I am a recovering over-planner. My natural habitat is a color-coded spreadsheet. In the past, my summer vacation plans looked less like a relaxing getaway and more like a military operation. Every restaurant was researched, every scenic overlook was scheduled, and every hour was accounted for. I believed, with every fiber of my Type-A being, that a perfect plan was the only path to a perfect trip.
Last summer, I learned just how gloriously wrong I was.
My partner and I had crafted what I considered the magnum opus of itineraries: a two-week road trip along the stunning Oregon coast. I had a binder. Yes, a physical binder in the 21st century. It contained tide charts for optimal beachcombing, sunset times for golden-hour photos, and reservations at three of the coast’s most blogged-about seafood shacks. It was, in a word, airtight.
The first three days went exactly according to the binder. It was lovely. It was predictable. It was… fine. On day four, as we were cruising down Highway 101, smugly on schedule, we hit a wall of stopped traffic. A state trooper eventually ambled over to our car and delivered the news with a shrug: a major landslide ahead. The road would be closed for at least 48 hours.
Panic. My beautiful binder, my meticulously timed plan, my tide charts—they were all useless. My immediate instinct was to check my phone, frantically searching for a new route that would get us back on track with minimal time lost. But the detour was significant, pushing us hours inland into a part of the state I’d dismissed as “flyover country.”
My partner, a Zen master in a flannel shirt, simply said, “Well, what’s over there?”
Defeated, I zoomed in on the map. A small town called Pine Grove. No famous restaurants. No epic cliffs. According to a quick search, its main claim to fame was the “Annual Lumberjack & Lavender Festival,” which, impossibly, was happening that very weekend. It sounded utterly ridiculous. It sounded perfect.
With a deep breath that felt like letting go of a rope I didn’t know I was gripping, I turned the car east, leaving my precious plan in a cloud of dust.
Pine Grove was a revelation. We checked into a charming, slightly crooked motel that wasn’t on any travel blog. We ate the best burger of our lives at a diner where the waitress called us “hon.” And the Lumberjack & Lavender Festival? It was a surreal, hilarious mashup of burly men throwing axes and delicate stalls selling lavender soap. We spent the afternoon cheering on log-rollers and the evening sipping lavender-infused lemonade under strings of fairy lights, listening to a surprisingly good local folk band.
We discovered a hidden swimming hole recommended by the motel owner, a crystal-clear lake unmarked on any tourist map. We spent a whole day there, doing nothing but floating and talking. It was the most relaxed, most joyful I had felt in years. There was no schedule to keep, no photo to stage, no reservation to make. There was only the present moment, and it was magnificent.
When the highway reopened, we did eventually finish our coastal trip. But the highlight, the memory that still makes us both smile, wasn’t in the binder. It was the chaotic, unplanned, lavender-scented detour.
This summer, I’m approaching things differently. My binder has been ceremoniously recycled. If you’re a fellow planner looking to inject a little magic into your summer, here’s how I’m learning to leave room for serendipity:
- Build in a “Buffer Day.” For every three or four days you plan, leave one entirely blank. No reservations, no goals. Just wake up and see what the day offers. It’s planned spontaneity, an oxymoron that works.
- Embrace the “Ask a Local” Gambit. Ditch Yelp for an afternoon. Walk into a local coffee shop or bookstore and ask the person behind the counter for their single favorite thing to do in town. Then, go do it. No questions asked.
- The 50% Rule. Plan your morning, but leave the entire afternoon and evening to chance. This gives you the security of a starting point but the freedom to follow a whim, whether it’s an intriguing side road or an invitation to a backyard barbecue.
Letting go of control is scary, but it’s not the same as surrendering. It’s an invitation. It’s trusting that the best parts of life, and of summer, are often the ones you could never have planned.
Photo by Denise Jans on Unsplash