All My Best Recommendations for Holidaying In New York At Christmas

At some point most people dream of spending a winter season in New York City. Christmas and New Year in Manhattan conjures up magical shop windows, New Years Eve in Times Square and hopefully some snow on the ground.

If you've never spend the holiday season in New York city, it is something you should consider even just for a few days. In 2011/2012 we got an apartment in Park Slope in Brooklyn and lived like New Yorkers for a month.

Here's my best tips on how to do that and what to expect.

Tip 1: Embrace Brooklyn, The Bronx, Harlem or Queens for Accommodation in New York

Accommodation in Manhatten is never cheap, however over the Christmas season when New York is one of the most popular destinations on the planet, it can be very expensive . Not only is it expensive, typically its very hard to find something affordable that has any kind of real kitchen.

While you may think that won't matter, its very hard to survive for a month paying probably around $6-10K for accommodation and NOT be able to prepare your own meals. Most of the accommodation options below will run $2500-$3500 for about 14 days so if you can reduce your stay to 2 weeks not having a kitchen will be a more manageable setup.

Manhattan hotels can be well priced if you get lucky, but that does mean that you have to eat every single meal out. While Brooklyn or Harlem has lots of affordable restaurants around, they can be hard to find in the middle of Manhattan. Locations like Park Slope in Brooklyn give you the option of choosing from heaps of restaurants on 5th or 7th Avenue. Likewise Harlem has many restaurants and cafes that line Frederick Douglass Boulevard and the side streets around that area. Mid town Manhattan does have some affordable eating for sure, but it is harder to find.

As an alternative to a hotel, you could of course try AirBnB, however since the borough councils have been very proactive in weeding out unlicensed short term accommodation on sites like these, the options are often no longer affordable. We used AirBnB in 2011 and paid just over $6000 AUD for a month in Park Slope (such an amazing apartment too), but when I look now I can't see anything under about $8,000 AUD and most average around $12K.

UPDATE December 2021 - Currently there seems to be a few around $5K for a month in Park Slope. I am assuming this is COVID related but if you are thinking of travelling right now, this link to AirBnB will give you a specific Park Slope Brooklyn search for a month over the holiday season. 

Tip 2: Be prepared to line up for food and tickets.

We didn't go out to the Statue of Liberty because the line up for tickets was 3 hours. Stuff that. We just took The Staten Island ferry and saw her that way. Its a great view from the ferry and when we were in New York, you couldn't go inside the Statue due to renovations so it seemed pointless to line up for 3 hours to see not much more than we could from a free ferry.

Apart from lining up for tickets, New Yorkers also line up for cafes and restaurants. As Australians we would usually just walk on but when you find out everything has lines you learn to get in that line pretty quick. Cafes and or restaurants typically prefer bookings and often have an entry for reservations and then another line for walk ins. Make sure you check with the door person if you have made a reservation. We made the mistake of lining up once thinking it was the way to get in and by the time we got to the door they had given away our reservation because they thought we weren't coming. So use your words and ask if you are not sure.

Tip 3: Broadway goes dark over the holiday season

I expected that because it was the busiest time of the year that we would have a plethora of shows to choose from. What I didn't realise is that Broadway goes dark for the main Christmas season so there are very limited shows running.

We went to Rock of Ages which was awesome and chose to go to some smaller more local shows . Check out some options on Viator who often has not just Broadway show tickets, but smaller off-Broadway shows as well. We went to My Sinatra that was playing at the time and really enjoyed it.

UPDATE: I'm not sure what the situation is at present with COVID but maybe keep this link so you can look up My Sinatra when things get a little more back to normal.

Consider:

As an alternative to seeing a live show, consider checking out all those famous New York filming locations you would recognise on a walking trip around the city.

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Tip 4: Find Smaller Music Venus

While it is always great to go to a big music event, New York has a surprising number of local smaller more personal music venues.

Of course the Bowery Ballroom is great and has a wide range of performers usually. Don't forget though that they have a multitude of venues so check out the venue page first so you don't accidently buy tickets for PIttsburg or somewhere.

• The Rockwood Music Hall has some great bands.
• Pete's Candy Store in Brooklyn has some amazing alternative acts. Don't miss a show there if you can avoid it.
• We got completely addicted to Freddy's Bar in Brooklyn. While they have live music acts the bar itself is very cool and they also have Trivia nights and open mike comedy too so check out what they have on offer.
• I don't feel like any stay in New York should miss a night out at The Apollo . Their specialty is cultural performances from song to dance to comedy even.
• If you can get to Smoke in Harlem - do it. We saw Gregory Porter there and it was amazing. Small, personal and filled with music lovers. They are also doing a live streaming service during lockdown which can give you an insight into what they offer. They are a Jazz club, however are very open to less strict forms of Jazz so you can see some great perfomers there.

Tip 5: Reconsider doing New Years Eve In Times Square

After doing it, in my personal opinion NYE in Times Square isn't worth it UNLESS you can spring for one of the major hotel events.

Being out on the street is freezing, crowded and disgusting by the end of the night (take my word for it). You will line up for hours and unless you have a ticket for an event, the numbers admitted are limited so you will have to be there very early to get in for free.

We decided to splash out and get a good location with dinner and drinks included. We spent $250 each for somewhere that was all inclusive and that had a balcony to watch the ball drop and while the ball drop was cool, the event was absolute shit.

We were lucky and went out on the balcony early so we did see the ball drop which was very cool, but they failed to tell everyone that there was limited numbers allowed out there and most people were locked inside for the ball drop. That would have sucked big time!

They ran out of all alcohol at 10:30 and didn't care. We didn't get any dinner because they ran out before they got to our table, and there wasn't even anything we could buy.

Unfortunately for them, Australian card providers allow you to challenge the charge for up to 6 months which I did and got my money back. Fortunately I had taken photos and video to support my claim because they tried to get my challenge dismissed. I had only just gotten a phone that could take photo and video and thank goodness I had recorded it because otherwise I might have been $500 out of pocket for 15 mins on the balcony and about 4 drinks!

I have known people who have purchased tickets at some of events at the big hotels which is what I would recommend. If you are spending $500, spend the $750 and have a night you will always remember.

Also be aware that there is so much traffic and so many people that getting a private car to pick you up anywhere in that area is a waste of time. We ordered one a few days before and they never showed up. Again the call centre said he was there but wouldn't give us his number and wouldn't listen when we said we hadn't got any calls. In the end we subwayed it home and I again cancelled the charge. If you do want to book a car, I would consider organising a pickup for at least 4 or 5 blocks away.

The bedlam of Times Square for NYE 2011/12

Confetti over the clock tower after midnight.

The Ball dropping to signify the countdown to midnight.

Tip 6: Plan some things before you go .

Tickets to any sporting events sell out fast. I knew I wanted to see both the hockey and football derby so taking the time and searching early meant we got both events and also good seats. If you are not Australian, a "Local Derby" is the game between the two local teams. In this case we saw Jets and Giants for footy and Rangers and Islanders for hockey at Madison Square Garden thanks very much!

There are a lot of websites that enable you to see what's going on, however please be careful where you buy tickets. I've always tried to use either Viator (who I know are reliable) or purchased tickets direct from the club or venue. Of course Ticketmaster and Ticketek (or similar in the US) are great but avoid anything you can't validate. I've known friends who have bought tickets to BIG events through less than reputable websites and have been left standing outside the venue on the night.

Stub Hub is a great place for sporting tickets because it enables season ticket holders to sell the tickets to events they don't want to go to. Please be aware of how you receive the tickets through Stub Hub though. If they are mailed to you, you don't want to have left Australia and still not received tickets. Check that they are emailable or you can pick them up at Will Call to be sure you won't spend the money and still miss out. Most are digital now, however it does pay to check because some tickets won't be released to the season ticket holder until not far before the event.

It is also legal to sell tickets in the US provided you don't make more than 10% profit I think it is. (Don't hold me to that percentage). This means that you often can get concert tickets for close to the original price when circumstances change and the holder can no longer attend.

The Jets - Giants game we saw while in New York.

Tip 7: Embrace Groupon

Groupon saved us so much money while we were in New York. I made a bit of a plan, used my process  consistantly and saved HEAPS of money.

I would work out what groupons I wanted to buy, sit with my laptop open and the order in my cart, call the restaurant (or wherever it was) and book making sure they knew it was a Groupon. Then after they had said yes my time and date was possible with a groupon, I would check out while I was on the phone and get the Groupon ID for the reservation.

This process I would consider essential for ensuring you can use the coupon while you are there.

Lots of popular groupons have black out periods over the holiday period, so you have to be sure the restaurant will take a Groupon booking before you purchase it. I doubt this would be necessary outside of the Christmas period though.

We got a great deal at a Russian restaurant in Brighton Beach and spent the night with the restaurant owners drinking Vodka and eating whatever they recommended. We also got a great night at My Sinatra a local show for like $15 I think it was.  We used Groupon for everything from Carousel rides to a 3 night stay in East Hampton. I would say we saved between $1000 & $1500 over the month we were there. Not to be sneezed at.

Just make sure you know your local address as sometimes you do have to enter it to qualify.

Tip 8: Learn early on the the subways aren't named after the destination.

If you are Australian you are used to the directions on the trains or trams telling you the destination as a suburb. So for example, the Gold Coast Airport train goes from the Gold Coast to the Brisbane Airport. That's not how it works in New York.

It can be very confusing however I'm sure it will be much easier now in the world of apps.

The declared destination is usually the last stop on the line, so don't look for the suburb you are going to as that won't help. There is the odd exception, but they typically aren't named for the destination. So if you are looking at a time board in the station and you are wanting to go to Queens you will be looking for the Fulton Street line AND depending on which way you are heading, you will be looking for either 6th avenue or Lefferts Boulevard. Those are the stops they show as directions so knowing you are heading to Queens won't necessarily help you. You would have to know if you are going toward either 6th Avenue or Lefferts Boulevard. See what I mean?

When you enter the station, check the boards that show the lines that run from that station and make note of the line and the last stop on the line. When you get to the platforms now you will know which train is going in which direction. Alternatively, you could spend all day going in the wrong direction, sometimes that's fun too! 

The other frustrating thing is that often there are no boards until after you've passed the gates, so get yourself a subway card before you do anything else. That way you can get in and always ask someone if you don't know.

Wikipedia List Of NY Subway Lines

The MTA Live Subway Map is much more descriptive than it used to be so maybe start there. Click the Live Map in black in the middle of the screen and then on whatever station you want.

Tip 9: Don't be put off by distances

Honestly, most of my followers will enjoy staying amongst the local suburbs way more than paying a bomb to be in a hotel on Manhattan. Knowing this don't be put off going to something in Flushing, or staying out at Sheepshead Bay. Once you are on the subway whether its 5 stops or 10 stops it doesn't really matter. You are on holiday, the subway is always very reliable and there is the added bonus that if you get on further out you are pretty much always guaranteed a seat for the whole trip.

Going from Park Slope to the Empire State Building takes around 35 mins on the subway. Going from Sheapshead Bay takes 45 mins. An extra 10 mins isn't going to make any difference and you will find everything heaps more affordable in Sheapshead Bay! Oh and you will be close to the beach out there too.

Tip 10: Dress local, act local and be local

I never have "travel clothes"! Ever. Actually that's not entirely true. I did by some khaki colored pants when I was in Africa mostly because the mossies seemed to LOVE my black pants, but it wasn't until after I chose the color that I realised I must have looked like I thought I was on safari everywhere I went. Who cares - they weren't cargo pants but still the color was very suitable for the dust I must admit.

I pride myself on wearing the clothes I wear in everyday life no matter where I am and if you do get to visit New York, please think about this. People in New York typically rush everywhere so if you are strolling along in your white sneakers, with your "I Love NY" T-shirt on immediately you can be spotted as a tourist. This doesn't matter in the overall scheme of things, but anytime you get anywhere near a tourist location you will be targeted by hawkers.

Now - I'm not saying don't wear your comfortable shoes. I'm always in mine , but just be aware that you will need to practice your travel face if you don't look like a local. Take your usual clothing. If you don't wear cargo pants with 14 pockets at home what on earth makes you think you will wear them on vacation?

Eat in the local establishments if you can. The further away from the more tourist areas you go, the more affordable food will become. It is difficult to find a large supermarket like we are used to in Australia, however smaller ones are everywhere and food is cheap in the US.

Bonus Tip: Check out these things to do in New York

Here is my worth it - not worth it list for New York. This is just my opinion based on what we did but hopefully it will help you out some.

Things We Loved

• The Empire State Buildling - pay the extra and go up for the day/night or evening ticket. It will be busy but just be patient and as people leave you will end up at the front of the rail. Also go into the bar and have the Empire State Cocktail before you leave. Its delish! Oh and listen to the story. The quality and speed in which they built that building is stunning!
• Staten Island for pizza - I don't know what it is but pizza on Staten Island is better somehow. Try Tony's
• Get the subway up and walk from 135th street in Harlem all the way down the island and cross the Brooklyn Bridge. Its about 10 miles but if you take the day, stop for coffee, lunch, browse some architecture and shops and cross the bridge in time for sunset its a great day.
• New York Aquarium. I don't usually do zoos or aquariums. I can't cope with caged animals but we had a friend working at the Aquarium so we went. It was better than I thought and I would recommend it especially for the kids.
• Get up to the Hamptons if you can. We spent 3 days up in East Hampton and loved it in winter. Its heaps quieter, there are still a lot of things open and the buses still run. Its a great kick back break from the city and you can get some great deals over the winter.
• 911 Memorial - superb. Bring tissues but excellent.
• Even if you don't know whats going on, head into a local bar to watch a footy match. The atmosphere is excellent.
• The Brooklyn Naval yard is worth the tour. The history and how its evolved is very interesting.
• There is a lot closed in Central Park over the winter but it is still worth a wander.
• The Highline is great but the Chelsea markets I was pretty non plussed with.
• Miss Mamie's Spoonbread Too in South Harlem was amazing. Southern food. OMG!

Not as great as we thought

• Statue of Liberty. The line was 4 hours long just for a ticket and then you had to line up for the boat. No thanks. We got the Staten Island Ferry for free.
• The coffee. Weirdly they don't seem to serve it as hot as we do. I wondered if its because everyone is walking with it, but I had no idea how much of a coffee state Australia is until we hit New York.
• The lack of restrooms is appalling. Like truely terrible. I wondered if it was any better before 9/11 but it is horrific now. Be prepared to pay for 2 beers every time you need to pee. Its unavoidable.
• The tipping. Now I don't mind tipping, but I do object to having to tip when you don't get great service. I didn't on occasion and actually got yelled at once! I was more resolute in my non tip when she yelled at me that's for sure. Overall my opinion is pay your service staff a decent wage and build it into the menu price so I don't have to pay them. You always have to factor it into the price so be careful because that $25 pizza can turn into a $35 pizza quickly.
• The public transport and stations can feel really unmaintained. I'm sure they are looked after but the weather contributes to what feels like grime everywhere. It's not a real concern but it does feel dirty. I was glad it was winter and I had gloves on more than one occasion.
• People can get very pushy shovey for the free Christmas events. I mean tourists not the locals. I got knocked over at the Christmas Tree at Rockefella Center and I'm not exactly a lightweight.
• The boathouse restaurant in Central Park. So not worth the money. It was expensive and rubbish. I would never recommend it.
• Magnolia bakery. Hmmm - not terrible but I lined up for 40 mins for what I though would be "the" cupcake of my life. It wasn't. It was OK but it wasn't amazeballs like I thought it would be.

So I hope I've helped you to plan and execute a winter in New York City. It is just amazing and there is no end of things to see and do. I will update this list as I think of things and of course please get in touch with any questions you might have.

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