How to Spend a Magical Holiday Weekend in New York City

As a child growing up in suburban New York (I didn’t meet my Texan husband until grad school), I yearned to go into Manhattan and ice skate in Rockefeller Center beneath the bright Christmas tree. So, when my 9-year-old daughter asked for a special holiday trip to celebrate her second COVID vaccination in December, I knew just where to go: the Big Apple. We planned a magical weekend in midtown, trying not to stray more than a few blocks from Rockefeller Center (with the exception of a design pilgrimage to a restored Eero Saarinen masterpiece).

Watching my daughter dance along Fifth Avenue after seeing the Rockettes will surely be one of my best memories. Read on for tips to create your own New York City holiday weekend magic.

WHERE TO STAY

SUPER GLAM: The Plaza Hotel

I adore Kay Thompson’s Eloise children’s books (most notably Eloise at the Plaza), so staying in the hotel where the fictional Eloise—and her nanny and turtle, Skipperdee—lived was a dream. Our room was decadent, with a marble-and-gold bathtub. Eloise herself even sent a room-service tray of macarons with a bottle of pink lemonade and a hand-written note saying she was in Paris and sorry to miss us. Before bedtime, my daughter begged to cartwheel down the hallway outside our room like Eloise.

“Of course!” I told her.

As Eloise would say, cartwheeling in pajamas is a must.

The St. Regis Hotel

Another grande dame of midtown is the St. Regis Hotel. Our room came with a butler named Nestor, who welcomed us to the seventh floor by saying, “Welcome to Seventh Heaven!” We could summon Nestor with a push of a button. He brought us morning coffee and tea, and we felt like movie stars. My daughter also loved perching in the window seat between sumptuous blue velvet curtains, peering down at the city.

WITH THE FAM

Margaritaville Resort Times Square

If your kids prefer swimming and exploring a large space to swanning around a glitzy lobby, try a room at the family-friendly Margaritaville Resort Times Square, which houses two restaurants, two bars, and a coffee shop. The view from the fourth-floor pool across Times Square is iconic, and the hotel is the perfect place to watch the ball drop on New Year’s Eve.

ON THE WAY HOME TO TEXAS

TWA Hotel

Designed by famed architect and furniture designer Eero Saarinen in 1962, this building, originally the TWA Flight Center adjacent to JFK Airport (and a five-minute walk from the present-day JetBlue check-in desk) was painstakingly restored to its Jet Age glamour. The TWA Hotel is among the most significant examples of mid-century modern architecture in the world, and wandering its swooping lobby and red-carpeted jetways feels like a dream.

Our room had a Saarinen womb chair for lounging, a view of the JFK Airport and the restored TWA plane now being used as a cocktail bar, period brass light switches, museum-worthy light fixtures, fun TWA pencils…the list goes on. A 95-degree rooftop pool completes this sophisticated escape.

WHERE TO EAT

The Russian Tea Room

Afternoon tea in this red-velvet-and-gold space was a highlight of our trip. From the gilded samovars and teacups to the delectable sandwiches (including tiny PB&J blinis) and desserts (our favorite was a chocolate mousse) to the unforgettable atmosphere, we loved this transportive meal.

The Living Room

Situated inside the Park Hyatt Hotel, the Living Room is a quiet respite serving delectable food in a low-key, lounge-style environment.

Food truck bagels, hot dogs, pretzels…and chestnuts roasted on an open fire…

Never underestimate the power of a hot pretzel on a cold day in New York.

DAYTIME GOOD TIMES

Museum of Modern Art

The MoMA has glorious design shops, three cafes, and hours of fascinating art to see. We especially loved the Automania exhibit, which brings together cars and car parts, architectural models, films, photographs, posters, paintings, and sculptures, ranging from Lily Reich’s 1930s designs for a tubular steel car seat to Andy Warhol’s Orange Car Crash Fourteen Times.

Rockefeller Center Ice Skating

Ice skating beneath the 85-year-old, 79-foot-tall Norway Spruce, aglow in more than 50,000 LED lights, is heavenly. Be sure to make reservations: we didn’t, and had to pay an exorbitant fee for a “Skate Now” Pass! (Worth every penny.)

NIGHTLIFE

Christmas Spectacular Starring The Radio City Rockettes

The Rockettes have been charming audiences at Radio City Music Hall since 1925. The Christma Spectacular show is jaw-dropping, with over-the-top costumes, flying tinsel, a 3-D flight with Santa, and a full orchestra.

Chalet de Ning at the Peninsula New York

Peninsula New York’s rooftop bar, Salon de Ning, transforms into the highly-anticipated Chalet de Ning for the holidays, featuring two chalet-inspired domes where guests can warm up as the temperature drops while sipping on a seasonal, expertly prepared cocktail and lights bites. This glamorous winter experience blends the snow-capped peaks of the Swiss Alps with the Manhattan skyline, creating both an intimate and tantalizing experience.

Connie at the TWA Hotel

Where else in the world can you relax aboard a restored TWA Lockheed Constellation L-1649A that’s been transformed into a cocktail lounge? Enjoy the sounds of Frank Sinatra singing “Fly Me to the Moon” and “Winter Wonderland” while you remain a stroll from your TWA Hotel room…and a short flight from home.

There’s nothing like New York City during the holidays, the most wonderful time of the year. (Especially this year…now that we are vaccinated and hopeful.)