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Trip Planning

“If you don’t get out of the box you’ve been raised in, you won’t understand how much bigger the world is.” – Angelina Jolie


As a child we very rarely went on vacation. In fact, I can only remember one that my parents took me on. They went on several themselves of course but I almost always got left in the care of my grandmother so they could relax and “get away from it all”. Apparently, I fell into that all category they needed to get away from, who knew. I believe as a result I love to go on trips and see the world as much as possible. Unlikely my folks however I prefer to have the family in tow. I feel that by exposing my children to the variety of experiences the world has to offer I better prepare them for adulthood, and they will hopefully have plenty of stories to share with their kids.

Like most folks Covid has caused delays and reschedules including the cancellation of our 2020 trip to the Pacific Northwest and 2021 spring break cruise to the Caribbean. Cabin fever settling in we are going to attempt an alternative spring break trip but will focus more on social distancing activities (better than a cruise anyway). As I begin the process of developing the itinerary, I thought it might be fun to write an overview of my processes.


In keeping with my theme of overcompensating for my childhood I prefer to handle vacations in a democratic fashion instead of dictating it to my family. This typically begins with me putting together a simple slideshow or presentation of suggestions. Being a family of 6 we have a great deal of diversity in interests so finding destination(s) that fit a cross section of tastes is paramount to a successful trip. Alexander (16) and I are big fans of museums and historical locations always seeking out ways to bring stories to life and connect with what we have learned. Dave (19) likes touristy locations but could care less about the placards of info and sees them as a drag on our progress from point A to point B. Phaedra (14) and Bridget (8) love the outdoors and want to run around in an open space, see something they’ve never seen and then stay in nice Airbnb where they can place “house”. Mom is as expected incredibly easy going and rarely pushes to have her way (so I have to be careful she doesn’t get cut out) but at the end of the day she loves to sit on a beach or on the side of a mountain to just take in the scenery.

Due to the diversity of tastes and heavily influenced by my addiction to geocaching our adventures have never once been limited to a single destination. They follow a road trip type layout with anywhere from a few hours to a few days dedicated to a single stop before moving on continuing in a large circle until we ultimately arrive back home. Once we’ve narrowed our main themes down (e.g. New York and Washington DC or Grand Canyon and Las Vegas) I begin filling in the gaps. The initial framework is built on a spreadsheet where I layout out at a high level the location we stay at (usually just a city name at this point), the mileage to get there, an estimate of time allocated to travel and major sites we hope to see along the way for each calendar day from departure to return. This must be revisited and updated as the plan develops.


Then it’s off to Airbnb, Vrbo, Kayak and the likes to try and find reasonably priced accommodations. In the beginning we camped everywhere we went. This was far more economical but difficult on an aging back and time consuming to setup and tear down every day. Hotels are easier to book but with three teenagers, a rambunctious 8 year old and a married couple it would require two rooms doubling the cost. As a result, we have become quite fond of home rentals and have even made large scale changes to accommodate staying in a house with amenities we are eager to exploit (e.g. pool, theater room, etc.)

Next comes my favorite part, the geocaches. Having geocached for going on 12 years now I find myself deeper and deeper into the realm of challenges. Currently I look for highly rated D/T caches, old caches (typically 2000 and 2001), caches with lots of favorites and a ton more esoteric examples not worth explaining. Because of this our route from point A to point B may snake significantly and even lead to additional days in an area. In 2018 we went to New York via the gulf touring nearly every state in the south!


Keeping in mind the tastes of each of our adventures I begin to scour the web for sites along our path both well known and obscure. There is a whole linty of sites used but my two favorites are Atlas Obscura and Roadside America. The latter of which has an interactive app (for a fee) that allows for flexibility and finding interesting sites on the fly. I document the attractions I am interest in on a separate tab with links to their page, addresses, hours, costs and anything notable (e.g. security check or reservation required).

At this point I usually reconvene with everyone and present what I have collected, and we discuss the merits of various lodging and attraction options. As you would expect we rarely if ever agree on any one thing, so we negotiate until there is a little bit for everyone. Being both the architect and driver I tend to have a little more pull in this area and there is always a healthy dose of caching and dad type adventure in there. In the early days of family trips I would build a map with all of those sites into a ZeeMap. Luckily Google Maps have improved, and I can now incorporate my interactive map with online spreadsheets. I usually add enough points of interests for 3 trips but being flexible and having backup routes has saved me on more than one occasion.

PLEASE NOTE: I had some issues with the web publisher program and this did not get published on the day intended. This was originally written for publish on 1/23/2021.

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