Chicago: The best laid plans

I tried to warn you- its not slowing down anytime soon. You are going to continue to be barraged by "Chicago this" and "Chicago that" for at least one more post (after this one).  Seriously.  You know you love it.

Here's a post about one of my favorite subjects.
"How to plan a trip."

Its no secret- I like to plan things.
What I've only recently finally learned about myself, though, is that I tend to under-estimate and over-complicate things.  A deadly combination.  But I will say, when it comes to planning trips, I've got a pretty good balance.

When I found out that we were really going to make this happen- this Chicago for the weekend thing- I could be found just about every night with no less than 15 internet tabs open on my computer.  Reading reviews, getting ideas, polling facebook friends, making reservations, saving maps, reading some more reviews, visiting groupon.  Its important when you only have 3 days to see a place you've never been, to know what you are walking in to.  How else will you know what you absolutely can't miss?

But here's the part that might surprise you- I actually don't plan EVERYTHING.

Here's our basic strategy:
We choose one thing for each day that you really want to do and plan for it.  Then, we have a list of other things you'd like to try to do and fill in the rest of each day with those things.  Usually we lay in bed at night and decide which "fluff" things we want to do the next day.  And we almost always have a back-up plan.  But we plan for the days "big event" to the nth degree.  Coupons, reservations, transportation, etc- all arranged ahead of time.

Here's how that played out for us in Chicago-

What worked:
The DIY Chocolate tour
So yeah.  This is my blog.  So I kinda feel ok about getting a little arrogant here once in a while.  But seriously, ya'll.  This one was B-R-I-L-L-I-A-N-T.  Ok, so I can't take complete credit for it.  RRL definitely helped.  But anytime it seems like maybe we took something and way over complicated it but somehow still pulled it off...that's the mark of yours truly.

When I saw a groupon for a Chicago Chocolate tour, I immediately forwarded it to RRL with the subject line "This is calling my name".  Sight-seeing via chocolate.  What could be better?
Well, I'll tell ya what could be better-
Sight-seeing via chocolate.
Without following a tour guide or her crowd.
(because that would have totally conflicted with the "just us" part of this trip.)
PLUS, we were quite certain (and correct) that we could get more chocolate for less money by doing it ourselves.

The website for the chocolate tour actually listed the chocolate shops they'd be visiting so I penciled the locations on to my paper map that also conveniently identified key landmarks.  So we'd buy some chocolate, walk a little bit, then stop at a landmark to sit and eat chocolate and see the sights.

Here's the tour:
Chocolate Mint Pie from Frango Cafe (here's a great reason to plan ahead. never would have found this one on my own, and its my favorite of all the places we ate in Chicago.  just a little sandwich/soda shop hidden behind the main eating areas at Macy's).  In addition to the amazing pie- we LOVED the Pesto Chicken Salad Sandwich.  YUM, I wanna go back.

And we didn't have to travel far to our next stop.  The basement of Macy's has an amazing chocolate/candy shop- which happens to carry Charbonnel & Walker chocolates.  CROWNS= DELICIOUS.

And while we are eating away inside of Macy's, we enjoyed these views (the museum about Marshall Field, the seven stories of shopping, crowned by the gorgeous Tiffany dome).  I nearly lost my chocolate pie looking over the edge of this balcony a little too quickly.

 Next stop, my least favorite, the Toni Patisserie.  We ordered the Brownie because it was supposedly the specialty, but it just tasted like a brownie.  But they did make a mean Arnold Palmer and the view from this corner cafe was fun- lots of good people watching.

Somehow I don't have a picture of the chocolate from our next stop- a Fannie May store.  Mostly I loved the history behind this chain store.  And I loved that we sat on the stoop of an old building to eat our treats while watching the passenger trains go by on an overhead track. 

Last stop- the most interesting and the one we were proudest of finding.  In a basement of a building, a sweet lady is living out her childhood dreams of making and selling her own candy.  The sea-salt caramel
"la-dee-dah" was DELICIOUS.  As was the bing cherry almond bar.  It just felt like we got a little peek into seeing someone accomplish a huge dream.  And we might have missed it if we hadn't done a little research ahead of time.

We ate these magical pieces with this view- from inside the Thompson Center

 a PERFECT afternoon.  seriously, this was my favorite date EVER.

As a side note- I'm thinking about doing this for a living.
Anyone want me to take you on a tour where we spend several hours seeing the sights all while eating Chocolate?  Bring your own paper map, skip lunch, and we'll be on our way!
YES, PLEASE!


The Boat Tour
Other than amazing places to eat, many told us that we should take an architecture boat tour.  This time we did opt to pay for the "official tour" feeling quite certain we could not recreate this one on our own.  I think the pictures pretty well speak for themselves (and this is narrowed down from about 4012923462 pictures we took in that 90 minutes).

 

This tour was an AWESOME way to get views of the city for the river and lake and learn fun facts about all of the cool architecture in Chicago.  LOVED THIS!

In the interest of transparency, here's
What didn't work:
The one thing everyone told us to do (well besides all the AH-MAZING restaurants) was Shedd Aquarium.  But it actually wasn't one of our "bigs".  So, on Saturday we just went out there.  When we arrived I was totally kicking myself for not planning this out more.  Why IN THE WORLD did I not do more planning for the one thing everyone recommended?  The fact that everyone recommended it should have told me that EVERYONE (and their mother, uncle, children, friend, sister, cousin) would be there on Saturday.  Sheesh.  The line just to get inside to purchase a ticket was TWO-FREAKING-HOURS (and a half).  We did not stay.  This is as close as we got.

And to make things worse, our "back-up plan" for the Aquarium was Navy Pier.  And any of the above listed everyone's relatives that were not at the aquarium... were at Navy Pier.  And its a Pier.  As in an unshaded piece of concrete sticking out into the water.  Which equals H-O-T.  Not our scene.  But we did ride the ferris wheel.  And didn't hate it (pictures of the great views coming up in the next post).  But we also left quickly.

All of that to say, when you take this approach of planning a few things really well, you have to be prepared that sometimes the things you don't plan will be a major flop.

Which means, the number one key to the success of any trip is not the plan itself, it is not even your own attitude toward the situation, above all else it is...
Who you plan to travel with.
And I'm gonna keep on choosin' him.

ABL