The best Christmas in NYC itinerary

Is there a more magical place during the holiday season than Manhattan? Maybe, but I haven’t found it yet. This Christmas in NYC itinerary has been a long time coming; I’ve been to New York during all four seasons, but never in the lead-up to Christmas. And I’m here to tell you that it can be done in just three days, as long as you’re prepared to hustle.

If you prefer a more leisurely pace, stay an extra day or two and allow for some more downtime or a spare night for a Broadway show. If you’re looking for a more generic plan for other times of year, my 4-day New York itinerary post will be the perfect starting point.

Moreover, “Christmas in NYC” doesn’t mean you have to spend actual Christmas Day there. No, because it’s alive with the holiday spirit from late-November through very early January, so you have several weeks in which to plan your NYC itinerary.

Here’s the best NYC itinerary for a Christmastime visit…

I built this itinerary for my Mom’s first-ever visit to New York City. Seeing Central Park and The Rockettes Christmas Spectacular have been on her bucket list for a long time, and being able to create a Christmas in NYC itinerary that ensured we did things important to her and things new to me and my family — all within a three-day window — was important.

Our goal was to walk as much as possible. After all, a big part of the NYC experience is just being out on the streets taking in the sights and sounds of the city. With that in mind, we decided to stay in the heart of midtown, just steps from Times Square. I always tell people who’ve never been to Manhattan that this is a great place to stay because of its proximity on foot to so many attractions and restaurants.

And the Hotel RIU Plaza Manhattan Times Square didn’t disappoint. In fact, I think it’s my new favourite Midtown hotel. A lot of hotels with “Times Square” in their names aren’t actually in Times Square at all — but this one is. Just steps from Seventh Avenue on West 47th Street, don’t confuse the RIU Plaza Manhattan with its sister property by a very similar name (the Hotel Riu Plaza New York Times Square).

If you have the option to add the breakfast for less than $22 per person when booking, do it! It’s a great buffet and you can only get it for USD$22 if you book it a day ahead at the front desk. That said, I’ve added some other breakfast options in the NYC itinerary below just in case you don’t want to do a hotel buffet each morning.

Before we dig in, I have three important notes:

1. I suggest creating a Google spreadsheet that you can download and/or copy and customize for your Christmas in Manhattan experience (you can find a sample here, which is for my four-day general itinerary). It’ll keep you organized and efficient.
2. You need reservations — for everything. Everywhere. Yes, even on Mondays and Tuesdays. I won’t even mention below that you need tickets in advance for something specific, because ev-ery-thing requires it during the holiday season.
3. Use my map below; download it before you leave to use it offline if you have to. Because if you’re following along with my itinerary, it’s going to save you time since I’ve got everything here plotted on it.

Your Christmas in NYC map

Alrighty, get your jingle bells ready and let’s do this.

DAY 1

Arrive as early as possible, whether it’s by bus, car, trail or air. With such a short stay, you need to maximize your time in Manhattan. Make your way into the city centre; if you arrive by air at LGA, I love taking the free Q70 LaGuardia Airport Bus. If you drove, find a secure parking lot in or near your hotel and leave your car put until the end of your trip — trust me, you don’t want to drive in Manhattan.

By noon, you should be dropping off your bags at your hotel even if your room isn’t ready. Just ask the bellman to hold your bags until you return later in the day.

If the weather isn’t co-operating, head to the TKTS Ticket Booth in Times Square to see if there’s a matinee with some last-minute tickets available. If the weather gods are on your side, however, you’re going to spend the afternoon walking to Ellen’s Stardust Diner for a singing lunch followed by a stroll up to Central Park. I suggest starting at the southwest corner of the park to see the Maine Monument, then Umpire Rock up to Tavern on the Green. I don’t really recommend eating there (the food is just OK), but the exterior decorations are stunning.

From here, head east along the south side of the Sheep Meadow (which will only be open if there’s at least six inches of snow) to the Central Park Carousel and continue east to the Chess & Checkers House and the Dairy; it has a great little gift shop and is a very photogenic building. Head northeast from here to find the William Shakespeare statue, which marks the start of The Mall and Literary Walk, should that interest you. Otherwise, keep going northeast on the path system until you reach the Alice in Wonderland statue.

Now you can zip all the way over to Fifth Avenue, which is the eastern edge of Central Park and decide whether you want to see The Met’s iconic front steps or head south again. Stay on Fifth Avenue as you walk back to Midtown so you can see the dazzling storefronts and window displays along the way.

It should be getting dark by now, so the street will be a vibe. Don’t miss checking out Dior, the Tiffany & Co flagship store — definitely make a point of going inside, too — plus Saks Fifth Avenue, St. Patrick’s Cathedral, The LEGO Store, Cartier, Bergdorf Goodman, Harry Winston and, especially, the Louis Vuitton store. It’s a WOWer, even if you’re typically not impressed by designer labels.

I added The Plaza to my NYC itinerary map because it’s definitely worth walking over before you descend farther along Fifth Avenue, but only guests are permitted inside this time of year. The exterior is beautifully decorated and the bellman outside behind the red ropes are equally photo-worthy (please ask permission first).

By nightfall, your hotel room will be ready and you’ll need some time to relax and refresh after a busy day. Just be sure you’ve already made a dinner reservation since every day is a peak day in Manhattan during the holidays. Based on many recommendations, we went to Becco on nearby Restaurant Row for its all-you-can-eat pasta extravaganza; it was good value for $36.95 per person but not a mind-blowing meal. Refer to my Restaurants – NYC list for alternatives.

Go easy on the booze at dinner because you still have a big night ahead of you! After stuffing your face, you’re walking to Rockefeller Center to do All The Things. From seeing its iconic Christmas Tree to riding up to The Top of the Rock and getting even higher on the new Skylift and even recreating your own picture on The Beam; in fact, just walking from the RIU Plaza Manhattan hotel to The Rock will be met with city lights and more holiday décor than you ever thought possible in such a small footprint.

But you must not leave until you ice skate at The Rink. If there’s one thing that screams “I did NYC at Christmastime,” it’s skating at Rockefeller Center. Mercifully, the skates are easy to get on and off and are reasonably comfortable, too. Plus, your ticket gives you access to a free locker so you can safely tuck away your boots and purse or backpack.

This will all probably take you until at least 11 p.m., and you were likely up early to travel, so it’s off to bed for you.

DAY 2

Rise and shine, tourista! This is your only true full day in NYC and you’re going to make the most of it.

Although it’s not the Christmasy-est thing to do in Manhattan, if you’re like my Mom and this is your first trip, you’ve got to do the Empire State building. I recommend the 10 a.m. time slot as it’s often the least-busy time to go up and down the elevators. You can walk from Midtown and stop for breakfast first at Best Bagel & Coffee; they’re among the best bagels in the city and it’s a very New York breakfast. Plus, it’s only another five to 10-minute walk to the Empire State Building from there.

Time for some free NYC Christmas markets, starting with the Bryant Park Winter Village. There are vendors galore, a free skating rink and loads of food kiosks, so have lunch here if you’re not still full from your massive bagel earlier in the morning. While you’re in this neck of the woods, if the weather isn’t great or you zip through the market quickly, the New York Public Library is right beside Bryant Park and it’s free and amazing and is also all dressed up inside for the holidays. (I wrote a little more about it in my New York City in the rain post, which may also come in handy if Mother Nature decides it’s too warm for snow.)

If you’re feeling spry, you can walk to the Union Square Holiday Market next — but it’s a good trek, so don’t be afraid to hop on the subway. Use GoogleMaps and toggle it to the “public transit” tab to get step-by-step directions. If you don’t have data in the USA, download the Airalo app and use my referral code (ANDREA6044) to get you USD$3/CAD$4.50 off your first eSIM purchase. You won’t ever want to take public transit in a new city ever again once you’ve done it with GoogleMaps!

The Union Square market is much smaller than Bryant Park’s but very similar, so if you’re still thinking about that nice ornament you didn’t buy, chances are good you’ll find it here. There’s also some good retail shopping down here if you have time, like my new fab find: Rothy’s. Shoes that make my bunions happy but my vanity even happier.

Once you’re all shopped out, take the subway back up to your hotel and put your feet up for a wee late-afternoon rest.

Your early dinner at Lillie’s Victorian Establishment (the W 49th St. location) will ensure you eat in at least one restaurant that takes its Christmas décor very seriously. For real, it’s basically vomiting garland in every direction — and it’s glorious. You need an early dinner reso because you’re off to see The Rockettes tonight! Lillie’s burrata appetizer and wagyu burger are both fantastic, BTW.

Walk from Lillie’s to Radio City Music Hall for your 8 p.m. performance and be prepared to be wowed. I went in thinking it would be all about the famous high kicks. Don’t get me wrong, there were a LOT of high kicks, but The Radio City Rockettes’ Christmas Spectacular was so much more; it was a light show, there were fairy drones, Santa is a central character (and, girl, he can SING!), there’s a musical theatre troupe making frequent appearances and there’s even a teeny-tiny little Nutcracker ballet dancer on pointe. I was blown away.

Pro tips: I recommend aisle orchestra seats on outside the centre rows; they’re slanted toward the stage and easy to see over the people in front of you (we had Row MM on the left aisle and they were expensive but fantastic seats). The dress circle is MUCH farther away from the stage than any other theatre I’ve been to globally so bear that in mind. Try to arrive no later than 7:30 p.m. at Radio City because the line to get in is very long and the bathroom lines inside match it; this theatre is enormous. There’s no intermission, so come well-fed and -watered and be sure you’ve emptied your bladder before showtime. 

When you come out of your show, cross the street to see the giant candy canes (pictured at the beginning of this post), then walk south on Sixth Avenue past W 50th St. Behold! There are giant red balls that await as you continue toward W 49th St. These huge ornaments (also plotted on the map above) are best viewed at night and they’re perfectly positioned for your post-Rockettes enjoyment.

If you still have energy to burn, and it’s a nice night, take in Times Square after dark — one of my favourite times to be there. It’s electric at night and it’s when the street performers are out in full swing. Otherwise, nighty-night.

DAY 3

Wakey, wakey — it’s your last day, but you were smart and booked a late flight home so you have most of the day to play with. Get up and at ’em early so you can get your bags into storage and check-out before the day has barely begun. Today is a mix of holiday displays and imperative NYC tourism.

Depending on how you feel, walk or take public transit to have breakfast at one of our favourite spots — In Common NYC. It’s in the heart of Hudson Yards, which is where today’s adventure begins. Order anything (no, really), because it’s all delicious. I love sitting and having a decaf mocha served in big, bowl-like mugs. Cozy yumminess.

Find your way over to the Vessel, which has re-opened (with new safety nets) after its years-long closure, but don’t feel you need to go inside to experience it. Simply walking around it if you’re short on time or don’t want to spend $10 will do the trick. Then check out the nearby SHED, which is an interesting piece of architecture, and feel free to pop into the Hudson Yards shops. There’s some nice holiday décor inside and public washrooms if you need one. But keep it quick — there’s no time for shopping this morning.

Now look for my pin on the map above called “Enter The High Line,” which is the starting point for this elevated city path — a must during any season. I wrote more extensively about The High Line in my NYC with teens post, which is chock full of great information even if you don’t have teens. Wander south and take in the compelling architecture, installation art, street murals and botanical info along the way. You’re going to get off The High Line at the pin I’ve titled “Exit The High Line for Chelsea Market” and then take a quick peek inside Chelsea Market, since it’s one of the oldest markets in North America.

Get out your GoogleMaps and head down W 15th St. to take the A/C/E subway line from 14th St/8th Avenue station toward the World Trade Center (just four stops). Exit into the Oculus and take it all in from the first or second level before going up to street level to see it from outside. Walk over to the 9/11 Memorial Pools to pay your respects to one of the city’s greatest tragedies before heading to the financial district.

Next up, you’ll walk south on Greenwich St. and go east on Thames St. and go south again on Trinity Place, where you’ll pass the stunning Trinity Church where Alexander Hamilton (and many of he and Eliza’s family) are buried. You can see Hamilton’s gravesite from the road but it’s also free to go into the cemetery if you’re interested and have time.

Go slightly south to Wall St. and take it to Broad St. to walk south again to see the Fearless Girl as she stares down the NY Stock Exchange building, which incidentally has outstanding holiday decorations and a tree that rivals the one in Rockefeller Plaza.

From here, walk west to Broadway and take it south towards Bowling Green. The famous Charging Bull is just before the fork in the road, but be sure to take a look at Bowling Green because it’s also beautifully decorated with all the trimmings.

Stay on the west side of Bowling Green and keep going south to Battery Park, now officially called The Battery. We’d hoped to ride on the SeaGlass Carousel but it’s closed for the season (still worth a peek into its glass shelter) and we also wanted to visit the Statue of Liberty Vista Point, but it’s under construction and inaccessible at time of writing, but you can hop up on a park bench near the construction zone and get a decent look at her. You won’t have time for a boat tour today, but come back one day and take the Staten Island Ferry instead of the paid tours to get the best vantage point for photos.

Pro tip: there will be dozens of official-looking people near the Staten Island Ferry entrance, trying to convince you that you need to pay for tickets. You don’t. They’re lying. Ignore them and go get your free ride if time permits!

We took the subway and went for lunch at Oscar Wilde after Battery Park, but I’m not sending you there. It’s decorated very much like Lillie’s Victorian and shares a similar menu (same owners) but the prices are higher and the food and service is inferior. Instead, I wish we’d gone to Rolf’s on Third Avenue, but because I can’t personally vouch for it, I left it off my Christmas in NYC itinerary map above.

No matter where you go for lunch, try to leave enough time to walk to Macy’s at Herald Square. Its decorations inside and out are not to be missed. There’s a big Santa’s Village up on the eighth floor, but we didn’t realize we needed a reservation just to view it — that’s new. If you’re visiting NYC during the holidays with little kids, this is something I’d prioritize and skip the financial district to do. Don’t forget to head to the fifth floor to experience the old-timey Macy’s wooden escalator, too!

It will likely be at least 4 p.m. by the time you walk out on W 34th St. and, gosh darnit, it’s a Christmas miracle that you’re still standing after all the walking I made you do. So, order yourself an UBER to get back to your hotel if you’re spent.

Speaking of UBERs, NYC in December is mayhem and if you need to get to the airport, I suggest public transportation. You can get to JFK and LGA using the Metro and a mix of the Metro and NJ Transit to reach EWR. Waiting for UBERs or a free taxi could mean you risk missing your flight (ASK ME HOW I KNOW).

I’d love to hear what you think of your Manhattan holiday adventure and if you have suggestions for this NYC itinerary, please leave a comment.

Happy holidays!

(What’s that? You drove to NYC? Then you should consider visiting the American Dream Mall in nearby New Jersey, too. It’s holiday-mania over there!)

 

DISCLAIMER: Rockefeller Center hosted our visit to its attractions but we’ve got the four-digit VISA bill to prove we paid for the bulk of this epic trip. All opinions and suggestions are my own, as always.