When to Plan and When to Let Go

I am a planner. While I’m pretty good at rolling with the punches should the plan fail, I still always have to have that plan in place. It’s one of the few traits my boyfriend and I don’t share.

When we were first dating and I started sharing my travel plans with Jo, I remember at one point he commented on how intense my planning was. If he were ever to take off and travel the world, he said, he would be more likely to throw some stuff in a bag, go to the airport, and just pick a flight at random.

Fortunately, when we travel together, our two extremes balance each other out.

Our Labor Day weekend in West Virginia was approached with minimal planning. We had a rough outline for the weekend: visit his parents at their cabin near Lewisburg, drive up to Harpers Ferry the next day, and return home through northern Virginia wine country. The rest – including where we’d sleep – was up in the air.

Entering Dolly Sods

Had we planned our trip more strictly, we might never have wound up in the Dolly Sods Wilderness – a chunk of Arctic tundra left in the middle of West Virginia from the last Ice Age.

There were a few wrong turns along the way. Our biggest mistake turned out to be trusting Google. For whatever reason, the route it calculated to get us from Lewisburg to Elkins took us along all these tiny, pig path, one lane roads where nobody would want to risk breaking down. We spent far longer than we should have looking for any hotel, let alone a decent one.

The next day, we had several options for a day hike midway between our hotel and Harpers Ferry. We decided to aim for the Cranberry Wilderness, but later realized we had been following directions to the wrong address and passed our destination by about two hours. But having a loose plan served us well there. We saw that a couple other hikes we had considered taking were nearby, so we went to Seneca Rocks and Dolly Sods instead.

It was my first experience not planning a trip down to the minute, and while there are places I think a little extra planning would have served us well, it was overall a great experience and made me feel a lot more comfortable with my long-term travel skills.

In many ways, travel is like cooking. If you know basic techniques, you don’t really need a recipe.

Likewise, in travel, I don’t have to book accommodations in advance and I don’t have to know exactly where the day will take me. I just need plenty of research in my back pocket and the skills to plan on the fly.


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