How To Plan The Perfect Holiday Trip In New York City

As the point of entrance for many immigrants arriving to gain residency in the United States and one of the most diverse cities in this melting pot of a country, 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 Years, but other cultural holidays like Hanukkah and Kwanzaa are also wonderful to experience in NYC. Visiting while the whole city is in celebration mode will infuse your whole stay with beautiful decorations and cheer, but you should have your stay planned out well before you step foot in the winter wonderland of New York City.

As our biggest holiday travel tip for the great NYC is to plan all your stops and accommodations ahead of time, it's important to actually know 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, albeit joyous, time of year. Reservations or advance booking may be a good idea, if not absolutely necessary. Not to fear, though, because our guide to planning a New York City holiday trip has everything from room and board to sightseeing and extracurricular activities in mind for the ultimate festive experience.

Stay somewhere spirited

The first step of 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 a more private rental, there are plenty of options to choose from in New York City that will have their own personal touch when it comes to the more festive months of the year.

Hotels in New York City during the holiday season seem to do everything they can to make guests feel like the spirit of Christmas is extra present during their stay. Classic and prestigious hotels like The Plaza and The Mark 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 needed around the holidays. New York City features a number of unique AirBnBs that add a little something extra to a vacation in the Big Apple, likely making for an experience that is a gift within itself, enough even without the wrappings. 

Eat where it's jolly

Everybody's gotta eat, and New Yorkers are all about their food. While there are plenty of places to grab a bagel and lox or a pizza pie in New York City — you can pretty much walk down any block and grab some grub — there should be 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 decorating for Christmas. For fans of rooftop views, The Greens at Pier 17 and Serra By Birreria both offer an atmosphere that is surprisingly cozy for rooftop eating and beautifully decorated.

It's almost impossible to talk about Christmas in New York City without talking about Rolf's. Although the German restaurant is popular with tourists all year round thanks to their massive, permanent display of Christmas decorations, the holiday season is really its time to shine, with even more ornaments and lights getting pulled out for the season. With thousands upon thousands of vintage ornaments carefully crafted into their displays, Rolf's is one Christmas experience that visitors can't be without to really be able to say they did Christmas right in New York City.

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. New drinks are featured every year. In past years, some actual fire was involved to concoct the Bad Krampus drink at Snowday's pop-up bar in Brooklyn, according to Secret NYC. A pink, pear-flavored drink called Partridge in a Pear Tree was also a popular order for its unique ingredients and the special bird-shaped glass it was served in. 

The holidays bring a number of dazzling pop-up bars to the city, sometimes even featuring some pretty unique experiences. Rockefeller Plaza 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 Plaza through the see-through domes.

As far as bars that are permanent fixtures to the city, though, Tavern on the Green is a great 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, they also bring the blistering cold with them, so bars act as the perfect shelter to sustain travelers' explorations of the city with one of many delectable warm spirits.

One Christmas tree your must see

The most important element of Christmas decor is the holiday tree, as it's the one thing the majority of households celebrating the holiday take part in.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 necessity, which is why you should plan for a stop in Rockefeller Plaza.

The live Norway spruce used at Rockefeller Plaza stands anywhere from 70 to 100 feet 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 part of Christmas traditions for nearly 90 years (via ABC7). 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."

All of Pauze's efforts lead to the grand lighting ceremony of Rockefeller Plaza's tree, which is not only a huge in-person event, but it's one that is also broadcasted live on TV. After the initial lighting, the tree stays lit for the majority of the day and night, a sight holiday visitors would be remiss in forgoing.

Pack your skates

Either pack your skates or rent them — either way, don't miss out on the stellar ice skating and 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, the most popular probably being Rockefeller Plaza. Just below the grand Christmas tree, the destination is known for its large public ice rink, where people enjoy gliding over the ice with their friends and family for a picturesque winter evening.

Other iconic New York locations that transform into ice skating venues during the holidays 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. This rink also has its own skate school for children and adults, so you can confidently skate laps around the rink in no time.

Whether you're traveling solo, as a family, or with someone special as a romantic getaway, ice skating is a great activity to partake in and there is practically nowhere better to do it than New York City around the holidays. Even for those lacking skating experience or skill, the restorative properties of stepping out on the ice to join the swarm of skaters will help to bring out the inner child in everyone. It's a joyful experience everyone should have at least once in their lifetime. 

Experience Hanukkah in a big way

Christmas isn't the only thing visitors should observe while in the festive city of New York. Hanukkah begins on December 18 in 2022, and the seven-day holiday will be celebrated all throughout the world by Jewish people. New York City contains 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, according to the Jewish Virtual Library. It's only natural that 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 public and free. Hanukkah, which is also referred to as 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" heavily showing off the city's festive spirit. Whether favoring 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 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 around, with many tied to the best tourist attractions the city has to offer. Central Park, which has its own movie tour, along with Rockefeller Plaza and a number of other hot spots in New York City are featured in a number of famous Christmas films, offering visitors ample opportunities to sink into the Christmas spirit.

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 special appearances at brunch. The huge, outdoor installation is in honor of Disney's new, nostalgic series "The Santa Clauses." The installation features many different areas based on North Pole destinations, 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, with so much to do it could be spread out throughout the season. Not only is there a Christmas tree lighting, but there's also a large ice skating rink and an open-air market that features local vendors and large companies for all your Christmas shopping needs. 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 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 join in the celebrations or simply observe the traditions, Kwanzaa is a great learning experience for the whole family. Behind each principle of the holiday is a valuable trait every person should try to exemplify in their life.

Harlem, a district rich with Black history, is a great place in New York City to visit during Kwanzaa. The Apollo Historic Theater is located in the neighborhood and frequently promotes programs that celebrate Black artists and stories, and their Kwanzaa celebration is no different. The theater hosts its annual celebration in 2022 for the 17th time on December 30th, titled Kwanzaa: A Regeneration Celebration.

Kwanzaa celebrations are typically centered on community, culture, and the arts. Your Queens' annual Kwanzaa event in South Queens is no different. The family-friendly, pay-what-you-can event is a cultural festival with music, food, and even a traditional African garb fashion show on the itinerary.

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 just might be a few steps above the rest in the festive lighting department, especially when it comes to a select few 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). But 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 in one YouTuber couple's 2022 holiday video, 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 to outdo themselves on Christmas lights. The neighborhood in Brooklyn even has bus tours that get led through the neighborhood, 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 hot in New York City year round, but those visiting during the holidays and trying to have the peak winter experience really need to check out the holiday markets that pop up in the city during the season. Columbus Circle and Brooklyn Flea in Dumbo both offer great opportunities for a few unique holiday finds, while the winter village in Bryant Park offers an iconic and picturesque setting within their maze of holiday vendors.

Columbus Circle is an annual pop-up holiday market that is located in the southwestern part of New York City's iconic Central Park. The market features around 100 food and gift vendors and, according to New York City's government website, runs from the end of November up to Christmas Eve in 2022.

Brooklyn Flea in Dumbo is one of the most unique and interesting holiday markets popular in New York City. With over 50 vendors who specialize in vintage and/or 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

The world loves watching New York City celebrate holidays, and it is the place to be for New Year's Eve. Millions of people not only flock to Times Square to wait for the infamous New Year's Eve ball to drop, but even more people all over the world tune in to the events in the city on their TV screens every year. While you should certainly be prepared for a huge crowd if you're wanting to see the ball drop in person, spending New Year's in the city is a worthwhile experience that everyone should have on their bucket list.

If celebrating in a massive crowd at Times Square and potentially appearing on TV screens everywhere isn't quite your thing, there are plenty of other ways to spend New Year's Eve in New York City. An interesting but potentially thrilling 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 firework display acting as the starting bell. If you're not quite ready to start in on your fitness resolutions for the new year, another popular way to celebrate the holiday is by attending one of New York's many New Year's Eve parties.