comedy shows. Be sure to buy your ticket in advance if you plan to do this. If comedy isn’t your thing, find some music, a Broadway play, or anywhere else to enjoy a show in this city full of talent.


Day 2:

Waking up after a jam packed day and late night requires a famous New York bagel. We went to Ess-a-bagel and had a delicious bagel with lox (we ate it too quickly to take a picture- sorry!). *Be sure to order ahead of time online so you can skip the long line here.*

Once you are filled up on breakfast, head down to the financial district of Manhattan to see some more iconic sites. Be sure to visit the Freedom Tower and the 9/11 Memorial. It is emotional and very impact to see first hand. If you want to visit the museum as well, be prepared for a long wait in line and give yourself enough time during the day to see it all. Freedom Tower is the tallest building in New York and also has a view point of the city at the top (also around $40 a person).


Next, take a short walk over to Battery Park to see the Statue of Liberty. If you’re up for it, there are ferries available to take you over to see it, but we simply enjoyed the view from the park.

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If you are up for more walking, head over to bustling Wall Street and continue down to the Brooklyn Bridge. Depending on if you have the time, walk all the way across the bridge into the Dumbo neighborhood of Brooklyn. We were short on time, so we walked about halfway across the bridge, enjoyed the views, and headed out to lunch.


For lunch, dine at the New York institution, Katz’s Delicatessen. I think we can confidently say the pastrami was the BEST sandwich we have ever had– and we’ve had a lot of sandwiches.


After lunch, spend the afternoon exploring another neighborhood. Visit Upper West Side, TriBeCa, West Village or even take a walk on the famous High Line.

Once you’ve enjoyed your afternoon, take some time to freshen up at your hotel (we stayed at The Lexington and had a great experience), and head out to a nice dinner- you deserve it! We went to Locanda Verde for dinner (we were there for a rehearsal dinner for a wedding- but we would highly recommend it for a nice dinner in the city).



And there you have it! That is how we planned as much as possible to do in New York within two days. If you have any questions for us, let us know.

Thanks for reading.

Emilie & Chris

Published by happilyaway

We are a married couple living in Chicago, and we are obsessed with traveling (probably like you). Unlike many travel bloggers, we have no intention on quitting our jobs and traveling full time because we actually love our jobs (shocker- I know) and we have a sweet puppy that we can't bear to leave for for than 3 weeks at a time. This hasn't stopped us from making all of our travel dreams come true. We are excited to share our adventures with you and help show you how you too, can travel the world- even while working full time. Emilie & Chris

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