Christmas in New York: A Magical 7-Day NYC Winter Itinerary

There are some cities that impress you… and then there’s New York.

In December 2016, my sister and I made a last-minute decision. We decided to spend Christmas and New Year’s Eve visiting my brother in New York City. Within minutes of landing at John F. Kennedy International Airport, we knew we had made the right decision.

The air was crisp enough to turn our noses red. The streets glittered with festive lights. The city had that unmistakable holiday energy that makes everything feel a little more magical.

The photo below was taken on the drive from the airport to my brother’s apartment. It perfectly captured how we felt. We were excited, slightly overwhelmed, and completely in awe of the city.

If you’re planning a winter trip, here’s how we spent seven unforgettable days exploring New York at Christmas.

Day 1: Central Park and 5th Avenue

We decided to spend Christmas Day wandering around Central Park. We strolled along Fifth Avenue. We finished the day by watching the sunset at 230 Fifth Rooftop Bar.

Central Park was surprisingly quiet and peaceful. I didn’t expect this considering it sits right in the middle of such a buzzing city. I also hadn’t realised just how big the park actually is! We wandered around the lake, passed under several bridges, and enjoyed the calm atmosphere. Because it was Christmas Day, it wasn’t crowded at all, which made the experience even more special. It was the perfect Christmas stroll — catching up with my brother while taking in the serene winter views.

From there, we walked to Fifth Avenue. The Christmas decorations were absolutely stunning. Just look at the display in front of Saks Fifth Avenue! I was far more interested in photographing the incredible window displays than actually going inside the shops.

We finished the day at 230 Fifth Rooftop Bar, one of New York’s most iconic rooftop spots.

Before arriving, we spent nearly half an hour on a plan. We tried to figure out how to sneak my 17-year-old sister inside. We even created elaborate backup plans. In the end, they didn’t even check our IDs.

The rooftop offers a breathtaking view of the Empire State Building, and although entry is free, the drinks are definitely priced for the view.

We ordered hot chocolate and coffee, wrapped ourselves in blankets, and watched the city lights come alive as the sun set.

They even had transparent igloos that seat up to eight people — but we preferred standing outside, taking in the skyline.

Seeing New York from above is something everyone should do at least once.

Day 2: Shopping at Macy’s!

Boxing Day meant one thing: shopping.

Visiting Macy’s Herald Square is practically a New York rite of passage, especially during the holidays.

The Christmas window displays alone were worth the visit. Each one was beautifully designed with vibrant colours and imaginative themes that had both adults and children stopping to admire them.

Inside, the store felt like a maze. But somehow we managed to navigate it and leave with plenty of gifts — taking full advantage of the Boxing Day sales.

Day 3: Lower Manhattan

(Wall Street, Staten Island Ferry, 911 Memorial and WTC)

We started the day by taking the subway to Wall Street. While many financial firms have moved elsewhere in recent years — partly due to flooding in Lower Manhattan — Wall Street still carries an iconic status as the historic financial heart of New York.

The first building we noticed was Federal Hall National Memorial, where George Washington was inaugurated as the first President of the United States and where the Bill of Rights was first proposed. The original building was demolished in 1812, and the current structure was built as a Customs House in 1842.

From there, we walked down to catch the free Staten Island Ferry across the Hudson River. It offers fantastic views of the Statue of Liberty, making it one of the best free experiences in the city.

On the way back, we passed the famous Charging Bull — which, interestingly, isn’t actually on Wall Street but nearby on Broadway at Bowling Green.

About a 10-minute walk away is the 9/11 Memorial. It’s one of the most sobering places in New York and serves as a powerful reminder of the attacks on September 11, 2001, which claimed nearly 3,000 lives. We didn’t go inside the museum as it would have taken several hours, but it’s definitely worth visiting if you have the time.

We also walked to One World Trade Center, built on the site of the former Twin Towers and now the tallest building in the United States. There’s an observation deck at the top with panoramic views, but unfortunately we ran out of time to go up.

Day 4: Exploring Mid-town Manhattan and Comedy Night!

We woke up incredibly excited to continue exploring — even my sister got ready in record time.

Our first stop was Grand Central Terminal, and it looked exactly like it does in the movies. The station felt enormous and full of energy. Above the entrance stands a sculpture of Minerva, Hercules, and Mercury surrounding the famous Tiffany glass clock.

The original station was built by Cornelius Vanderbilt in 1869. After a major accident in 1902, steam trains were banned in Manhattan, leading to electrification and the construction of the larger station that officially opened in 1913.

The central information booth with its iconic four-sided clock has become one of the most famous meeting points in the city.

Next, we visited the United Nations Headquarters. As a PPE graduate, I was particularly excited about this stop. The complex was designed by Brazilian architect Oscar Niemeyer.

After grabbing lunch (and doing plenty of shopping along the way), we headed to Times Square. Many people warned us to avoid it, but as Londoners we’re used to crowds and busy city life, so it didn’t bother us. The flashing lights, massive billboards, and constant buzz make it an unforgettable experience.

While we were there, we spontaneously decided to watch a comedy show — and it turned out to be one of the best decisions of the trip. We laughed so hard we were practically in tears. It was also my sister’s first time in a comedy club, which made it even more memorable.

Day 5: Chelsea / Greenwich Village

We started the morning with a walk along the High Line — a 2.3 km elevated park built on a former railway line on Manhattan’s West Side. It only opened to the public in 2009 and has quickly become one of the city’s most unique attractions.

The pathway is lined with beautiful plants (many native to the U.S.), art installations, and incredible views of the Manhattan skyline and the Hudson River. We also found plenty of quiet spots to sit, relax, and people-watch.

Afterwards, we stopped at Chelsea Market for lunch. The entrance alone looks promising, and inside there are countless food stalls and shops selling everything from handmade jewellery to quirky souvenirs.

Next, we walked to Greenwich Village and stopped by the building used as the exterior for the Friends apartment — which was very cool to see in person. After exploring the neighbourhood (and quietly following part of a walking tour), we went to Joe’s Pizza — literally one of the best pizza spots in New York. The queue alone proved how popular it is.

Later that evening, we walked to Washington Square Park, home to the famous Washington Square Arch and the heart of New York University. We sat by the fountain for a while, people-watching and resting after our long walk.

When we decided we were in the mood for jazz, a quick search led us to Fat Cat Jazz Bar. It had a relaxed atmosphere with live music, ping-pong tables, board games, and a great crowd. We grabbed a deck of cards from the bar and played games while waiting for the jazz set to start. It was unpretentious, fun, and full of raw musical talent — definitely a place I’d recommend.

Day 6: Brooklyn & Basketball Game!

We dedicated a full day to exploring Brooklyn — though honestly, we could easily have spent much longer there.

We started with breakfast at IHOP. We had to see what the hype was about, and WOW — the portions were huge (and delicious!).

Afterwards, we walked across the Brooklyn Bridge early in the morning before the crowds arrived. We spent nearly an hour taking photos and enjoying the views.

Next, we visited the Brooklyn Heights Promenade, which offers stunning views across the East River toward Manhattan. From there we walked to DUMBO (Down Under the Manhattan Bridge Overpass), a neighbourhood that has transformed from abandoned warehouses into a vibrant area filled with restaurants, shops, and creative spaces.

That evening, we went to our first ever basketball game — one of the highlights of the entire trip!

Day 7: Day of Museums!

New York has so many incredible museums that it’s impossible to see them all in one trip.

By the time we packed our bags and got organised, we only had time to visit two: The Metropolitan Museum of Art (the Met) and the American Museum of Natural History.

Both were incredible and easily places you could spend an entire day exploring.

The Met:

History Museum:

We also spent a day visiting Washington D.C. (which I’ve written a separate blog about) and a few more days shopping before heading home.

Honestly, I can’t even explain how much I love New York. It’s just… cool. There really isn’t another word for it. This was one of my favourite trips ever, and I wouldn’t hesitate to go back in a heartbeat.

Have you been to New York — or are you planning a trip there? Let me know in the comments below! 🗽✨