The ultimate holiday season weekend in Manhattan

Something 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.

I get it. New York during the month of December is a magical time 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 fun and festive things. Landing in NYC at nighttime is ideal – those twinkling skyline lights grace the city all year long.

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 the full 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 – because one day, it could be 70ºF, and the next, you’ll be ever so grateful you packed a scarf and gloves. Keep your footwear practical and comfy. I also like to carry around a canvas tote wherever I go 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 of when you’re planning your trip. Most people who visit the city for the holidays don’t realize how easy it is to breeze through the top seasonal attractions. That’s why 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 takes advantage of seasonal ingredients and flavors (last December, I had a croissant monkey bread). Cardamom buns also 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. First stop: Rockefeller Center, baby! Perhaps the most iconic Christmas tree in the city (the world?), you don’t truly feel how grand it is until you’re standing in front of it (the lighting ceremony is on December 4). Resist the temptation to lace up your skates here – the rink at Bryant Park is much better.

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 going to skate, do it here (it's free if you bring your own skates). Then, munch on treats in 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 the market fatigue, walk down Fifth Ave to Washington Square Park, home to another iconic, massive tree (the lighting ceremony is on December 11).

End your festive tour at the New York Stock Exchange Christmas tree (the lighting ceremony is on December 5) – perhaps the most underrated tree in the city, but no less dazzling. 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 pizza is on your must-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 elevated 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 is the oldest continuously operating bar and restaurant in NYC. It gets extremely busy once the garlands go up, so definitely make a reservation.

Day 2

Now that we’ve checked off the most popular sightseeing 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 wander this historic neighborhood, admiring the decked-out stoops of the beautiful brownstones 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 include Greenwich Letterpress (for stationery, Christmas cards and wrapping materials), Abbode (they do beautiful custom same-day 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.

I can’t recommend a trip to New York without a museum or gallery visit. It’s not necessarily festive, but it’s a cozy culture fix – not to mention 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. I’m desperate to visit Annie Leibovitz’s Stream of Consciousness at Hauser & Wirth, which is on until January 11.

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

After dark: While the Rockettes put on a fabulous, joyful show during the holidays, tickets are incredibly competitive, so if you can’t snag one, head uptown to Lincoln Center to see the ballet (the Nutcracker begins November 29), live jazz (Big Band Holidays runs December 18 to 22) or the New York City Philharmonic (Sounds of the Season runs December 14 to 15 and Elf in Concert runs December 19 to 22).

Day 3

Morning: This is a go-to formula for me on the 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 ones lining the Conservatory Water, where you can watch the ducks and sailboats circle the pond.

How to spend the day: Sit down for 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. My favorite tea is on the top floor of Bergdorf Goodman, 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.

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, go ahead and book that flight for cherry blossom season.