Road Trip Planning: The Dangers of Over-Planning

I’ve been a planning addict since I was a child. One of my favorite childhood games was to plan out my entire adulthood – from where I would live to who I would be: a famous writer with a gorgeous mansion overlooking the ocean. My friends and I would take turns spinning a globe I had in my bedroom and holding our fingers over it. Wherever our fingers ended up point would be the start of a long plan as to whether we’d travel there, or we’d marry someone from there, or if we’d live there.

So – it’s not surprising I grew up to be such a planner that I over-plan! Well, at least I used to – I’m better now thanks to some help from friends and boyfriends along the way.

Do you over-plan, too? Ever catch yourself getting carried away and planning every moment of your road trip or any other vacation? Why does it matter? Isn’t it great to have it all worked out before you go?

Yes and no. It’s great to be organized enough to ensure your road trip is fun. If you don’t plan much you’ll be very likely to end up spending your whole vacation dealing with problems – not being able to find a hotel room, your car breaking down, getting lost. Plus, by planning your road trip, you can find out all about fun things to do both along the way and at your destination and do them!

But, if you over-plan you run into a number of problems. One of the biggest problems is that you miss the amazing magic of serendipity. You’ve got every second planned, so you’re rushing to the next item on your checklist, missing every cool serendipitous thing that pops up along the way.

The Story of the Road to Hana
When my husband and I traveled the Road to Hana in Maui, we gave it an entire day just to get to Hana, so we could soak it all in. We’d stay overnight in Hana and then return the next day. The Road to Hana is an extremely winding and very tight two-lane road more appropriate for smaller cars, which were common when it was built (compared to the SUV’s of today).

As we drove to Hana, we wondered how anyone could go all the way to Hana and back in one day and live to tell the tale. It was a hair-raising experience with tons of blind curves. Trucks and SUV’s came speeding around these blind curves heading right at you – you had to honk your horn so they’d know you were there! Nevertheless, this crazy drive was recommended as a one-day excursion in practically every guidebook I read (read my article about travel guidebooks to help avoid getting burned).

We had a great time as we could stop at every beautiful waterfall, beach and overlook to enjoy the views. All-day, we watched people flying by, trying to get to Hana and back in one day, missing everything. They flew by while we climbed up to see the twin falls and they flew by when we stopped at a cute little shop to buy snacks. They flew by while we watched surfers on a beach and they flew by while we explored an old church. They missed it all – especially the driver as the driver can’t look at anything but the road unless he or she wants to crash!

Every road trip can be like the Road to Hana – exploring everything and enjoying every minute, or a white-knuckled race to the next thing. Slowing down and not planning too much into your vacation can allow for serendipity to work its magic.

Road Trip Planning

Watch Out for the Drill Sergeant!
Another problem with over-planning is you become a bit like a drill sergeant – “Let’s go, move it on out! Next item to do: have fun! Hurry up, will you?” It reminds me of Clark Griswold in National Lampoon’s Vacation – especially when he says, “Well, I’ll tell you something. This is no longer a vacation. It’s a quest. It’s a quest for fun. I’m going to have fun and you’re going to have fun.” He says this right before he breaks into Wally World and holds the security guard hostage.

It’s a real danger of being a control freak – going off the deep end! Obviously, Vacation is a parody, but most people agree it’s pretty realistic on some levels. You just can’t control everything and when you try to, you just become overbearing and desperate.

Disappointment is another problem with over-planning. I can promise you that you will be disappointed in your road trip if you over-plan everything down to the minute. All that obsessing means that nothing will satisfy your hopes! You’ve built it up in your mind and made that vacation more like heaven than something that could happen here on Earth.

What to Do?
The very best way to approach planning your road trip is to plan things, but leave nice buffers of time in every day to just enjoy, soak up every moment, and stay open to serendipity that might lead you to some sight you’ve never heard of but turns out to be the best of the trip or some restaurant that has the most delicious food you’ve ever eaten (and wasn’t in the guidebook). A gentle balance is key to your very best vacation – let serendipity happen!

Leave a Comment