New York in Winter: How to Plan a Festive City Break Without the Stress

When to Go

The festive season starts properly in late November, around Thanksgiving, and runs into the first days of January. Each stretch has its own character.

Late November and early December are the sweet spot for most people. The lights are up, the markets are open and the crowds have not yet reached their peak. The Rockefeller Center tree is usually lit in early December, and the lighting night itself is best avoided unless you enjoy standing in a pen for hours. Go a few evenings later and you will see exactly the same tree with a fraction of the elbows.

The week before Christmas is the busiest and most expensive time of year. Hotels fill up, restaurants book out and Fifth Avenue becomes a slow shuffle. If those are the only dates you have, book everything you can in advance and plan your sightseeing for mornings, when the city is noticeably calmer.

January is the underrated option. The tree usually stays up into the first couple of weeks, hotel rates drop after New Year and Restaurant Week, which tends to run from late January into February, makes some of the city’s best dining rooms surprisingly affordable. It is colder, though. Daytime temperatures often hover just above freezing, and a wind blowing off the Hudson can make it feel a great deal worse.

Before You Fly

British travellers do not need a visa for a holiday in the United States, but you do need an approved ESTA before you board. It is an electronic travel authorisation for countries in the Visa Waiver Program, and airlines check it at check-in, so it is not something you can sort out on arrival. Every traveller needs their own, babies and children included, and it is linked to the passport you apply with. Renew your passport and you will need a new ESTA too. Applications are made online, and many people prefer to have their ESTA form checked before it goes off, since a mistyped passport number is one of the most common reasons for a wasted application. US authorities recommend applying at least 72 hours before travel, but there is no reason not to do it the day you book your flights.

While you are at it, check that your passport is a biometric one (look for the small gold chip symbol on the cover) and take out travel insurance with generous medical cover. Healthcare in the US is famously expensive, and a slip on an icy pavement is not the souvenir anyone wants.

Getting Into the City

Flights from London take around seven to eight hours, landing at JFK or Newark. JFK is the more convenient choice for most of Manhattan, though Newark is often cheaper and the train link to Penn Station is quick.

From JFK, the AirTrain connects to both the subway and the Long Island Rail Road. The subway is the cheapest way in, but after a long flight with suitcases, the LIRR to Penn Station or Grand Central is far more comfortable. Yellow cabs from JFK to Manhattan charge a flat fare, which takes the guesswork out of it, although traffic in December can turn a forty-minute journey into ninety.

Once you are in the city, you can tap a contactless card or phone at the subway turnstiles, so there is no need to queue for a ticket.

The Festive Classics

Start in Midtown, where most of the postcard moments are within a few blocks of each other.

The Rockefeller Center tree stands above the ice rink between Fifth and Sixth Avenues. For the classic view, come in from Fifth Avenue and walk down the Channel Gardens towards it. Skating on the rink beneath is a lovely idea in theory, but sessions are short, tickets are timed and it can be crowded. Book ahead or simply watch from the railings with a hot chocolate.

Across the road, Saks Fifth Avenue runs a light show on its facade in the evenings, and the windows along Fifth Avenue are worth a slow walk after dark. Macy’s at Herald Square has its own famous displays, along with a Santaland that families tend to book well in advance.

Bryant Park, a short walk away, hosts the Winter Village every year, with a free-entry rink (you pay to hire skates if you have not brought your own), a ring of little glass-walled shops and a few warming food stalls. It is the most relaxed of the big festive spots and a good place to start an evening.

Beyond Midtown

If you only see Midtown, you will miss some of the best of the season.

Dyker Heights, in southern Brooklyn, is where residents go wildly over the top with their Christmas lights. Entire houses disappear under giant nutcrackers, inflatable reindeer and enough bulbs to light a small town. It is a long subway ride, so go on a weekday evening and wrap up well, as most of the viewing happens on foot.

The New York Botanical Garden in the Bronx runs its Holiday Train Show through the season, with model trains winding around miniature New York landmarks made from bark, leaves and seeds. It sounds quaint, and it is, but adults tend to enjoy it as much as children.

For something more theatrical, the Radio City Christmas Spectacular with the Rockettes is a New York institution. The high kicks are as precise as you would expect. Matinees are often easier to book than evening shows.

Staying Warm (and Sane)

The secret to a happy winter city break is not to fill every hour. New York rewards wandering, but in December your toes will have opinions about it, so build in time indoors.

The city’s museums are perfect for this. The Met is vast enough to swallow an entire afternoon, and its Christmas tree and Neapolitan crèche are a seasonal highlight. MoMA is easier to tackle in a couple of hours, and the Frick, smaller still, is a calm escape from the crowds outside.

Food halls are your other refuge. Chelsea Market, Urbanspace venues around Midtown and the stalls in Grand Central’s lower level let you warm up and eat well without committing to a full sit-down meal. Save your restaurant bookings for the evening, and reserve popular places early, especially in the run-up to Christmas.

Finally, plan your days by neighbourhood. Crossing Manhattan several times a day in December traffic is the quickest way to lose an afternoon.

Good to Know

• Sales tax is added at the till rather than shown on price tags, and tipping of around 18 to 20 per cent is expected in restaurants.
• Layers beat one enormous coat. Shops, museums and the subway are heated, sometimes enthusiastically.
• Waterproof boots with a good grip make icy pavements and slushy kerbs far less of a hazard.
• New York is five hours behind the UK, so give yourself an easy first evening.

A City That Earns Its Reputation

New York in winter has a way of living up to the films, provided you get the practicalities out of the way first. Sort your paperwork early, choose your dates with care and leave a little space in each day. The city will fill it soon enough.

By S.Guys

Image credit – Dreamstime.com