I have never been someone who arrives in a new city with no idea what we are going to do. Before we leave, I have usually researched enough activities to fill approximately three vacations and attempted to fit most of them into one.
Years ago, my vacation-planning system started with a Groupon membership to the Maryland Science Center. The reciprocal museum benefits gave us a starting point in almost any city we visited. I would create a TripTik, add every museum, historic site and possible stop I could find, and then turn the whole thing into an itinerary.
We rarely followed it exactly.
I still overplan vacations, although the tools I use have changed. I also understand the purpose of all that planning differently now. The itinerary gives us structure, but the larger collection of research gives us room to change it. When something is unexpectedly closed, the weather refuses to cooperate or the people on the vacation turn out to have opinions, I already know what else is nearby.
The plan starts with too many possibilities
When I begin researching a trip, I am not particularly restrained. I want to know about the major attractions, but I also want to find the smaller museums, historic sites, unusual stops and places we might only visit if we happen to be nearby.
I put everything on the map.
Some of those places become anchors for the trip. Others are possibilities that may never make it onto the actual itinerary. But mapping them all helps me understand the geography of a city. Two attractions that sound as though they belong together may actually be on opposite sides of town. Something that seemed too minor to plan a day around may be directly next to another place we already want to visit.
I can also begin to see which activities naturally fit together and how much time we will lose moving from one part of a city to another. That matters when traveling with children, but it also matters when traveling with any group of human beings who eventually want to eat, sit down or stop looking at historic plaques.
Then I build the itinerary
Once I have the oversized collection of possibilities, I begin turning it into actual days.
I look at locations, opening hours and anything that needs to be reserved in advance. I think about which places are most important to us and which ones would be nice if the timing works. I try to avoid traveling back and forth across the same city unnecessarily.
Then I inevitably put too much into each day.
I have become somewhat better at recognizing that looking at a map is not the same as moving several people through an unfamiliar city. There is travel time, parking time, waiting time and the mysterious stretch of time that disappears whenever everyone has to leave a hotel room.
Still, I would rather begin with more options than we need. The plan might say we can visit four places. That does not mean we must visit all four. It means that when we finish the second activity, we already know what else is nearby and can decide what makes sense.
The itinerary is not a binding contract
Our actual trips rarely look exactly like the original plans.
A museum is unexpectedly closed. It rains. Something takes twice as long as I expected. We discover a place that was not part of the plan at all. Someone is tired, hungry or simply finished participating in my carefully constructed educational experience.
Sometimes we move an entire day around. Sometimes we skip something I really wanted to see. Sometimes an attraction I researched extensively loses out to something we noticed from the car.
The planning is still useful because we are not starting from scratch every time something changes. I already know which options are nearby, which ones require reservations and which activities could work better on another day.
Overplanning is what allows us to be flexible.
My planning system has changed
The Maryland Science Center membership was once the beginning of the process. I could look at the reciprocal benefits available in a city and build outward from there. The TripTik helped me see the route, add stops and begin organizing the trip geographically.
I still use TripTik, but now it is one piece of a larger planning process. I gather information from different places, map the options and gradually turn all that research into a day-by-day plan.
The technology makes it much easier to move things around, check current information and find alternatives. It also makes it possible to collect far more possibilities than any family could reasonably visit.
I am not entirely sure that last part is an improvement.
What has changed more than the tools is how I think about the finished plan. I used to see the itinerary as the trip we were supposed to take. Now I see it as one possible version of the trip.
There are things we definitely want to do, things we would really like to do and things that are useful to know about if we have time. There are also activities that work as backups when the weather changes or when the original plan turns out to be unrealistic.
Not every researched attraction needs to become part of the vacation for the research to have been worthwhile.
Planning for the trip we are actually taking
The same itinerary will not work for every family, or even for my own family at every stage.
The ages of the children matter. The length of the trip matters. The reason we are traveling matters. A short pre-camp trip has different constraints from a longer family vacation. A city we have visited repeatedly requires a different kind of plan from a place none of us has seen before.
Our interests and energy levels also change. Something that worked beautifully on an earlier trip may no longer make sense. Something we skipped years ago may suddenly be exactly what one of the children wants to do.
That is part of why I keep planning rather than simply reusing an old itinerary. I can begin with what I already know, but I still have to think about the particular trip and the people taking it.
What I am going to share
Over the years, I have accumulated a lot of travel plans. Some were followed more closely than others. I want to begin sharing them here, including the research that went into them, what we actually did and what I would change if we took the trip again.
These will not be definitive guides to everything a family should do in each destination. They will be the plans I created for my family, with the parts that worked, the parts that did not and the options we researched but never reached.
I still enjoy building a very detailed itinerary. I also know that the itinerary will change once the trip encounters weather, opening hours, traffic and my actual family.
That does not make the plan a failure. It means it did its job.
