How To Plan The Perfect Holiday Trip In New York City

New York City is pretty much the perfect place to get away for a holiday trip. Not only does the Big Apple go all out for Christmas and New Year's, but other cultural holidays like Hanukkah and Kwanzaa are also wonderful to experience. Visiting while the whole city is in celebration mode will infuse your stay with beautiful decorations and cheer, but you should plan your trip well before stepping foot in the winter wonderland of New York City. 

By planning all (or most) of your stops and accommodations ahead of time, you'll have a better idea of where the jolliest of memories can be made. While winter is considered the off-season for the bustling metropolis, the holiday season is quite a busy time of year. Reservations and advanced bookings are a good idea, if not absolutely necessary, to eat at popular restaurants and score your ideal hotel room. Not to fear, though, because our guide to planning a New York City holiday trip has everything, from festive accommodation options to holiday activity suggestions, to help ensure your time in NYC is filled with Yuletide cheer. 

Stay somewhere spirited

The first step in planning a trip full of holiday magic is staying somewhere that embodies the spirit of the season. Whether you prefer to stay in one of the best Christmas hotels the city has to offer or the privacy of a short-term rental, there are plenty of options to choose from — and many accommodations add their own personal touch during the festive months of the year.

Hotels in New York City during the holiday season seem to do everything they can to immerse guests in seasonal cheer. Classic and prestigious hotels like The Plaza and The Mark Hotel dazzle in their lavish, traditional-style Christmas decor. For travelers wanting a more out-of-the-box experience, though, Moxy Times Square's pop-up holiday display is an eclectic Barbie's dream come true, complete with an overload of pink holiday trees and similarly themed decor.

Though they are generally missing the grandiose holiday presentation, private short-term rentals can give travelers that home-away-from-home feel, which can be especially welcomed around the holidays. The city features a number of unique Airbnbs that add a little something extra to a vacation in the Big Apple, though new laws now restrict vacation rentals in New York City, which may impact availability. 

Eat where it's jolly

New Yorkers are all about their food. While there are plenty of places to grab a bagel with lox or a pizza in New York City, you should give special consideration about where to eat during the holidays. To get the very best holiday experience, you'll want to check out some of the restaurants that go all out with Christmas decorations. For fans of rooftop views, The Greens at Pier 17 and Serra By Birreria both offer a surprisingly cozy atmosphere for rooftop eating and beautiful decorations.

It's almost impossible to talk about Christmas in New York City without talking about Rolf's German Restaurant. Although the restaurant is popular with tourists year-round thanks to its massive, permanent display of Christmas decorations, the holiday season is really its time to shine, when Rolf's adds even more ornaments and strings with lights. With thousands upon thousands of vintage ornaments carefully crafted into its display, Rolf's is unmatched in its holiday exuberance. 

Enjoy the holiday spirit at creative bars

New York City restaurants aren't the only businesses that like to get creative during the holiday season. Bars in New York not only go the extra mile with decorations, but bartenders also come up with some pretty amazing alcoholic concoctions for their holiday menus, adding new, inventive drinks every year. To sample some holiday-themed, creative cocktails, check out Snowday in Brooklyn, a seasonal pop-up bar. In past years, Snowday's mixologists have used fire to create its Bad Krampus drink, while a pink, pear-flavored drink called Partridge in a Pear Tree has been a fan-favorite due to its ingredients and bird-shaped glass.

Along with Snowday, the holidays bring a number of other dazzling pop-up bars to the city, while year-round establishments make special arrangements for the holiday season. Rockefeller Center is home to cozy igloos in the winter, as City Winery transforms its outdoor space into pockets of reservable private domes. Guests are able to sip wine while enjoying 90 minutes of the iconic Rockefeller Center through the see-through domes.

Tavern on the Green is also a popular place to go for a drink while soaking in the city's festive spirit. The long-time hot spot has its own tree lighting and features live music throughout the month of December. Beautiful as the holidays are in New York, the winter months can also bring the blistering cold, so bars act as a perfect shelter to sustain travelers' explorations, offering cozy atmospheres and warm spirits.

One Christmas tree you must see

The centerpiece of any Christmas decor is the tree. Over 90 million homes had at least one Christmas tree displayed in their house in 2021, according to the American Christmas Tree Association. For those wishing to dive into the Christmas spirit while in New York City, visiting one of the most famous Christmas trees in the world is a must, which you'll find in Rockefeller Center.

The live Norway spruce at Rockefeller Center stands anywhere from 70 to 100 feet tall, depending on the year, and with around 50,000 LED lights, a Swarovski crystal-encrusted star, and plenty of preparation, the huge holiday tree has been a NYC Christmas tradition for nearly 90 years. The man who has scouted and selected each tree for the last three decades, Erik Pauze, takes upholding the tradition to heart, telling The Center Magazine, "All year, almost every day, I'm thinking about this year's tree, next year's tree, and maybe the tree after that."

Each year, all of Pauze's efforts lead to the grand lighting ceremony, which is not only a huge in-person event but also broadcast live on TV. After the initial lighting, the tree stays lit for the majority of the day and night — a sight holiday visitors to NYC shouldn't miss. 

Pack your skates

Pack your skates or rent them — either way, don't miss out on the stellar ice rinks that pop up all over New York City during the holidays. Locals and visitors alike take advantage of the frigid temperatures and well-maintained ice rinks spread throughout the city in the winter, though the most popular rink is located at Rockefeller Center. Just below the grand Christmas tree, the plaza is known for its large public ice rink, where people enjoy gliding with their friends and family for a picturesque winter evening.

Other iconic New York locations transformed into ice skating venues include Central Park and Bryant Park. Wollman Rink has been a favorite for those visiting Central Park, which has accumulated its own host of winter traditions since 1949. If you've never skated, this rink offers its own skate school for children and adults, so you'll be able to confidently skate laps around the rink in no time.

Whether you're traveling solo, as a family, or with someone special for a romantic getaway, ice skating is a great activity — and there's practically nowhere better to do it than in New York City around the holidays. It's a joyful experience everyone should try at least once in their lifetime. 

Experience Hanukkah in a big way

Christmas isn't the only holiday observed in the festive city of New York. The seven-day holiday of Hannakuh is celebrated throughout the world by Jewish people, and New York City is home to the second-largest Jewish population in the world — second only to Tel Aviv in Israel — and has over double the number of residents than Jerusalem. Needless to say, the Hanukkah celebrations in NYC are some of the best, and the city is home to the largest menorah in the world, standing at a whopping 32 feet tall. The lighting of the menorah right outside of Central Park celebrates the beginning of the holiday every year.

In fact, there are plenty of menorah lightings that happen throughout the city, a lot of which are completely free. The Festival of Lights is especially unique in New York City, with many celebrations being held right under the stars. The most prominent of these outdoor events is Chanukah on Ice, which takes place at Wollman Rink in Central Park and features a large menorah made completely out of ice.

Take your cue from the movies

Some of the most iconic Christmas movies have taken place in New York City, with films like "Elf" and "Miracle on 34th Street" showing off the city's festive spirit. Whether you favor a classic film or a more modern tale, movie buffs will enjoy visiting all of their favorite movie spots in New York City.

While wandering around the city can lead to some pretty great finds, Free Tours by Foot actually has a holiday tour specifically for iconic films set in New York City. The walking tour company operates on a pay-what-you-can policy, though their holiday film tour does use the Metro, which requires a small fee. Tour guides also suggest bringing a little hot chocolate money so you have something to warm you up while wandering the city.

Many of the iconic movie spots in NYC are also some of the most festive areas, with many tied to the best tourist attractions the city has to offer. Central Park, which offers its own movie tour, and Rockefeller Center are both featured in a number of iconic Christmas films.

Immerse yourself in an actual winter wonderland

While New York City itself is like its own winter wonderland, there are spots within the city where that feeling is even more concentrated. The Watermark at Pier 15 transforms into the North Pole during the holiday season, with Santa even making a special appearance at brunch. The huge, outdoor installation features many different areas based on the North Pole, including Santa's workshop, his living room, and the ever-important sleigh.

The Bank of America Tower's front yard at Bryant Park turns into its own massive winter village during the holidays. Along with a Christmas tree lighting ceremony, the park also hosts a large ice skating rink and an open-air market with both local vendors and international artisans to help you with your holiday shopping. For children who may be a little too shy to step out on the ice rink, Bryant Park's Le Carrousel is open through the winter, even on Christmas Eve and Christmas Day.

Don't miss out on Kwanzaa

If you schedule a trip to New York City between December 26 and New Year's Day, you'll also be able to take part in some Kwanzaa celebrations. Kwanzaa celebrates African culture and history, with the heart of the holiday being its seven principles that promote community and individuality. Whether you observe the holiday or just wish to join in the celebrations, Kwanzaa is a great learning experience for the whole family. 

Harlem, a district rich with Black history, is a great place in New York City to visit during this time. The Apollo Historic Theater is located in the neighborhood and frequently promotes programs that celebrate Black artists and stories. Apollo's annual Kwanzaa celebration is no different. 

The annual event called Your Queens in South Queens is another popular festival. Kwanzaa celebrations center around community, culture, and the arts, and this cultural event is highlighted by music, food, and traditional African garb fashion shows. 

See the most festive neighborhoods

New York is known as "the city that never sleeps," and residents seem to be extra jolly at night. While Christmas lights are popular all over the world, NYC may be a bulb above the rest in the festive lighting department, especially when it comes to a few specific neighborhoods. Some of the very best areas to see Christmas light displays are not business districts or urban parks (although Shine Bright at Hudson Yards is pretty amazing). Instead, residential neighborhoods like Dyker Heights and Whitestone take the cake for the best light shows at night. 

Whitestone in Queens is home to a number of Christmas-loving residents, whose homes you can see on YouTube videos, but one tends to steal the show come the holidays. Kevin Lynch, whose home has been dubbed "Santa's Corner," completely covers his two-story home with lights every year, complete with a Christmas village and a number of moving and stationary figurines.

Dyker Heights, though, is probably the most well-known residential neighborhood in New York City for extravagent Christmas lights. The neighborhood in Brooklyn even has bus tours for the lights, though you can walk on your own as well. For travelers with a love of extravagant, ultra-tacky Christmas lights, swinging by Dyker Heights would be a great addition to a holiday trip in NYC.

Shop some holiday markets

Shopping is great in New York City year-round, but those visiting during the holidays should check out the holiday markets that pop up in the city to grab some last-minute gifts. Columbus Circle and Brooklyn Flea by the DUMBO Archway offer great opportunities for unique holiday finds, while the winter village in Bryant Park provides shoppers with an iconic and picturesque setting within its maze of holiday vendors. 

Columbus Circle is an annual pop-up holiday market located in the southwestern part of New York City's iconic Central Park. The market features around 100 food and gift vendors and typically runs through November and December. Brooklyn Flea is one of the most unique, interesting, and popular holiday markets in New York City. With over 50 vendors who specialize in vintage and homemade goods, the items found at this market are bound to be different, if not one of a kind. 

Start the new year out right

New York City is one of the best places to celebrate New Year's Eve. Millions of people flock to Times Square, waiting for the iconic New Year's Eve ball to drop, while millions more watch the festivities from their TV screens at home. If you want to see the ball drop in person, you should prepare to deal with a huge crowd. However, spending New Year's in the city can be a worthwhile, memorable experience to cap your holiday visit to NYC. 

If celebrating in a massive crowd at Times Square isn't quite your thing, there are plenty of other ways to spend New Year's Eve in New York City. One interesting way to start off the new year is to go for a run. The New York Road Runners' Midnight Run is a 4-mile run at Central Park with a midnight fireworks display that kicks off the event. But, if you're not quite ready to start your fitness resolutions minutes into the new year, another popular way to celebrate the holiday is by attending one of New York's many New Year's Eve parties.