6 Winter in New York Travel Tips For An Enchanting NYC Christmas

Winter in New York City Travel Tips

Winter in New York City.

The very idea conjures an image of snowflakes catching in the golden glow of a streetlamp, while faint strains of Silver Bells drift from a busy restaurant into a street “dressed in holiday style.”

Thanks to NYC Christmas movies like Elf, I’ve always wanted to see winter in New York. When we selected a destination for our second annual mother/daughter “Christmastime in the City” trip, New York City naturally won out.

We had a magical time during our long NYC weekend in December 2019. But our NYC Christmas trip gifted us with a few less than pleasant surprises. Don’t worry, I’m here to share all the lessons we learned on our NYC Christmas trip. Even with our stumbles, this is a trip we’ll never forget.

Read on for my very best winter in New York travel tips!

#1 Plan Ahead 

I’m far from alone in my desire to see New York at Christmastime. Thanks to New York holiday attractions like the Rockefeller Center Christmas tree, Christmas shopping on 5th Avenue, and of course, the infamous New Year’s Eve Ball Drop in Times Square, the holiday season is the busiest, most expensive time of year to visit. As a result, it’ll behoove you to book plane tickets and NYC accommodations as soon as you’ve decided on a NYC Christmas trip.  I ended up on a major struggle bus when I started looking into Manhattan lodging.

I really wished I’d booked two hotel rooms for our New York winter weekend. Instead, I faffed about, watching room prices soar as the holidays inched nearer. Finally, I panic booked a dodgy five-story walk-up in Midtown. It’s by far my biggest regret of the trip. Since we spent an average of 13  – 14 hours out of the apartment every day, we should have stayed in hotel . . . . You know, where we would have had a working elevator, customer service support, and probably not homeless people sleeping in the building’s awning.

But I’d gotten really stuck on trying to replicate the accommodations we’d had the year before in Boston. We’d rented a three-bedroom apartment through Stay Alfred on Washington Street and it worked perfectly. New York City and Boston might have their similarities, but their housing markets – even for tourists – are drastically different.

New York City doesn’t do short-term rentals so don’t book one.

If you want a short-term rental in Manhattan, fuhgeddaboudit. New York State cracked down on short-term rentals in 2018, essentially banning Airbnbs and VRBOs. In early 2019, a judge overturned this law, but it’s still not the most comfortable market to dabble in.

I found our two-bedroom apartment on Booking.com. It seemed legitimate enough and the interior of the apartment worked great for us. However, when we arrived, we found a building wrapped in scaffolding. Inside, we could either climb five flights of stairs or take a tiny freight elevator that made me fear we’d end up requiring a visit from the New York City Fire Department. Most telling, the informational signage in the apartment basically demanded we give the listing a five-star review. In other words, they wanted us complicit in dubbing other New York City travelers into booking these less than desirable digs. No thank you! 

#2 Choose your Manhattan, NY accommodations’ location carefully

Sure, I’d heard that you shouldn’t stay in Midtown. So I went right ahead and ignored that wise advice. . . .

(Technically we stayed in NoMad, but the Empire State Building was only a five-minute walk away.)

Since the main NYC Christmas attractions are between 34th and 57th streets, I figured why not stay in the thick of it? We’d only be in New York City for three full days, so it seems more efficient than staying somewhere that required a decent subway ride. But my idea of staying in a “central location” kind of backfired. I didn’t even know you could be too conveniently located!

We found it difficult justifying taking the subway only two or three stops down the line. If we headed up to the theatre in Times Squares or Central Park, we almost always opted to walk. Like proper Midwesterners, we failed to factor in two-minute-long red lights. Let me tell you, it takes a lot longer to walk a mile in the city than it does in the country! In hindsight, I’d have preferred to have stayed farther afield and popped out right at our destination each day.

But perhaps the biggest downer about Midtown is its distinctive lack of personality. We almost always returned to our apartment via 5th Avenue where dining options were limited to chains and Korean barbecue. Since we’d spent all day on our feet, we sadly never ventured further east or south to enjoy the offerings of neighborhoods like Murray Hill and Gramercy. Instead, we ended up eating at the Heartland Brewery on the first level of the Empire State Building twice – pleasant but not exactly the pinnacle of NYC’s available culinary experiences.

#3 Avoid SantaCon

Let’s cast our minds back to a quiet Saturday morning in New York City in December 2019. Thanks to flight delays, we reached our Manhattan apartment well after midnight. Mom and I headed out into the NoMad/Flatiron neighborhood to grab some breakfast items. As we emerged from the basement of Trader Joe’s, we found Third Avenue filling with twenty-somethings in Santa costumes. As we continued on with our day, the entire island teemed with these Santa-clad individuals.  

Turns out, we’d accidentally timed our winter in New York visit with SantaCon. This Santa themed pub crawl originated in San Francisco to the mid 2000s. Many other cities around the world host SantaCons, but New York City holds the largest, most notorious event. We’d have preferred not to share NYC sidewalks with drunken revelers decked out in their best festive apparel.

It’s hard to avoid something when you don’t even know it exists. So I’m telling you right now – SantaCon is a thing. You can either get into it or avoid it. If you’re over 30, you probably want to avoid it. Do yourself a favor and Google Santa Con dates before  scheduling your NYC Christmas trip.

#4 You CAN be spontaneous on a NYC Christmas trip

Despite New York’s popularity during the holiday season, it surprised me that you didn’t need to book theatre tickets in advance. Unless you’ve set your heart on a particular show, don’t book ahead of time. Yes, you really can bank on last minute ticket availability.

Don’t believe me? Consider that the Christmas Spectacular at the Radio City Music Hall has up to five daily performances. With nearly 6000 seats in the Radio City house, you better believe rush tickets exist for nearly every performance. If you don’t want to stand outside at the TKTS discount ticket booth in Times Square, download the TKTs app a few days before your visit to get a sense of what’s available. Then just purchase the tickets in the theatre lobby when you’re in the city. If you’re using a tourist pass like the New York Pass, see if there are any in app deals on popular shows.

#5 Consider Visiting NYC Mid-Week

As four Midwesterners, our first two days – Saturday and Sunday- proved overwhelming. And since we were staying in Midtown, we got to muddle our way through the New York streets in a sea of equally confused and disoriented tourists. In fact, the very first group activity we did  – a bus tour of lower Manhattan – ended with us trapped on the bus’s upper deck, in the rain, while we sat in traffic on the West Side Highway.  Welcome to New York?

Then Monday arrived. The crowds dispersed. Lines at tourist attractions shortened. We’d gotten our bearings and winter in New York started to feel, well, magical.

A midweek trip isn’t always possible. (It wasn’t for us!) But if you can make it happen, I’d recommend scheduling NYC Christmas trip for midweek. If you must go over the weekend, do the best of brace yourself for hordes of people. Also try visiting areas like to 5th Avenue and Rockefeller Plaza late in the evening after crowds disperse.

#6 Don’t do A NYC Christmas trip as a first time NYC visitor

I’d visited New York City two times before we made our NYC Christmas trip. New York City serves up sensory overload even at the calmest time of year. I’m no New Yorker, but my faint familiarity with street and subway layouts proved helpful in the NYC Christmas mayhem. 

My poor sister-in-law had never been to New York before. Naturally she wanted to visit many of New York’s “top ten” tourist attractions. With so many people in town for holiday festivities, we found extra-long lines at attractions like the Empire State Building. Busy streets also slowed down how quickly we could navigate from one place to another. It proved not an ideal time to be itching to get to the top of every building or grab a photo of every iconic NYC site.   

My Winter in New York Takeaways

If I could do it all over again, I’d probably focus my visit on seeing holiday lights, eating well, doing a little shopping, wandering around Central Park, and visiting a few favorite haunts like the Metropolitan Museum of Art and Cloisters. If you can, try to simply exist in New York at Christmas. If you can let go of your NYC checklist, you’ll fully enjoy winter in New York.

I’m so happy we saw the tree in Rockefeller Plaza and skaters spiraling on the ice in Central Park. I loved sipping hot apple cider as we wandered the Bryant Park Christmas Market. The Christmas Spectacular at Radio City Music Hall is hands-down one of my favorite Christmas memories ever.

If you’re contemplating whether a winter in New York trip is right for you, my best advice is to just go. It’s an unforgettable experience and these tips will help ensure you have a spectacular trip.