5 day itinerary for New York City

Over Labor Day weekend, Barry and I were able to take a trip to the Big Apple! I had only been there for a day when I was 13, and Barry was a toddler on his only trip, so we really counted this as the first time for both of us. I’ve spent time in other large cities, like Los Angeles, Atlanta, and Houston, but New York is truly unlike anything I’ve ever seen. The contrast of old and modern, the history and the industry, the sheer number of buildings and people and cars…

With the enormity of the city, the history, culture, shopping, and tourist sites, you could easily spend a month there and not see everything you want to. So many people have asked me, “Oh, did you see (this)? Did you go (there)?” And often my answer is no, because we only had 5 days! 4 1/2 really, because the last day we had to head home after breakfast. But we tried to pick a little of the best of everything – activities and events that were important to us and lots of fun!

Day 1

• We arrived at LaGuardia airport late morning and picked up a ride to our hotel. (More on that in my Tips and Tricks post.) We stayed on the north side of Times Square because we wanted to be centrally located and able to walk places, and it really wasn’t much more expensive than staying in Jersey or Brooklyn.
• We grabbed some lunch from one of the many food trucks on our way to Central Park. You could wander the park for a while on foot, but be warned, it is HUGE. We opted to go with a horse-drawn carriage tour and it was wonderful! There are a ton to choose from, but I recommend NYC Horse Carriage Rides. We got to see the main attractions in the park and stop for some photo ops. Our tour guide was a wealth of knowledge about the park, all the movies filmed there, and the iconic buildings in the area.
• Last stop before dinner was going to a taping of the late-night show Gutfeld! If you’ve never been a part of a studio audience before, it is fascinating to see behind the scenes. Tickets are often free; you just have to request them in advance. Whatever your favorite show is, check it out. 😊 When we travel, I try to pick experiences that are out of the ordinary or unique to where we are, and this was definitely both! We met some great people and had a blast. Dinner was at an Irish pub in Times Square. I’m not going to put a link for it, it was fine but not great. There are several to choose from though, and you typically don’t need reservations. Try to find one with live music!

Day 2

• The original plan was to go to Liberty Bagels for breakfast, which is a New York classic, but we were short on time so we ate at our hotel before taking the subway to Battery Park. From there we took the ferry to the Statue of Liberty and Ellis Island. The Statue was awe-inspiring, and you can feel the history in the air. I found it fascinating that over half the tourists there were international, and I loved seeing them be so excited about this symbol of America. We chose not to go up to the crown, as it sounded a little more strenuous than what we wanted to do, haha!
• In between Battery Park and the 9/11 memorial is a great little place called Joe’s Pizza. It’s been visited by dozens of celebrities – their photos are all over the walls! They don’t have much indoor seating and the line was out the door, but don’t let that stop you. The slices were big, cheap, and it’s the best thin crust pizza I’ve ever had.
• We spent the afternoon at the 9/11 Memorial Museum. It is very well done, beautiful and tragic. Being there was a sobering experience, and honestly something I think everyone should see. We must never forget.
• After a busy and slightly emotional day, we went back to the hotel to change clothes, and then had dinner at Tavern On The Green. Ok, this restaurant is a splurge, but if you get a chance, eat here. It was our favorite in the city. They have a beautiful patio with string lights, a live band that was doing oldies/jazz favorites, couples would spontaneously start dancing, and we loved everything we ate here. It really was a perfect ending to our day.

Day 3

• We started the day off with brunch at a cute little restaurant called Jams. It has great food and a funky, botanical vibe. The rest of the morning was spent “window shopping” along 5th Ave. Every fancy, boujee, expensive store you can think of is here, and some fun ones too! I got a few photos of Tiffany’s, and Barry loved the 2-story Lego store.
• To throw some sports into our trip, we went to a Yankees Game. (I wasn’t kidding when I said we did a little bit of everything.) Our first choice is always football, but since the Seattle Seahawks didn’t happen to be playing in New York that weekend, we went with baseball. We do like watching baseball in person, and Yankee Stadium did not disappoint! It’s easy to get to because the subway station is right next to the stadium. The food was good and the fans were so much fun. Even though we didn’t win, at the end of the game Barry and I decided to be Yankees fans. 😊
• This evening we went to the Empire State Building to watch the sunset. The weather was pretty cloudy, but it was still beautiful to see the city lights come alive. Afterward we got dinner in Little Italy at a place called Piacere, which means pleasant or delight in Italian.

Day 4

• Another tweak to the plan – we were going to head to New Jersey and visit the original Carlos’ Bakery – of Buddy the Cake Boss fame. Yes, I am a baking nerd. However, after learning it would be about an hour on the train just to get there, and he has two locations in Times Square, we decided to skip the long trip. We still went and got some cannolis and wandered around Times Square. This is also a good time to check out Rockefeller Center if you haven’t already.
• For a little culture, we spent the afternoon at The Met. If you love museums you could easily spend the whole day here – it’s that big. It took us 3 hours to get through half of the first floor, and it is two stories. We even had to ask one of the employees where the exit was.
• After a quick dinner near the theater district, it was time for Broadway! There are so many great shows here, the hardest part might be choosing one. This time we decided on Harry Potter and the Cursed Child. Not too hard a decision really, if you know our family you know we are big Harry Potter nerds. The talent was incredible, and the special effects were truly magical! (See what I did there? 😉) We got a late-night snack in Times Square, which was just as busy at midnight on a Sunday as it had been at noon. They’re not kidding when they call this the city that never sleeps!

Day 5

• Our last morning in New York! We had breakfast at a French restaurant, La Grande Boucherie. It’s a little fancy, with delicious food and covered courtyard seating that stretches for a block. After this, we checked out of our hotel and grabbed an Uber to the airport, to head home.

See my post on Tips and Tricks for NYC for a few more things we learned along the way that might be helpful if you’re heading to the Big Apple anytime soon. It was a busy trip, packed full of adventure, and there’s still so much more to do! I’m not a big city girl, and I don’t think I’d ever want to live there, but visiting is fun!