Itineraries: My Fear of Missing Out

Confession: I am a type A personality. Not THE most type A of all type As, but still pretty type A. As an attorney, I am also predisposed/trained to identify all potential negative outcomes of a situation and to try and avoid those outcomes. Some call me a "pessimist," but I tend to consider myself a realist about what things are most likely to go wrong. Which leads me to research. And planning. And planning. If I have a plan, I try to have a back up plan. And research on the back up plan. 

Conversely, J is the world's biggest optimist. He's not naive, but he chooses to believe and/or hope that things will work out for the best. And if they don't, he deals with the situation when it occurs.  He does some background investigation, but does not have tripadvisor/yelp/lonely planet on his "top ten websites" the way I do. He's probably  definitely the happier and calmer of the two of us. 

The "no vehicular traffic" road I accidentally instructed J to drive
down in Jerusalem. Excellent travel planning on my part.

Our travel/life philosophies never seem more divergent than when we are getting ready to take a trip.  Particularly when we are headed to a destination that has so! much! to! see! I feel an overwhelming urge to allot every moment and make sure I am getting my time and money's worth out of an experience, and that I'm not missing something very cool that I would have known about if I had just bothered to google my destination. However, as you may expect, this has led me on several occasions to become very frustrated when things don't go exactly according to plan. And, probably, it has led me to miss out on some spontaneous, cool adventures.

These people definitely have an itinerary. 

In doing my research (sigh sigh, I know) on our trip to India, I've read a lot of horror stories about people who found it completely overwhelming to prepare their own itineraries, who say NOTHING goes according to plan there, and to throw all expectations out the window. You can imagine this is my personal version of hell when it comes to vacation planning. So in an effort to avoid the inevitable frustration of having my plans go awry, I have tried to take a much more "relaxed" approach to planning this trip. For each destination we have, I have booked accommodations because I have irrational fears of ending up homeless on the streets. I have booked transportation from city to city. And for a few activities we have planned (e.g. a hot air balloon ride), I have made reservations (tip: never on travel days). And other than that? I've made lists of big attractions in each of the cities we are visiting and have "graded" them in terms of 1) must sees; 2) would be cool to see; and 3) if we happen to be passing by and feel like stopping. I've grouped them geographically to try and use our time most efficiently. And that's about it. I am trying to "under" plan the trip to make sure that I leave time for side trips and unanticipated events without losing my mind. It's not perfect, and it's not the most type B way to travel, but I think it's progress!

My idea of what a Type "B" traveler looks like.

So here I ask my readers: When you travel, how detailed are your itineraries? Are you a "plane ticket and go" kind of person? Or do you need to sync your watches with other members of your travel party to ensure everyone's on schedule? Any tips?

*Note: This blog post inspired by this post authored by a much better blogger than me--and I'm proud to count her as a colleague and friend too!