Taylor-Stoop-NYC

A woman in front of Lotte tree in New York City.

Even though New York City is a year-round destination, visiting during the holiday season is extra special. From late November through the end of December, the city shines with the most beautiful Christmas decorations, bright lights, festive shows and more. To experience the best of it as a first-timer, it’s a must to visit NYC for at least 3 days and follow a thorough Christmas itinerary.

From admiring the Rockefeller Tree to dining at one of the best Christmas restaurants, there’s no shortage of amazing NYC holiday activities for those visiting for the first time! In fact, there is something for everyone to enjoy that will get them into the holiday spirit.

Discover the best things to do during the holiday season in the Big Apple in this 3-day NYC Christmas itinerary.

**Please note that this blog post uses affiliate links, meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like.


Pin the Below Image to Keep Handy

3-Day NYC Christmas Itinerary for First-Timers

Planning a Trip to NYC in December during Christmas Time:

A woman enjoying all the holiday decorations during a 3-day NYC Christmas itinerary.

It’s not a secret that New York City is a major international hub, so it’s easy to find flights to and from the Big Apple worldwide. The top three New York airports are John F. Kennedy International Airport, Newark Liberty International Airport and Laguardia Airport. You can find affordable flights through Skyscanner.

The MTA subway is the most convenient way to get around New York City. There is also a bus that goes around the city and runs similarly to the subway. It’s best to download the MYmta and TrainTime apps to plan trips, track trains, purchase tickets, etc.

Other ways to get around NYC when following a Christmas itinerary are by taxi or rideshare (Uber or Lyft). You can also download Curb to haul a cab digitally.

Suppose you’re traveling within the Tri-State area. In that case, it’s best to take public transportation like NJ Transit or the Long Island Railroad into Penn Station, the Metro-North into Grand Central Terminal and Amtrak into the Moynihan Train Hall at Penn Station.

Other ways to get into Manhattan include taking a bus into the Port Authority Bus Terminal and riding the PATH train (from New Jersey) into the World Trade Center, Christopher Street, 9th Street, 14th Street, 23rd Street and 33rd Street.

You can also take ferries to and from NYC, like the NY Waterway, NYC Ferry, Staten Island Ferry, Trust for Governors Island, Liberty Landing Ferry, NY Water Taxi, Seastreak and Statue Cruises.

During the heart of Christmas time, you can obviously drive into the city. If you choose to do that, it’s best to plan your travels ahead and be prepared for heavy traffic, delays and large crowds. Always arrive early for reservations, shows, etc.

Where to Stay for 3 days in New York in December:

A woman enjoying the magical decor at The Peninsula New York.

When planning a New York Christmas trip for the first time, it’s best to stay in Midtown Manhattan because that’s where all the main holiday attractions are. Discover where to stay in NYC at Christmas.

Even though there are a plethora of hotels ranging from all budgets and a wide selection of rental properties to choose from, below are my personal recommendations for where to stay in Midtown:

Luxury Accommodation: The Plaza

Boutique Accommodation: Refinery Hotel

Mid-Budget Accommodation: Moxy NYC Times Square

Budget Accommodation: Yotel New York Times Square

3-Day NYC Christmas Itinerary: Long Weekend New York Christmas Trip

A woman in front of an Upper East Side Christmas stoop in NYC.

If you’re asking yourself, “Is Christmas in New York worth it?” you must follow the 3-day, long weekend itinerary below for your first visit. It’s a complete guide to the most iconic, must-visit spots.

The holiday season in New York City is the time of year when you don’t want to miss out on all the best places that will provide you with holiday cheer. Enjoy your trip!

Day 1 of a NYC Christmas Trip:

See the Rockefeller Center Christmas Tree:

A woman enjoying the magic in Rockefeller Center during a 3-day NYC Christmas itinerary.

After arriving in New York City and checking into your hotel, the first landmark you must visit during your NYC Christmas itinerary is the Tree at Rockefeller Center. The tree is lit from early December through early January.

Not only can you admire this iconic NYC Christmas landmark from close up and afar, but you can also watch the ice skaters or even participate in the fun yourself at the Rink at Rockefeller Center. As you skate, you can admire the colorful lights on the giant Christmas tree and the stunning gold angels surrounding the rink.

Also located at Rockefeller Center are the giant red ornaments, Christmas lights and candy canes that are perfect for photo opportunities!

If you want to warm up and enjoy a snack, Ralph’s Coffee Truck is a festive pop-up in Rockefeller Center where you can enjoy hot chocolate, coffee, muffins and more.

For those visiting NYC for the first time ever, I also recommend purchasing tickets to Top of the Rock. This observation deck is located 70 floors high, at the top of Rockefeller Center. At Top of the Rock, you can enjoy the best views of many major New York landmarks.

Visit Bryant Park Winter Village:

A woman enjoying the Bryant Park Winter Village during a long weekend NYC Christmas itinerary.

Another iconic Christmas location in New York City that you must visit on your first day is Bryant Park Winter Village.

If you love magical Christmas markets, Bryant Park Winter Village will amaze you! Throughout all the 180 stands, you can enjoy delicious food for lunch, like cheese wheel pasta, raclette, mochi cookies, babka, hot chocolate from Max Brenner, bao buns, apple cider donuts and more. There are also stands selling jewelry, clothing items, artwork and trinkets.

Also located at the Bank of America Winter Village is a beautiful Christmas tree to admire. If you don’t ice skate at Rockefeller Center, try to do so at Bryant Park. The ice rink is larger than the one at Rockefeller, and it’s free unless you rent skates and need a locker for your belongings, which is an extra cost!

The other best things to enjoy at Bryant Park Winter Village are to visit The Lodge Bar + Food Hall, a rinkside open-air, après-skate venue, book a cozy igloo to warm up in and experience the Curling Café & Bar, which includes a curling lane and heated dome. You must make a reservation to book an igloo or enjoy curling.

Admire the Bright Lights at Hudson Yards:

A woman admiring the Christmas lights at Hudson Yards in New York City.

One of the top things you cannot exclude from your New York City Christmas itinerary is seeing the magical lights at Shine Bright at Hudson Yards, presented by Wells Fargo.

From Bryant Park, walk off the tasty treats you consumed by making your way to Hudson Yards. Not only can you admire the unique Vessel and two million gold Christmas lights in the mall, but you and your party can also enjoy free photo opportunities with Santa Claus and get some holiday shopping done.

Check Out the Macy’s Windows:

A woman in front of Macy's Herald Square during the holidays.

As you make your way east from Hudson Yards, don’t forget to pass by and admire the Macy’s windows and displays in Herald Square.

Not only does this major department store have some of the most magical holiday window displays in Midtown Manhattan, but there’s also a lit-up “Believe” sign on the façade of the building.

If you have young children, you must visit Santaland at Macy’s Herald Square to meet the big guy!

Enjoy Festive Food and Decorations at Eataly:

A woman enjoying the decorations at Eataly during a NYC Christmas trip.

A festive place for dinner to add to your 3-day NYC Christmas itinerary is Eataly’s SERRA by Birreria rooftop.

Overall, Eataly is an Italian marketplace comprising different restaurants, pizzerias, bakeries, bars, retail stores, markets and a cooking school. You can find Eataly in numerous cities around the world and there are three locations within New York – the Flatiron, the Financial District and now Soho.

Eataly Flatiron has a seasonal rooftop restaurant and bar called SERRA by Birreria. Meaning “greenhouse” in Italian, SERRA offers a seasonal, rustic menu reflecting the Italian countryside and Alps during Christmas time.

You can enjoy mulled wine, seasonal Italian cocktails, hearty dishes and more at this magical rooftop and restaurant. Even if you don’t visit Eataly during your Christmas trip, you must add it to your bucket list any other time you visit New York City.

Spot the Christmas Tree in Madison Square Park:

Madison Square Garden Christmas tree.

After savoring a delicious dinner at Eataly, walk across the street into Madison Square Park to admire the beautiful Christmas tree!

What’s iconic about this park during the holiday season is that it held the country’s first public Christmas tree lighting in 1912. It’s also home to the original Shake Shack, where you can treat yourself to a delicious milkshake as a dessert.

Warm Up in an Igloo at 230 Fifth Rooftop:

A woman in a heated cabin at 230 Fifth Rooftop during Christmas time.

If you’re looking for a great place to have a fabulous time, you must add visiting the igloos at 230 Fifth Rooftop Bar to your NYC Christmas itinerary. With the best views of the Empire State Building, you can enjoy 230 Fifth Rooftop’s igloos through a reservation system or via walk-in based on availability.

At 230 Fifth, you can enjoy different types of warm, boozy, and non-alcoholic beverages, tasty snacks and meals, along with heated cabins that are also available on a first-come-first-serve basis.

Day 2 of Christmas in NYC Itinerary:

Have Brunch at Tavern on the Green:

Located in Central Park West, Tavern on the Green is an elegant New York City staple that has served U.S. presidents, royalty, Hollywood stars and artists from around the world.

This iconic restaurant has been around since 1934 and enjoying a holiday brunch is a must to add to your NYC Christmas itinerary. During a holiday brunch at Tavern on the Green, you can enjoy a 3-course menu selection by Executive Chef Bill Peet from 9 am to 3:30 pm every Saturday and Sunday from late November through the end of December.

Some top food items you can enjoy during brunch at Tavern on the Green are potato pancakes, Scottish salmon, a vegetable frittata and spiced egg nog crème brûlée to name a few.

The dining spaces at Tavern on the Green offer countless views overlooking the park. It’s even more special during a snowstorm.

Go Ice Skating in Central Park’s Wollman Rink:

Ice skating at Central Park during a 3-day NYC Christmas itinerary.

After brunch, walk off your meal in the beautiful Central Park. New York City’s grandest park has numerous walking trails, ponds, biodiversity, a zoo, horse and carriages, a castle and an ice skating rink.

Wollman Rink is an iconic rink located in the southern part of Central Park. Unlike Rockefeller Center and Bryant Park, Wollman Rink is surrounded by nature. Ice skating at Wollman Rink is special because many great films, like Home Alone 2 and Mr. Popper’s Penguins, were shot at this spot.

Stroll through the Columbus Circle Holiday Market:

Before leaving Central Park, head over to the holiday markets for more shopping. The Columbus Circle Holiday Market is an elegant location for art, jewelry, delicious food specialties and clothing apparel.

Also situated near the Columbus Circle Holiday Market, next to Central Park, is The Shops at Columbus Circle. You can shop from popular stores like Alo, Diptyque, J Crew and Tumi, dine at iconic restaurants like Momofuku Noodle Bar and enjoy seasonal events.

Explore the 5th Avenue Holiday Windows:

A woman enjoying the Saks Fifth Avenue windows.

As you head back to your hotel to relax, walk along 5th Avenue to see all the decorative storefront windows that showcase trending fashion items.

The best holiday windows to see on 5th Avenue are Saks Fifth Avenue, Bergdorf Goodman, Cartier, Louis Vuitton, Bulgari, Tiffany and Co., Christian Dior and Harry Winston, to name a few.

Of all the holiday windows in Midtown Manhattan, Saks Fifth Avenue has the most magical display and iconic light show you cannot exclude from your NYC Christmas itinerary. During the evening, from 4:35 pm to 10:35 pm, you can enjoy an incredible 10-story themed light show in front of Saks. Each light show is repeated at regular intervals of around 10 minutes and it will leave everyone amazed.

While in the area, stop by the astonishing St. Patrick’s Cathedral to view all the peaceful nativity scenes. If you have time, attend a mass at St. Patrick’s Cathedral. It’s a breathtaking experience!

Transport to a German Christmas Market at Rolf’s:

A woman enjoying mulled wine at Rolf's in New York City.

A 3-day NYC Christmas itinerary for first-timers must include visiting Rolf’s German Restaurant in the Gramercy neighborhood.

Rolf’s is one of the most iconic Christmas restaurants in New York City because it’s decked out in festive ornaments, Christmas lights, garlands, wreaths and dolls. It will transport you to a German Christkindlmarkt since it boasts traditional Bavarian dishes like bratwurst with potato pancakes and glühwein (German mulled wine).

Please note that you must make a reservation to dine at Rolf’s by visiting the actual restaurant. If you don’t get a reservation, you can always visit Rolf’s as a walk-in for a festive drink at the bar.

If you can’t get a reservation at Rolf’s, I recommend visiting Pete’s Tavern, another cozy Christmas restaurant and bar with festive décor. Great restaurants are not too far away, like Angelo’s in Little Italy and Nom Wah Tea Parlor in Chinatown, two of my favorite places.

Venture to Brooklyn for the Dyker Heights Christmas Lights:

A woman enjoying the Christmas lights at Dyker Heights in Brooklyn during a NYC Christmas itinerary.

After savoring a delicious meal in downtown Manhattan, either take the subway, hop in a taxi or rideshare and head over to Brooklyn’s Dyker Heights neighborhood for the best Christmas lights!

Overall, Dyker Heights pays homage to the most over-the-top Christmas light decorations with life-size Santas, nutcrackers, snowmen, Christmas village houses and more. There will even be Christmas carolers in the neighborhood, and some homes will sell hot chocolate and baked goods to visitors.

Visiting Dyker Heights is one of the best things to do in NYC on Christmas Eve. It’s a great way to ring in the holiday. There are many incredible Italian restaurants where you can savor a Feast of the Seven Fishes (an Italian-American Christmas Eve tradition).

The best time to see the bright lights in Dyker Heights, Brooklyn is at night. It’s also a great way to wrap up your second day during your NYC Christmas itinerary.

Day 3 New York Christmas Itinerary:

Fuel Up at La Grand Boucherie:

Start with breakfast at the art-nouveau La Grande Boucherie in Midtown on the final day of your New York Christmas trip. It’s an elegant French restaurant that has incredible items to help fuel you for your day, from omelets to breakfast sandwiches.

You can also enjoy Christmas specials at La Grand Boucherie during the holiday season!

Watch the Radio City Christmas Spectacular:

A woman in front of Radio City Music Hall in Midtown Manhattan.

A 3-day itinerary for a NYC Christmas trip for first-timers must include seeing the Radio City Rockettes perform in the Christmas Spectacular.

For around a century, the Rockettes have been an icon in New York City, especially during the Christmas season. They also entertained USA troops during wartime and performed at presidential inaugurations.

From November to January, you can enjoy the Christmas Spectacular with the Rockettes at Radio City Music Hall in Midtown Manhattan. It’s a 90-minute show with festive musical productions, synchronized dance performances, fascinating backdrops and featured Santa Clauses and other Christmas icons.

The Radio City Christmas Spectacular will leave you awestruck regardless of age! There are numerous shows throughout the day, especially on weekends.

Make Memories at Afternoon Tea at The Plaza:

A woman in front of The Plaza Hotel during Christmas time.

A first trip to NYC for the holidays is made extra special by booking an afternoon high tea experience at The Plaza Hotel.

From early November through New Year’s Eve, visitors can enjoy afternoon tea at The Plaza’s beautiful Palm Court. It’s decorated beautifully for the holidays with elegant Christmas trees and garlands. During a tea experience, you can sip festive flavors, savor English finger sandwiches and make memories with loved ones.

Since the popular early 2000s film Eloise at the Plaza was filmed at this iconic NYC hotel, you and your family can enjoy Eloise Tea on select days. Santa Claus also visits The Palm Court, so watch for him too!

Book your high tea experience at The Plaza Hotel 30 days before your preferred dining date. Hotel guests can make reservations with the concierge anytime before their check-in date.

Shop through Union Square Holiday Market:

After high tea, relax at your hotel before heading downtown to Union Square to enjoy more NYC Christmas markets.

The Union Square Holiday Market is internationally renowned for selling unique gifts made by local New Yorkers and features award-winning NYC restaurants and retailers.

From mid-November through Christmas Eve, stroll around the holiday market, shop for loved ones, and treat yourself to home goods, candles, delicious treats, beautiful clothing and more.

Dine at Lillie’s Victorian Establishment:

A woman enjoying a drink at Lillie's Victorian in Union Square.

A NYC Christmas itinerary is only complete with visiting another holiday-themed restaurant. Lillie’s Victorian Establishment and its sister restaurants, Oscar Wilde and Papillon Bistro, boast stunning Christmas décor in an old-world setting.

Lillie’s Victorian Establishment has two locations – Times Square and Union Square. After strolling through the Union Square Holiday Market, head to Lillie’s Victorian for dinner or a festive cocktail.

Located in a Victorian setting, you can savor delicious American fare at Lillie’s Victorian Establishment. Please note that you must make reservations to dine here during Christmas time. However, you can visit the bar area as a walk-in.

Adventure to Lower Manhattan for More Magic:

A woman admiring the Christmas lights in Zuccotti Park in Lower Manhattan.

To conclude your long weekend New York City Christmas trip, you must head downtown to Wall Street in the Financial District to see the beautiful tree at the New York Stock Exchange. The décor on the Stock Exchange building itself is also to be admired.

Zuccotti Park has an enchanting light display with a giant Christmas tree near the NYSE. It’s a hidden gem in New York City and one of the only places you won’t find a heavy crowd.

While in Lower Manhattan, you must also head over to the World Trade Center to see the peaceful fountains, walk through the 9/11 Memorial Museum and head into the Oculus to shop and walk through the holiday market. (This year, there is a roller skating rink at this spot!)

If you have extra time, go ice skating at Brookfield Place, see the Christmas tree in Washington Square Park or visit another NYC festive-themed pop-up bar like Miracle on 9th Street!


Rockefeller Center - one of the top places to visit in NYC during a 3-day Christmas itinerary.

Discover other great destinations you must visit at least once:

Sydney, Australia

Rome, Italy

London, England

I hope you all find this 3-day NYC Christmas itinerary helpful for your first holiday trip. If you have any questions, please email me at info@browneyedflowerchild.com.

Click here to book a cooking class in New York.

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., NY State Capital: Albany, Time Zone: Eastern Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my NYC Christmas Look:

Click here to shop my Poshmark closet!

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2 Comments

  1. Kim Deer on December 1, 2023 at 9:35 pm

    Love, love, love this 3 day guide for a fabulous experience in NYC during Christmas time ~ I have been to most of these places and it never gets old. It’s so magical in New York during the holidays. I enjoyed all your beautiful photos ~ it really is getting me into the holiday season. Can’t wait to decorate this weekend ~ love you, mom 🤷‍♀️❤️💚🎄

    • Taylor Deer on December 3, 2023 at 5:29 pm

      Thank you mom! You’re right, Christmas in the city never gets old! Love you too!

Leave a Comment





Taylor-Stoop-NYC

A woman in front of Lotte tree in New York City.

Even though New York City is a year-round destination, visiting during the holiday season is extra special. From late November through the end of December, the city shines with the most beautiful Christmas decorations, bright lights, festive shows and more. To experience the best of it as a first-timer, it’s a must to visit NYC for at least 3 days and follow a thorough Christmas itinerary.

From admiring the Rockefeller Tree to dining at one of the best Christmas restaurants, there’s no shortage of amazing NYC holiday activities for those visiting for the first time! In fact, there is something for everyone to enjoy that will get them into the holiday spirit.

Discover the best things to do during the holiday season in the Big Apple in this 3-day NYC Christmas itinerary.

**Please note that this blog post uses affiliate links, meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like.


Pin the Below Image to Keep Handy

3-Day NYC Christmas Itinerary for First-Timers

Planning a Trip to NYC in December during Christmas Time:

A woman enjoying all the holiday decorations during a 3-day NYC Christmas itinerary.

It’s not a secret that New York City is a major international hub, so it’s easy to find flights to and from the Big Apple worldwide. The top three New York airports are John F. Kennedy International Airport, Newark Liberty International Airport and Laguardia Airport. You can find affordable flights through Skyscanner.

The MTA subway is the most convenient way to get around New York City. There is also a bus that goes around the city and runs similarly to the subway. It’s best to download the MYmta and TrainTime apps to plan trips, track trains, purchase tickets, etc.

Other ways to get around NYC when following a Christmas itinerary are by taxi or rideshare (Uber or Lyft). You can also download Curb to haul a cab digitally.

Suppose you’re traveling within the Tri-State area. In that case, it’s best to take public transportation like NJ Transit or the Long Island Railroad into Penn Station, the Metro-North into Grand Central Terminal and Amtrak into the Moynihan Train Hall at Penn Station.

Other ways to get into Manhattan include taking a bus into the Port Authority Bus Terminal and riding the PATH train (from New Jersey) into the World Trade Center, Christopher Street, 9th Street, 14th Street, 23rd Street and 33rd Street.

You can also take ferries to and from NYC, like the NY Waterway, NYC Ferry, Staten Island Ferry, Trust for Governors Island, Liberty Landing Ferry, NY Water Taxi, Seastreak and Statue Cruises.

During the heart of Christmas time, you can obviously drive into the city. If you choose to do that, it’s best to plan your travels ahead and be prepared for heavy traffic, delays and large crowds. Always arrive early for reservations, shows, etc.

Where to Stay for 3 days in New York in December:

A woman enjoying the magical decor at The Peninsula New York.

When planning a New York Christmas trip for the first time, it’s best to stay in Midtown Manhattan because that’s where all the main holiday attractions are. Discover where to stay in NYC at Christmas.

Even though there are a plethora of hotels ranging from all budgets and a wide selection of rental properties to choose from, below are my personal recommendations for where to stay in Midtown:

Luxury Accommodation: The Plaza

Boutique Accommodation: Refinery Hotel

Mid-Budget Accommodation: Moxy NYC Times Square

Budget Accommodation: Yotel New York Times Square

3-Day NYC Christmas Itinerary: Long Weekend New York Christmas Trip

A woman in front of an Upper East Side Christmas stoop in NYC.

If you’re asking yourself, “Is Christmas in New York worth it?” you must follow the 3-day, long weekend itinerary below for your first visit. It’s a complete guide to the most iconic, must-visit spots.

The holiday season in New York City is the time of year when you don’t want to miss out on all the best places that will provide you with holiday cheer. Enjoy your trip!

Day 1 of a NYC Christmas Trip:

See the Rockefeller Center Christmas Tree:

A woman enjoying the magic in Rockefeller Center during a 3-day NYC Christmas itinerary.

After arriving in New York City and checking into your hotel, the first landmark you must visit during your NYC Christmas itinerary is the Tree at Rockefeller Center. The tree is lit from early December through early January.

Not only can you admire this iconic NYC Christmas landmark from close up and afar, but you can also watch the ice skaters or even participate in the fun yourself at the Rink at Rockefeller Center. As you skate, you can admire the colorful lights on the giant Christmas tree and the stunning gold angels surrounding the rink.

Also located at Rockefeller Center are the giant red ornaments, Christmas lights and candy canes that are perfect for photo opportunities!

If you want to warm up and enjoy a snack, Ralph’s Coffee Truck is a festive pop-up in Rockefeller Center where you can enjoy hot chocolate, coffee, muffins and more.

For those visiting NYC for the first time ever, I also recommend purchasing tickets to Top of the Rock. This observation deck is located 70 floors high, at the top of Rockefeller Center. At Top of the Rock, you can enjoy the best views of many major New York landmarks.

Visit Bryant Park Winter Village:

A woman enjoying the Bryant Park Winter Village during a long weekend NYC Christmas itinerary.

Another iconic Christmas location in New York City that you must visit on your first day is Bryant Park Winter Village.

If you love magical Christmas markets, Bryant Park Winter Village will amaze you! Throughout all the 180 stands, you can enjoy delicious food for lunch, like cheese wheel pasta, raclette, mochi cookies, babka, hot chocolate from Max Brenner, bao buns, apple cider donuts and more. There are also stands selling jewelry, clothing items, artwork and trinkets.

Also located at the Bank of America Winter Village is a beautiful Christmas tree to admire. If you don’t ice skate at Rockefeller Center, try to do so at Bryant Park. The ice rink is larger than the one at Rockefeller, and it’s free unless you rent skates and need a locker for your belongings, which is an extra cost!

The other best things to enjoy at Bryant Park Winter Village are to visit The Lodge Bar + Food Hall, a rinkside open-air, après-skate venue, book a cozy igloo to warm up in and experience the Curling Café & Bar, which includes a curling lane and heated dome. You must make a reservation to book an igloo or enjoy curling.

Admire the Bright Lights at Hudson Yards:

A woman admiring the Christmas lights at Hudson Yards in New York City.

One of the top things you cannot exclude from your New York City Christmas itinerary is seeing the magical lights at Shine Bright at Hudson Yards, presented by Wells Fargo.

From Bryant Park, walk off the tasty treats you consumed by making your way to Hudson Yards. Not only can you admire the unique Vessel and two million gold Christmas lights in the mall, but you and your party can also enjoy free photo opportunities with Santa Claus and get some holiday shopping done.

Check Out the Macy’s Windows:

A woman in front of Macy's Herald Square during the holidays.

As you make your way east from Hudson Yards, don’t forget to pass by and admire the Macy’s windows and displays in Herald Square.

Not only does this major department store have some of the most magical holiday window displays in Midtown Manhattan, but there’s also a lit-up “Believe” sign on the façade of the building.

If you have young children, you must visit Santaland at Macy’s Herald Square to meet the big guy!

Enjoy Festive Food and Decorations at Eataly:

A woman enjoying the decorations at Eataly during a NYC Christmas trip.

A festive place for dinner to add to your 3-day NYC Christmas itinerary is Eataly’s SERRA by Birreria rooftop.

Overall, Eataly is an Italian marketplace comprising different restaurants, pizzerias, bakeries, bars, retail stores, markets and a cooking school. You can find Eataly in numerous cities around the world and there are three locations within New York – the Flatiron, the Financial District and now Soho.

Eataly Flatiron has a seasonal rooftop restaurant and bar called SERRA by Birreria. Meaning “greenhouse” in Italian, SERRA offers a seasonal, rustic menu reflecting the Italian countryside and Alps during Christmas time.

You can enjoy mulled wine, seasonal Italian cocktails, hearty dishes and more at this magical rooftop and restaurant. Even if you don’t visit Eataly during your Christmas trip, you must add it to your bucket list any other time you visit New York City.

Spot the Christmas Tree in Madison Square Park:

Madison Square Garden Christmas tree.

After savoring a delicious dinner at Eataly, walk across the street into Madison Square Park to admire the beautiful Christmas tree!

What’s iconic about this park during the holiday season is that it held the country’s first public Christmas tree lighting in 1912. It’s also home to the original Shake Shack, where you can treat yourself to a delicious milkshake as a dessert.

Warm Up in an Igloo at 230 Fifth Rooftop:

A woman in a heated cabin at 230 Fifth Rooftop during Christmas time.

If you’re looking for a great place to have a fabulous time, you must add visiting the igloos at 230 Fifth Rooftop Bar to your NYC Christmas itinerary. With the best views of the Empire State Building, you can enjoy 230 Fifth Rooftop’s igloos through a reservation system or via walk-in based on availability.

At 230 Fifth, you can enjoy different types of warm, boozy, and non-alcoholic beverages, tasty snacks and meals, along with heated cabins that are also available on a first-come-first-serve basis.

Day 2 of Christmas in NYC Itinerary:

Have Brunch at Tavern on the Green:

Located in Central Park West, Tavern on the Green is an elegant New York City staple that has served U.S. presidents, royalty, Hollywood stars and artists from around the world.

This iconic restaurant has been around since 1934 and enjoying a holiday brunch is a must to add to your NYC Christmas itinerary. During a holiday brunch at Tavern on the Green, you can enjoy a 3-course menu selection by Executive Chef Bill Peet from 9 am to 3:30 pm every Saturday and Sunday from late November through the end of December.

Some top food items you can enjoy during brunch at Tavern on the Green are potato pancakes, Scottish salmon, a vegetable frittata and spiced egg nog crème brûlée to name a few.

The dining spaces at Tavern on the Green offer countless views overlooking the park. It’s even more special during a snowstorm.

Go Ice Skating in Central Park’s Wollman Rink:

Ice skating at Central Park during a 3-day NYC Christmas itinerary.

After brunch, walk off your meal in the beautiful Central Park. New York City’s grandest park has numerous walking trails, ponds, biodiversity, a zoo, horse and carriages, a castle and an ice skating rink.

Wollman Rink is an iconic rink located in the southern part of Central Park. Unlike Rockefeller Center and Bryant Park, Wollman Rink is surrounded by nature. Ice skating at Wollman Rink is special because many great films, like Home Alone 2 and Mr. Popper’s Penguins, were shot at this spot.

Stroll through the Columbus Circle Holiday Market:

Before leaving Central Park, head over to the holiday markets for more shopping. The Columbus Circle Holiday Market is an elegant location for art, jewelry, delicious food specialties and clothing apparel.

Also situated near the Columbus Circle Holiday Market, next to Central Park, is The Shops at Columbus Circle. You can shop from popular stores like Alo, Diptyque, J Crew and Tumi, dine at iconic restaurants like Momofuku Noodle Bar and enjoy seasonal events.

Explore the 5th Avenue Holiday Windows:

A woman enjoying the Saks Fifth Avenue windows.

As you head back to your hotel to relax, walk along 5th Avenue to see all the decorative storefront windows that showcase trending fashion items.

The best holiday windows to see on 5th Avenue are Saks Fifth Avenue, Bergdorf Goodman, Cartier, Louis Vuitton, Bulgari, Tiffany and Co., Christian Dior and Harry Winston, to name a few.

Of all the holiday windows in Midtown Manhattan, Saks Fifth Avenue has the most magical display and iconic light show you cannot exclude from your NYC Christmas itinerary. During the evening, from 4:35 pm to 10:35 pm, you can enjoy an incredible 10-story themed light show in front of Saks. Each light show is repeated at regular intervals of around 10 minutes and it will leave everyone amazed.

While in the area, stop by the astonishing St. Patrick’s Cathedral to view all the peaceful nativity scenes. If you have time, attend a mass at St. Patrick’s Cathedral. It’s a breathtaking experience!

Transport to a German Christmas Market at Rolf’s:

A woman enjoying mulled wine at Rolf's in New York City.

A 3-day NYC Christmas itinerary for first-timers must include visiting Rolf’s German Restaurant in the Gramercy neighborhood.

Rolf’s is one of the most iconic Christmas restaurants in New York City because it’s decked out in festive ornaments, Christmas lights, garlands, wreaths and dolls. It will transport you to a German Christkindlmarkt since it boasts traditional Bavarian dishes like bratwurst with potato pancakes and glühwein (German mulled wine).

Please note that you must make a reservation to dine at Rolf’s by visiting the actual restaurant. If you don’t get a reservation, you can always visit Rolf’s as a walk-in for a festive drink at the bar.

If you can’t get a reservation at Rolf’s, I recommend visiting Pete’s Tavern, another cozy Christmas restaurant and bar with festive décor. Great restaurants are not too far away, like Angelo’s in Little Italy and Nom Wah Tea Parlor in Chinatown, two of my favorite places.

Venture to Brooklyn for the Dyker Heights Christmas Lights:

A woman enjoying the Christmas lights at Dyker Heights in Brooklyn during a NYC Christmas itinerary.

After savoring a delicious meal in downtown Manhattan, either take the subway, hop in a taxi or rideshare and head over to Brooklyn’s Dyker Heights neighborhood for the best Christmas lights!

Overall, Dyker Heights pays homage to the most over-the-top Christmas light decorations with life-size Santas, nutcrackers, snowmen, Christmas village houses and more. There will even be Christmas carolers in the neighborhood, and some homes will sell hot chocolate and baked goods to visitors.

Visiting Dyker Heights is one of the best things to do in NYC on Christmas Eve. It’s a great way to ring in the holiday. There are many incredible Italian restaurants where you can savor a Feast of the Seven Fishes (an Italian-American Christmas Eve tradition).

The best time to see the bright lights in Dyker Heights, Brooklyn is at night. It’s also a great way to wrap up your second day during your NYC Christmas itinerary.

Day 3 New York Christmas Itinerary:

Fuel Up at La Grand Boucherie:

Start with breakfast at the art-nouveau La Grande Boucherie in Midtown on the final day of your New York Christmas trip. It’s an elegant French restaurant that has incredible items to help fuel you for your day, from omelets to breakfast sandwiches.

You can also enjoy Christmas specials at La Grand Boucherie during the holiday season!

Watch the Radio City Christmas Spectacular:

A woman in front of Radio City Music Hall in Midtown Manhattan.

A 3-day itinerary for a NYC Christmas trip for first-timers must include seeing the Radio City Rockettes perform in the Christmas Spectacular.

For around a century, the Rockettes have been an icon in New York City, especially during the Christmas season. They also entertained USA troops during wartime and performed at presidential inaugurations.

From November to January, you can enjoy the Christmas Spectacular with the Rockettes at Radio City Music Hall in Midtown Manhattan. It’s a 90-minute show with festive musical productions, synchronized dance performances, fascinating backdrops and featured Santa Clauses and other Christmas icons.

The Radio City Christmas Spectacular will leave you awestruck regardless of age! There are numerous shows throughout the day, especially on weekends.

Make Memories at Afternoon Tea at The Plaza:

A woman in front of The Plaza Hotel during Christmas time.

A first trip to NYC for the holidays is made extra special by booking an afternoon high tea experience at The Plaza Hotel.

From early November through New Year’s Eve, visitors can enjoy afternoon tea at The Plaza’s beautiful Palm Court. It’s decorated beautifully for the holidays with elegant Christmas trees and garlands. During a tea experience, you can sip festive flavors, savor English finger sandwiches and make memories with loved ones.

Since the popular early 2000s film Eloise at the Plaza was filmed at this iconic NYC hotel, you and your family can enjoy Eloise Tea on select days. Santa Claus also visits The Palm Court, so watch for him too!

Book your high tea experience at The Plaza Hotel 30 days before your preferred dining date. Hotel guests can make reservations with the concierge anytime before their check-in date.

Shop through Union Square Holiday Market:

After high tea, relax at your hotel before heading downtown to Union Square to enjoy more NYC Christmas markets.

The Union Square Holiday Market is internationally renowned for selling unique gifts made by local New Yorkers and features award-winning NYC restaurants and retailers.

From mid-November through Christmas Eve, stroll around the holiday market, shop for loved ones, and treat yourself to home goods, candles, delicious treats, beautiful clothing and more.

Dine at Lillie’s Victorian Establishment:

A woman enjoying a drink at Lillie's Victorian in Union Square.

A NYC Christmas itinerary is only complete with visiting another holiday-themed restaurant. Lillie’s Victorian Establishment and its sister restaurants, Oscar Wilde and Papillon Bistro, boast stunning Christmas décor in an old-world setting.

Lillie’s Victorian Establishment has two locations – Times Square and Union Square. After strolling through the Union Square Holiday Market, head to Lillie’s Victorian for dinner or a festive cocktail.

Located in a Victorian setting, you can savor delicious American fare at Lillie’s Victorian Establishment. Please note that you must make reservations to dine here during Christmas time. However, you can visit the bar area as a walk-in.

Adventure to Lower Manhattan for More Magic:

A woman admiring the Christmas lights in Zuccotti Park in Lower Manhattan.

To conclude your long weekend New York City Christmas trip, you must head downtown to Wall Street in the Financial District to see the beautiful tree at the New York Stock Exchange. The décor on the Stock Exchange building itself is also to be admired.

Zuccotti Park has an enchanting light display with a giant Christmas tree near the NYSE. It’s a hidden gem in New York City and one of the only places you won’t find a heavy crowd.

While in Lower Manhattan, you must also head over to the World Trade Center to see the peaceful fountains, walk through the 9/11 Memorial Museum and head into the Oculus to shop and walk through the holiday market. (This year, there is a roller skating rink at this spot!)

If you have extra time, go ice skating at Brookfield Place, see the Christmas tree in Washington Square Park or visit another NYC festive-themed pop-up bar like Miracle on 9th Street!


Rockefeller Center - one of the top places to visit in NYC during a 3-day Christmas itinerary.

Discover other great destinations you must visit at least once:

Sydney, Australia

Rome, Italy

London, England

I hope you all find this 3-day NYC Christmas itinerary helpful for your first holiday trip. If you have any questions, please email me at info@browneyedflowerchild.com.

Click here to book a cooking class in New York.

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., NY State Capital: Albany, Time Zone: Eastern Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my NYC Christmas Look:

Click here to shop my Poshmark closet!

2 Comments

  1. Kim Deer on December 1, 2023 at 9:35 pm

    Love, love, love this 3 day guide for a fabulous experience in NYC during Christmas time ~ I have been to most of these places and it never gets old. It’s so magical in New York during the holidays. I enjoyed all your beautiful photos ~ it really is getting me into the holiday season. Can’t wait to decorate this weekend ~ love you, mom 🤷‍♀️❤️💚🎄

    • Taylor Deer on December 3, 2023 at 5:29 pm

      Thank you mom! You’re right, Christmas in the city never gets old! Love you too!

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