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As I shared a few weeks ago, we ultimately landed on NYC as our 2023 anniversary trip! It wasn’t exactly on our radar for places we wanted to go, but the timing worked out perfectly with a work conference I’d be attending in the city, so we capitalized on having most of the nights in the hotel already covered. Three days and change is not a lot of time to explore, especially when we both had work to do, but I think we did a great job of finding the bleisure in our visit.

Here’s how we spent our time:

Day 1, Sunday

We almost gave up our seats on our flight to JFK when they increased the payout to $700 per person, but they ultimately didn’t need us to! Instead, we arrived on time to NYC, around 2pm. We got a Lyft to the Henn na Hotel New York, where we were greeted by a dinosaur! Definitely a fun way to kick off the trip. We then grabbed some snacks from a nearby CVS and settled into our room.

We ventured into Times Square, which was quite busy, and made our way to the New York Marriott Marquis, so I could check in for my conference. After picking up my name badge, we made our way to Monkey Bar for dinner. We didn’t have reservations, but we were lucky to get a table in their bar area – definitely would recommend it for a cool atmosphere with good food, though be prepared for a more expensive evening! We stopped by nearby Paley Park for a view of the fountain (and a cute photo opp) before taking the subway back to our hotel for the night.

Day 2, Monday

I spent most of my time in meetings due to the conference, and Tyler spent the day working from the hotel. While we got the chance to hang out in the afternoon for a bit before my dinner with my agency (and watch some Ted Lasso), this was by far the least time we spent together. That being said – I still got to eat some great meals with my work partners!

  • Junior’s on Broadway – while I didn’t get a slice of the cheesecake they’re best known for, I did get to start my day with a very classic breakfast. Prices felt quite reasonable, and the location is right in the heart of Times Square.
  • Lodi – I met a new partner here based on her recommendation as a local, and it was a seriously great lunch spot. I really enjoyed both my pasta and my salad, as well as their patio dining in Rockefeller Plaza. This was just what I wanted – highly recommend.
  • Del Frisco’s Double Eagle Steakhouse – my agency brought several clients together for dinner, and we had a great time. It’s definitely decadent! Despite it being a steakhouse, I got the scallops, which were quite good. You can find this outside NYC too.

Day 3, Tuesday

We both kicked off the day with more meetings and work. I met a partner for breakfast at Michael’s New York, which was a super old school spot. It was very tucked away, but worth a trek – we even met Michael! I then headed over to the New York Marriott Marquis for my morning meetings, before meeting a different partner for lunch at Joe Allen. I really liked this place, which felt like a hole in the wall, despite being a five minute walk from the hustle and bustle of Times Square.

From here, I actually bumped into Tyler on the street, which was a fun surprise! He was looking for lunch, so I joined him at Carmine’s. I snacked on a cannoli while he got a plate of enough pasta to feed an entire family – he brought back a lot of leftovers to the room! I wrapped up my meetings with a stop at Ground Central Coffee (which was very good, I’d recommend it) and then made my way back to the Henn na Hotel New York.

Now that I’m in my second trimester, I’m higher energy than I was during my first trimester travels, but I was still beat come 5pm. We opted for a low-key night in the hotel, watching TV and eating our leftovers from Carmine’s. Tyler also popped out for a quick visit to the nearby Taco Bell Cantina (they serve alcohol!), but we called it an early night.

Day 4, Wednesday

This was fully our day to spend together and see the city! Of course, since we have a toddler at home, and this trip essentially functioned as our babymoon, we capitalized on our time to ourselves and had a very lazy morning of watching TV in bed. Becoming parents has definitely impacted how we travel, even when we don’t have the kiddo in tow, and I gotta say – I really appreciate the opportunity to sleep in!

Of course, we did eventually venture out. We had a great lunch at 5 Napkin Burger, which lived up to its Google reviews hype – I’d definitely get the patty melt again! From there, we walked over to the Walter Kerr Theater to see Hadestown. This show had come highly recommended by several of our friends, and I thought it was really good. The music is great, but you should definitely know the Greek myths it’s based on going into it.

The show let out close to 5pm, so we wandered around for a bit before packing up that evening. Stops included another visit to Taco Bell Cantina, as well as Amorino Gelato and Cafe – a perfect walking dessert! – and Carnegie Pizza. Since we flew out the next morning, we definitely got in all our snacks (and steps).