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 isn’t 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 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. Not sure if you then pass the lines.

Evening

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

Chelsea Piers

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, the other is The Central Park Boathouse. Both are a tad expensive. Boathouse has a cheaper side.

Afternoon

If you want to see all the Christmasy stuff, walk down 5th Avenue (from Central Park). The fun starts around 59th Street, all the way down to 51st Street, which is Rockefeller Center. The tree is amazing, but be prepared in that area to get stuck in the crowds. There are great store windows and Saks Fifth Avenue has a light show. Pro-Tip: Go down the elevator at the tree and head to the skate rental shop. Don’t rent, but this will give you a bird’s eye view of the tree. If you can, walk out of the shop, turn right. There are stairs that you can take a fantastic picture of the tree.
Fifth Avenue in that area is impossible to get to, depending on the day and time. I went on Saturday night at 6PM. You can see the crowds in the video.
Head down to Bryant Park for the holiday village. There is ice-skating there to. I heard this year it was very crowded – I have not yet been, but I’ve always been able to find cute stuff to purchase. I don’t eat there. I do recommend the Bryant Park Grill – but make a reservation.
Macy’s would be next on 34th Street (between 6 & 7 Avenue). It’s got lots of decorations and a Christmas village. Go into shop at one of the World’s Largest Department stores. They also have a first-time ever carousel.
If you are ready for a Tall Building – head east to 5th Avenue ant 34th Street for The Empire State building. Be prepared for 2 hour waits. It’s Christmas. It’s crowded. Go figure. Buy tickets online for the best buy.

Evening

You can either head toward Grand Central – and eat at one of the food courts underground, The Brasserie (Make a reservation) or the famous Oyster Bar (only M-F – make a reservation.) There is also the Capital Grill (200 Park Avenue). Alternatively, go further east for dinner to an area called Murray Hill. Starting from 3rd Avenue and 27th Street, up to 42 Street, there are loads of places to eat (these are a few that I’ve gone to and like, but there are many along 3rd Avenue)

Docks-Seafood
Sinigual – 640 3rd Avenue, Mexican
Leslie – Mediterranean
Mazu – 495 Third Avenue – Chinese
Bubo – 515 Third – Amercian
Humus Kitchen – Mediterranean, Israeli (31st and 3rd)
Ruby’s – Burger and Salad (31st and 3rd)
Norma – Italian (31st and 3rd)
Blue Mountain Asian – Asian Fusion 396 3rd Ave
The Banc – Irish Pub

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)
Oculus
Bull on Wall Street
Financial District Christmas Tree 11 Wall Street

Evening

Downtown West Side area
Battery Park Brookfield Place
Santa Village
Skate
Eat at Brookfield Place

Day Four

Depending on what time your flight leaves (if flying) Leave at least 4 or 5 hours before your flight. It can take as little as an hour to get their but as much at 2.5. I am an Uber person when it comes to airports. Many people take public transportation, but with suitcases, I don’t find it pleasant. There are share rides like Uber that are less expensive than private.

If it were me, I would pick one of my favorite museums and call it a day. The museum can be 2 or 3 hours and it’s loads of walking. My top two are:

Museum of Natural History
The Met

Other fantastic museums are:

The Museum of Modern Art
The Whitney

If a museum feels a bit rushed on your last day,

Run over to Bloomingdale’s and see their holiday floor. Grab some last-minute gifts.
Go to the Lower East Side and have brunch at my new favorite restaurant, Fossetta. Check out the “vintage” stores and pick up something unique.
Go to Canal Street (Chinatown) and pick up a knock off designer bag. Check out my tips for shopping there! Grab a bit to eat — recommended places here.
Take a cab to Greenwich Village or Soho – walk around the streets and enjoy your last minutes. Grab a bite to eat.

I could not put every possible thing into this 4-day itinerary, and in fact, I think it is too much — but use it as a guideline to plan your trip.