4 Days in New York City Itinerary (part I)

It has always been on my bucket list to visit New York City in the fall, so for my 40th birthday, we headed to the big apple. We spent 4 days in New York City enjoying the beautiful October weather and exploring the city. Since we had both been to NYC in the past, we weren’t interested in doing the typical tourist things. We wanted to explore different neighborhoods and eat and drink our way through the city. Here’s what we did and some lessons we learned along the way.

Hotels

After researching hotels, I knew I wanted to use our Marriott points to stay at the historic and luxurious St. Regis on 5th Avenue. I wanted the old and classic NYC feel, not new and modern. However, I didn’t have enough points for all four nights, so we stayed two nights at the Moxy Chelsea and two nights at the St. Regis. We typically try to stay in one hotel, but I’m actually glad we split our stay as it allowed us to explore different neighborhoods.

Moxy NYC Chelsea

I stay at a lot of Marriott hotels, and I will say that I’ve never experienced such a rude welcome as we did at the Moxy. Maybe that’s just a New York thing. The location was convenient and close to the subway and train stations. We took a lovely walk through the flower district from the train station to get there. Honestly, I didn’t even know there was a flower district until we were walking on the sidewalk surrounded by gorgeous flowers and plants.

The rooms here are tiny, which I knew when booking. However, they do a good job of making the most out of the limited space. The best part of our stay at the Moxy was the incredible view from our corner room.

St. Regis

After our two nights at the Moxy, we headed to the St. Regis. We checked in the day before my actual birthday so I would wake up 40 in the luxurious room. I used our suite nights to upgrade to a beautiful suite. Unlike the Moxy, there was a warm welcome, and our suite provided more than enough space! It was exactly as I imagined.

Day 1 in NYC: Chelsea

We took a redeye to New York, which was ultimately a horrible idea. I have something I like to call “redeye amnesia” – I book a redeye thinking it will give us an extra day of vacation, we can’t sleep a wink on the plane, we then spend the entire first day miserable, and I swear never to do it again, but then I do it again. So our first day was a bit rough, but we did get out and explored Chelsea. 

Chelsea Market

Whenever we visit a city, we find ourselves at the local market. The combination of delicious food and good shopping in a casual environment is a great way to spend an afternoon and experience the city as locals do. With this in mind, we headed to Chelsea Market! I could honestly spend a day eating my way through the market. We started with a drink outside in the crisp fall air at Hearth. It is a cute spot right outside the market for drinks and snacks.

After a drink, we headed into the market to try Los Tacos No. 1. I’d read about the tacos, and a colleague recommended them, so we waited in line to try them. As Californians who eat a lot of Mexican food, we weren’t sure the tacos would live up to the hype, but they did! They were simple and delicious! These were some of the best tacos we’ve ever had. I highly recommend a trip to the market, if for nothing else, to try the tacos!

We walked The High Line back to our hotel. The High Line is a 1.45-mile-long elevated city park and path built on a former New York Central Railroad spur. Imagine a beautiful trail with trees elevated a story above the street. If you exit the back of the Chelsea Market and go upstairs, you are on the trail. It was a nice walk back to our hotel for a much-needed nap. 

Since we were still tired, we had a lowkey night. We headed to this tiny and intimate bar near our hotel, La Noxe. I read about La Noxe online and made reservations in advance. The bar is tucked inside the 28th street subway station and is a little difficult to locate. It was dimly lit with chill music and only a few tables. While I love this environment, Mark likes a more lively atmosphere. We sat at the bar and enjoyed drinks and tapas.

Day 2 in NYC: West Village

Initially, we wanted to stay in West Village, but there were only a few hotel options, and none were Marriott properties, and I wanted to use our points. So on our first full day, we took the subway and explored West Village. We completely fell in love with this neighborhood.

We started with brunch at Quality Eats. It was recommended by a colleague who used to live in West Village. It’s a cute restaurant with fun drinks and good food. They have two locations in the city.

After brunch, we walked passed Carrie Bradshaw’s stoop on our way to Dante. It is roped off, so you can’t go on the stoop, but I got a picture on the sidewalk.

Dante has won many awards over the years, and in 2022 it was number 36 on the best bars in the world list, so we had to go. (In 2019 it won World’s Best Bar.) We were fortunate to get seats at the end of the bar with a great view of the bar and restaurant. I ordered a cocktail, and Mark enjoyed one of their famous martinis, the Dante Martini. Dante is an Italian cafe, but since we just ate brunch, we only had drinks. It was a great spot to sit, enjoy a cocktail, and watch the bartenders mix drinks. I think Mark would have been happy sitting there all afternoon. And the fall decor was stunning.

After our drinks, we walked and shopped along Bleecker Street. We made a stop by Magnolia Bakery for a sweet treat. Their cupcakes were delicious!

That night we had dinner reservations at Bar Primi, but we struggled to get there. We never truly learned or understood where to get on the subway to ensure we were heading in the correct direction. Sometimes I asked for help, but people weren’t so interested in helping tourists; gotta love that NY charm. One of the subway stations was closed, so we ended up at some random station trying to catch a taxi to make it to dinner. We were late, but thankfully they held our table. We overindulged in pasta and bread while soaking in the bustling energy of a busy NYC restaurant.

To end our evening, we headed to a small karaoke/piano bar, Sid Gold’s Request Room. Neither of us sings, but we thought it would be fun entertainment, and it definitely was. Having a pianist playing along elevates the karaoke experience. The people who sang were incredible! I felt like we were at a Broadway performance. I felt bad for the one or two drunk people who sang as if they were at a typical karaoke bar; the talent performing that night was next level. I even took some videos because I swore one of them had to be famous. If you plan on going, be sure to make reservations. There is limited seating and there is a time limit, so be sure to be on time for your reservation.

To truly end our evening, we headed to a deli around the corner from our hotel for a late-night snack. I wish we had delis like this by our house! It was the perfect salty and cheesy sandwich.