Planning to a Fault

I was born a planner.

It’s just how my mind works. So it was natural for me to plan out my first international trip six years ago with Casandra in detail.

Months before departure, we had worked out our flights to Greece, hotel in Athens, transportation and key sites of interests to visit together. But similar to someone who was in the closet, I hid my real plan from her. This included ridiculously detailed lists of every place we would be – addresses and phone numbers, maps to and from these various destinations, directions by car and/or by foot, how long it would take to get to each destination, the best days to do each based on weather and location, cost and hours of operation if applicable…and in some cases even a picture or two to ensure we knew what to look for.

And maybe I compiled all of this in a 3-ring binder.

Now, this was before the rise of the smartphone. That’s my excuse. But even then, I knew my OCD had gotten the better of me and it would surely frighten Casandra to see this side of me.  So I hid these print outs in my backpack and read through them like porn while she was in the shower or away. Once we had done something for the day, I had to check it off my list and start thinking about how we were going to get to the next thing. I just couldn’t help myself.

During our trip to Greece, the only part of our plan that seemed to work out was our hotel. Everything from the flight, to our cabs, to the places we visited all had varying ways of unraveling which we will write about later. And you know what? I loved every single minute of it. When I finally stopped worrying about the how and whens, I was able to just absorb the plethora of moments right in front of me. We still saw everything we wanted to and many things we never imagined because we stumbled upon them after getting lost roaming around. Our best experiences time and time again were the ones we never expected. And isn’t that what life is about? To live it as it comes.

Fast forward to the present and 25+ countries under my belt, and I can’t help but smile when I think of that trip to Greece and how it helped confirm my career choice in life – hint: it lets me plan the hell out of some plans – but more importantly how to leave room in my trip to just travel. So how do I plan a trip today?

Things I always do:

  • Book flights with reasonable departure times and secure a window seat
  • Book lodging prior to landing
  • List out key things I want to see or devour (I love cocktails and a good meal.)
  • Check visa entry requirements
  • Check electrical outlet type/voltage
  • Confirm native language and learn the basic phrases.
  • Confirm currency
  • And yes, I still have a ‘quick list’ printed out just in case wifi doesn’t work that has key addresses and such. But it’s never longer than a page so I don’t have to be ashamed of it.

That 3-ring binder from Greece has been retired to the shelf and serves as a reminder to not suffocate a trip by planning it down to the t – let it breathe…you’ll be amazed at everything you can take in.

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