Wandering 2.0

In the early days, wandering was mostly a state of mind.

Endless days of summer spent in my top bunk overlooking the willow tree directly outside my childhood window. Fan aimed in my direction, book resting on my lap. Daydreaming the day away.

Later—wandering—was one of the ways that I knew Rob and I were just right. In the early days of dating we’d get in the car on Sundays and head somewhere. We’d choose a general direction, usually toward the water, but the other details were joyfully fuzzy. New cape towns, antique stores, road side diners, New England windy roads. It’s an awesome feeling when you find a fellow wanderer. 

Wandering took on a whole new meaning after kids. Preschool meant 2 hours of time—too little to accomplish much and too much to wish away, so we—Will and I— would set out for the unknown while his older brother tackled the alphabet. We’d visit parks, take walks, and discover hidden worlds in plain sight. 

One particular day “killing time” led us to an oddly named museum and a meaningful volunteer opportunity with a dotted line connection to the job I hold today.

The magic of wandering, for me, is that it’s an act of faith with no intended return on investment and yet strangely again and again it is how I get things done. How my insides refocus, reenergize, figure out “what’s next.”

Wandering is not for everyone. I remember declaring to a family member that I often would “pick a new exit” and go explore during those baby-in-tow preschool days. My kin examined me strangely. “That could be dangerous.” So could crossing the street, but I do that too, I thought.

Others spend their entire lives wandering—building careers around the freedom of the unexpected. I am not that person. I am driven by my to-do list, benchmarks that let me know where I am in relation to where I am hoping to go.

Wandering is exercise for my mind. A way to blow off accumulating mental steam. Wouldn’t want to do it all day every day but a healthy dose is needed to keep the cranial weight at bay.

Lately it’s been a mostly solitary activity. “We’re just going to drive around and see where we end up!” isn’t an appealing opener to two teens.


At the beginning of this summer we took a long awaited tropical vacation—the kind of vacation that necessitated planning to make the most of a place that we might not get back to for many "somedays." So we (my thirteen-year-old adventurer actually) plotted one planned activity and one eating destination per day for our twelve days away. 

A colleague of Rob’s suggested an app that would accompany us on our travels. I immediately protested. “I am not going to listen to some guy talk at us all day!”

But by day two or three of the “together time” I’d rosily imagined, I’d had enough of the bickering in the backseat.

”How about that app?” I suggested.

From that point on, the voice who we affectionately named Jason was our private tour guide, nudging us toward non conventional adventures.

“If you want to experience the most beautiful beach known to locals, turn right here!” Jason would say.

“By now you may have noticed that Kauai is full of chickens. Can you guess how many chickens there are to humans on the island?” (The answer is 5 to 1, by the way.)

He told stories about ancient Hawaiian tribes and warned us not to take any of the beach rock. “Each and every day people mail back the rocks they take from Hawaii because bad luck has fallen their way.”

We laughed. Surely he was kidding. 

But when we went to mail postcards, we asked the person behind the desk and she confirmed, “Yes, rocks routinely arrive in the mail addressed to the closest post office from where they were taken and we return them. It is very annoying.”

Jason led us to hidden waterfalls, scenic vistas, and an off-the-beaten path artisan town. He suggested a rope bridge where we dangled over a river and were rewarded by meeting a photographer in her studio on the other side. We heard stories of island settlers and the origins of trees that have been there for hundreds of years. 

We grew so accustomed to hearing his voice that when toward the end of our vacation we realized we’d made it all the way around the island and listened to all he had to say, a melancholy settled in.

We decided our final day on the island would be spent revisiting our favorite places. Amusingly most of the things we returned to originally were suggested by ”Jason.”

A travel app is different then spontaneously picking a new exit but its results were the same. The feeling of embracing an unplanned adventure, of taking the road less traveled.

The blessing of feeling recharged, refocused and appreciative that I am raising future wanderers. Even if the wandering is satellite guided.


Wherever you’re wandering this summer…enjoy!

P.S. Thank you, gypsyguide.com.

1 comment:

  1. Hi Holly! I am a co-worker of Rob's in the Atlanta office. He shared with me your blog and in reading the "wandering" post I am in love! I too am a wanderer and so is my husband. We love to just go where the road leads! I admit, I like to plan also, but Nathan has made me more open minded about wandering. "Let's just go until we get there" is our motto. We are taking a trip to Yellowstone this month and yes, we have planned it...somewhat. We've left open some time to just wander. I look forward to reading more of your blog! Mary Jane Cagle