Welcome to the first installment of the Un-Planner’s Guide, a wholly un-serious and unusual approach to travel itineraries.

I’m Katie, and I’ll be your host through approximately one-and-a-half days of New York City, NY.

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Yes, this hat is part of our required tour guide uniform.

 Trip Pre-work:

  • Know about the trip, in my case, AT LEAST a year in advance.
  • Book your flight accordingly, apparently for domestic flights the magic number is 54 days for cheapest fares.
  • Have ample time to pack and let that dwindle down to months, weeks, days and mere hours before your trip.
  • Go out to dinner with friends and/or family the night before your flight.
  • Struggle to pack within the window of 12 a.m. to 2 a.m. (Stop mid-packing to justify your procrastination.)
  • Sleep for 2 hours.
  • Wake up to leave for airport and hate yourself a little bit.

Day 1 (or Day 1/2):

Getting There

  • Be at airport.
  • Go through security rigamarole.
  • Fly.

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  • Land and realize you lost half your day because of time changes. Curse.
  • Rideshare from the airport to your hotel and get stuck in traffic. Learn your lesson and take the subway for the rest of the trip.

Ice Cream Break

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It has to be soft serve. From a truck. No exceptions.

  • Wrangle large group of Filipinos (who are your family so it’s okay) and proceed.

Oculus – World Trade Center Transportation Hub

  • Take subway to get to the Oculus, which is the World Trade Center’s transportation hub.
  • Exit train and enter Oculus. Be impressed. Take a moment to admire the architecture.
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The structure of the Oculus was like being inside the skeleton of great beast.

National September 11 Memorial

  • Cross the Oculus, meaning just walk straight across it and up a flight of stairs, and you’ll find yourself back at street-level and able to walk right over to the National September 11 Memorial. There’s a museum there, as well.
  • Visiting the memorial, as you would imagine, is a truly sombering experience. But beautifully moving, too, if you take in not only the construction of the memorial but the fact that they place white roses next to the names of the people being remembered on their birthdays.
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The day we visited, there were two birthdays.

One World Observatory

  • Check out One World Observatory. It’s just a short trip across the street. The building itself if stunning, but it also offers you 360-degree views of the city from 100 stories up.
  • The trip up to the observatory does require admission, so expect to pay about $30+ for a single person.

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If you were to ask me what part of the city this way or what any  of those buildings were, I couldn’t tell you. They had these tablet thingies for purchase that you could point out at the city, like a virtual tour guide, but I was more keen on just looking.

Chinatown (And Little Italy, Sort Of)

  • Find that after all the subway riding and walking you are famished, as one ice cream alone cannot hold you down.
  • Fumble through the subway with your herd and somehow make it to Canal Street.

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  • Arrive late enough that most of the shops are closed, but just in time for the restaurants to be bustling with business.
  • Let your dad pick the place, though his relationship with Google is tentative at best, and then let him lead the way (???).
  • Walk into an unfamiliar neighborhood almost to the point of concern until you reach Shanghai Asian Manor. Note that this restaurant only accepts American Express or cash.
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Eat delicious food and not realize until later that this is actually a really popular place.

  • Leave and enjoy the light sprinkles of rain as you walk. Let your family make ill-advised hat purchases at a souvenir shop about to close.
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Pass up Little Italy (sad-face) because majority rules to go to Times Square.

Times Square

  • Arrive in Times Square and be baffled by the fact that the city is still buzzing at 11:00 p.m. on a Wednesday. Assume that maybe all the huge electronic billboards are making people think it’s still daylight.
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SO BRIGHT. MY EYES.

  • Be horrified by the discount store-looking nightmares that are parading around as notable characters. Pull your unsuspecting aunts away from a particularly disturbing Minnie Mouse and Woody.
  • Decide you’ve had enough of these shenanigans and decide to turn in so you can get up early for more exploring tomorrow.

Well, that’s it for the first part of The Un-Planner’s Guide to NYC! Come back next week for part deux.

Your Humble Host,

Katie