
“You’ll lose him – you’ll lose him for sure”, is what everyone said when we announced plans to take our 6-year-old, ‘spirited’ child to Times Square for New Year’s Eve. Guess what – we didn’t lose him. In fact, he actually turned 21 today, so I guess I’m not that bad a parent after all….I mean, he’s not HERE, but I know where he is. For the last 13 years, my office has been in New Jersey while I work from Texas. And, before that, I spent treasured times in the city with close cousins – we commuted, by train, ALONE, from Long Island, ….when we were children. Can you imagine? Times were different (we tell ourselves). Nonetheless, New York City has always had a special place in my heart and if pressed, I honestly could not tell you how many times I’ve been there. Whether it was for a luxe vacation, a budget vacation, just a dinner, summer or fall, I’ve seen it all there. But, I can confirm for you that there’s no city I’ve seen that compares to NYC during the holidays.
Take the picture of Radio City above. If you were standing in this spot right now, you could literally pivot around and see Rockefeller Center with its skating rink serving as the most luxurious and well-tread tree skirt any Christmas Tree ever had. Pivot again and spy Saks Fifth Avenue’s windows and light show. If you picture in your mind’s eye the scrolling electric beacons that dress Times Square and the Theatre District, that’s just a sampling of what you’ll see at Christmastime across entire swaths of the city. And, it’s sincerely holiday cheer – ok, fine – the commercial side is probably manufactured to some degree. But, you certainly get the impression the city revels in it, too. It’s not just for show – the city, its inhabitants and its tourists, find a way to get along and actually, dare I say, share some good will. Even if it’s only for a moment. There are lots of cities where you can go outside and just walk. But, few cities where you can bundle up and walk among the tourist traps and the honking horns of midtown, into the pristine rolling hills of Central Park, and then on to shopping that rivals Rue de Faubourg of Paris in a single stroll. It’s a long stroll. Work with me on this.
Think ahead (as always) on what you’ll want to do while you’re there. Is it all casual? Or, will you also need to fit in some dress clothes for The Rainbow Room or Lincoln Center? You can always adapt your activities around what you’ve brought, or buy more (my preference), but you will want to look smart and be comfortable regardless.

How does a Texan dress for snow?
Dressing for your walking trip through NYC is directly proportional to your level of enjoyment. There’s an art to this:
- Dress in layers – this isn’t just something to say – it’s a fact
- Underwear
- I recommend silk underwear – it breathes in a way cotton doesn’t. And, if you’re new to the northeast at winter, you don’t yet know that they like their interiors to be a balmy 92F at all times. Layers.
- Casual top of any variety – I like flowy, my men wear T-shirts
- Sweater
- Scarf (or, 2 – they’re $5 each on the sidewalk)
- Coat – I had a nearly frozen southerner in NYC once tell me “You know how they say leather coats are the warmest in the world?” No, no one has ever said that who experienced actual cold. Get wool, get quilting, get down….get smart.
- Gloves
- A hat – Texans don’t understand the hat part, but it’s key. I have a HUGE head and a ton of hair. So, I’m usually comfortable with ear muffs, but cover your EARS
- Underwear
- Cute shoes? – leave them at home. You need at least 2 pair of durable boots and comfortable socks. I really can’t overstate how much you’ll be walking. Just assume you’ll never get a cab – then if you do, you’ll be pleasantly surprised.
- If it’s going to be REALLY cold, grab some foot warmers. I discovered them last year in Montreal – Heaven in a self-activating pouch
- If you DO have to bring fancy shoes for an event, note that New Yorkers commute around in sensible footwear – you’ll carry your nice shoes in a bag that gets coat-checked, after you swap-out, with your outer coat when you arrive. They think of everything.
- Packing mix and match pieces that all coordinate has never been so vital – you might find yourself wanting to wear everything at once someday – and, if they all match, you’re in business.
- Bring cash – most places will encourage/require you to check your outerwear – you’ll want to tip at least a little
- I recommend a plastic bag you can stick your gloves and hat into that they can sling over the hanger of your coat. Otherwise, shove those pieces into the coat pockets and slide one end of the scarf down the arm of your coat – less likely to fall off and get lost that way.
I’ve chosen to pop over to the city from New Jersey for dinner on more than one occasion – it’s always worth it. But, this is especially true November – December. Maybe you’re bridge-and-tunneling it, so you’ll likely stay close to train stations. There’s the Oyster Bar in Grand Central Station (with Holiday markets popping up left and right). Then, you make your way back down toward the PATH and find yourself near Bryant Park, with alas, more Holiday shops. Sip, stroll, repeat.
Say you have just enough time for dinner, but you gravitate near the Park. Plan ahead and make reservations at Tavern on the Green. Yes, it’s back and better than ever – but, don’t forget your reservations. And, if you’ve never done it before, I recommend a carriage ride through Central Park. It’s in fact controversial these days – are the horses well cared for? There are 2 sides to that story, so I won’t direct you either way – do your own google-search and decide. I will say that doing it once is enough for me – I’m not going to use it as a standard mode of transportation. But, as a slice of Americana – I just couldn’t say no.
“Better to see something once than to hear about it a thousand times.”
Asian Proverb
(I can’t confirm it’s referring to New York, but I think it is)
Not a shopping fan? How about pop-up ice skating – right in the middle of things. Bryant Park, Central Park, again – Rockefeller Center beneath Prometheus? That’s all pretty Christmas-y. The latter costs the most and has the longest lines. Among the 3, if this is your cup of tea, I’d aim for Bryant Park.
Museums? Um, they’ve got your museums. Here are just a FEW of my favorite NYC art museums:
- Metropolitan Museum of Art (ok, fine – yeah, duh….but, even if you’ve been a million times. Go see the Angel tree at Christmas) BTW – if the lines are insane, and they will be, as you face the museum, you’ll see a small entrance down below and to the left….it’s for groups. I play dumb and use this entrance; I haven’t been turned away yet. Good luck.
- Natural History Museum – I’ve grown weary of the crowds at this museum, but if we’re talking Christmas, their Origami tree is really worth the hassle. OK fine. There. I admitted it….I’m looking at my origami souvenir ornament right now.
- Museum of Modern Art (and, an amazing hamburger just nearby @ The Burger Joint in the Parker Meridien Hotel….let your nose guide you….bring cash)
- And, don’t miss the museum’s LARGE gift shop across the street from the museum itself.
- The Guggenheim – Frank Lloyd Wright – if all you do is stare at the building, it’s worth the trip. But, while on the upper east side – stop by a cozy wine bar. Rest your feet. You earned it.
- The Morgan Library and Museum – Not far from the New York Public Library and what a pleasant little surprise. For decades, I didn’t even realize it was there just waiting for me to discover it.
- Cooper-Hewitt – a hands-on Design museum. I wasn’t initially enamored, but it sucks you in, where you stay for hours. And, their gift shop has some of the best and most unique shopping in town.
- Neue Galerie – New to me (I’m not trying to be funny….I’ve really just discovered this gem). Klimt. Enjoy.
I don’t need to tell you there’s nightlife in Manhattan, right? You’ve heard the song: it doesn’t sleep. Well, that’s not exactly been my experience. But, I will tell you that if you’re looking for dessert or a cocktail at midnight, you’ll have no trouble. So, break out of your routine and live like a New Yorker – sleep a little later, eat a little later, be a grown up a little later and squeeze in a show in between. New Yorkers also see shows. And, whether you’re interested in a top-billed ticket like “Hamilton”, or what’s now a tried and true staple like “Wicked”, they’ve got you covered. If it’s “Hamilton” you want, you might want to call your American Express Platinum Concierge (still….in 2019…but, it’s Christmas). Go checkout your options. My advice is to buy at least 1 set of tickets on-line to your dream show right now – before you leave. And,then while you’re there, see what you can pick up on the fly. There’s always TKTS and there are box offices at every venue. You’ll have options. I’ve even picked up tickets outside of a theatre from groups who pre-purchased a block of tickets and a few guests couldn’t make it. Someone always has to cancel during cold and flu season. For face-value, that’s reasonable and fair – I didn’t get taken. But, use your judgment. And, if you’re not down for a live show, check out the numerous cinemas around town. I really like the IFC in Greenwich Village. In addition to first-run films, they’ve got a curated collection of off-beat Noir-ish Christmas offerings. And, in a city of X-million people – there will be a theater showing “It’s a Wonderful Life”, I have no doubt.

If you’re there for Christmas, you’re probably already thinking of visiting St. Patrick’s Cathedral. I guess it’s my upbringing, but celebrating the season in church just brings it home to me – dogma aside. It’s the spirit of togetherness, celebration, and new hope. Even if you’re only there to take in the structure, the art, or the music – it’s always an experience that reminds me for at least a short time each year, that we can be collectively reverent whether it’s for spiritual or just nostalgic reasons, it’s still there inside us.

Where to stay is a question of no small concern – NYC is one of your pricier destinations and you’re going at one of its busiest times of year. You see where I’m going with this – if you didn’t book early, you’re going to be staying out or paying $$$. Still, I’d encourage you to think long and hard about where to stay if you’re looking to economize and consult someone who knows the city. To someone who says, ‘I don’t mind staying out a bit’, I’d say: Trains are a great option in NYC – download the CityMapper app and hope for the best. But, trains breakdown, they get delayed, they’re crowded, they have maintenance at the MOST inopportune times (read: just when you’ve planned your curtain time down to the minute). Cabs can get expensive, but they’re usually abundant….except during shift-change, which is right before your dinner reservations. And, pray that it doesn’t rain – you’ll never get a cab in the rain. Theoretically, someone does, but I don’t know who. And, Uber/Lyft are a great option now, but be aware of “peak time”, which seems to be my waking hours. Point is – you’ll want SOME things to be within walking distance. Don’t plan the whole of your 3-4 night vacation to be very far from where you want to do your sightseeing. There are a TON of New York City hotels – you can find one within your price range-ish. And, be wary of those bearing only a few stars. I’m an intrepid traveler and I’ve had to pack-up and leave a few times when the 3 stars I was “OK” with were discovered to be either ill gotten or just far too generous. You have your health and safety to think of; I’m not just referring to the absence of a Nespresso machine. If you’re staying near Times Square for New Years Eve, or the days leading up to NYE, give consideration to the crowds. We were once greeted at a 5-star hotel with a disclaimer that said the elevators might be quite delayed due to the volume of guests – I kid you not….30min to get an elevator at times. By contrast, I offer the Michelangelo Hotel. I’ve stayed here a few times for NYE and was surprisingly insulated from the crowds and chaos. When I’ve been before, I was always able to walk the sidewalks of Times Square on the big night without being corralled into the barricades you see on TV. I called this year to ask whether brandishing their room key would give me the same advantage – they said it’s dependent on NYPD who will decide day-of. That’s a bit of a gamble at their prices, but it’s an option. A comfy one that allows you to watch the lights and crowds from your window, follow the ball drop on your TV, and pop a bottle of fine champagne in bed. There are worse things.
Manhattan doesn’t roll up its sidewalks on Christmas Day, New Year’s Day, or even Thanksgiving for that matter. Although, pack your patience for the crowds and the parades. You’ll have your pick of restaurants whether you want a casual bite, some tradition, to rub elbows with Broadway elite, or you’ll have what she’s having. Just plan ahead and check for adjusted hours. If you’re still looking for that after dinner cocktail and maybe dessert, I have to put in a plug for a favorite literary haunt and round table.
I’ll follow-up with a post profiling some classic Holiday films set in New York City. I’m not letting this one go – there’s no place like Manhattan at Christmas. You have to see it to believe it. The vibrant spirit, the crispness on your face, maybe some snowflakes in the air, and familiar tunes played by sidewalk buskers. For goodness sake – carts hawking CHESTNUTS on 5th avenue.
I’m not naive – I know there’s a bit of a racket looking to cash in on some of the sights and sounds I’m encouraging you to take in. (I’m picturing Charlie Brown admonishing me for over-commercializing Christmas – thunk-thunk on the metal tree). And, while I’m a bit of an off-beat, boutique shopper, myself, and while I abhor crowds, there is still something magical about just standing still in the Macy’s on 34th Street and knowing that Santa Clause once worked there.