Why I Spend Time Planning My Vacations

I included a quote in one of my Twitter posts yesterday as I was simultaneously planning three of my upcoming trips:

“A schedule defends from chaos and whim.” – Annie Dillard

I love that quote because it reminds me that scheduling is necessary to keep me sane but also a constrictor.  The last thing I want to do on vacation is defend from whim!  With each trip, I’m getting better at finding the balance.  I used to pack every minute in to see two days worth of attractions in one, in that stereotypical if it’s Monday, it must be Barcelona syndrome (sorry Mom!).  My trips lately have been more serendipitous, with open time that sometimes means stumbling upon a soccer game in Fes or stopping to watch a moose courting ritual in Denali.

My balance these days has been to schedule one thing that I don’t want to miss for every day of vacation.  That gives me something I look forward to and a slight structure to my day while still leaving plenty of wiggle room.  And I try to make just-in-case hotel reservations (or throw my camping gear in the car) so that I’m not wandering around looking for a place to stay in the middle of the night.  It just doesn’t seem safe to me, especially when traveling solo, and especially because I’m batting a 0 when it comes to finding acceptable options on the night of arrival.

In the meantime, I still research the heck out of my destination.  Some of it is logistical: things like gathering train schedules, maps, and average costs.  I do that so I don’t stress while I’m actually traveling and in fact, being armed with that kind of information makes it easier to change plans on a whim.  Some of the research is “armchair travel” with reading on the attractions, restaurants, and unique accommodations at my destination (anyone else want to sleep in a Slovenian wine barrel village?).  And more recently, I’ve been researching the local history and culture of my destination to better understand where I’m headed.

In the end, sometimes I feel like I know more about my upcoming destinations than some locals do (it works both ways: I’ll admit to not knowing everything about Richmond, either!).  Maybe that takes the mystery out of things, but I have so much fun in the reading and anticipation that I’d never give it up.  I can get months worth of enjoyment leading up to a single week-long trip.  The only problem with that is that a week to explore somewhere new ends up seeming less and less adequate since there’s more and more I want to see and understand.  It’s a great problem to have and amazing inspiration to realize I’ll likely be returning and thus can just enjoy the time I do have.

Are you a planner or do you prefer to go with the flow?

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Editor and Lead Author at The Girl and Globe
Becky loves hiking and the outdoors, reading a good book on a rainy day, practicing yoga with friends, cooking with Sinatra in the background, relaxing with her husband and a good glass of wine, and above all: travel. Read more about Becky.

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  1. Scott says

    I’ll plan, but many times I find the plans are overly ambitious, which is frustrating. I like the sound of only one don’t miss opportunity per day – I may try that on my next trip.
    How do you organize all your research? I’m trying to pack lighter and would like to keep as much as possible on my tablet, but not every locale/attraction makes that easy!

    • says

      @Scott, I like to compile all of my information into Word documents, which you can then keep on your tablet. I’ll copy details on addresses, opening times, confirmation numbers, and even pictures of maps into a single document. I usually end up with two separate files: one with everything on my “don’t miss” list (along with those hotel addresses, etc.) and a second one full of other information in case I do find myself with more time on my hands.

  2. Nat says

    I like to read about places, activities, etc, and put them all in a word document. But I’ll actually print it out booklet style to take with me (and also put a digital version on my phone). Mostly, though, I just love to read about places, and I try not to overplan, instead, know enough to have lots of options when time comes to choose.

  3. Drew says

    Definitely a planner, but like you, as I have traveled more and more over the years, I have slowed the pace. This summer, I will be in France for 10 days, and I have booked a “just in case” hotel to start. That will change. I want to focus on WW I and WW II battlefields and memorials, and I will do lots of research and planning. Back in Paris, less planing but still lots of research. I also find time to take a book into a park everyday and read.

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