The 'Things Will Go Wrong' Guide to Family Vacation Planning (And Why That's Totally OK!)
- Heather
- May 12
- 3 min read
You know that moment when you're staring at your vacation planning checklist, feeling overwhelmed by all the "perfect family vacation" advice out there? Let me tell you a secret: even the most organized moms have vacation mishaps. I speak from experience—I once had to buy a car during our vacation because our original car broke down and after two failed repair attempts we ran out of options! And that's exactly why I'm here.
What if I told you that planning for things to go wrong is actually the key to a more relaxing family vacation? Stick with me, because I'm about to show you how embracing the chaos can lead to your most memorable family adventures yet.
The Reality of Family Vacation Planning (And Why Perfect Isn't the Goal)
Let's be honest: family vacations rarely go exactly as planned. Someone gets a cold, the weather doesn't cooperate, or your perfectly researched restaurant is mysteriously closed. But here's the good news: these "mishaps" often become your favorite family stories!
Why Traditional Vacation Planning Advice Falls Short
It assumes everything will go according to plan (when does that ever happen?)
It creates unnecessary pressure for perfection which means more stress for mom
It doesn't account for real-life family dynamics
Your Stress-Free Family Vacation Planning Blueprint
1. The "Everything's Fine" Planning Framework
Instead of trying to prevent everything from going wrong, we're going to plan for it!
Create a flexible daily schedule with built-in buffer time
Research backup activities for weather changes
Keep a list of nearby urgent care centers (just in case!)
Pack a "chaos kit" with essential problem-solvers
I even created a guide for this and it's free.
2. The Sanity-Saving Packing Strategy
Forget perfect packing - aim for "good enough" with these tips:
Pack outfits in gallon bags - perfect organization not required!
Create a "first day survival kit" that's easily accessible
Remember: most destinations have stores if you forget something
Use packing cubes to keep everyone's items separate and organized
Keep a family "laundry bag" for managing dirty clothes
3. Setting Realistic Expectations (With Everyone)
The secret to happy family travelers? Managing expectations:
Have a family meeting to discuss what could go wrong
Let kids contribute to the backup plan ideas
Agree on a family motto like "Adventure is never perfect!"
4. The Art of Schedule Flexibility
Make your plans elastic with these strategies:
Build in "buffer blocks" - 30-60 minute windows with no planned activities
Keep a running list of "anytime activities" that can fill unexpected gaps (Uno Splash is a great option. We always keep it in our truck for anytime.)
Create "swap slots" where activities can be easily exchanged
5. Make Travel Part of the Adventure
Transform travel time from tedious to terrific with our Road Trip Rescue Kit!
Turn car rides into story time with audiobooks or family storytelling
Play travel scavenger hunts from my printable Road Trip Games Pack
Pack screen-free activities like quiet individual games and puzzles
Try my tested car activities that keep kids engaged for hours:
Get your complete Road Trip Rescue Kit with dual scavenger hunts, would-you-rather games, and state challenges here: Road Trip Games Pack
When Things Go Wrong (Because They Will!)
Just remember, the goal isn't to prevent all problems - it's to handle them with grace and maybe even a laugh!
Your "Keep Calm" Action Plan:
Take a deep breath and remember: this will be a funny story later
Have a few "emergency joy" activities ready (card games, silly songs, etc.). Get it here.
Keep a running list of "vacation plot twists" to laugh about later
The Most Important Thing to Pack: Perspective
Here's the truth: your kids won't remember if everything went perfectly according to plan. They'll remember how you all handled the unexpected together, the laughs you shared, and the adventures you had - even if they weren't the ones you planned.
Pro Tip: Start a family tradition of sharing "favorite mishap moments" at the end of each vacation day. It helps everyone see the fun in the imperfect!
Ready to Embrace the Chaos?
Download my free "Perfectly Imperfect Vacation Planning Guide" which includes:
Flexible planning templates
Backup plan worksheets
The famous "chaos kit" packing list
"Emergency joy" activity ideas
Click here to get your free guide: Perfectly Imperfect Vacation Planning Guide
Remember: The best family vacations aren't the perfect ones - they're the ones where you all grow closer, even (or especially) when things go wrong!