Christmastime in the City - Itinerary for a New York City Trip (with a bonus day trip to Philly)

Last week, I shared all about Joey and Lauren’s New York City proposal (if you want to read their story, click here), but this week, I thought I would share the itinerary from our trip.

My mom, sister (Nicole), Lauren, and I started planning our girls trip about a year out, which was nice because it gave us some time to save up money and to decide exactly where we wanted to go and what we wanted to do.

On Monday, we flew from Charlotte, NC, to Newark, NJ. Once we landed in Newark, we took the NJ Transit into Penn Station. From there, we took the subway north to our Airbnb in Harlem. For dinner, we took an Uber back into the heart of the city and ate at Cassidy’s Pub & Restaurant. I highly recommend the fish and chips with a Guinness. After dinner, we took a night ride in Central Park in a horse drawn carriage. Even though it was really cold for this southern girl, the horse ride was fantastic! Our driver was so sweet, and it was apparent that she loved her horse and her job.

Tuesday was a long day. Our morning started early, and we took the subway down to the 9/11 Memorial & Museum. If you’re a museum go-er, this museum is a MUST. It’s absolutely incredible! As you’re walking through the museum, you see all of the news reports, the articles of clothing and office supplies that were found in the streets, and you can even listen to recorded phone calls of people calling their loved ones to let them what was happening. Talk about gut wrenching and tear worthy. When you tour this museum, I really encourage you to stand at the reflecting pools and take some time to close your eyes and breathe either before or after walking though the museum. After the 9/11 Museum, we headed down to the Lower East Side and grabbed some hoagies (subs) at a Bodega called Green Star Foods. I’m not sure if we were just super hungry or not, but those were some of the best hoagies I’ve ever had. Then we walked down the block to The Tenement Museum. The Tenement Museum is a different kind of museum. You pick the tour you want to take (we did “Hard Times”), and the tour guide leads you through some rooms of the tenement building. You explore the ideas of the different families that immigrated to the U.S. and some of the trials they faced. This museum isn’t a “tourist” museum per se, but it is extremely informative, and I liked the local feel it offered. After that museum, we grabbed some coffee at the Starbucks across the street and then made our way to Rockefeller Center. We had to kill a little time so that Joey could make it up the observation deck and prep for the proposal, so we literally walked in and out of some shops, trying to be as discrete as possible. I was so afraid we were going to give the proposal away. Once we took the elevator up to the observation deck of Top of the Rock, Joey asked Lauren to marry him! After I snapped some photos of Joey and Lauren, my mom, Nicole, and I made our way across the street to watch The Radio City Rockettes Christmas Show. I’m not sure exactly where Joey and Lauren ate and what they did, but after the Christmas show, my sister, mom, and I ate in the little plaza at Rockefeller Center, and then grabbed some celebratory cupcakes from Magnolia Bakery.

Wednesday morning, my mom and sister visited a news station while I did a quick engagement session in Central Park with Joey and Lauren. After saying our “goodbyes” to Joey, Lauren and I hopped on the subway and caught up with my mom and sister. We took a tour of the city on a “Hop on Hop Off” bus, and then headed to Chelsea Market for lunch. After lunch, we got back on the bus and rode all the way down the island to the Brooklyn Bridge. This bridge is pretty iconic, so I was super excited to get to walk on it. After taking in the view, we rode the subway back up to Times Square and did everything Christmas. We walked in toy stores and found the Christmas trees and light displays. With it being our last night in NYC, we had to get pizza. We stopped at John’s Pizzeria for dinner, and then satisfied our sweet tooth with a little gelato at Amornio. I loved getting to walk through the city at night. The locals were still hustling from one place to another, and the tourists were walking slowly, stopping to photograph everything and enjoy the Christmas season.

Thursday morning, we checked out of our Airbnb and made our way to Philadelphia. We rode the subway into Penn Station and then took the NJ transit all the way to Hamilton Station, where my uncle picked us up and then drove another 30 minutes to Cherry Hill, which is just across the river from Philly. I would strongly suggest getting yourself an uncle who has sweet tea and a pretzel waiting for you in the car when you arrive ;) We ate panzerottis for lunch and then drove into downtown Philly, where we checked into our hotel for the night. We walked all over the city, including stopping in the Comcast building to watch a holographic Christmas show, and walking through Charles Dickens “A Christmas Carol” at the Wanamaker Building (now known as Macy’s). Of course we had to stop into my favorite place, Reading Terminal, and have the best cannolis. After finding the Christmas tree in City Hall, we finished our trip with some Philly cheesestakes. I even made a quick trip to Wawa.


This will go down as one of the best trips we’ve ever taken, and there’s talks of another one! There is something truly special about visiting the city during Christmas. 10/10 would recommend

Here are a few traveling suggestions for NYC (and even in Philly):

  • Book an Airbnb vs. a hotel to save some $$$.

  • Look at all three airports when purchasing tickets - JFK, LaGuardia, and Newark.

  • Don’t be afraid to buy one way tickets because sometimes they’re cheaper.

  • Make sure your ticket offers overhead storage if you’re only packing a carry-on.

  • Look into Groupon and other resources like City Pass to save some $$$ on museums and other attractions.

  • Always allow extra time for travel while in NYC.

  • The subway and walking are the fastest ways to get anywhere (cheapest too).

  • Don’t be afraid to ask some locals for help with the subway.

  • Know your Enneagram number and the numbers for your traveling companions/pay close attention to people’s personalities so that you can avoid getting frustrated with each other (may or may not know this from personal experience).

  • Let everyone pick a thing or two that they want to do while on the trip.

  • Pack tea bags, you can always get a cup off hot water at a coffee shop.

  • Eat where the locals eat.

  • Grab a portable charger.

  • Don’t just travel somewhere once, go multiple times and do different things.

I hope this was helpful for y’all, and I can’t wait to hear about your next trip!