Taking a Bite Out of the Big Apple

Vacation Planning: An Example of My OCD Organizational Skills

My husband and I are taking a trip this fall. We’re going to one of my favorite places on Earth, New York City, for our first anniversary.

Dark CityRyan’s never been to the Big Apple, so half of my excitement is thinking about watching him take in the city for the first time. I’m convinced he’ll love it, but it will leave him exhausted. I know it. I’ve done all the touristy things before and don’t really want to do them again. I’d rather experience NYC like a local. Because Ryan’s never seen most of them and has several on his must-see list, though, we are compromising by doing half and half.

I plan trips like I plan anything else – down the the minute details with lists upon lists and sublists and spreadsheets and possibly even graphs.

In a word – obsessively.

I get nervous that we’ll have these random amounts of time with which we don’t know what to do and where to go. I hate moments like that on vacation. My husband and I have the exact same feelings about trips: Do as much as possible. You can relax when you sleep.

(Example: We couldn’t just sit at the beach longer than 45 minutes on our honeymoon. We literally don’t know how to sit still while on vacation.)

And I’m getting off topic. Anyway, we sat down last night to make a master list of the things we just have to do. It’s color-coded. Each item has a ranking. Intense. From there, we’ll plan our days out by borough, and then I’ll memorize the subway and bus system. I refuse to be that tourist looking at a map. Refuse.

So, here’s what we have so far:


  1. Central Park
    1. Natural History Museum and Hayden Planetarium – top of my list. If we see Neil DeGrasse Tyson, I will die of happiness. Die.
    2. Central Park – Ryan wants to walk through it. I kind of want to run it every morning since our hotel is nearby.
    3. FAO Schwarz – “I want to go to the toy store from Home Alone.” – my husband, verbatim. Easy to see why I married him, huh?
  2. Midtown
    1. New York Public Library
    2. MOMA – ohmygodohmygodohmygod. Can’t wait.
    3. Bryant Park
    4. Legoland in Times Square – please see comment next to MOMA
    5. Rockefeller Center
    6. Wicked on Broadway – Tickets are outrageous, but I’ve been told that if you hit the box office first thing in the morning, you can get cheap tickets. We may try it. Wicked is my favorite, but my husband will probably fall asleep. So, there’s that.
  3. Lower Manhattan
    1. World Trade Center
    2. St. Paul’s Chapel
    3. Please Don’t Tell (PDT) – Google it
    4. Employees Only
    5. Death & Co.


  1. Williamsburg
    1. Brooklyn Brewery
  2. Prospect Heights
    1. Brooklyn Botanic Garden
    2. Prospect Park
  3. Coney Island – Because I am Italian
  4. Windsor Terrace (?)
    1. Green-wood Cemetery – No, we’re not morbid. It’s got a lot of cool stuff to do, and it looks absolutely beautiful. I’d like to see the Civil War project.
  5. Honestly, I just want to walk around Brooklyn and pretend I live there.

The Bronx

  1. Yankees game. Duh. Can’t wait to see those Bronx Bombers. 

Can we see all that in 4 days? No. We’ve got some cutting to do. And I’m still getting back recommendations on local hot spots from friends and acquaintances that live in NYC. Speaking of, do you have any ideas? Let me know in a comment below.

*I get all the Brooklyn areas mixed up, because they are so close to each other on the map. If I mess something up, please let me know in a comment!

photo by: nosha
1 Comment
  • Ryan Arthur
    June 27, 2013

    I can’t wait and we can get it all done if we just don’t sleep. Also you forgot the 5 am bars we will be going too!

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