4-day itinerary

Pro-Tip: Do not try and push everything in on a 4-day trip unless your goal is to check the boxes to say you been here and saw NY. A 4-day itinerary is going to give you a taste of everything in a fairly leisurely way, while at the same time, hoping to show you how Manhattanites experience the city. Of course, you can mix and match – and add or remove things. This itinerary is specifically for the December holidays – whether you’re here for Christmas, Hanukkah, or a Birthday – or just to enjoy the city, It is more adult/teen oriented and is gleaned from not only my own experiences, but from those I’ve been reading all over the internet. If you love where you are, don’t rush through it to get to the next place. Enjoy the journey.

Pro-Tip: There are bagel places all over Manhattan. They don’t have to be a planned thing to do. My favorite is H&H. I want a bagel now.

Arrival:

If you arrive at your hotel at 3 or 4 in the afternoon, today is NOT THE DAY to run around like a crazy person. I am assuming you are staying in the Times Square area. But, if you haven’t booked your hotel yet, here are alternative places that are also central, and really nice:

Hotel Options***

Pro-tip: If you go after January 2, you can still see all the holiday lights and decorations, and hotels are up to 50% less than in December.

Get Started

Head Downtown to the West 30s.

The Vessel- This is amazing, and going up and seeing the views is spectacular. I have a gazillion shots of this. I can’t believe someone built it, but maybe that’s just me. If you go at twilight, it now lights up.
Hudson Yard Shops and decorations
Hudson Yards has great places to eat, not only in the Mall (top floors) but also on the street level at Little Spain which is slightly away from the shops. Just ask people.
There is also, of course, the The Edge – but everything I have been reading says STAY AWAY now due to 2.5 hours waiting in line.
Pro-Tip: If you eat at Peak with Priceless and spend $60 per person, you get a free Edge ticket

Evening

Next: Either the Chelsea Piers area OR Union Square. You can do both, but I would be very tired, but that’s me, and I like to relax.

Chelsea Piers

Chelsea Piers Area. Either walk Downtown on the highline (which starts at Hudson Yards) or take a bus down 9th Avenue to Chelsea Piers. MTA Bus: M11 – 9th Ave and get off at 23rd Street. Walk West toward the Hudson River.

Little Island – very cool park with great city views
Pier 59 – Has lots of eateries and also a great view of the city from the roof park
Museum de Arte – this was a fabulous digital, interactive art museum. I spent about 90 minutes there. Amazing. Click here for my recap and photos

You can stay in that area and eat dinner at Pier 59, (the food court) , can eat at City Winery (nice place, ok food, make a reservation). There are also a gazillion restaurants all around Chelsea. Click here for a list. I haven’t tried all of them, but they are cheaper and less crowded than anywhere near Times Square. There is also Chelsea Market, but personally, it’s fast food and CRAZY INSANE crowds. At least during December.

Alternate route: Union Square

Union Square – Holiday village and Farmer’s Market. Farmer’s Market is on M, W, F, Sa – the Holiday market has food, and hand-crafted gifts.
Barnes and Noble Bookstore- a tradition
My favorite area of town to dine in is Park Avenue South, from Union Square up to 27th Street. Here is my list Click Here

Day Two – Holiday Cheer

Morning

Find a bagel place near your hotel. Or any diner, a place that serves breakfast. We have something like 26,000 restaurants. Trust me, you’ll find one! Just ask at the front desk. I can’t recommend it because I don’t know your hotel. You don’t have to stand online at many places. If you go to the Upper West Side, on Columbus Avenue/Amsterdam Avenue, you will be where NYers are and away from Tourist City.

Start on the west side of Central Park. Spend 1 or 2 hours, but this will depend on your ability to tolerate cold weather. Please don’t support Horse Rides as they are abused. My favorite place in the park is the Reservoir, which is on West 85th Street. The views are beautiful.
There are two great places to eat inside the park. One is Tavern on the Green

Day Three – Brooklyn and Lower Manhattan

Everyone says they want this, so I’m going to start with the Brooklyn Bridge: You need to decide if you want to cross from Brooklyn or from Manhattan. People say the views going into Manhattan are amazing, but if you want to see Dumbo, that won’t make sense! In addition, you CAN turn around and look at Manhattan as you walk.

Pro-Tip: Dress in comfortable walking shoes, a down coat, sweater, hat, mittens, and scarf. It was 30 degrees yesterday, and that wasn’t even the bridge where it is colder.

Start in Manhattan: You can take the East River Ferry to Wall Street and walk to the entrance, which is right near City Hall. Or, Just make it easy and take an Uber! Lastly, there are many subways. The main subway is the East Side Green Line (4,5,6) and get off at City Hall. OR, take the ferry to Wall Street.
Directions to Ferry: Take a bus across 42nd Street or 34th Street (which is closer) and go all the way to the East River Ferry. The Ferry will take you to Wall Street, and it’s a 15-minute walk from there.
When you do this, is up to you. The earliest ferry is 6:45 AM so you will miss the Sunrise over the Bridge.
Alternatively, there are multiple subways to get to Dumbo. Then walk over the bridge if you want to catch the Sunrise.
When in Dumbo, there are lots of things to explore.
This website is all about Dumbo – click here

Afternoon

Take a ferry back to Wall Street and explore the South Street Market. Lots of places to eat and very festive.
Walk to the 911 Memorial.
911 Museum (90 minutes to 2 hours)
Bull on Wall Street
Financial District Christmas Tree 11 Wall Street