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Serendipitous Travel

Skip the online research. The best travel experiences are almost always unplanned.

By Marie Sherlock

In the spring of 2014, my husband and I were in Italy for my Turning 60 European Adventure. We'd just toured the Basilica of St. Francis in Assisi and were strolling the streets of this beautiful hill town when we encountered a couple dozen older men, all decked out in white, and sporting enormous balloons on their heads.

Small boats decorated with flowers. Next Avenue
Combat Naval Fleuri (Naval Battle of the Flowers) in Villefranche-sur-Mer, France  |  Credit: Marie Sherlock

Weird got weirder: They were accompanied by three white convertible sports cars and a couple of loudspeakers, blaring the themes to "Star Wars" and "2001: A Space Odyssey." They eventually marched down the street, in a parade of sorts, as I stood slack-jawed — and completely mesmerized.

It's those unexpected, wholly serendipitous, out-of-the blue experiences that make travel truly magical.

I will always consider this encounter to be among my most memorable travel memories, just as I will always wonder what the heck those guys were doing that day in Assisi.

We plan our trips, sometimes ad nauseum, so that we don't miss any must-see-bucket-list destinations. But it's those unexpected, wholly serendipitous, out-of-the-blue experiences that make travel truly magical. And make for the very best travel stories — a huge perk.

Here are some tips for ensuring that your travel adventures contain as much serendipity as possible.

Keep Your Schedule Open

Serendipity is "something interesting or pleasant happening by chance." (Italics mine.) So, by definition, you can't plan for serendipitous events. Oxymoron, right? But you can cultivate the kind of openness needed for those fortuitous travel moments to occur.

Because magic needs oxygen. So, as much as possible, leave your travel plans flexible. Plan, by not planning.

Take those White Balloon Head Guys. That day in Assisi, the sight-seeing portion of our day had (ironically) ended. Our "plan" was to relax and enjoy Assisi. In any event, we could not have scheduled this particular phenomenon because here was nothing online that gave us even a hint as to what was going on.

A group of people with balloon-like hats. Next Avenue
"Balloon Head Guys" in Assisi  |  Credit: Marie Sherlock

Keep Your Mind Open

Along with that open schedule, pack an open mind. By doing so, you've made the decision to be a traveler versus a tourist.

"When you travel, always go with an open and curious mind."

What's the difference? For the most part, tourists stick to sightseeing, tour groups and bucket lists. Think "if it's Tuesday, this must be Belgium." The goal of travelers is learning about the world and its people. Think of philosopher Ralph Waldo Emerson: "Life is a journey, not a destination."

"When you travel, always go with an open and curious mind," says Janet Hanpeter, a San Diego globe trotter with 87 countries under her belt who publishes the blog Planet Janet. "That's what travel is all about — a fascinating cultural exchange."

An added perk: Travelers often end up spending far less money on their journeys than tourists. Staying in smaller towns, eschewing the spendy tours, eating at authentic, hole-in-the-wall restaurants. A win-win!


Wander. Explore. Go a Little Marco Polo!

With your open schedule — and mind — it's time to do some exploring.

Ali King, of Portland, Oregon, has visited six continents and crossed countless items off her bucket list. Still, she says, "the very best part of travel is when you walk the backstreets, just meander and people-watch."

Don't Google the daylights out of every possibility — which is, truly, the antithesis to exploring.

She and her daughter were roaming around San Miguel de Allende, Mexico when they came across a wedding callejoneada: a dancing and singing procession that ushers guests from the ceremony to the reception. They gazed in awe as the revelers, along with enormous "bride and groom puppets" (called mojigangas) and a mariachi band, weaved their way through the narrow streets.

Give yourself permission to wander. Don't Google the daylights out of every possibility — which is, truly, the antithesis to exploring. There's something about happening upon an event — the thrill of "discovering" it for yourself — that adds to the magic.

A group of people celebrating in the street. Next Avenue
Wedding in San Miguel de Allende, Mexico   |  Credit: Marie Sherlock

"Your chances of experiencing serendipity are greatly increased when you're open and receptive and firmly in your explorer mode," agrees Hanpeter.

Consider Solo Travel

In 1982, I went on a month-long tour of Europe with a group of young people from Australia. Who, in their 20s, wouldn't want to hang out with a busload of fun-loving Aussies for four weeks? It was a blast! Still, I can't recall a single serendipitous travel event during that entire month.

But on a solo backpacking trip around Ireland in 1983, the stars were smiling down on me.

I arrived in Galway schlepping my huge backpack and looking (I'm pretty certain) lost. A trio of locals walked up to me and one fella asked, in that beguiling Irish lilt, "Would you be looking for a place to stay then?"

If solo travel is no longer in the cards for you, "find opportunities to break away from the group and wander on your own."

Turned out that Seamus O'Flaherty owned a B&B. He, Mickey MacNamara and Mary Kelley (I am NOT making these names up) became my fast friends for the next three days. We went to pubs, watched Irish TV together, and hiked out to the coastal burg of Salthill, "to see the sun go down on Galway Bay."

If solo travel is no longer in the cards for you, "find opportunities to break away from the group and wander on your own," says Hanpeter. She was doing just that in Antalya, Turkey when she happened upon four older men sitting at a sidewalk cafe. Hanpeter's openness and smile were enough for this gregarious group to invite her to sit and have coffee, oranges and pomegranates with them.

"I made some Turkish friends and was blessed with another priceless travel experience," she says.

Embrace the Bumps on the (Literal and Figurative) Road

Stuff happens when you're traveling. Mishaps can derail your best-laid plans, from lost luggage to sprained ankles to horrific weather. A trip to Provence began inauspiciously when my husband and I arrived in Nice to a downpour of biblical proportions. It was no fun lugging our baggage from the airport to Villefranche-sur-Mer, our ultimate destination.

As it turned out, that wildly inclement weather led to the postponement of an annual event — Combat Naval Fleuri (Naval Battle of the Flowers). It was scheduled for earlier that day; we would have totally missed it. Two days later we were rewarded with a perfect Mediterranean day and a quirky tradition of boats, festooned with flowers, circling the Villefranche-sur-Mer harbor.

I didn't Google this event and assumed it commemorated some historic maritime skirmish. How wrong I was. The "battle" part occurs when folks on the boats toss flowers to those on the dock and then the spectators lob the flowers back at the boats. Hundreds of carnations and mimosas arced back and forth. Crazy, travel bliss!

Reach Out and Touch Someone

Many, if not most, great travel memories have to do with the people we meet. To maximize your chances of connecting with locals, you need to do those things that locals do: hang out in town squares, frequent off-the-beaten-path cafes, speak their language (learn some foreign phrases), roam the backstreets.

And take the bus.

On that same Irish backpacking trip, I was on my way (by bus) to Cork when an older woman sat next to me. Bridget Fitzgerald and I ended up talking for the next hour. When we arrived at her stop —the small town of Cahir — she asked the bus driver to wait (she may actually have told him to wait; they were on a first name basis) while she bought me "tea."

And he did. He and a couple dozen passengers cooled their heels while this lovely Irish woman bought me a sandwich at a little cafe nearby.

Forty years later and I've forgotten what the Blarney Stone and the Book of Kells looked like but I still remember Bridget Fitzgerald, her kindness, and how she got an entire busload of people to sit tight while she bought me lunch.

The essential truth revealed by that serendipitous encounter — that people are good the world over — is the most important lesson I've learned from traveling.

Marie Sherlock
Marie Sherlock practiced law for a decade before turning to writing and editing in her 30s — and never looked back. She's worked as the editor of several publications and is the author of a parenting book (Living Simply with Children; Three Rivers Press). She spends her empty-nest days writing about travel trends and destinations, simplicity, spirituality and social justice issues. Read More
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