6. Hot cocoa at Le Maison du Chocolat

Decadent hot cocoa at Le Maison du Chocolat in NYC

To me, nothing really says winter like a steaming mug of hot cocoa. I prefer black coffee 90% of the time, but you can’t beat a nice rich cocoa while enjoying holiday festivities. While there are plenty of trendy places throughout the city to grab a quality cup of hot chocolate, only a few come with the added bonus of a much needed low-key setting.

Le Maison is an amazing Paris-based chocolatier which serves tasty treats and the best hot chocolate in the city. The vibe and presentation are both great and the shop is located nearby all the touristy activities including Rockefeller Center and FAO Schwartz. I really love how the whipped cream is served in a separate bowl. The staff was so nice and friendly and even gave us a free truffle to sample.

Location: 119 W. 56th Street

7. Rockettes Christmas Spectacular at Radio City Music Hall

Christmas at Radio City Music Hall in NYC

Seeing the Rockettes Christmas Spectacular is always a contender for top touristy things to do during the holiday season. The Rockettes have been dazzling audiences around the world with their dance moves (including their famous eye- high kicks) at Radio City since 1925.

If you do have the time and spare cash, this is a great show for anyone seeking a fun high spirited production. For some reason, this sign always reminds me of Home Alone 2 in the scene where Kevin is checking out all the iconic city attractions with All Alone at Christmas playing in the background. This is one of my favorites scenes in either of the movies although I prefer the first one overall.

Even if you can’t make it to the show, I recommend walking by to check out the festive seasonal decor which includes a giant red tree. Radio City Music Hall is already a standout site that you cannot miss due to the huge neon sign.

8. Central Park

Winter day in Central Park

Nothing could be more romantic during the New York winter season than taking a stroll through Central Park. The early morning hours are actually quite peaceful. As I walk around the park, I am reminded of all the great scenes from Home Alone 2. If you are fan, you will likely also remember Kevin’s adventures in the big city as you make your way through this quaint park.

Take in the beautiful city views, watch the skaters glide by on the Wollman rink, and simply enjoy a little peace and quiet before embarking on the craziness in Rockefeller Center.

If you are lucky, you will get to see the park covered with a fresh dusting of snow. Do not get your hopes up through as snow is quite rare this time of year. Nevertheless, the park is beautiful anytime of year and especially tranquil and rejuvenating during the cold winter season.

9. Holiday markets and shopping

FAO Schwarz in NYC

There are a number of great holiday shopping markets scattered throughout the city. The best is a European inspired Winter Village at Bryant Park. Here you will find over 170 holiday shops, plus specialty food and drinks, at an open air market. While here, you may also want to check out New York’s only free ice rink (skate rentals apply). Although admission is free, it’s not really that “free” when you have to pay $30 for skate rentals. Despite having my own skates, I still wanted to check out the main rinks during my first time in the city – maybe next time.

I recommend investing in a good pair of skates if you live nearby, as they will easily pay for themselves in just 2 visits. Years ago, I purchased figure skates at Dick’s Sporting Goods for $40 with a free shake sharpening. Let’s just say, I have already saved myself hundreds of dollars on rentals as I skate pretty much all winter on Philly’s gorgeous rinks. On a side note, Philly’s holiday lineup is pretty spectacular as well and really underrated in my opinion.

Free ice skating at Bryant Park in New York City

The Columbus Circle Market near Central Park and the Union Square market should also be added to your itinerary if you love shopping and have the extra time. And don’t forget about FAO Schwarz, which recently reopened at its’ new location in Rockefeller Center. Although it looks nothing like it did in Home Alone 2 (I found the decor so much more whimsical in the movie where in real life it looks more like a generic toy store), you can still play the floor piano like Tom Hanks in Big!

The piano from Big at FAO Schwartz in Rockefeller Center

10. The Macy’s Thanksgiving Day Parade

Grinch balloon at the Macy's Thanksgiving Day Parade in NYC

I watch it on TV every year, but decided to rough it up and get up at 3am for the 2 hour drive over from Philly. It was cold, I was tired, I had to go to the bathroom for hours on end but couldn’t risk losing my front row view – but in the end it was worth it. I loved watching all the iconic character balloon floats march by live in person.

2025 will mark the 99th year of this beloved US event. Millions (including me) will either be tuning in or maybe even braving the cold NY winter to watch this beloved American tradition. Seeing all the action in person after dozens of TV airings is quite the experience. At 50 to 60 foot tall, the balloons are so much larger than you would expect. It was a windy day when we attended so the balloons were a bit lower than usual but that didn’t take away from the excitement. And of course, the holiday season officially kicks off with the arrival of Santa to close out the parade.

Although the parade does not start until 9am, you will need to get here by 6am to score a front row view. Although it is a bit inconvenient, not to mention boring, to get here so early, this really is a bucket list contender for anyone wanting to check one of America’s longest standing holiday traditions off their bucket list.

Note: Any pricing details/hours are current as of 2025. Please check with each individual business for updates.

How crowded is the city this time of year?

Let’s just say, I was shocked by the insane level of crowds. They show Kevin by the tree in Home Alone 2 like it’s empty. It’s a different story in real life: don’t expect to be gazing at the tree alone! However, if you want to experience the Big Apple in the most festive way possible, it’s worth the hassle.

With all the extra pizazz and excitement, I would say that this is the most wonderful time of the year in NYC. While the romanticized media version of Christmas in the City may be far from reality, plunging yourself into all the craziness (at least once!) is a totally exhausting, yet exhilarating once-in-a-lifetime experience. I would definitely do it all again!