The ultimate holiday season weekend in Manhattan

One of the things I love most about New York City is how it wears the seasons like a perfectly tailored suit. Once the winter holidays roll around, that suit is velvety red with white trim, and everyone wants to try it on.

And it's easy to see why. New York during the month of December is a magical place to go ice skating, see majestic Christmas trees, stroll through holiday markets and sip seasonal cocktails at cozy pop-up bars. Here’s how to plan a festive, wintry weekend in Manhattan to experience it all for yourself.

When to arrive: Maximize the holiday cheer by landing the night before you want your trip to begin, giving yourself at least two full days to experience all the festive fun. Landing in NYC at nighttime is ideal. Those twinkling skyline lights set the scene perfectly for the holiday scene that awaits.

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How to get from the airport: You’re in luck. We have a complete guide for this! Here’s how to get to and from each of NYC’s airports.

Getting around town: We have a guide for this, too, though I always opt for the subway or bus (and the occasional ferry, because it rocks). Here's a detailed guide to getting around in NYC.

Where to stay: Keep in mind that holiday cheer comes with a high price tag at NYC hotels (even the low-cost ones), but the Plaza is not the only hotel where you can live out your Eloise at Christmastime dreams. The Beekman in the Financial District celebrates the season with an enormous twinkling tree. If you don’t care much about decked halls, MADE is a fabulous budget option. For the ultimate luxury holiday experience with all the trimmings, go to Lotte New York Palace. Eloise would love this place, too.

What to pack: It’s all about layers in December – one day, it could be 70ºF (21ºC), and the next, you’ll be ever so grateful you packed a scarf and gloves. Keep your footwear practical, comfy and ideally warm. I also like to carry around a canvas tote in case I pick up any souvenirs (and it’s carry-on friendly).

Book everything in advance: Make reservations for everything you possibly can, from your ice-skating time slot to holiday pop-up bars.

Day 1

Today is all about seeing those iconic sights you think about when you’re planning a trip to NYC. Most people who visit the city for the holidays don’t realize how easy it is to breeze through the top seasonal attractions; this itinerary may seem jam-packed, but trust me, you can cover a lot of ground in one day.

Morning: Start the day with a seasonal pastry from one of New York’s phenomenal bakeries. I love how Librae Bakery in the East Village makes full use of seasonal ingredients and flavors (one December, I tried a croissant monkey bread). Cardamom buns always remind me of the holidays, and La Cabra and Smør make very fluffy, flavorful versions.

How to spend the day: See the sights by starting in Midtown and working your way to Manhattan’s southernmost tip. Make your first stop the Rockefeller Center, baby! It's home to perhaps the most iconic Christmas tree in the city. You won’t truly feel how grand it is until you’re standing in front of it (the lighting ceremony is on December 3). Resist the temptation to lace up your skates here – the rink at Bryant Park is much better.

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Walk down Fifth Ave and then over to Sixth and wander around Bryant Park, stopping to shop along the way if you still have some gifts left to buy on your list (though I usually save my dollars for independent shops downtown – more on that tomorrow).

Bryant Park is pure holiday magic at this time of year, thanks to the adorable winter village and ice rink. If you’re planning to skate in NYC, do it here (it's free if you bring your own skates). Then, munch on treats from the holiday market, like babkas, Belgian fries, raclette and apple cider donuts.

Hop on the subway down to the Union Square holiday market for more festive shopping. The stalls here are very similar – or in some cases the same – as the ones at Bryant Park, so if you’re feeling market fatigue, walk down Fifth Ave to Washington Square Park, home to another iconic, massive tree (here the lighting ceremony is on December 11).

End your festive tour by the Christmas tree at the New York Stock Exchange (the lighting ceremony is on December 4). This is perhaps the most underrated tree in the city, but no less dazzling than its peers. Then, ride your reindeer over to the nearby Beekman Hotel for cozy pre-dinner drinks.

Dinner: Pop back up to Gramercy for a snuggly dinner at Friend of a Farmer, a family-owned, farm-to-table spot that feels more like the countryside than Manhattan. Chicken pot pie, shepherd’s pie and short rib are favorites. If you missed the reservation window, or if a slice of New York pizza is on your must-try list for this visit, it doesn’t get more New York than Joe’s Pizza, a short jaunt away on 14th St.

After dark: I’m a sucker for a holiday bar. There’s something elevating about sipping a cocktail surrounded by pretty garlands, red bows, twinkling lights and tiny Christmas villages. Pete’s Tavern is across the street from Friend of a Farmer, and it's the oldest continuously operating bar and restaurant in NYC. It gets extremely busy once the garlands go up, so definitely make a reservation. 

For a literally elevated experience, make a reservation for one of the cozy, private (and heated) rooftop Chesa chalets at the Peninsula Hotel, where you can sip wine and snack on Swiss specialties and fondue.

Day 2

Now that we’ve checked off the most popular sightseeing stops in December, today is about seeking out less obvious (but just as fun and festive) experiences.

Morning: Grab a coffee and bagel sandwich from Cafe Panino in the West Village and take a wander round this historic neighborhood, admiring the decked-out stoops of the beautiful brownstone houses and shop window displays.

How to spend the day: I always love browsing the shops in the West Village, especially when I have gifts to buy for loved ones. Some of my favorite shops are Greenwich Letterpress (for stationery, Christmas cards and wrapping materials), Abbode (they do beautiful same-day custom embroidery), Three Lives & Company (for Lonely Planet books, of course) and Big Night for the coolest, most colorful items for your kitchen (I particularly adore the groovy glassware).

When you’ve exhausted your feet and your credit card, stop for lunch at Faicco’s Italian Specialties, an iconic Italian sandwich shop that prepares one of the city’s best chicken cutlets.

It would be impossible to recommend a trip to New York without adding in a museum or gallery visit. It’s not specifically festive, but it’s a cozy culture fix, and NYC hosts some of the best exhibitions on the planet. Walk up from the West Village to Chelsea and pop in and out of the many galleries in the West 20s between 10th and 11th Aves. 

Dinner: There are two types of food the West Village especially excels in: brunch and Italian. And what could warm you up more after a day of walking around in the chilly winter air than a bowl of pasta? A few no-frills places where you’ll likely be able to snag a table are Malaparte, Malatesta and Piccolo Angolo.

After dark: The Rockettes put on a fabulous, joyful show during the holidays at Radio City Music Hall, but tickets are incredibly sought after, so if you can’t grab one, head uptown to the Lincoln Center to see the ballet (the 2025 season of The Nutcracker begins November 28), live jazz (Big Band Holidays runs December 16 to 21) or the New York City Philharmonic (the Sounds of the Season concert runs December 13 to 14 while Home Alone in Concert runs December 17 to 20).

Day 3

Morning: This is my go-to formula for New York weekends: take the subway up to Butterfield Market on the Upper East Side (either the Madison Ave or Lexington Ave location), pick up a seasonal pastry and coffee, and perch on a bench in Central Park. I love the benches lining the Conservatory Water, where you can watch the ducks and sailboats circle the pond.

How to spend the day: After a morning amble round Central Park, escape the cold with a hot cup of tea. You could try for a coveted table at the Palm Court at the Plaza Hotel, which is especially lovely once the holiday lights go up. But my personal favorite tea is served on the top floor of the Bergdorf Goodman department store, overlooking Central Park. If you’re traveling with children or want something more whimsical, sip tea like the Mad Hatter would at Alice’s Tea Cup, between Central Park and Broadway.

So that's your holiday weekend covered; your sleigh awaits to take you home. But like I said, New York wears its seasons well, so if you can't make it in December, plan ahead and book a flight for cherry blossom season in April.