Wander Intentionally
Pick one daily anchor to give yourself baseline confidence, then leave the rest of your route open for zero-stress discovery.
The key to a low-stress itinerary? Enough planning to feel confident with enough flexibility to explore.
Hi. I’m a recovering Over Planner. I’ve always felt that planning helps me manage uncertainty. I genuinely enjoy researching places, building maps, learning what exists nearby, figuring out how different neighborhoods connect – seriously, ask my husband how much time I spend planning things that we may never even do!
However, rigid itineraries make me want to crawl out of my own skin. If there’s no margin, no room to breathe, then we become pressed for time, rushed to get from thing to thing, instead of being present and enjoying the experience.
So I created an approach that I call Intentional Wandering, which is basically planning not to plan.
Itinerary planning is really an exercise in curation and expectation management. Everybody gets to throw ideas into the pool, but every idea does not automatically become something the group has promised to do. This is where my ABC Lists come in. My ABC-list approach to creating an itinerary was built specifically around sorting those possibilities into shared priorities rather than trying to cram everything into one trip.
Start with an Anchor
Choose one thing that gives the day direction. Your anchor could be a museum, historical site, dinner reservation, playground, neighborhood, scenic view, one A-list attraction.
Then research the area around it: Coffee shops, bookstores, historic buildings, playgrounds, snack options, parks, public art, markets, scenic streets, odd little stores, local places that look interesting but don't necessarily deserve a reservation and a color-coded calendar invitation.
You're not scheduling them or committing to any particular location. You're just becoming aware that they exist.
Then walk out the door.
Turn down the interesting street, stop for fancy coffee, wander into the record store, let the kid play in the sand, take the photo, listen to the street musician, investigate whatever weird building just caught your attention.
Research gives you the confidence and flexibility gives you the freedom to get a little lost on purpose.
Your Map Is a Menu, Not a To-Do List
This distinction matters. I save TONS of places to maps. More places than we could ever realistically visit.
And I do so with intention because I'm creating options for Future Ashley. When we arrive somewhere, I can look at the map and say, "Oh! There's a bookstore two blocks from here," rather than spending 25 minutes standing on a sidewalk searching "things to do near me" while everybody slowly loses the will to live.
The research happens before the trip, not in the middle.
The decisions happen when we actually know the weather, everyone's energy level, what time lunch ended, whether the museum was amazing and took four hours instead of two.
Try It Now
Choose one anchor for a day. Then research what's near it: food, parks, bookstores, weird things, practical things, places you'd be delighted to stumble across.
Save the possibilities. Resist the urge to schedule them.
Then ask: What is today's anchor and what can remain flexible?
See It In Action
The No Place Like Anywhere planning system isn't just theory, it’s quite literally how we plan every single trip, staycation, and family getaway without losing our minds. See how Step Five works in the real world below.
One day in Paris began with my son’s second-highest priority: the sewer museum.
He was five years old and totally obsessed with pipes. So obviously we were going to tour les égouts de Paris.
After the museum, we meandered toward the Eiffel Tower, sat at a café, chased pigeons, wandered through the Latin Quarter, ate crêpes, rested near Notre Dame while somebody played accordion, stumbled onto a percussion group, eventually made our way to dinner, found a playground where the kid could burn off whatever energy remained, and the only part of the day that was “planned”? The starting point.
By the time we got home that night, we had walked nine miles and used the Métro a few times. Our feet hurt, our bellies were full, and we all went to bed happy.
It sounds exhausting when I type it all out, but nobody felt burned out because we weren’t racing between reservations. We stopped when we wanted, rested when we needed, followed whatever looked interesting.
We had a direction, not a rigid schedule. That’s intentional wandering.
It isn’t showing up somewhere without doing any research and hoping the universe entertains you.
Intentional wandering works best when you do enough research that you can make informed spontaneous decisions once you’re there.
The No Place Like Anywhere Planning System
I don't want to help you plan a so-called perfect trip. That sounds stressful as hell, tbh. I do want to help you create a travel experience worth the time, money, and energy you put into it!
While I often write about traveling as a family, the same approach works if you’re traveling solo, with a partner, with friends, with your parents, or with twelve people who all have different opinions about breakfast.
Let’s figure out what you actually want from this experience. Then we can build around that.
The No Place Like Anywhere Planning System
I don't want to help you plan a so-called perfect trip. That sounds stressful as hell, tbh. I do want to help you create a travel experience worth the time, money, and energy you put into it!
While I often write about traveling as a family, the same approach works if you’re traveling solo, with a partner, with friends, with your parents, or with twelve people who all have different opinions about breakfast.
Let’s figure out what you actually want from this experience. Then we can build around that.