3 things I’ve learned from planning long, multi-city road trips

When I get back from a trip, I spend a lot of time mulling over how I think it went and what I would do differently if I could take the trip all over again.

I just can’t help myself. I am what I am.

​Recently, Hubby and I have done a couple of major multi-week, multi-city road trips. Here are a few lessons I’ve learned from planning long, multi-city road trips.​

Woman sitting in the driver's seat of a car looking at a paper map.

1. Plan for things to go wrong…because THEY WILL

​Hubby and I had a run of pretty rotten luck during which we had outbound flights canceled on three consecutive trips: a flight from Denver to Rapid City, South Dakota; a flight from Charlotte to Denver; and a flight from Baltimore to Las Vegas.

During that attempted trip to South Dakota, things went so monumentally sideways that we ended up having to turn around and fly back home, completely canceling the trip. The next year we attempted the trip again, thinking we could avert disaster by flying to Denver and then driving to Rapid City.

​​No such luck. That flight was canceled too. Not even joking a little bit.

After a little bit of “I can’t believe this happened to us again!” I got to work. Fortunately, on that trip, we were automatically rebooked for the next morning. I did try to get us to Denver that day, but it didn’t work out. So, we adjusted our itinerary and flew to Denver early the next morning and everything went very smoothly (finally!).

But then a few days later our rental car developed a leak in the fuel intake tube, so at a gas station in Gillette, Wyoming, our rental car was making a large puddle of unleaded as Hubby was fueling up.​

That is not what you want.​

After more than 30 minutes on the phone with the rental car company, we located a replacement car at the airport in Casper, Wyoming. We were heading to Casper for the night anyway, so that worked out just fine. Plus we got a primo upgrade.​

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2. Build breathing room into your itinerary…and then add a little more​

While I love road trips, they can really wear me out. You can feel like you’re constantly on the move, without as much downtime as needed for your physical and mental health.​

Or sometimes, I think it can feel more like you are constantly on the move than you really are. If you’re the keeper of the itinerary, you have to think about drive times, hotel arrival times, etc., constantly keeping an eye on the clock to make sure you can get in everything you want to before heading to the next stop. That’s tiring.​

My advice is to adjust your itinerary, to build in the space you need for rest, longer drive times than anticipated, and other things possibly going wrong.

Because things will go wrong (see above).​

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3. Do and see all the things you want​

Now after reading the above point, I’m going to sound like I’m contradicting myself. (Very well then I contradict myself!)​

When all is said and done, the things I regret the most after a trip are the times I decided NOT to make that stop or see that extra site, or do that late activity.​

I’ve never regretted getting a little less sleep than I wanted so that I could see that extra waterfall, take that evening stroll over the cobblestones to get yet more gelato, or try to see the Milky Way in that national park.​

So when I’m on the road and I find myself asking myself “Should we?” I want the answer to be YES!

But if, on the other hand, what you really want is an early evening, lying on your hotel bed while eating takeout for dinner and watching your favorite show…then that’s great too.

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