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THE ULTIMATE 4 DAYS NEW YORK ITINERARY

Looking for the ultimate 4 days New York Itinerary? There’s so much to see and do in New York, it’s difficult to squeeze all the best sights into such a short trip in any given season. However, this 4 days New York itinerary in winter is designed to help you make the most of visiting the Big Apple during the festive months.

Factors include weather (yes, it will be cold, with average temperatures ranging from seven to minus two degrees Celsius – and there’s always the possibility of snow), the months you’re planning to visit (and therefore the holidays, festivals, and other events that take place during that time), plus a focus on specifically winter-themed activities and attractions you don’t want to miss if you’re visiting New York in the winter and how to see New York in 4 days. Here are the top NYC rooftop hotels.

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4 DAYS NEW YORK ITINERARY

The Ultimate 4 Days New York Intinerary – New York in the Winter

Map provided by Wanderlog, a vacation and road trip planner

While booking your trip to New York City, you will want to stay in the right area that is close to all the attractions. Here are the ultimate places to stay in New York City for first-timers. The ultimate hotels in New York City have amazing rooftop pools with great views.

Please note that many of the attractions mentioned here are currently closed and activities/events are suspended due to the Covid-19 pandemic. For the latest information, check ahead of time with the venue to see if it is open and running as normal. Of course, always wear a mask, social distance, and take necessary precautions to ensure your New York visit is a safe and healthy one.

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Ice Skating in Central Park in January

Day 1 of 4 Days New York Itinerary – Manhattan 

Start your wintery 4 days in New York adventure in Central Park, which is just as beautiful in the cooler months as in the warmer ones, especially when it snows and the pond freezes over. Even if there’s not real snow, during the free Winter Jam festival there are snow machines to ensure a flurry of flakes!

Sled down the hills, go ice-skating at the Wollman Rink, or simply walk around breathing in the fresh, crisp winter air – just make sure you’re wrapped up warm with plenty of layers.

When the weather gets too chilly, make your way to one of the great museums nearby. Not only do the museums offer a respite from the winter chill as well as fascinating exhibitions, but there are often impressive festive decorations to enjoy too. 

The Museum of Natural History is known for its themed Origami Holiday Tree (the 2019-2020 theme was dinosaurs) and this tradition has been going on for 40 years. The Metropolitan Museum of Art also has a special seasonal holiday tree, lit up and decorated with gorgeous ornaments, accompanied by festive music.

Next, make like Audrey Hepburn and head down to Fifth Avenue to admire the incredible window displays by high-end retailers such as Tiffany & Co., Saks and Macy’s, to name but a few. Sometimes window shopping is as fun as the real thing.

By now you’re sure to have worked up a bit of an appetite and the best remedy to a day on your feet in the cold is by warming up with a hot drink. Heading to the Upper East Side, you’ll come to Serendipity 3, an establishment made famous by the 2001 movie Serendipity, starring John Cusack and Kate Beckinsale (essential watching as a NY-set rom-com with a Christmassy theme).

An alternative is The Russian Tea Room – a historic NY institution that has been serving high tea for more than 90 years. Continuing with the Russian theme, end your first day in New York by catching a festive performance of The Nutcracker by the New York City Ballet at The Lincoln Center. 

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4 Days New York Itinerary

Day 2 of 4 Days New York Itinerary – Manhattan 2

Fuel your body for a second day of sightseeing around Manhattan with a hot chocolate from Dominique Ansel Bakery, topped with a marshmallow flower.

From here, it’s up to Union Square to peruse the Union Square Holiday Market, which sells everything from festive ornaments to winter fashion to NY souvenirs (all perfect holiday gifts for loved ones), plus there’s plenty of hot food and drink to satisfy the munchies brought on by cooler weather.

Nearby Union Square is the famous Strand Bookstore, a large independent bookstore that has all kinds of titles, plus it’s great to wander around on a cold day. Check out their website before you visit, as sometimes there are literary events held at the store.

Continue your bookish tour of the city with a visit to the New York Public Library. The building itself is as impressive at the literary collection. There’s a free one-hour tour you can take of the library, which includes the Rose Main Reading Room and some of the library’s exhibitions.

Heading north, you’ll reach some of New York’s most recognizable landmarks, such as Times Square (look out for the ball on New Year’s Eve) and the Rockefeller Center. Of course, the Rockefeller Center is well-known for its giant Christmas tree, and if you time your visit right, you may get to witness the lighting ceremony.

In the evening, make your way down Broadway to see a show or simply to watch the dazzling lights and billboards advertising current performances. If sport is more your thing than theater, head to Madison Square Garden. Winter is ice hockey season and watching a fast-paced New York Rangers game at this impressive venue is a true “New York in winter” experience.

If you have time, squeeze in a drink at 230 Fifth Rooftop Bar, one of the city’s best al fresco rooftop bars. During the winter, there are heaters and the bar provides red robes, so you’re sure to feel cozy while enjoying your drink and a stunning view of the Manhattan skyline.

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4 Days New York Itinerary

Day 3 of 4 Days in New York Itinerary– The Bronx & Brooklyn

Though it’s a little out of the way, a journey north of Manhattan will bring you to the New York Botanical Gardens. Every year, this space puts on a Holiday Train Show in a greenhouse, featuring miniatures of New York landmarks, such as the Empire State Building, with miniature trains winding through.

(To replicate this in real life, during any Sunday on your 4-day itinerary for New York in winter, you can travel between Manhattan sightseeing spots on the vintage Holiday Nostalgia Train – run by the New York Transit Museum.)

Down in Brooklyn, get your holiday shopping fix at Smorgasburg Winter Market and/or the Brooklyn Flea. Antiques, vintage fashion and collectible items mix with winter-themed knick-knacks (plus hot food, cocoa and warming drinks).

If you need a museum fix and to warm your toes after meandering the outdoor markets, pay a visit to the Brooklyn Museum. One of the city’s largest museums, the building holds more than 1.5 million artworks!

After dark, head even further south to the neighborhood of Dyker Heights, famed for its impressive Christmas lights. Some of the residents here even hire professional companies to deck out their homes with illuminated holiday-themed displays!

Day 4 of 4 Days in New York Itinerary – Ski Trip

Taking a day trip out of New York City, take to the slopes, and enjoy a day of snow sports. The best way to do this is by joining a tour, which will provide transport as well as equipment for rental, and lift passes, etc. Here are a few locations to consider: Mountain Creek (Vernon, NJ), Thunder Ridge (Patterson, NY), Hunter Mountain (Hunter, NY), Mount Snow (West Dover, VT), and Belleayre Mountain (Pine Hill, NY).

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4 Days New York Itinerary

Events in New York in the Winter

Of course, the activities you decide to do while visiting New York during winter will largely depend on which month you’re visiting in. There are lots of exciting events and festivals that take place during the winter months, which you may wish to factor into your New York trip:

Hanukkah (December)

Thursday 10th – Friday 18th December 2020, Sunday 28th November – Monday 6th December 2021

To celebrate the Jewish Festival of Lights, head to Prospect Park, where the world’s largest menorah is lit for all eight days and nights of the festival. 

Christmas (25th December)

As you may have guessed already from the suggested activities and attractions listed in the recommended 4-day New York in winter itinerary above, there are plenty of Christmassy displays and events that take place in the city in the lead-up to Christmas Day.

However, if you don’t celebrate Christmas, you may be a little disappointed on Christmas Day itself – as this is usually a quiet day that people spend with friends and family, and many establishments will be closed for the holiday. 

If you’re looking to celebrate Christmas, dress up and head to church for services and carol recitals. If you’re not Christian, you may wish to spend this day in Chinatown or Koreatown, which is usually buzzing on Christmas Day – filled with people who don’t celebrate the holiday!

New Year’s Eve (31st December)

Watching the ball drop in Times Square is iconic, but be mindful that it is very crowded, very cold and you’ll be waiting around for a long time. You may prefer to ring in the New Year at a local bar or restaurant, so look around for ideas.

No Pants Subway Ride (January)

Tuesday 12th January 2021

As the name suggests, this is a day where people ride the subway without pants. What started as a joke in 2002, this cheeky idea has become a much-beloved annual event and has spread from New York to more than 60 cities around the globe since its inauguration!

Lunar New Year (January or February)

Friday 12th February 2021 (Year of the Ox)

Also known as Spring Festival or Chinese New Year (though it is celebrated by many Asian nationalities), Lunar New Year is best celebrated in Chinatown or Koreatown. You’ll see plenty of red-and-gold decorations, lanterns, dragon and lion dances, and more in the run-up to the New Year. There are also dates of significance pertaining to seeing family, sharing gifts, as well as giving and receiving red packets of money. 

Super Bowl (February)

Super Bowl LV Sunday 7th February 2021

The most important sporting event of the year in the United States, the Super Bowl is an annual championship game that decides the winner of the National Football League (NFL). 

On top of the sport, it’s also a major event in advertisers’ calendars for the famed Super Bowl commercials, and the cherry on the top of the cake is the half-time performance. Previous Super Bowl halftime performers have included Lady Gaga, Beyonce, Jennifer Lopez, Madonna and more.

Even if you’re not big into sports or don’t follow the NFL, you’ll still want to get involved and soak up the atmosphere of this major event. Find a sports bar playing the game, though make sure you plan ahead as it may be very crowded!

New York Fashion Week (February)

New York Fashion Week takes place twice a year – once in September and once in February. The events last between seven and nine days, with international designers, buyers and press coming together for everything fashion related. 

Many shows are for industry only, but you can buy tickets for open-to-the-public shows, or simply hang around NY’s cool spots to catch a glimpse of some of the world’s most famous fashion icons.

Westminster Kennel Club Dog Show (February)

If you’re an animal lover, you may be interested to know that the annual Westminster Kennel Club Dog Show takes place in New York during February. The show has been hosted in the city since 1877 and is also televised. 

Valentine’s Day (14th February)

Visiting New York for Valentine’s Day can be busy and expensive, but incredibly romantic. There’s plenty to see and do in the city for cupid’s annual holiday. Popular spots to visit during this time include the Empire State Building, Times Square (where many couples propose, tie the knot, or renew their vows in front of the Valentine’s hearts) and Central Park (for a horse-drawn carriage ride). 

If you’re staying in New York over Valentine’s Day, make sure you book accommodation and any restaurant reservations well in advance to avoid disappointment. 

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4 days in NYC

Other Things to See in New York City

If you have time during your 4 Days in New York I would suggest making your way down to the Hudson Yards to see the Vessel. You can make a reservation ahead of time to climb to the top of The Vessel for amazing views. The World Trade Center Memorial is another must-stop on your adventure through New York City.

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4 day new york itinerary

Other Things to Do in 4 Days New York Itinerary in the Winter

Did you find this 4-day itinerary for New York in winter helpful in planning your trip, or the event guide that details which holidays and festivals are going on during each month? Alternatively, do you have anything to add or recommend to be added to the itinerary, to make a NY winter trip even more special? Let us know in the comments below.

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