If you get to see NYC all wrapped up for the holiday season, consider yourself lucky. Sure, it is crowded and potentially cold, but something about the city during this time of year is magical. Growing up just outside of NYC, and living there later in life, means I spent a lot of time wandering the city during the holidays. Thinking about it stirs up nothing but happy memories for me.

While I don’t frequent many of these places during other times of the year, even the most tourist resistant New Yorkers can’t help but enjoy the spectacular sites, holiday windows, and glistening trees.

If you are in New York for the holidays, you will want to do the things that everyone wants to do during this time. You will want to make like Kevin McCallister and hit the ice in Central Park. Squeeze together to gaze at the Rockefeller Christmas tree. And parade down 5th Avenue looking at the holiday window displays.

This is not an itinerary that takes you ‘off the beaten path’. These popular spots are well worth it during the holiday season for a truly unforgettable NYC Christmas Experience.

NYC Christmas

photo by Anthony Quintano via Flickr

Couple of things to note about this itinerary.

  • I refer to Avenue of the Americas as 6th Avenue, they are the same.
  • Walking around the city is my favorite way to explore it, so this itinerary has a lot of walking. It is easy to take cabs or hop on the subway more frequently if you aren’t interested in so much walking.
  • 20 City blocks = 1 mile

Hop on the Subway and get yourself to Herald Square. It’s a central point in the city, so lots of trains stop there. The B, D, F, M, N, Q, R, W stop at 34th St. Herald Square while the A, C, E, 1, 2, 3 stop at 34th street Penn Station.

8:30am – Macy’s Herald Square Window Display 

New York City Christmas

Photo by Sarah via Flickr

Macy’s always has a Miracle on 34th Street Holiday theme, with additional windows and stories. Each year the display gets bigger, brighter, and more interactive. These windows are some of my favorite, I always make sure to check them out each year. Starting your day here means there will be a lot less people.

  • For the GPS: 151 W. 34th street
Detour → Got kids? Make a stop at Macy’s Santaland. It is on the 8th floor of Macy’s Herald Square Store. Santaland is a North Pole Village filled with elves, reindeer, sparkling lights, and of course, Santa. It’s magical for kids (and adults) and opens the day after Thanksgiving and runs through Christmas Eve. Head here first thing in the morning to beat the crowds.

Walk down Broadway to 29th St. where you can grab some strong coffee and a quick bite to get energized for the day. ~7 minutes

9:00am – Stumptown Coffee in the Ace Hotel Lobby

New York City Christmas

Good coffee and attention to detail make this a quality coffee stop in a central spot. The high ceilings and vintage-y feel of the coffee shop are comforting. Drink your coffee people watching in the window, or lounge in the hotel lobby for awhile.

I always get the Nitro Cold Brew when stopping in at Stumptown. The cold brew, infused with nitrogen, is creamy and smooth and so delicious, even in the cold of winter. If drinking a cold beverage is not in the cards, the cappuccinos and lattes are excellent.

  • For the GPS: 18 W. 29th St.

Walk down one block to 28th street and hop on the subway NQR headed downtown. Go three stops, and get off at 8th st. NYU. ~ 1 minute

10am – Washington Square Park 

New York City Christmas

Photo by Andy Cross via Flickr

This is one of my favorite Christmas trees in the city. Of course, it’s best to see it at night when it is lit up, but it is pretty cool during the day. 

Take a stroll around the park, one of the most iconic in the city. NYU is nearby and a good detour if you have kids looking at colleges.

  • For the GPS: Washington Square Park

The Washington Square Arch marks the entrance to 5th Avenue. Walk uptown on 5th Avenue for your lunch break. 12 blocks up 5th Avenue gets your to 18th street. Turn right crossing Union Square W and Park Ave. S until you hit Pete’s Tavern. ~15 minutes 

11am – Lunch at Pete’s Tavern 

New York City Christmas: Pete's Tavern

Photo by Dr. DeNo via Flickr

Pete’s Tavern is a NYC institution; the oldest bar in the city. Fun fact, my parents almost rented an apartment above it, but decided it would be too noisy. The Tavern goes over the top during Christmas; decorated with trinkets, trimmings and old-fashioned lights.

The food is decent, a lot of options to choose from, but not out of this world. You are coming here for the experience, more than the quality of the food.

  • For the GPS: 129 E. 18th St.

Walk up Park Ave to 23rd street (you can hop on the subway here, but you will have to transfer) and turn left and walk one avenue block to the NR subway stop at 23rd and Broadway. ~10 minutes

Take the subway 6 stops uptown and hop off at 5th Ave/59th Street. Walk down 59th Street (the park should be on your right). When you hit 6th Ave, turn right into the park. Follow signs, the rink is about ¼ mile into the park. ~5 minutes

1pm – Ice Skating at Wollman Rink in Central Park

New York City Christmas - Ice Skating in Central Park

photo by Young Sok Yun via Flickr

There is no more classic a holiday activity in NYC than skating in Central Park. This ice skating rink is bigger and cheaper than Rockefeller Center. And during the day (especially if it’s during the week) it will be less crowded. If you want to hang out in this famous park for longer, check out these ways to stay active in Central Park.

  • For the GPS: 850 5th Ave.

Exit the park from the same spot you entered and walk past the subway stop. Turn right down 5th avenue. Stop to check out the Apple Store, the windows at Bergdorf Goodman, and the sparkling display at Tiffany’s. At 56th street (Abercrombie is on the corner). Walk a couple hundred feet in and you will be at Momofuku. ~12 minutes

3pm – Crack Pie at Momofuku Milk Bar

New York City Christmas: Crack Pie at Momofuku Milk Bar

photo by Wally Gobetz via Flickr

This NYC sweet spot is an excellent place to take a break and refuel from your ice skating adventures. It is a small door, and if there isn’t a line outside, you might have trouble spotting it, so keep your eyes peeled. Since you just spent the last hour or so ice skating, feel no guilt indulging in any of the unique and delicious desserts Momofuku is famous for. Chef Christina Tosi (of Master Chef) is the brains behind this incredible dessert bar.

Crack Pie should be one of the choices you make. I don’t think I can even describe the incredible taste of this pie. Savor every bite. If you can handle the cold, the cereal milk soft serve ice cream is another incredible choice.

It is not a sit down place, so take your treats and eat them as you head toward Radio City Musical Hall.

  • For the GPS: 15 W. 56th St.

Leave Momofuku and continue walking down 56th street. Turn left onto 6th Avenue and walk to 50th street. ~8 minutes

4:30pm or 5pm – Radio City Christmas Spectacular 

New York City Christmas: Radio City Christmas Spectacular

photo by Bob Jagendorf via Flickr

This is a classic NYC Christmas experience. Locals and tourists head to this show to see the famous Rockettes every year. I have gone at least 5 times in my life; from a kid to an adult. It has never failed to disappoint me. Something about this show really puts you in the Christmas spirit.

During the week, shows are at 5pm, on the weekend they are at 4:30pm. I would recommend going to the early evening show then heading out to see the tree and have dinner afterwards. Check out the full schedule here.

  • For the GPS: 1260 Avenue of the Americas

When you exit Radio City Music Hall, walk down 50th street and you will end up right in Rockefeller Center. Check out the beautifully decorated windows at Anthropologie on the corner before you turn and see the tree.

6:30pm – Rockefeller Center Christmas Tree

New York City Christmas: Rockefeller Center Christmas Tree

My family tradition: Chug a beer in front of the Rockefeller Center Christmas Tree.

Turning the corner and seeing this famous Christmas tree gets me every year. I love hearing all the little mutterings of “Wow!” and “Ooohh!” when people see the tree. It will be crowded. There is no getting around it. Your photo will have tons of other people in it, but that is okay! Take some time to watch the people ice skating (don’t do it-too expensive and too long a wait!), and just take in all the happiness around you!

When you are done, walk through Rockefeller Center, and exit on the other side of the skating rink (angels line the walkway) and St. Patrick’s Cathedral towers ahead. Turn right down 5th Avenue. Check out the windows at Saks Fifth Avenue at 50th street right when you come out of Rockefeller Centre. As you are walking down 5th Ave. Turn left onto 45th St. Crossover Madison and Vanderbilt, then turn right onto Park Ave. Naples 45 is in the Metlife Building. ~15 minutes

Detour→ Not interested in eating just yet? Head down 5th avenue to 42nd street and Bryant Park. From late November through the beginning of January this holiday market is one of the best in the city. The holiday market has 125 different vendors selling a huge variety of goods. On Saturday’s the market closes at 9, during the week it closes at 8, and on Sunday’s it wraps up at 6.

7:30pm – Dinner at Naples 45 

New York City Christmas: Dinner at Naples 45

photo by Patrick Copley via Flickr

This wide open Italian restaurant with wood burning pizza ovens, a huge bar, and great outdoor patio (though you won’t be sitting at it during the winter!). It is popular with folks who commute into the city from Grand Central Station, and happy hour can get crowded. It is laid back and comfortable with tasty food and decent prices. I used to hang out here a lot as my friend was a bartender – I always knew I would be getting a great meal.

  • For Your GPS: 200 Park Ave. (Metlife Building)

If you have had enough for the day, hail a cab or hop on the subway at Grand Central Station (4,5,6,7). If you still have energy, continue strolling in the area, you will eventually find a place to grab a drink or people to watch. 

Late night – Cocktails at Lantern’s Keep 

New York City Christmas: Drinks at Lantern's Keep Bar Inside the Iroquois Hotel

photo by Jeff Kocan via Flickr

I would recommend Lantern’s Keep for quality cocktails in a quiet atmosphere. It is on 44th street between 5th and 6th Ave, inside the Iroquois Hotel. It is small, cozy, and a great place to warm up and wind down after walking around the city all day.

  • For the GPS: 49 W. 44th Street

If you follow this itinerary walking from place to place it should result in about 1 hour and 20 minutes of walking, and 4 miles. Of course this doesn’t factor in meandering around the parks, ice skating or stairs in buildings. Overall, it’s a solid itinerary that covers a lot of the classic holiday events in NYC. 

I typically stay with friends and family while in the city, but if I happen to need a hotel. Booking.com is my go to source for booking a place to stay. If you check out the New York City Page, there are tons of deals and filters. Plus, if you happen to book through my link, I make a little extra $$ at no cost to you!