City Breaks, Going Solo, Road School

Road School: Chicago–The Unplanned Plan

Please see note at the bottom of this post for an explanation of this photo.  Thanks!

Please see note at the bottom of this post for an explanation of this photo. Thanks!

Several weeks ago, my sister-in-law sent me a text: what’s the name of that museum in London you told me about?  I looked at the date and I looked at the time and replied: you’re at the airport, getting ready to board the plane right now, aren’t you?  And then I laughed.  Because I literally cannot imagine being that laid back about travel plans.  Yet she is.  And do you know what?  I saw her photos.  I heard her stories.  She had an amazing trip.

For my second Road School post, I thought I’d go ahead and step right out of my comfort zone.  I’ll be in Chicago this weekend, a city I’ve never visited before.  And I have two full days there (plus one night and one bonus morning before I depart); having this amount of time, solo, in a new city, typically sets me off on a planning frenzy.  Which made me wonder–what would it look like if I simply didn’t plan?

Guiding Questions:

How important is it to have a planned itinerary when exploring a new city?  Is it better to plot and schedule, or to go with the flow?  Which type of trip is more enjoyable?  Which type of trip is more interesting?

Thus, I will spend one of my two full days in Chicago with plans and reservations–an entire itinerary.  I will leave the other day open.  I will not even set my alarm clock.  I will simply see what happens.

This two-day experiment, like my last Road School adventure, will be documented in photo form, live on Instagram.  And I will not tell you which day was planned and which day was unplanned–you’ll have to guess.  And then vote for which was your favorite day.  Though I have to wonder–does planning to do this count as a plan?  Gah!  I’m hopeless!

Note: It is impossible to include original photography for pre-trip posts featuring plans to visit a place I’ve never been.  Thus, I for Road School ‘Plan’ posts, I shall include an original shot that has nothing to do with the location I’ll be visiting, yet in some way expresses the spirit of my guided question.  

This post’s photo says something like ‘come along with me–it’ll be fun, I promise!’  What?  You didn’t get that from the photo?  Ah well.  I tried.  It was taken at the Phipps Conservatory in Pittsburgh, PA. 

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