I just finished typing and it ended up being really long, but I hope you can find something useful in my post. I got carried away with reliving our trip. Lol Please excuse any typos as I did this post from my phone.
We just got back from a 5 day trip there June 5th. It was my first time and my husband had only spent one day there 30+ years ago. We had a fantastic time and covered quite a bit, but still left plenty undone. Our days were long because we wanted to see so much, but it was worth it. We walked so much as our hotel was centralized to a lot of things and you'd be surprised how quickly you can walk those blocks. 20 blocks (walking north/south) is only about a mile so going from 54th to 34th isn't as bad as it sounds and you can really see the city when you walk it. Our hotel was just a few blocks south of Central Park between Broadway and 8th Avenue. (Around corner from Ed Sullivan Theater) We did use the subway some which ended up being fairly easy especially on the day we went downtown to the Financial District. I will tell you that we didn't put a big priority on eating in nice restaurants as we are more about seeing things than sitting in a restaurant. Plus we have great restaurants here. We frequented this great local 24 hour cafe/ deli by our hotel and got breakfast there everyday which held us over for hours. We often snacked through the day from local places and then shared dinner somewhere. It worked for us, but I know everyone is different and some consider the dining experience as an integral part of their vacation.
As far as activities, there's so much to do. We didn't end up doing any museums except the 9/11 museum as we just didn't have time and didn't want to spend all our time inside. Here's a summary of our days:
-Arrival night-set out around 8pm- stroll through Times Square, ate at local gourmet burger joint, and walked down to Bryant Park to explore which was quiet and beautiful on a weeknight late
-1st full day- explored Grand Central Station area- took a cool free 2 hour guided walking tour (we did tip) that covered Grand Central Station, Chrysler building, and the area. Did an additional hour with tour guide after main tour ended (us and and one other tourist) and got to see more private areas. It was so cool to learn the details and really understand what you were seeing. Also went to the NY Public Library (must see Rose Reading room), Bryant Park in the Daylight which was full and had a concert/ event going on, Rockefeller Center, and St. Patrick's Cathedral (breathtaking) which recently came out of restoration - walked everywhere
-2nd full day- I think this was my favorite day. We started with the subway downtown to the very tip of the island and walked along waterfront to Finanicial District. Explored Wall Street, Federal Hall, Trinity Church (Alexander Hamilton and a few other noteworthy people are buried here), Fraunces Tavern, Battery Park, rode Staten Island Ferry round trip to see SOL from boat (didn't do tour), 9/11 Memorial & Museum, caught subway from Occulus to Brooklyn around 10pm and walked back across the Brooklyn Bridge at night (breathtaking views and so much fun), and then finished with a late night visit to the Empire State building.
This was an amazing, long, emotional, and wonderful day. Our only regret was that we didn't leave ourselves enough time at the 9/11 museum. We spent about 40 minutes at the outside Park/ pools and then went into the museum at 5:30pm (Museum closed at 9:00pm) Since we are the types that want to see/ read almost everything, we only made it through about half of the museum. We missed one whole section completely and definitely want to go back someday to complete it. After it closed, we spent some more time outside at the memorial pools to just reflect on what we experienced and see them at night. They quickly closed the park for the night though and that's when we caught the subway to Brooklyn and did the bridge followed by ESB which were both wonderful.
-Day 3- slept in as we didn't get back until almost 2am. Walked to Lincoln Center to see outside and get same day Broadway tickets at the tkts booth there. Spent the next 5 hours exploring the southern half of Central Park. So beautiful and such a great NY experience. Went back to hotel to get ready for Broadway show. Saw School of Rock 3rd row center with tickets we bought that morning. Theater was full and the show was amazing! The kids and Jack Black character were so good. I highly recommend it and I'm so glad I waited to buy tickets as these 3rd row center same day tickets were the same price as back row balcony view in advance. We grabbed a late dinner and then headed back.
- Full day 4- walked down to 34th street near Macy's, spent about 20 minutes in area and inside exploring- saw old wooden escalators, etc; walked down to Penn Station / Madison Square Garden area and found entrance to High line. We walked entirety of High Line and exited in Chelsea and did a little exploring and ate at Chelsea Market (lots of variety- foodie place). Then we explored parts of Greenwich Village and went to Washington Square Park. From there we took a subway back to Rockefeller Center for our timed entrance to Top of the Rock. We timed it to stay long enough to get daylight views, sunset, and nighttime views. Stunning! We then walked down to the Upper East Side passing famous real estate like Park Ave, Bloomingdales, 5th Avenue, etc on our way to Serendipity for an appetizer and shared dessert . (Bucket list item for me) Another great day.
Departure Day was mostly just picking up a few gifts for the kids and walking back up to Columbus Circle and past a few areas we wanted to quickly revisit
For us, it was an amazing trip filled with things we could never do with our kids for that long- architecture, walking neighborhoods, etc... Of course we left so much untouched like many of the famous museums, but we feel like we got a wonderful taste of a great city and hope to someday return. I know you didn't ask for a play by play trip report, but it was my first time thinking it through/ typing it out and it just came out that way. I know I enjoy reading others itineraries and what they did so maybe it will be helpful to some. If you have any specific questions, let me know. I love planning trips and helping others if possible.