Five Rules to Plan an Unreasonable Itinerary (Without Losing Your Mind)

So you want to take a movie-montage worthy trip with scenic views, museums, fun eats, and too many quirky stops to make sense? Here’s our How- To!

Our trips often include sunrise hikes, roadside attractions, national parks, weird museums, local restaurants, scenic overlooks, and enough miles to make Google Maps question our sanity. 

And somehow…it usually works.

Not because we’re lucky. Not because our kids are unusually patient. And definitely not because everything goes according to plan.
It works because we’ve learned a few rules that make overpacked itineraries surprisingly doable.

1. The Journey Deserves Equal Billing
Too many trips are built around a destination. We’re just as interested in everything between Point A and Point B.

Many times people plan the majority of their time and funds to be spent at the main destination- we don’t! Plan for some extra travel days so that you can soak in some extra experiences. I usually spend the same if not more time planning stops along the way as I do activities at our final destination- but more on that in Rule #3!

2. Find Your Non-Negotiable
Every trip has one thing that cannot be missed. Maybe it’s a hike, a restraint, a beach, an experience!
Figure out your non-negotiable first, everything else becomes flexible around it.

When weather changes, traffic happens, or kids melt down, you know exactly what you’re protecting—and what you can let go!

3. Plan the random

The best adventures are really happened on accident. While I love a good spontaneous stop at a quirky roadside attraction, to really have a experience pack trip takes a little bit of extra planning.

A quick Google search of the route that you’re taking or the small towns that you’re passing through can reveal a local restaurant that’s a must-see, a quirky museum, or even the world‘s biggest pistachio. I utilize Google and ChatGPT to help get some general suggestions and then I narrow them down based on proximity and what peaks are interest. I try to have at least one or two planned stops per travel day. 

4. Plan to not have a Plan

This might be the most important rule.

Have a backup. Actually…have three.

Know which stops are optional, which hikes can be shortened, what you’ll skip if you’re running behind.

A rigid itinerary breaks the moment something unexpected happens.

A flexible itinerary bends without ruining the trip.

So much of this is relaxing your mindset about travel, not everything has to be a MUST. Try to create a priority list for each day or section of your trip- then if weather happens or you end up finding a side trail that you really wanna hike, you can easily swap things around without feeling tied to a checklist of things that you have to do that day. 

5. Don’t focus too much on where you are staying.

This might be the thing that most will disagree on. 

We don’t travel to spend all day at the campground or hotel so we don’t invest a lot of funds into this aspect.

As long as it’s clean, safe, and comfortable enough to recharge, we’re happy. The campground/hotel is home base—not the destination. Our kids love a pool or hotel breakfast as much as the next so occasionally we will spring on something a little fun, but we typically are a little bit more reserved on our lodging.

So…Why Are We Like This?
Because life is short.
Because there are too many beautiful places to see and too many stories waiting just off the highway.
Because we’d rather come home tired than wondering what we missed.
Our itineraries might look unreasonable on paper, but they’re built around what matters most to us: shared experiences, unexpected adventures, and memories our kids will talk about long after they’ve forgotten where we slept.


So go ahead. Add the extra stop.

Take the scenic route.

Pull over for the world’s biggest ball of twine or that tiny diner with five-star pie.


Your itinerary might be unreasonable.
But your memories will be unforgettable.

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