The Adventure of Trip Planning - My Personal Process
I love to travel, but honestly, sometimes I think I love the planning just as much as the trip itself. There’s something about digging into a new place, finding little gems, and building out a loose plan that feels like its own little adventure.
So where do I start?
I usually dive straight into online exploring. It’s fun, it gets my energy up, and it makes me excited for whatever’s ahead.
I bounce between:
Google Maps to see what’s nearby
Tripadvisor for restaurant scouting
Copilot (and yes, ChatGPT too) for ideas based on what I already enjoy
What about you—what do you like to explore when you’re somewhere new? I’m usually looking for things that are budget‑friendly, unique, or local. And if there’s an easy water activity, I’m absolutely in.
I usually start with an AI prompt like:
“Tell me about budget‑friendly, unique, or local things to do near…”
or
“Tell me about notable things to do near…”
My personal go‑tos:
Eclectic shops
Local history
Disc golf
Wineries and breweries
Tubing, kayaking, paddle boarding
Thrifting
Roller coasters (of course)
Once I find one anchor—like a great thrift store or a cozy little winery—I can usually build out the rest of the trip from there. Some of the tiniest, most interesting spots are nearly impossible to find unless you go digging.
I drop everything into Google Maps lists because:
It keeps everything organized
I can see how close things are to each other, which makes planning the day so much easier
If you’re curious, I wrote a whole post about how I use Google Maps to plan trips.
After that, I start exploring restaurants. I use the same kind of prompts to figure out where to eat. Something like:
“Tell me about notable restaurants near…”
And because I’m always thinking about budget, I follow up with:
“Tell me about the best restaurants in the area that offer great value.”
Now for the nerdy part.
Compiling the details.
I like to gather the general area, hours, and any special features I don’t want to miss. It helps me intentionally plan the “when” and “where” of the trip.
Sketch the plan.
From there, I outline a general plan based on operating days. I start with the things that matter most to me or have the tightest time restrictions, and then I build everything else around them.
A few other things I keep in mind:
I like my adventures to be partial‑day. Ideally, I start early and wrap up in the early afternoon. But if something requires an evening, I just shift the whole day later. And I always leave room for one day with no commitments at all. A great trip, in my opinion, needs a mix of structure and freedom.
More help from AI.
If you’re planning something more specific or you’re working with a tight timeline, AI can make things even easier. It can design walking maps based on operating hours or even color‑coded maps of different types of sites.
Just make sure to double‑check the accuracy. On my trip to the Scranton area this summer, AI gave me a list of attractions in northern Massachusetts and suggested a festival that had already happened a month earlier. So… always verify.
Keeping the trip realistic.
What is your structure? Ensure that you plan days that fit you (and your travel companions) style.
I prefer partial days - either starting in the morning and wrapping up by the mid-afternoon or start later for an evening activity. I also mix in a day without plans, so I can savor flexibility and impulsivity.
Wishing you great adventures ahead.
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