
I hate flying.
There’s just something utterly unnatural about crowding into a pressurized cylinder with wings, blasting into the sky, hurtling over 500 mph at 36,000 feet, and pretending to relax in cramped quarters for hours on end.
It may be the safest way to travel, but then, when your car breaks down you can pull over. Engine trouble at 36,000 feet presents few options other than dropping.
Of course, air travel offers other charms before you even take off. Long lines, screaming kids, security and customs headaches, canceled flights, bad weather, lost luggage, and time zone exhaustion.
But there’s no sense whining.
My wife loves to travel, so despite my aerophobia and monastic, homebound predisposition, I pack a bag and follow her lead. She’s an experienced traveler who handles all the details, so I have no excuse but to get on the plane and deal with it.
Truth be told, once the plane lands, I thoroughly enjoy the places we visit. And interestingly, the greatest joys are often not found in the celebrated tourist locales.
The best experiences are the unexpected ones, off the beaten path.
Disappointment inevitably ensues
There was an article that caught my eye in the Wall Street Journal by travel writer Sebastian Modak titled, “Shred Your Bucket List: Why ‘Must-Do’ Travel Plans Are Ruining Your Vacations.”
In the article, Modak reminds us that the term “bucket list” was popularized by a 2007 film starring Morgan Freeman and Jack Nicholson. Faced with cancer diagnoses, both men decide to travel the world and see everything on their bucket list before time finally catches them.
Modak notes:
Surprising no one, the travel industry quickly turned the concept into a way to sell vacations and make people feel like more-humble travel pursuits—a camping trip in a local state park, a repeat visit to a city you love—were somehow lesser.
Seems these days, if you haven’t been to Paris, experienced the Northern Lights, walked the Wall of China, kissed the Blarney Stone, and visited a host of other approved bucket-list destinations, you are pitied as a sad, provincial soul.
Some people talk about their vacations like it’s a game of one-upmanship, or a competition. “Hawaii? Oh no, dear, you must visit Milan.”
It’s all a bunch of poppycock.
Some of the best experiences my wife and I had took place in seemingly unremarkable places, at home and abroad. Once, during a multi-state road trip, we ended up in a remote motel fifteen feet from a railroad track.
We bought a cheap bottle of wine with some crackers and cheese and sat in rockers on the porch outside our room. Across from us was a rough-looking but friendly biker couple, sitting in chairs outside their motel room.
We struck up a conversation.
They pointed out an old pickup truck in the parking lot, with a broken down three-wheel motorcycle in the bed. The biker dude, smiling with a missing tooth, said, “We broke down in Alaska on the trike. Cost too much to fix or ship home, so we bought that old truck for a thousand bucks to take the trike home. It’s been a helluva trip!”
We spent the next hour swapping stories, talking about life and travel, and laughing. Our road trip would later take us to many bucket list destinations, like Mount Rushmore, yet the evening spent in that dusty old motel with the biker couple is more memorable to me.
Modak points out in his Wall Street Journal article:
When hype builds a place up in your mind to epic, life-defining levels, disappointment inevitably ensues. I’ve come across dozens of stories of deflated travelers (Chichén Itzá? ‘Too many vendors.’ Niagara Falls? ‘Pointless.’) These tales speak not of bad destinations but false expectations.
My wife and I experienced this last year during a trip to Italy.
No doubt, Tuscany is lovely, and we visited endless towns and must-see sights like the Leaning Tower of Pisa (it’s exhausting to climb up) and Michelangelo’s David at the Accademia Gallery of Florence. But overall, we were a bit underwhelmed.
The tourist sites are crowded, commercialized, overpriced, and stressful to get to. We often found ourselves ambling down backstreets to quiet cafes where we could relax, interact with the proprietors, and get a more realistic sense of everyday Italian life.
My favorite experience was when we visited a hidden-away sculptor’s studio in the town of Volterra. The sculptor invited us in, and we got to explore his studio and watch him work with alabaster.

Sculptor in Volterra. Photo: John P. Weiss
Michelangelo’s David was stunning, and I’m glad I saw it. But I have much fonder memories of the little sculptor’s studio, off the beaten path, in a back alley of Volterra.
The places in between, the ones not found on bucket lists and tour programs, often hold more authenticity and magic.
The places in between
In 2022 my wife and I took a trip to Scotland.
We booked with a well-regarded, small tour group consisting of only twelve people plus our two guides. It was a whirlwind trip and we saw amazing sites and events like the annual military tattoo in Edinburgh.
Other sites included the Falkirk Wheel, numerous castles, the Jacobite Steam Train (of Harry Potter fame), a Highlands tour, the magnificent Kelpies, and more.

The mythical Kelpies in Helix Park, Scotland. Photo: John P. Weiss
Yet it was the little known haunts and experiences off the beaten path that were the most memorable to me. For example, one day we landed in the town of Oban and were set loose for a few hours of shopping.
My wife ran off exploring with another woman in our group, and I set out with my rangefinder camera for some local street photography. I grabbed a coffee and sat down next to a wonderful woman and her dog.

Woman and dog in Oban, Scotland. Photo: John P. Weiss
“Is the Fanta for you or the dog?” I said with a smile.
“Oh, now don’t be silly, young man. It’s for both of us,” she said with a twinkle in her eye.
We chatted for nearly a half-hour and I learned that she moved to Oban many years ago from Ireland. I shared that my grandmother was born and raised in County Kerry, Ireland. She told me how much she loved Oban, which is why she settled in the town.
The sun was shining, the air was fresh, and the conversation was lovely. Unhurried and true. I asked if I could take their picture, and she said, “Only if you focus on the dog.”
Despite all the notable places I experienced in Scotland, this friendly and completely random exchange with a local woman was particularly memorable and special to me. Maybe because, unlike tour guides and their canned speeches, this chat with a local in downtown Oban was devoid of any contrivance or agenda.
I got to see what it felt like to be a local.
When you have no expectations, reality has an easier time impressing you. — Sebastian Modak, Travel Writer
This is what I mean about “the places in-between.” There’s nothing wrong with seeing the tourist sites, but some of the real magic of travel is found in the little moments and unremarkable places.
I think the best memories come from experiences where time slows down. Where we, and the others we’re interacting with, can just be ourselves and enjoy the moment in all its honesty and truth.
Hurtling ourselves into the unknown, again and again
At the end of our Scottish tour, we got to spend three days aboard a lovely mini-cruise ship called the Glen Etive.
We floated down scenic lochs and occasionally boarded a small tender to visit sites like the Isle of Jura and the Jura Distillery. Up until then, the trip was often hectic, as we crammed into vans and raced all over to castles and tea rooms and historic sites.
We saw a lot, but we were also exhausted.
The three-day cruise aboard the Glen Etive (refer video below) was one of our favorite aspects of the trip. It’s not something you’d normally find on a bucket list of Scottish must-see experiences, which proves the point of the Wall Street Journal article.
As Sebastian Modak wrote in his article:
For some, visits to iconic spots may help to define a life well-lived. But for others, it will be the unexpected moments too nuanced to make a top-ten list. And the only way we find those, I’m afraid, is hurtling ourselves into the unknown, again and again.
If you want to find a bit of serendipity, head off the beaten path and look for the places less traveled.
They’re often not a bucket list item. Sometimes they’re just a park bench next to a talkative, Italian pensioner. Or an obscure artist’s studio blocks away from the main attractions and street vendors.
The point is, take everyone’s recommendations with a grain of salt.
What excites someone else may bore you. Better to chart your own course, explore the path less taken, and be sure to bring your camera.
Because you never know what you’ll find exploring those in-between places.
Before you go

I’m John P. Weiss. I write elegant stories and essays about life. Often illustrated with my photography and artwork. For the latest, check out my free Saturday Letters here.
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This post was previously published on Medium.com.
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Main image credit: My wife (left) with fellow travel aboard the Glen Etive in Scotland. (John P. Weiss)




