How to Plan a Magical Holiday Trip to New York City

Before we moved to New York, we came here during the holidays as often as we could. We had just seen Hamilton when 2016’s famous blizzard hit and we were snowed into Manhattan for an extra day – pure magic for this snow-and-city-lover! While I can’t promise you snow or Hamilton tickets, but I have plenty of ideas for making your holiday visit magical.

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1. Prepare for the Weather

Spoiler alert: it’s going to be cold. Follow the adage that “there’s no such thing as bad weather, just bad clothing” and think of your future self while you’re packing. When you’re strolling past the Bloomingdale’s windows after dark, will that coat be enough? Can you pair it with an extra-warm sweater, or layer a jacket underneath?

It might be worth it to buy or rent a warmer coat, simply because you’ll enjoy your trip so much more if you’re not freezing every time you walk outside. If it snows (you lucky thing), you’ll want to be able to pull on your boots and rush outside without worry. Speaking of snow, stay somewhere you love – I’d pick SoHo or near Central Park – so you can revel in the snowy magic without getting stuck in a cab or on the subway.

read the posts: How to Dress for Winter, Winter Travel Capsule, Rent the Runway

2. See the Holiday Sights

There are plenty of fantastic things to do and see in New York all year round, but December brings its own set of city sights. Pick the ones that feel most magical to you and skip the rest – what’s the point of trekking through the Christmas Market at Union Square when you’ve really been dreaming of ice skating in Central Park?

• Just before it gets dark (you know, like 3pm), get a perfect cup of cocoa from Jacques Torres and take a walking tour of the best store windows and holiday decorations. I have a route for you in the map at the bottom of this post, but my favorite windows are always at Bergdorf Goodman.

• The jumbled streets of the West Village are perfect for getting lost on purpose and stumbling upon plenty of classic New York vignettes. It’s photogenic neighborhood to begin with, and even more so when it’s dressed up for the holidays. Pairs well with brunch at Cafe Cluny.

• Go ice skating. Buy tickets in advance if you can, or arrive when the rink opens for the day. The rinks at Rockefeller Plaza and Bryant Park each have a fantastic Christmas tree – but if you want to look like you might be skating through a Naif Christmas dinner plate design, Wollman Rink in Central Park is the way to go.

• From Columbus Circle and Union Square to Bryant Park and the Grand Bazaar, there are Christmas markets in just about every neighborhood. While they’re not all the same, you’ll probably want to choose just one to shop through during your visit.

• SoHo’s stylish storefronts are extra-beautiful this time of year. One morning, grab a coffee or cocoa at Maman and wander through the cobblestone streets to window shop for a while. If you prefer an uptown aesthetic, wander the Upper East Side to see some of the poshest decorations (and homes) in the city.

• Plenty of hotels and restaurants set up festive holiday lounges for an après-ski feeling in the middle of the city. My personal favorite is at The Standard East Village, where the Winter Garden is filled with yurts, serving fondue and mulled wine. The Standard High Line has a Winter Wonderland complete with skating, and Gallow Green transforms into a cozy rooftop ski lodge. Reserve in advance (email wintergarden@standardhotels.com for the yurts!) or show up early.

3. Add Some Classic New York

You’re in New York! Mix in a few classic NYC spots, just because you can. Find a perfect skyline view, see some of the world’s best museums, eat a slice of pizza on the street. And don’t worry – there are bound to be Christmas trees and holiday decorations just about anywhere you go.

• Catch a wonderful skyline view from one of my favorite spots: Top of the Rock, the Ides Bar at the Wythe Hotel, or the DUMBO waterfront by Jane’s Carousel.

• Spend a while taking in the smaller museum collections at The Frick, the Morgan Library, or Neue Galerie. If you have more time, head to The Met or The Whitney. It’s not really a museum, but the New York Public Library on 5th Avenue is home to the famous Rose Reading Room and a wonderful Christmas tree.

• See a show! From the Radio City Christmas Spectacular to musicals like Come From Away, it’s hard to go wrong. Try using TodayTix if you haven’t booked in advance.

• Stalk The Skint for free and cheap things to do in the city every day – it’s perfect for last-minute plans. You just might find yourself in line for a free gourmet hot dog at 3pm, and that is quite New York.

• Speaking of street food, be sure to pick up your favorite: mine are Shake Shack, Gray’s Papaya, and pizza-by-the-slice (dollar pizza or Joe’s, thanks). Follow it up with a cookie from Levain, Maman, or William Greenberg (the best black-and-whites!).

read the post: My Favorite Things to Do in New York

4. Balance the Cold with Coziness

Even in frigid weather, I like to walk as much as I can – but I also like to balance it out with lots of super cozy spots. The kind of place where you’re almost surprised to find there isn’t a tartan throw blanket tucked into your chair… but maybe you could bring your own? Here’s what I suggest:

• New York is full of jazz clubs perfect for ducking in from the cold to enjoy some live music and a couple drinks. In the West Village, head to Blue Note Jazz or Village Vanguard. In Harlem, there’s Ginny’s Supper Club; in Midtown, Birdland Jazz; on the Lower East Side, The Back Room. Central Park’s Tavern on The Green also has live music – and dancing – during the holidays.

• Is there a beverage cozier than cocoa? I’m beginning to make my way through the best hot chocolates in New York, and these are top of my list: Jacques Torres’ super-rich sipping chocolate, blooming hot chocolate by Dominique Ansel, thick cocoa topped with a giant homemade marshmallow at City Bakery, and lavender hot chocolate from Maman.

• Settle in for a movie at Nitehawk Cinema in Williamsburg, where you can order a themed cocktail to match the feature film – and some tacos, too. This is what all those dine-in AMCs want to be when they grow up.

• Bemelmans Bar at the Carlyle is the chicest and coziest of hideaways, even if it isn’t very hidden. At Ralph Lauren’s Polo Bar, you might actually find that tartan blanket tucked into your chair! The Lobby Bar at the Bowery Hotel is a bit more casual, with armchairs and a roaring fireplace. If you’re looking for a more secretive spot, book a table at Please Don’t Tell or BanzarBar.

• If I wax poetic about each of these restaurants, this post will never end. Just trust me that these are all cozy, wonderful, and you might see me there: Palma (West Village), Epistrophy (NoLIta), Bakeri (Greenpoint), La Mercerie (SoHo), Cafe Lalo (Upper West Side), Cafe Cluny (West Village), Sweet Chick (multiple locations), Her Name is Han (NoMad), While We Were Young (West Village), The Smith (multiple locations, get mac & cheese and don’t skip the photo booth!).

• On a cold night after a busy day, act très local and just stay in. Watch a good movie and order delivery from Seamless or Caviar – be sure to list your room number if you’re ordering to a hotel!

what to wear in New York City

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