What To Do In New York CITYYYYYYYY!

{me and huck and the flat iron, september 2010}

Touristy Stuff, Only Cooler
Skip the lines at the Empire State Building. Top of the Rock is faster and just as tall.
Skip the Statue of Liberty. Walk the Brooklyn Heights Promenade instead. You'll see the Lady and all of Manhattan's skyline, plus you can say you went to Brooklyn, which is exciting! (Wave at Montague Street for me while you're there!)
Skip Grimaldi's and get Juliana's. Same family, same ovens, smaller line. Get ice cream at the Brooklyn Ice Cream Factory for dessert, and then walk back to Manhattan across the big girl.
Get tickets to a taping of something. Jimmy Fallon is my favorite. Sign up for tickets in advance, and if they're all booked you can always try the standby line day-of.
Skip Times Square, and visit Union Square instead.
(Unless you want to see the four story Forever 21. The four story Forever 21 is totally worth the hassle of Times Square.)
Skip the cupcakes at Magnolia and get the banana pudding instead.
If you go to Ground Zero, be sure to check out the old graveyard across the street. It's really rad in there.
If you're going to do a museum, I suggest the MoMA. The MoMA cafe is especially worth it.
You know what's every bit as fun as you think it's going to be? FAO Schwarz. I mean it. Go there.

Shopping? Yes, You Will Be Shopping
On a weekend, nothing beats the Brooklyn Flea Market and the Smorgasburg.
Spend most of your time on and around Broadway south of Houston, and on 5th Avenue south of the 23rd Street. Zara, Topshop, Madewell, H&M, Barneys CO-OP. Be sure to wander down Spring and Prince and Wooster when you're in SoHo. That's some of my favorite places down there.
For a real New York experience, you're going to want to hit up a Sample Sale (racked.com will keep you posted.) Be sure to wear your cutest underpants for when you strip to your skivvies next to model-types. This sounds horrifying, but it's good for you, you should try it once.
Go to Mood and pretend you're on Project Runway.  (M&J Trimming is fun.)
Department stores are fun to wander through. I really like Bloomingdales a lot.

Good Things To Eat
Shake Shack. Get the Shack Stack. You won't need to eat for the rest of your life.
Eat a Levain cookie, but whatever you do, don't look up the calorie information on that sucker, you'll regret it.
Benny's Thai in the Financial District (hole in the wall, and sooooo goooooood).
Iron Chef Sushi in Brooklyn Heights (tell them Natalie sent you, and order the MONKEY ROLL).
Falafel in the West Village
Bubby's in Tribeca
Amy Ruth's in Harlem (I've been dying to check this place out, you'll have to tell me how it is)
John's Pizza on Bleecker Street

Other Fun Stuff
Pick an Avenue and walk it. Any Avenue will do. (I like Fifth.)
Ride the subway for funsies. Just, not from 8-10AM and not between 4 and 6PM and not any time after midnight, unless you want a different kind of funsies. I like the N/R line, goes right down the middle.
Get lost in the west village. You're going to get lost down there anyway so you may as well say you did it on purpose.
Go stare at hipsters and do some thrifting in Williamsburg.
Go see my lover the Flat Iron building and then wander around Eataly because that place is BONKERS.
Check out the bathroom at Bryant Park. It was named the third best public restroom in the nation!
Pressed for time? Do a bus tour. I know I know. They're actually kind of fun.

Things that aren't worth it:
Waking up early to stand outside the Today Show windows. Please don't stand around and scream at Al Roker. You won't feel good afterward. Same goes for any restaurant anywhere near Times Square. The Lego Store is lame, but the M&M store sells gold M&Ms!

Bonus Extra Credit:
Take a You've Got Mail pilgrimage to the West corner of 69th and Columbus to see The Shop Around The Corner (next to the L'Occitane). Then wave at me, you're in my neighborhood!