3 Things I’ve Learned from Planning Long, Multi-City Road Trips

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Have you ever found yourself staring at a sprawling map, plotting out an epic road trip that spans multiple cities and states? As exhilarating as the journey can be, planning it can sometimes feel like solving a Rubik’s cube while juggling five flaming torches. Trust me, you’re not alone in this! Planning long, multi-city road trips has been an ongoing saga for me and my hubby over the years, and I’ve picked up a few valuable lessons along the way. Buckle up; we’re about to embark on a tour of practical road trip wisdom.

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1. Plan for Things to Go Wrong… Because THEY WILL

Let’s be real: if Murphy’s Law had a vacation home, it would reside smack dab in the middle of your meticulously planned road trip itinerary. No matter how carefully you plan, something will inevitably go awry. And that’s okay!

I remember the time when Hubby and I had a streak of disastrous luck where our outbound flights were canceled on not one, not two, but three consecutive trips. Denver to Rapid City? Canceled. Charlotte to Denver? Canceled. Baltimore to Las Vegas? You guessed it—canceled. The cherry on top was an aborted trip to South Dakota where things were so catastrophically messed up that we had to turn around and fly back home. Determined not to be defeated, we attempted the trip again the following year, thinking that flying to Denver and then driving to Rapid City would be foolproof. Spoiler alert: it wasn’t.

The South Dakota Debacle

When that Denver flight was canceled too, after a bit of “I can’t believe this happened to us again!” I rolled up my sleeves and got to work. Fortunately, we were automatically rebooked for the next morning. Let’s just say we learned that having a backup plan for your backup plan is never a bad idea.

A few days later, just when we thought our luck had turned, our rental car developed a leak in the fuel intake tube. Picture us at a gas station in Gillette, Wyoming, watching our rental car leak gallons of fuel while Hubby was filling it up. Fun times! After more than 30 minutes of frantic phone calls, we found a replacement car at the airport in Casper, Wyoming. We were headed there for the night anyway, and as a silver lining, we got an upgrade. Huzzah!

Travel mishap	How we handled it
Outbound flight canceled	Rebooked for the next morning
Fuel leak in rental car	Found a replacement and got an upgrade
Multiple flight cancellations	Rerouted and adjusted itinerary

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2. Build Breathing Room Into Your Itinerary… And Then Add a Little More

I adore road trips, but let’s not sugarcoat it—they can be physically and mentally exhausting. Just thinking about all the logistics can sap your energy, making it feel like you’re constantly on the move even if you’re not.

The Myth of Constant Motion

When you’re the keeper of the itinerary, you’re perpetually tracking drive times, hotel check-ins, and how long you can dawdle at each stop without derailing the entire plan. It’s like being a general in a logistical war, armed only with Google Maps and gas station snacks. This is why you need to build flexibility into your itinerary—then add a little more for good measure.

Allow yourself some buffer time for rest, unexpected detours, and the inevitable hiccups that will crop up like weeds in your meticulously manicured garden of plans. Trust me, you won’t regret it.

Here’s a crisp, straightforward table to make you see the wisdom of adding more flexibility:

Situation	Without Breathing Room	With Breathing Room
Flat tire	Panic and potential delay	Small delay, but manageable
Unplanned detour	Stress about getting back on schedule	Enjoy the detour without time pressure
Traffic jam	Major stress and rescheduling required	Frustration minimized with buffer time

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3. Do and See All the Things You Want

Now, I know what you’re thinking: didn’t you just advise slowing down and giving yourself some leeway? Yes, I did. But here’s where the paradox kicks in: the moments I regret most in our trips are usually the ones where I decided NOT to make that extra stop or see that additional site. Confounding, right?

Saying “YES” to Adventure

When you’re on the road and you find yourself teetering on the edge of a spontaneous decision—should we make that extra stop? Visit that quirky roadside attraction? Chase that waterfall?—just say YES.

I’ve never once regretted sacrificing an hour of sleep to see a breathtaking sunset, an awe-inspiring waterfall, or to savor an extra scoop of gelato on an evening stroll. On the contrary, these are often the highlights of our trips. So, when I’m on the road and face that tiny internal debate, I steer myself toward embracing the moment.

But, and this is a crucial but, if all your heart desires is to collapse on the hotel bed with takeout, while binging your favorite show, that’s perfectly fine too. Balance is key!

Decision	Regret Level	Satisfaction Level
Skip extra site for sleep	High	Low
Make extra stop for memory	Low	High
Early night in for rest	Low	High

3 Things I’ve Learned from Planning Long, Multi-City Road Trips

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