Somewhere outside of Barstow, my girlfriend Kate and I had our first real road trip fight.
It was over a gas station burrito.
Yes, really.
I’d been driving for four hours, she was starving, and I kept saying “just one more exit.”
By the time I pulled off, neither of us was speaking.
And honestly, I felt kind of ridiculous.
Because the road was gorgeous, the sky was huge, and we were being petty over lunch.
That day taught me something.
A great trip with your person isn’t about the destination alone.
It’s about how you treat each other when the miles get long.
So here’s everything I’ve learned the hard way.
Talk Before You Pack a Single Bag
The best thing I ever did for a trip happened at my kitchen table, with coffee.
Kate and I sat down and asked each other what we wanted from the week.
I wanted open road and zero schedule.
She wanted a few real dinners and at least one morning to sleep in.
Neither of us was wrong, but we’d never said it out loud.
So now I always ask three questions before any trip.
What’s one thing you absolutely want to do?
What’s one thing you’d happily skip?
And what’s going to stress you out?
That last one is sneaky good.
It’s kind of like clearing the weeds before you plant anything.
Pacific Coast Highway for the Romantics
If you want a road trip that does the romance for you, drive the Pacific Coast Highway.
I love it so much it’s almost embarrassing.
The road hugs the cliffs, the Pacific is this deep steel blue, and the air smells like salt and eucalyptus.
Kate rolled her window down near Big Sur and just laughed for no reason.
I’d go in spring, when the hills are still green.
Stay a night in Cambria or Carmel instead of rushing through.
And pull over at every turnout you can.
Seriously, every one.
Some of our best moments were at a gravel pull-off, sharing a thermos and watching waves hammer the rocks.
Blue Ridge Parkway When the Leaves Turn
Fall on the Blue Ridge Parkway is my favorite kind of slow.
The speed limit tops out around forty-five, so there’s no point in being in a hurry.
The mountains go copper and gold, and the morning fog sits in the valleys like spilled milk.
Kate and I rented a little cabin near Asheville with a porch and two mismatched rocking chairs.
We drank cider, played cards, and barely checked our phones.
If you only have a long weekend, this is the one I’d pick.
Book your lodging early, because leaf season fills up fast.
And bring a warm layer for the evenings, since the temperature drops quicker than you’d think.
It’s cozy in a way that’s hard to fake.
🗼 I Wrote a Book About My Japan Travel Catastrophes!
Before I landed in Tokyo, I thought I was the “Final Boss” of international travel. Spoiler alert: I WASN’T. 😅
🚅 I boarded the wrong Shinkansen and ended up in THE WRONG CITY. I confused locals with my “expert” bowing that was more awkward than accurate. I accidentally stumbled into a high-stakes Kendo practice thinking it was a tourist show. Sound like something you’d do?
“Things I Wish I Knew Before Going to Japan” is your shortcut to avoiding ALL my cringe-worthy mistakes. ✨ Inside, you’ll find practical, LIFE-SAVING tips on etiquette, transport, money, and hidden gems that will save you time, money, and a whole lot of confusion.
Utah’s Red Rock Country for Adventurous Pairs
If your partner likes a little dust on their boots, point the car toward southern Utah.
Moab, Zion, Bryce, Capitol Reef, all within a reasonable drive of each other.
The first time I saw Delicate Arch at sunset, the whole rock glowed like it was lit from inside.
Kate grabbed my hand and neither of us said a word.
That’s the thing about big landscapes.
They make you quiet, and being quiet together is underrated.
Start hikes early, because the desert heat is no joke.
Carry way more water than you think you need.
And pick one or two big hikes instead of cramming in five, because sore legs make for short tempers.
Maine’s Coast for the Slow Travelers
Maine is where I go when I want to exhale.
Drive up Route 1 and let yourself wander through the little harbor towns.
I’m kind of obsessed with the smell of the docks in the morning, all salt, rope, and fresh coffee.
Kate and I split a lobster roll on a picnic table in Camden, and I swear it ruined all other lobster rolls for me.
Rent a cottage if you can, even for two nights.
There’s something about a kitchen with a window facing the water that makes you want to cook together.
Pack a rain jacket, because the weather changes its mind a lot.
But honestly, a foggy day with a hot drink and a good book is half the reason to go.
Route 66 for the Nostalgia Lovers
Route 66 is part history lesson, part scavenger hunt, and totally worth it.
You won’t drive the whole thing, and you don’t have to.
Pick a stretch, like Arizona into New Mexico, and just soak it in.
We stopped at a retro diner outside Seligman where the milkshakes came in those tall metal cups with extra left in the canister.
Kate still talks about that milkshake.
The neon signs, the old motels, the quirky roadside oddities make it feel like a movie.
My advice is to leave room in your schedule for random stops.
Some of the best memories on that road were things we never planned.
And keep a little cash handy, because a few of the smaller spots still don’t take cards.
Sit Down and Talk Money Early
Money is the quiet troublemaker on almost every couple’s trip.
I learned this after a trip where I booked a fancy dinner without asking.
Kate smiled, but I could tell she was doing math in her head the whole meal.
So now we set a rough daily budget before we leave.
We decide what’s worth splurging on, and what we’ll gladly skip.
For us, great views and good food are worth it, while fancy hotels are not.
Figure out your version.
And if one of you earns more or has less wiggle room, talk about it kindly and honestly.
It’s a lot easier to be generous when nobody feels cornered.
Give Each of You a Real Job
Every road trip needs a driver and a navigator, and the roles matter more than you’d think.
I used to hog the wheel because I’m a control freak, I’ll admit it.
Kate finally told me she felt like luggage.
Oof.
Now we trade off every couple hours, and the passenger runs the music, the snacks, and the directions.
It sounds small, but it keeps things fair.
If one of you hates driving at night, the other takes the dark stretches.
If one of you gets carsick reading maps, switch jobs.
Being a team means both people feel useful, not just along for the ride.
Don’t Overpack Your Days
My biggest mistake early on was trying to see everything.
I’d plan six stops in a day and then get cranky when we ran behind.
Now I follow a simple rule: one big thing per day.
Maybe it’s a hike, a town, or a sunset spot.
Everything else is a bonus.
That leaves space for naps, long lunches, and wrong turns that turn out to be the best part.
If I had a trip coming up this weekend, this is what I’d do first.
I’d cut my list in half, then cut it again.
You’ll remember the feeling of the trip way longer than the checklist.
