The Road to Serendipity

Every travel tale needs a plot twist—a fluke, a folly, a fortunate turn that leads to new worlds. In 1754 Horace Walpole gave name to these happy accidents: He called them “serendipities,” a term derived from the ancient Persian name for Sri Lanka. To Arab traders, Serendip was an isle of enchantment. To modern travelers, serendipity is the one thing every trip needs—but that no one can plan. Maybe you can’t go out and find serendipity, but you can develop a mind-set that embraces daring, openness, and whimsy. Here are ten around-the-world ways to pack awe into your next trip.

1. Acquire a Talisman

Big sky, broad vistas, clean air, and solitude: I needed them all, so I flew to Arizona and set out on a solo road trip to the Four Corners. Giddy with new freedom and blasting Neil Young, I resisted dozens of photo ops before finally pulling over to a red rock-valley vista in the Painted Desert. A lone woman was selling handmade silver and stone jewelry—modest pieces, her own creations. We chatted; she was Navajo and from the region. I chose a small carved-green-stone turtle necklace and bought it, not knowing why. I wore it the entire trip. Nothing but happiness came my way. I kept it on for years, always remembering my road trip, the promise of new beginnings, and the woman who made my talisman.

Lesson: A perfect storm of impulse shopping and magical thinking? Not to me. The power of my talisman comes from positive feelings, personal engagement, and happy memories of a specific time and place.

2. Encounter a Mystic

It was a hot day in Hue, Vietnam. At the end of a dusty walk I bumped into a man in a nón lá (conical hat), a cigarette stuck to his lower lip. He asked me something—for money perhaps?—and I waved him away. I walked a few steps farther and he asked again. Something clicked. I stopped in my tracks. Did this man just ask if I’d like a poem? I turned around. He repeated: “Can I read you my poem?” From memory he recited “Mộng Vàng” (Gold Dream), first in Vietnamese and then in English. I was stunned—his poem was a lamentation on love and loss, an elegy to the river that feeds his town.

The boat of the moon carrying dream,

Sinking in the clear, quiet air.

Oh, the river of lights,

Lets gold dreams drift ...

We spoke haltingly and he told me about his life along Hue’s Perfume River. I thanked him, shook his hand, and gave him a bit of money. He smiled and gave me a copy of his poem—he wrote, “Have a good holiday. Many thanks, Hoài Lê Công”—and continued his way down the road. Was it all a dream?

Lesson: Be open—to people, to engagement, to whatever the road delivers. And listen to what’s happening around you. Enlightenment could be just around the corner.

3. Go Far to Find Home

Marriner’s Lookout is a grassy plateau that provides a spectacular view over Apollo Bay, a retro-cool surf town on Victoria’s Great Ocean Road, and into the swells of the Bass Strait. In the off-season cold winds scare away most sunset seekers, and I found myself blissfully alone here. Just as I started to walk down the hill, a couple headed up the trail. We all said hello and kept walking, but our accents caused us all to stop. In the haystack of travel we were three needles from Washington. We quickly discovered how much we had in common—we all lived in D.C., worked in media, loved to travel, and chose to end the day gazing at the sea. We headed off to dinner together, where Jack talked me into a kangaroo steak, I talked him into Prickly Moses Spotted Ale, and Mindy kept us in stitches. We would never have met back home—and yet there we were, breaking bread halfway around the world.

Lesson: Travel is full of surprises—one of which is having the chance to reflect on home. You may travel to the ends of the Earth and finally befriend someone from your own town.

4. Stay Home to Go Far

With one of the largest populations of Ghanaian Americans in the nation, Washington, D.C., is a cultural convergence point between. So when my friend Eric Ofori Asamoah invited me to an “outdooring” I thought, Why not? I like the outdoors. Turns out that the event is also known as a naming ceremony—it’s the first day a newborn is taken outdoors, given a name to mark its social identity, and welcomed into its ancestral community. For one night, an empty warehouse off the Beltway in Virginia was transformed into a village party near Kumasi, Ghana. Polyrhythmic music pounded, conversations in the Twi language soared, men in gold-embroidered robes and women in kente fabric and pastel-colored gowns made their rounds. Kids nibbled at mountains of cassava, plantain, and tilapia while old guys sipped Guinness and people of all ages danced. A village chief appeared, visiting from Ghana, and paraded through the masses under the shade of gilded parasols. We all partied until dawn and Eric said to me, “See? I knew you would like Ghana!”

Lesson: You don’t have to go very far to see the world.

5. Embrace the Distance

One day while lunching at the Serra Cafema safari camp in northern Namibia’s remote Kaokoland, I had the chance to observe a camp manager instructing a pair of trainees. The day’s lesson: filling glasses with ice and water. It seemed like a simple task until I saw the trainees fumble ice and spill water as if they were serving martinis on the Titanic—post-iceberg. The manager explained that the young employees were Himba women who had lived pastoral lives before entering a modern workforce. In the nomadic realm of the Himba, handling ice is a foreign practice, just as building a mud-and-mopane hut would prove impossible to me. Since ice has been noticeably absent in West Africa for thousands of years, it’s no surprise that these new hires need a how-to. Turns out the incongruous part of the picture was not the ice-cube training program—it was my own need to drink ice water in the Namib desert.

Lesson: No matter how far you’ve traveled to get somewhere, many of the locals have traveled even farther in their own way to show you hospitality.

6. Follow a Whim

When I visited New Orleans seven years ago, I wanted to check out 632 Elysian Fields, the fictive home of Stella and Stanley Kowalski in A Streetcar Named Desire. Like Blanche DuBois, I’ve always depended on the kindness of strangers and could not overcome my desire to knock on the screen door. An old man shuffled from the darkness and said hello. He knew why I was there: I was a pilgrim, like many before me. He’d lived in the faded white shotgun—which is nothing like the tenement in the play—for years and had weathered Hurricane Katrina there. A tide of gentrification was forcing him out, but he was equivocal. He would miss the odd visitors and his home’s mysterious allure. But in art as in life, “the show must go on,” he said.

Lesson: To paraphrase Blanche, sometimes you don’t want realism—you want magic! Follow your travel desires and who knows what memories you’ll make? By the way, the house’s current tenant is A Bicycle Named Desire, a bike rental company.

7. RSVP Yes

A few years ago my friend turned 70. He embraced it as a milestone and an opportunity to revisit a place he loved. His wife planned the party and issued the invitation. She promised that anyone who could get to Altaussee, a serene lakeside village in the Salzkammergut region of Austria, would have a room with a view and a time to remember. Who could say no? Then again, saying yes meant scheduling time away from work, clearing the calendar, buying an expensive ticket, finding a dog sitter, budgeting expenses, and—the hardest part—accepting that my summer vacation was determined by someone else ... And a senior citizen at that! I eventually said yes. The upshot: one of the best trips of my life, loaded with laughter, food, togetherness, and mountain air memories. The birthday was someone else’s but the present was mine.

Lesson: Just say yes. Rise above saying no all the time. Embrace someone else’s travel ideas and you may discover that the thing you needed was something you never would have looked for.

8. Make a Wish

About 15 years ago I made a strange trip to Bali. The local spirits had their way with me, and my vacation was bedeviled by un-paradisical ills, including spooky weather, botched plans, personal squabbles, and food sickness. Everyone has had a trip like that. It ended with a stay at Tugu Bali, a lovely small hotel on Canggu Beach. I remember floating in the pool and thinking to myself, Someday I’ll return here with someone I love and the trip will be perfect. Then I forgot all about it—until a year ago. My partner planned a surprise weekend in Bali and kept the details to himself. We landed at night and drove to the hotel. Bali’s tourism had boomed in the intervening years, with a motley horde of hotels glowing everywhere. We drove for an hour and pulled into a driveway. I got goosebumps before I read the sign: Tugu Bali. I’d never told Chris my story, yet from a thousand hotels, he chose the one where I’d made a wish so long ago.

Lesson: Leave a bit of yourself wherever you go—in the form of a wish, a sight unseen, a stone unturned. And don’t give up on a destination—you may return to love it all another time.

9. Holiday With the Locals

One man’s holiday is another man’s workday. A year ago we decided to sidestep the reindeer and spend Christmas in Sri Lanka. The roads are abysmal, and you need a driver if you hope to travel from coastal Galle to Nuwara Eliya’s tea plantations to the sacred city of Kandy and the cave temple of Dambulla. Our driver, Nuwan Amila, guided us with humor and expertise. In a nation of Buddhists, Hindus, and Muslims, Nuwan was a Christian, married with kids. When we realized that our holiday would take him away from his family on Christmas Eve, we tried to send him home with cash—but he would have none of it. So we all enjoyed a yuletide feast, Sri Lanka-style, with spicy curry, grated coconut, and beer. Nuwan told us about growing up during the Sri Lankan Civil War, a 26-year conflict that ended in 2009. Massacres and bombings were so common that when Nuwan’s family traveled by bus they took separate lines so that if one bus exploded, the rest of the family would survive. Santa’s gift to me, at the base of Sri Lanka’s Lion Rock, was a reminder of how mercurial life’s lottery can be, how precious our time together is, and how much you can learn by striking up a conversation.

Lesson: A world of experience can separate a traveler and a local, so go with a generous heart and find ways to engage with locals and hear their stories.

10. Remember to Laugh

Hiking the Inca Trail is a traveler’s dream, but it’s also hard work. Part of the meditative magic of mechanical movement is that it has the power to unlock the mind. But at the end of a long day on the trail toward Machu Picchu, such unbridled introspection can lead to unexpected events. This is how I found myself flat on my back in a near-frozen stream, icy rivulets of Andean water racing down my neck and back, my toothbrush sailing into the valley. As far as serendipitous moments go, this one was a cold snap. But before I could gather my wits and drag myself out of the water, I looked straight up to the heavens and noticed, for the first time, the constellations above me. I would never had seen the Southern Cross with such clarity had I not slipped on a stone and slid into a sudden stream of consciousness.

Lesson: Don’t lose yourself in your own thoughts. Travel is a chance to check yourself at the door and dive into the world around you. At the very least, you should watch where you’re walking.