Magical Secrets to Enjoying New York City At Christmas

My daughter, two sisters-in-law, and I recently returned from the perfect New York City Christmas trip! And we can’t stop talking about how great it was! So, if you’re planning a holiday trip to NYC and don’t know where to start, I’m sharing all of our secrets to enjoying Christmas in New York City like a professional!

The key to any successful vacation starts months before you go, with strategic planning and budgeting.

Giant Christmas Balls at Rockefeller Plaza

Before You Go

First of all, I recommend going in December so you don’t miss the glorious holiday sights and shows! Additionally, it’s much more merry to have a few good friends with you for a fun, shared experience.

Secondly, when you first plan to go, set your budget and begin researching and prioritizing your travel experience. At the bottom of this post, I’ve saved you time by listing the most noteworthy sites on our personal trip!

There’s so much to do and see in NYC! So, if you only have a few days, it’s crucial to plan both structured and non-structured days while you’re there. On our last day, we left the itinerary for the entire day blank because we knew we’d see things that we would want to check out more thoroughly. It was a strategy that ended up working perfectly.

Third, sign up for a rewards credit card where you can earn big discounts on flights, hotels, or meals, such as the Chase Sapphire Preferred® Card, Citi Double Cash® Card, or Blue Cash Preferred® Card from American Express. Then (and this takes some courage and restraint), put all of your purchases on the card to begin earning points toward your trip. You’ll pay it off in full at the end of each month.

I use the Southwest Rapid Rewards® Plus Credit Card, but I am planning to switch to one that earns rewards at a faster rate.

Once you’re ready to book your trip, be sure to use any rewards you’ve accumulated toward your flight and/or hotel.

Be Properly Prepared

If you’re like me, you prefer to stay in the heart of New York City. We stayed at NYC’s conveniently located third-largest hotel, the Sheraton Times Square Hotel. It was within walking distance of almost everything we wanted to see in Manhattan. The hotel was lovely, and the service was admirable. For you coffee lovers, there’s a Starbucks inside the lobby.

Once the plane and hotel reservations are made and it’s getting close to departure time, be sure to arrive at the airport two hours before your flight time. Our plane left at 6:20 AM, and though we checked in one hour ahead, our bags did not make it to NYC until our second day of the trip. We were informed this was due to our bags being rerouted as a result of our late check-in.

Another important consideration when packing is to be sure to check the weather in NYC, which can be fickle at times. In wintertime, you’ll need warm clothing, gloves, neck scarves, and something to cover your head and ears, which freeze quickly in the cold. It also rains a lot in NYC.

Another issue is knowing the baggage rules for your flight so your suitcase is below the maximum weight limit. You don’t want to have to throw something away at check-in or be forced to check your carry-on.

Getting Around New York City

NYC has one of the most efficient transportation systems in the country! Between the subway and bus system, the more expensive but infinite taxis, and other car services, you’ll have no problem getting to your destination. My New Yorker nephew and others warned us not to ride the subway at night for safety, but it’s fine during the day. (We did ride it at night and had no issues.)

If your hotel doesn’t have airport transportation, your best bet is a taxi or Uber/Lyft/Via to arrive at your hotel. DO NOT, and I repeat, DO NOT rent a vehicle to drive around NYC if you can help it. They have an entire traffic system of their own, and you can easily get pulverized by millions of other vehicles around you. Also, parking is very expensive.

Tip: Use a taxi app like Curb to avoid waiting for a cab in busy areas.

The cheapest travel option is to purchase a bus/subway MetroCard. (the subway runs 24/7), The price is very reasonable at $2.90 per ride. If your MetroCard runs out of money, you simply purchase additional rides at any subway station.

Plus, if you stay in the heart of Manhattan, you can get anywhere you want by walking or using the subway, even to New Jersey, across the waterway! I’ll have to admit, when there were few riders on the subway, my daughter kept us entertained with pole dances.

Additionally, the Staten Island Ferry offers free ferry service between Staten Island and Manhattan. The NYC Ferry provides affordable ferry routes connecting waterfront neighborhoods (e.g., East River, Rockaway, Governors Island) at $4 per ride.

Faith clowning on the New York City Subway

We’ve Arrived

My daughter and I met one sister-in-law at the baggage carousel in LaGuardia. Along with a fellow passenger from our hometown (the airport rerouted her luggage, too, which is how we met), we shared an Uber to our nearby hotels. It took over an hour to go just six miles due to rush hour traffic. Another tip: whenever you leave to go anywhere in NYC, give yourself at least 20 extra minutes to get there. Siri (and we) got easily confused while walking around Manhattan.

After settling in at the hotel, we grabbed hot dogs from a street vendor and walked to a nearby pub. There, we met up with my other sister-in-law and her son, who lives in New York.

We enjoyed a welcome drink before my nephew took us to a surprise show, “Sunset Boulevard.” It was funny, and the singing was incredible. However, if you’re looking for show-stopping theatrical effects, skip this one.

All of the plays we attended took place in gorgeous, eclectic theaters, each over 100 years old. They alone are worth the trip. Dressing up for Broadway theaters is not necessary, and you should be comfortable with whatever you wear to view the shows.

After the show, we went to a nice sushi restaurant nearby. It was my first time trying sushi, and I have to admit I wasn’t a fan.

Beautiful chandelier at Radio City Theater

Three Inspirational Places to Eat in NYC

Restaurants, especially Irish Pubs, are everywhere due to the large Irish population. This is a city that’s packed with great places to eat. Our favorite Irish Pub was the Playwright Celtic Pub. It was super cozy and full of holiday ambiance. Plus, the food was divine.

An absolute don’t-miss, over-the-top restaurant that my nephew took us to was Oscar Wilde. I’ve never seen so much Christmas in one place! It was everywhere!

As a Christmas nut, I was in heaven! Oscar Wilde decorates for every holiday, but even when it’s not a holiday, this place is crammed with personality. Even if you don’t eat there, at least walk through and see the history and view the decor of this magical place.

We saved Serendipity 3 until our last night in New York City! And boy, was it worth the wait! Besides enjoying our own intimate, little decorated dining nook, we loved the vibrant decor and personality of this unique place!

Serendipity 3's famous frozen hot chocolate

Serendipity 3 is the home of the famous Frozen Hot Chocolate (try the Red Velvet flavor), and it’s a must for any traveler! They have fabulous drinks and desserts, and the food is yummy, too.

Moreover, it’s best to make a reservation for Oscar Wilde and Serendipity 3 before you go to New York, as both places remain packed most of the time.

Serendipity 3 Times Square, New York City

Top Priorities to See in NYC in Two Days

We had four glorious days in New York City, so prioritizing what we wanted to see and experience was vital. Below is our itinerary, which I highly recommend.

Day 1: Statue of Liberty and Ellis Island: The story and detail of this copper and iron lady are amazing! Be sure to reserve your tickets prior to your trip via statueoflibertytour.com, the official site that provides transportation via ferry from Battery Park.

Allot at least five hours for this tour so you won’t be rushed. You can purchase tickets for just the pedestal, or you can go up into the crown. Be sure you’re able to navigate the 162 stairs to the crown because there’s no elevator up there. Also, check out these important tips for your visit to Lady Liberty.

That evening, we had tickets to see The Lion King at the amazing Minskoff Theater. It was beautiful and riveting. The actors were amazing, and the special effects were breathtaking.

Day 2: Walking Tour of Manhattan: We spent the day walking along Fifth Avenue and its surrounding areas. There were lots of Christmas sites, but I highly recommend doing this at any time of the year. On the way, we saw such great sites such as:

Louis Vuitton’s Gigantic Suitcase
Trump Tower
Radio City Music Hall
Grand Central Station, where we ate lunch
New York City Public Library – the largest library in the USA
Macy’s Department Store, Tiffany’s, and other flagship stores
FAO Schwarz Toy Store
Multiple Beautiful Historic Churches and Architecture
Amazing department store windows
Don’t miss Laderach Swiss Chocolate, the best chocolate I’ve ever eaten! (And I’ve been to Switzerland!)

We ended the day at the Rockefeller Center, enjoying the majestic Christmas Tree and accompanying sights. It was interesting to see NBC’s and Jimmy Fallon’s television studios.

The majestic Rockefeller Christmas tree 2024

Top Priorities to See in New York City Day 3

Day 3: The next day, we were up bright and early to see the 911 Ground Zero Museum and The One World Trade Center Observatory. Both experiences, though vitally different, were well worth our time. My daughter, who was a baby at the time of 911, was profoundly affected by all she saw and heard at the museum. It was beautiful, sobering, and well-presented.

After a brief lunch at the amazing Oculus nearby, we headed up the sky pod elevator to the 102nd floor of the One World Observatory at Freedom Tower. The elevator itself was a fun experience, but the 360-degree views from the top of Manhattan were breathtaking.

Another suggestion is to go up around 3:30 PM so you can catch the sunset from the top of the world around 4:30 PM. This tip was recommended by one of my nephew’s New York friends, and we’re happy that we followed her advice.

After a gorgeous sunset, we took the trip back down to Earth and headed to the subway to Times Square. It was time to catch the late show for the Rockettes at Radio City Music Hall.

Now, I’ll have to admit that I wondered how a bunch of women known for kicking their legs in the air could keep us entertained for a couple of hours.

All I can say is that their Christmas show was amazing! So much pageantry was incorporated into this show that I can’t rave enough about it! The special effects, the dancers, and the storyline grab the attention of the audience and hold it prisoner!

I can say that we were all disappointed when the show was over because we wanted more!

The Survivors Stairs in the 911 Memorial Museum

Top Priorities to See in New York City Day 4

Day 4: This was our last day in NYC. We started with a short stroll to Central Park, where we bought yummy crepes from a street vendor. We enjoyed them on a bench where we could see The Plaza, the posh hotel in “Home Alone 2, Lost in New York.” I also found the site where the Bird Lady fed the pigeons in the movie.

Scenic bridge at Central Park in New York City

Like the Bird Lady, we fed the birds our leftovers. Several squirrels came right up to my daughter so she could feed them the toasted nuts we had bought.

Warning: don’t let them eat out of your hand. They are wild animals and will bite!

We spent six hours strolling the park, enjoying bridges, fountains, and ice skaters at Wollman Rink. We didn’t take the time to go to the small zoo. But we did enjoy a ride on the colorful carousel for only $3 each!

There were street vendors, musicians, and performers all over the park. We took a peaceful carriage ride through the park with a guided tour from our young driver. We saw the famous “Friends Fountain” (shown at the beginning of every Friends TV episode) and the John Lennon Memorial. It was right across the street from the historic building where John lived and was killed.

We also saw the building where Denzel Washington lives. Our young driver pointed out several interesting facts, and it was a nice reprieve from the fast and furious pace of our short trip to the city.

That night, we had reservations at Serendipity 3 in Times Square, then visited one of the local bakeries for some New York Cheesecake. It was a wonderful and restful way to wind down a lovely trip.

Serendipity 3 Restaurant at Times Square

Regrets That We Didn’t Visit

Of course, we didn’t get the chance to see everything we wanted. I really wanted to see the New York Stock Exchange and experience the energy of the place, but there wasn’t enough time. Additionally, I regret foregoing the opportunity to visit Chinatown, America’s largest Chinese community.

Other regrets include our failure to visit one of the thriving Christmas markets in NYC. Bryant Park Winter Village offers shopping, ice skating, and hot chocolate in its cozy Igloos. Additionally, the famous Dyker Heights Christmas Tour offers an enchanting tour of one of the country’s most outstanding neighborhood Christmas light displays.

I’m also sad we didn’t get to see “Wicked,” the sensational Broadway show that’s taken the country by storm. Maybe this just means I need to go back soon. Plus, I really wanted to explore Rockefeller Plaza more, get our photo made on the Beam, and experience the Skylift.

I don’t regret forgoing The Empire State Building. We could see it from the One World Observatory, and that was good enough. My nephew’s friend advised us to skip the inside tour as it’s a bit disappointing. We also viewed the historic Brooklyn Bridge from the Observatory Tower.

Other worthy places to visit in NYC include Madame Tussaud’s Wax Museum, New York Botanical Gardens, and The Metropolitan Museum of Art.

Conclusion: Secrets to Enjoying New York City

All in all, I think New York City is one of the best Christmas destinations in the country. It’s really hard to explore such a massive city in just four days. A week is best if you can swing it.

However, no matter how many days you have, it’s totally worth your time. My family and I now have a wonderful trip to remember. And it was made even better because we shared it together.

NYC is such a lively place, and there’s absolutely no other place quite like it. I can’t wait to go back!