Do you think you could handle a NYC Weekend Itinerary to see all there is to see in the Big Apple? New York City is one heck of a city. Even a week in the city and you would still have so much more to see. From Broadway, local performances, shopping, great food, so many landmarks and parks, NYC has something to offer for everyone. If you were to ask anyone how long to plan your visit, they’ll tell you that you need four days minimum to see enough to get a feel for NYC. I’m here to tell you that it’s entirely possible (albeit exhausting) to see a huge part of the City in just a weekend if you can’t make it for a longer trip. Pack light (I’d recommend a backpack only, so you can walk around with it before stopping at your accommodation) and be sure to wear your most comfortable shoes because this itinerary is FULL of tons of walking! I wouldn’t say a trip to NYC for only 2 (plus a couple hours) days is ideal, but this itinerary will provide a great trip for the time! If you want to follow this itinerary, download the PDF version below!
Day 1 of your NYC weekend – Arrive and get right to sightseeing!
Arrive in NYC! (via plane, train, etc.)
The earlier the better, so you can take advantage of every hour you have! We began our morning bright and early and took a bus from Newport, RI to Providence where we hopped on an Amtrak train for a three-hour ride into the city. We arrived in Penn Station just before noon, so half our day was essentially used up. We got right into walking around. Since it was lunchtime, we opted for a classic New York pizza. Hard to go wrong with that! Since we arrived at noon, we stopped for a quick slice of NYC pizza, which is a must for your trip!
Depending where you arrive, walk or take the subway to 42nd Street to see Times Square and Broadway
We made our way north along 7thAvenue or so, meandering along the way. Our first destination was Times Square, which was overwhelming with performers, lights, tourists, and shops. I had visited the City a couple times prior to this, but it was my first time showing someone that has never been here, let alone to America. We walked around Times Square for a bit, taking in all the lights and people. It’s a great place to people watch. Make sure to meet the Naked Cowboy if you hit up Times Square, and definitely try to see it at both at night and during the day if you’ve never been! Although it’s a NYC staple, I wouldn’t spend a whole lot of time here right now, since you’ll be coming back to it later on to see it at night if you follow this itinerary, which is far more spectacular.
From Times Square, you can either walk East on 42ndtowards Bryant Park, or follow our path North towards Rockefeller center and Radio City Music Hall.
We decided to continue our trek north, which is what I would recommend, since there’s a lot to see up that way, and you can take your time walking down 5thAve for some shopping! Along the way we stopped to see the building housing the Tonight Show (starring Jimmy Fallon), Radio City Music Hall. If we hadn’t gotten into the city as late as we did, we were going to do a tour of one of them but opted out to save some time. We found an adorable summer pop-up bar in Rockefeller Center and decided to rest out feet for a bit. After enjoying a glass of rosé, we continued to walk around. I would recommend spending some time enjoying Rockefeller Center – there’s pop-up events year-round and ice skating in the Christmas season! From Rockefeller, you can go and view the St. Patrick’s Cathedral on 5thAvenue. It is easily one of the most beautiful buildings I’ve ever seen! If you have time, you can shop along 5thAvenue!
From Rockefeller Center – walk towards Grand Central Station and continue toward 42ndStreet to see the Chrysler Building.
Grand Central station gets a lot of hype, which is uncommon for a train station. After leaving St. Patrick’s, we made our way to Grand Central Station to take a peek inside the gorgeous lobby of the station. We didn’t stay long, as it is just a train station and there’s really not a lot to do. It is definitely worth peeking in and looking up – I never knew that the station’s ceiling is ornately painted with constellations! Walk towards the Chrysler Building – another famous building that you don’t want to miss on your NYC weekend.
Walk south on 5thAve towards the Empire State Building, Madison Square Park, the Flat Iron Building, and Union Square Park.
At this point, we were heading back to my friend’s apartment, where we were staying for the weekend. She lives in the East Village, so we could have taken the subway, but we decided to walk from here. We got a quick dinner but continued our explorations on the walk home. We walked into the Empire State Building, past Union Square Park, Madison Square Park, the Flatiron building, and finally made our way back to her East Side apartment. You can definitely go into and up the Empire State Building if you get there when the line isn’t too long. For us, the line was too long, and we had plans to meet up with some friends in a few hours, and still wanted to save some energy for the evening. The Flatiron building is one of my favorite buildings in NYC because of its unique architecture and is a great photo op!
Head to your accommodation for some down time.
At this point, you are probably getting tired and need a rest or to call it a night. I had plans to surprise another best friend of mine that lives outside the City, so I spent a couple hours relaxing before getting ready to head out for the evening. We rendezvoused to have some drinks but called our “day 1” for the itinerary done once we got back before going to get drinks. I’ll leave it up to you if you relax or follow our footsteps and have a night on the town! Note to self and anyone reading: if you are planning to go out at night, you need shoes with straps on the back of your heels to get into most places!
Day 2 – Probably the longest day of walking during your NYC weekend!
Good Morning NYC!
As I mentioned at the beginning of this post – the earlier the better! We were up and ready to see some more of the City around 9 AM, which was still early enough to avoid some crowd, but I would try to get out even earlier if possible! We grabbed a coffee and a pastry to go to take with us and made our way southwest from my friend’s apartment, a few blocks away from Union Square Park.
Start out at Washington Square Park and the NYU area
Our first main stop this morning was Washington Square Park! Although there was a festival going on, it was still fun to see all the arts and people enjoying the sunshine. I would definitely recommend hanging out here for a bit, it’s near NYU so there’s a huge variety of people there.
Walk towards Broadway to Houston Avenue and Canal Street
The area around Houston Avenue is split into “NoHo” and “SoHo” which are north of Houston and south of Houston avenue, respectively. There’s tons of shops in this area, along with local art. If we wanted to, we could have spent the whole day shopping in this area, so I’d definitely set out a good chunk of time here. There’s big name brands like Zara, cheaper shops with super cute clothes, as well as little local boutiques with unique items. We spent a couple hours shopping around and grabbed a quick snack at a little Irish pub on a side street. Definitely feel free to explore the side streets – there’s a lot to see! We opted to skip Canal Street, but there are tons of knockoff items available on the sidewalks from vendors. Be prepared to bargain but know your limits and walk away if the vendors start to get too pushy or unfriendly.
Hop in an Uber or Taxi towards the One World Trade Center for a great early dinner at Eataly
We hopped in an Uber after shopping around to head down to Eataly for a late lunch/early dinner. I highly recommend visiting Eataly if you like Italian food (or even just pizza), it’s a must to include for your NYC weekend trip! Consider making a reservation – although not necessary, it can get super busy! The restaurant boasts an incredible Italian market that you walk through prior to being seated, and then has an incredible view of the Trade Center. I could have walked around the little marketplace for hours, just admiring everything that they had to offer.
9/11 Memorial, One World Trade Center, and Oculus
From Eataly, walk down to the Trade Center to view the 9/11 Memorial. We visited both the North and the South Tower Memorial, just a quick walk from one another. It is so humbling visiting these memorials and is such a contrast in comparison to the rest of the hustle and bustle of the city. It is very quiet and solemn there. You may see people crying, some people just staring, some leaving flowers, photos, or trinkets in memory of loved ones. It brought me to tears, but the memorial is so phenomenally composed, it is definitely something I would recommend going to see. Be sure to be respectful to the people and their families that were affected, I was upset seeing some people take selfies leaning on the memorial (leaning on the memorial is actually not allowed).
In the area of the Trade Center, you can see the tallest building in NYC, the One World Trade Center. Although we didn’t go in, they do offer a ticket to the top for the best views of the city. We walked past the Oculus and decided to go in for a quick peek but left after realizing it was a mall. When we left, we saw a really great acapella group on the street, which lifted my spirits after taking in the power that the Memorial has.
Walk to Battery Park and the Statue of Liberty
Battery Park is another cute park that NYC has to offer, but you can see the Statue of Liberty from this one! There are ferries that travel to and from the Statue throughout the day to get a better view and some closer pictures. Since we were pressed for time (still had more to see!), we just enjoyed the view with a glass of wine at the little outdoor café in the park after taking some photos.
Walk towards Wall Street and the Financial District
Since you’re already at the southern end of Manhattan, walking to Wall Street doesn’t take too long. It’s a great option, even if you have no interest in finance (I don’t understand stocks, but the area is unique and a great place to take a look at some historic buildings). We made our way to Wall Street to see the New York Stock Exchange, Financial District, and the Wall Street Bull! I wanted a photo with the bull, but the line was ridiculously long, so we skipped that. I don’t know if the line for the bull is always as long as it was that day, but if it was as long as that day, I would skip out on waiting so long for a picture since you’re experiencing so much in this NYC weekend itinerary.
Hop on the subway to 86th Street to enjoy Central Park in the late afternoon right before sunset
At this time it was late afternoon, but we still had a couple hours of sunlight left, and I have always loved Central Park. There’s not a whole lot of time in this itinerary to truly explore Central Park but squeezing it in here is about the best option that we saw. We took the subway to 86thstreet and walked in the upper east side towards the Metropolitan Museum of Art. Enjoying a Blair Waldorf moment (or would I be Serena since I’m a blonde….?) I got a photo sitting on the Met steps. We enjoyed a big hot pretzel and a hot dog as a snack while walking down towards another subway station through Central Park on the Upper West Side. By the time we got done walking through Central Park to the subway station, it was a getting a bit dark, so we hopped on towards Times Square.
Take the subway to see Times Square at night before heading back for an early night.
We grabbed the subway into Times Square to see the lights at night. It’s difficult to explain how bright the area really is, but it is definitely a sight to see! I will point out that it is definitely more crowded at night than during the day. We didn’t spend too long here since we had already seen it, but snapped a few pictures, got a couple souvenirs, and made our way back to the apartment for an early(ish) night. Trust me, after this long day, you’re going to want all the rest you have before heading out the next morning!
Day 3 – Time to leave!
Pack up your belongings and strap them on for a couple hours before departing
Aside from day 1 where you’ll be walking around with your backpack most of the day, your last day during your NYC weekend is another reason why packing light for this trip is important! You don’t want to be carrying around a huge suitcase or duffel, plus with such a short trip you really only need 3 outfits total. We left around 8 AM but could have left earlier to enjoy a nice brunch.
Catch a subway up to the Metropolitan Museum of Art or Central Park
This is another spot that you can squeeze a little bit of Central Park into. We had until about 1 PM before we had to leave the City, so we had some time. If you don’t and got to NYC earlier on day 1, squeeze this into day 1 since you’ll already be closer to that end of town on that day! We decided to spend some time inside the MET to enjoy the history and art that the incredible museum has to offer.
Hop on the Subway to Chelsea Market and the Meatpacking District to walk along the Highline
It’s a bit of a ride from Central Park to this end of town but is the perfect place to end your trip if you’re departing from Penn Station. If you’re leaving from Grand Central, you could swap the MET and Highline to end your NYC weekend. We didn’t have a chance to really look around inside Chelsea Market, but we took our time on the Highline Park walkway. Chelsea Market is full of artisan crafts, products, and operates kind of like a farmer’s market. The Highline Park is a high-rise park constructed of old railway parts, pretty cool to see some of the history being repurposed! Keep an eye on the time, then head back to Penn Station (or subway station to head to the airport).
Can you handle this adventure packed NYC weekend itinerary???
This weekend was a ton of fun, but not for the faint of heart! We walked about 15 miles each day, so bring your comfiest shoes! It was a high paced, super fun weekend, but I’m proud of how much we got done in such a short amount of time. It’s definitely the way to experience the city if you are pressed for time, but still want to see as much as you can! Of course, there’s a lot that we missed, but we hit most of the major sights in Manhattan! Did I miss something super important? Other things you could see or do along the way? Let me know in the comments!
Are you heading to NYC during Christmastime? Be sure to check out this guide to NYC at Christmas for all the things you don’t want to miss!
A big thank you to my dear friend Jp for taking all the photos for me this trip! You can check his Instagram out here!