January, February, and March might not sound very tempting at first, but hear me out. Yes – there’s a decent chance of colder and rainier weather, BUT the advantages also weigh heavy.
Prices for accommodation are at an all-year low. This your chance to score a (very) good deal on an upscale hotel in Manhattan. Fancy a room amidst New York’s towering skyscrapers? Go for it!
Plus, you will share the city with fewer tourists and more real New Yorkers – who tend to flee from the heat (and said visitors) during the hot and humid summers. Check out this curated 5-day winter-itinerary. New York is never a mistake.
day 1 | Walk Manhattan
Make sure you wear comfortable shoes for this one. We’re going for a walk. Though Manhattan’s reputation suggests otherwise, one of the best ways to explore the heart of New York is by foot. I like to start at the northern end of the High Line, a former rail trail that has been converted to a green walkway.
The 1.5 mile (2.3 km) park is located on the western side of Manhattan and runs from Hudson Yards through Chelsea and the Meatpacking District all the way down to West Village. Strolling along the park provides perfect elevated street views. Pick up a coffee at the popular Chelsea Market and let those first impressions of the big city sink in.
Once back on street level, treat yourself to an authentic slice of New York at Bleecker Street Pizza, located in the heart of West Village. Or build yourself a bagel at the Manhattan location of the Brooklyn Bagel & Coffee Company. I know, this sounds like tourist 101, but look around you. These ain’t just your fellow passengers on your inbound flight – this is real New York.
Once recharged, make your way further south. Browse a few stores in fashionable SoHo, try a sweet Cannoli in Little Italy and observe an intensively played session of Mahjong in Chinatown’s Columbus Park. When you look up, your destination for the day finally comes in sight.
At the southern tip of Manhattan, One World Trade Center (the highest building in the Western Hemisphere) and the adjacent 9/11 memorial site pays tribute to the city’s painful modern past and its unwavering optimism and pride. You can’t squeeze more into your first day. Get some rest.
day 2 | Explore Lower Brooklyn
If Brooklyn were a separate city, it would form the fourth largest city in the United States. This is why I strongly suggest exploring the borough in smaller doses. A great place to start is Brooklyn Heights. Be warned – roaming the picturesque streets of this neighborhood will likely have you check rental prices instantly.
Steps away is the Brooklyn Bridge Park, nestled along the East River waterfront. The park is subdivided into different piers and provides some greenery even in winter. The real treat are the unobstructed views of the lower Manhattan skyline. Even though the Brooklyn Bridge is right in front of you, you don’t want to head up there just yet.
First, make your way a little bit further north. Wait, you see another structure spanning the East River? That’s Manhattan Bridge. And the many industrial-style buildings around you comprise the DUMBO district – Down Under Manhattan Bridge Overpass.
Finally, it’s time for a walk over the iconic Brooklyn Bridge. The promenade walkway can be accessed at Anchorage Plaza. From there, the only thing that you have to do is enjoy the dramatic views of Manhattan – and to watch out for the many bikes speeding across the overpass.
A stroll over the bridge is a highlight of any trip to New York City. Once you reach the Manhattan side, turn left and take a walk through Wall Street. Make sure to say hi to the iconic Charging Bull and wave to Lady Liberty from the waterfront at Battery Park.
day 3 | From Harlem to Grand Central
Today, it’s time to explore yet another distinct neighborhood. A quick ride on the northbound A-train will bring you to 125th Street, one of the liveliest streets in Harlem.
The intersecting Malcom X Boulevard provides for even more ways to spend your time in Harlem: Explore historic music venues, indulge yourself with colorful street art, and browse a few of the colorful stores.
If you’re in for the full experience (and happen to be there on a Sunday or Wednesday), head over to one of the many churches for a traditional Gospel service. The Abyssinian Baptist Church and the Bethel Gospel Assembly are particularly welcoming to visitors.
No trip to NYC is complete without a stroll through Central Park. And given that you currently find yourself at its northern end, you get to explore the whole park. A couple hours will suffice to see the impressive Reservoir (named after Jacqueline Kennedy Onassis), enjoy the view from Belvedere Castle, and to simply take in NYC's green lung.
Upon exiting Central Park at its southern end, walk along iconic 5th Avenue, marvel at the historic Plaza Hotel, and top your day off with a visit to Grand Central Station.
The Beaux-Arts design of the Main Concourse is omnipresent in movies and TV series. And now you’re here! Do make sure to take a closer look at the ceiling. The thick turquoise paintings show various astronomical signs – its partial inconsistencies are an open secret.
One minute away from the station lies my favorite green space in New York: Bryant Park – which boasts an ice rink in winter. What are you waiting for? Change your shoes and skate off into the night.
day 4 | Trendy Williamsburg & A Broadway Show
Remember what I said? Brooklyn is huge. And today we’re exploring its northern neighborhoods. Make the East River State Park the starting point of your walking-tour through trendy Williamsburg.
While it’s home to the famous weekly Smorgasburg food market during summer, the park provides for equally pretty views of upper Manhattan in winter.
From there, make your way further inward. Do you have some extra space in your luggage? Good. You might need it after visiting some of Williamsburg’s thrift shops. Pies n Thighs is a great stop for some mouthwatering soul food.
A couple stops on the L-train will drop you in one of New York’s fastest changing areas. Bushwick is home to a growing crowd of young creatives who fuse a variety of influences into these streets.
A visit to Nowadays, a large event space and gastro venue, will provide for the essential Bushwick feel. No matter what you do, you can easily spend a full day exploring these artsy neighborhoods.
Given you’re not staying for one of Nowadays’ extensive parties, make your way back to Manhattan. Tonight, it’s time for a Broadway show. Another upside of your winter-trip to NYC – you might just find yourself in the city for the biannual Broadway Week.
Scoring a 2-for-1 deal for one of Broadway’s most famous shows has never been easier. Plus, the simultaneously happening Restaurant Week will let you enjoy some fancy food at restaurants throughout the city for a fixed price. Enjoy!
day 5 | From The Met to Top of the Rocks
This is already your last day – but I promise, we’ll make the most of it. Start your day with a visit to the enormous Metropolitan Museum of Art. No matter if you’re interested in seeing an entire ancient Egyptian temple, impressionist paintings by Van Gogh or Monet, Roman marble statues or Samurai swords, you’ll find it here.
In fact, this is the largest art museum in the United States and holds a collection of more than 5,000 years of arts from all corners of the world. So there really isn’t an excuse to skip The Met.
Why not combine your day at the museum with exploring another neighborhood? Stroll along Lexington Avenue in the posh Upper East Side and grab a bite at the Lexington Candy Shop. That name is misleading, and their club sandwich game strong.
Saying goodbye (for now) to NYC is never easy. But from Top of the Rock it’s at least a bittersweet farewell. If you only want to access one of the many observation decks in New York, make it this one.
Only from the top of the Rockefeller Center, you have unobstructed views down the island of Manhattan. Only here, the massive Empire State Building sits right in front of you. To see the city transform from day to nighttime on a clear winter day will be one of the most memorable experiences of your trip. And it will definitely make you hungry for more.