NYC Trip 2026 - Day 1, Part 1/Heading To NYC, The W Hotel, The Theater District And Missing Madonna

 Our flight on Day 1 of our trip to NYC was scheduled for late morning, so we were able to wake up at a decent hour in the morning and drive to the airport.

 

Doug, Bri and I were very ready to be in NYC and our flight was on time and very smooth (we like to fly into Newark)...

 

In typical Lisa fashion though, something had to go slightly awry. I was enjoying my in-flight entertainment (I was watching "Stumble") and nature called. I returned to my seat where I had paused my show, but my screen had completely frozen up...

 

The bottom photo in the collage shows where my show got stuck. Just like that.

 

It wasn't doing anything. I called over the flight attendant and he said he could reboot my particular screen - which he tried. Nothing. Luckily, I had loaded a couple of shows on my phone that I could watch, but it was slightly bothersome. He gave me some Delta points toward another flight for my inconvenience, so that was nice. And right before we were about to land, the screen finally rebooted and started working again. I would say about 45 minutes had passed. So, I am not sure what took it so long to straighten itself out.

 So we land, grab an Uber and head into the city. Per usual, we go through the Lincoln Tunnel - which is absolutely nuts every time. There are about 20 lanes that eventually merge into TWO. It's crazy...

 

After about 45 minutes (maybe an hour), we get to our location - the W Hotel...

 

This is the hotel where we always stay. It is located smack in the middle of the theater district (47th Street and Broadway) and that is where we like/need to be. And it is very comfortable. The only downside, it is also located right in Times Square. And Times Square gets more crazy crowded every single year. I would like to try to stay somewhere else away from Times Square eventually, but for all the shows we see when we visit, the W just makes the most sense.

This is the lobby/bar. We had drinks here a couple of times during our visit...

 

 This was our room (we were on the 48th floor)...

 

Bri sleeps on the pull out couch when we stay there. She has the whole living area to herself.

 

 We settled in and were getting a bit hungry. We looked online to see what was around us and Doug suggested an Italian restaurant called "Sicily" for dinner. That sounded great and it was a few blocks away, so we could walk.

 

When we exited the hotel and started walking through Times Square, we noticed a very large crowd gathering around the famous red steps. Guard rails were going up. We saw a large double decker bus with drag queens on it, so we assumed it was something for Pride Month. We wanted to get the heck out of there because it was so crowded and we needed to get to the restaurant. We squeezed our way through the gathering crowd and finally got to some streets that weren't insane.

 

It was a nice walk...

 

Walking through the theater district, there are so many marquees for so many amazing shows...

 

We saw "Beetlejuice" at the Marquis Theatre ("Stranger Things, The First Shadow" is there now) and "Hamilton" at the Richard Rodgers Theater during past visits...

So funny story - the very large crowd gathering in Times Square was doing that for a reason. It wasn't until we got back to the hotel from our dinner that we found out what that reason was.

 

Madonna - yes THE Madonna - did a surprise 15 minute pop up concert in the middle of Times Square to kick off Pride Month...

 

But...D, B and I had no idea, totally walked by and missed it.

 I am not much of a Madonna fan nowadays, but back in the 80s and 90s, I was a big big fan. So it would have been really cool to see her in person. But no, we were chowing down on our Italian meal instead. Oh well.

 

In my next post, I will share the food we were chowing down on instead of seeing Madonna perform. We also did some shopping in Times Square after all the hubbub was over.