One morning in June, I opened my email to find an itinerary for a trip — a “transformational journey,” rather — that would begin that very day. I quickly packed a bag and caught a last-minute flight from Berlin, where I live, to Lisbon.
By the time I landed, I’d received another email, this one containing a bulleted list of questions: “What’s your ‘story’ about who you are, where you are from, what you do? Are you being the Victim or Creator of your life? Hint,” the email continued, “the best way to go from Victim to Creator is to ask yourself the very questions I asked in my previous email: ‘What do I want?’ and ‘What do I need to do now to get it?’”
The emails were from my “travel mentor,” Michael Bennett, co-founder of Explorer X, a Seattle-based agency that creates custom trips designed to provide a “life-changing travel experience.” Explorer X is part of a growing group of companies specializing in what’s known as transformational travel. If experiential travel signifies engaging meaningfully with the people, history, environment and culture of a destination (like a local, not a tourist), then transformational travel is supposedly the next step: Engage so meaningfully, the trip actually changes you.
This can mean extreme adventure travel, as with companies like Britain-based Pelorus, which offers heli-skiing guided by retired military on active volcanoes in Kamchatka, and immersions with indigenous cultures in Angola and Papua New Guinea. Or it can mean wellness-inflected, small-group trips aimed at building fellowship, as with a slew of female-focused companies like WHOA Travel, which connects its groups with local women to “create experiences and friendships that will change the way you view the world and yourself forever.” There is often a sustainability or public service angle. A newer iteration doubles down on the element of surprise. Black Tomato, a New York- and London-based agency, recently debuted a “Get Lost” service, which drops travelers into remote destinations, requiring them to find their way out (tag line: “You need to get lost to find yourself”).
And it’s not just the niche agencies. In a 2018 survey by Skift, a travel industry news and research site, 54 percent of respondents ranked the importance of transformational travel as seven out of 10 or higher.
Transformation, it seems, has permeated the mainstream.
Michael Bennett of Explorer X was one of the four co-founders in 2016 of The Transformational Travel Council, which leans into the writings of the American mythologist Joseph Campbell, particularly his notion of the “Hero’s Journey,” with an acronym-heavy set of principles that would make a Burner blush (Follow the PATH: prepare, adventure, think, honor. Travel with HEART: humble, engaged, awake, resilient, thankful).
Preparing for the trip
But what did this mean in actuality? This past spring I swallowed my skepticism, and, within a few days of contacting Explorer X, was on the first of two hourlong Skype calls with Michael, engaging in “The Call to Adventure.” The phrase is borrowed from Campbell, but in this case it meant a conversation about my travel history, preferences and goals for this trip: both “the outer journey” (the trip itself) and “the inner journey” (my personal transformation narrative). “If you want to travel more meaningfully, how can you, Charly, go out there and use this trip to really create some shift in perspective and see the world through new eyes?” Michael asked.
He had done some Googling and quickly made me for a journalist, but we agreed I should take the trip like any other transformational traveler. Was there a challenge I was facing right now in my life? A feeling with which I would like to reconnect? After calculating that I should probably not forge a transformational journey around my recent frustrations with the German tax authorities or the ambient existential boredom that seems to accompany the onset of early middle age, I touched on my struggle to write the novel I’ve been plugging away at for a year. “But I don’t know if a writer’s retreat is going to be the most exciting transformational journey,” I said.
“Well I’m just taking notes here,” Michael spit-balled, “but it’s like, maybe you’re writing the next chapter in your story.” This seemed, if a bit too wordplay-dependent, as good an inner journey as we were likely to come up with, so we moved on to logistics.
An Explorer X trip can cost many thousands of dollars and since my budget was bottom of the barrel, it became clear I would be going somewhere in Europe, where I live, and for not very long. Beyond that, we decided to keep it mysterious in the lead-up to “Day Zero,” the sci-fi term Explorer X uses for the day of departure. That date was the only concrete piece of information I was given.
I did, however, receive reading and viewing material (travel essays by the likes of Pico Iyer and Paulo Coelho; “Finding Joe,” a tedious, 2011 documentary about Joseph Campbell, featuring the pro skater Tony Hawk and the New Age guru Deepak Chopra, among others) and suggestions that included throwing a dinner party before my trip where I recite for my friends a “Traveler’s Blessing,” and then ask them for their “thoughts and prayers” to “guide me through the difficult times.”
The journey begins
What were these difficult times? They were certainly unrelated to my arrival, I realized, as I was whisked from the Lisbon airport in a black sedan with tinted windows by the driver and a local guide. After dropping my bags at a hotel on Lisbon’s central Praça do Rossio, the guide, Edgar Miguel Rodrigues, took me on a walking food tour of central Lisbon. We tried ginjinha, a smooth, sour-cherry liqueur, ate bifana, Lisbon’s signature sandwich of garlicky pork steak, washed down with green wine, and tasted cheeses and chorizo at the covered Mercado Da Baixa, as I pondered what a food tour had to do with my inner journey.
“Some people love the tourist boom,” said Edgar, 35, who grew up in Lisbon and now lives 20 minutes outside the city, as we wove down bustling Rua Augusta toward the city’s newly developed waterfront. “But some feel that Lisbon is becoming a theme park, just like Barcelona.” He went on to tell me that almost every single Lisbon native he knows now lives either in the deep outskirts or shares a home with several others.
I felt the heaviness of this, which seemed to take literal form as we ate our way through the city center, sharing oysters at a restaurant set in a former monastery in the Chiado district, walking the hills of Alfama to sample pastel de nata. Edgar dropped me off at the hotel at the point of bursting and informed me that my next guide would soon arrive for — I’m not kidding — an evening food tour, coinciding with the Feast of St. Anthony.
The guide was knowledgeable, particularly about sardine harvesting and local agricultural politics, but by hour seven, I was starting to come a bit unraveled. Having never participated in a guided tour into which I had very little input, I didn’t have much of a basis for comparison. But the breakneck pace and constant chaperoning felt suffocating, and the only viable option seemed to be drinking heavily until I joined a cluster of middle-aged women dancing wildly to an onstage band playing pimba, an up-tempo style of Portuguese shlock-pop, in a packed Alfama square.
If transformational travel just meant heavily regimented travel with extra reading material, I was struggling to understand the appeal. Then again, it was only the first day.
The next morning, moderately hung over, I was in the back of a car headed for Sintra, a forested town in the foothills of the Sintra Mountains known for its pastel-hued villas and palaces. My newest guide, Susana, also a local, asked me to choose a palace listed in my itinerary. This felt inexplicably difficult, perhaps because I’ve never much enjoyed touring palaces, or maybe because I had acclimated to giving up control.
“Which one is your favorite?” I asked.
“They are all very nice,” she replied. “It depends what you like.”
I countered, “And what do you like?”
This went on longer than it should have until we found ourselves descending the spiral stone staircase of the initiation well at Quinta da Regaleira, a gauche and fantastical neo-Manueline estate built in the early 1900s by an eccentric Brazilian entomologist nicknamed “Monteiro Millions,” who filled it with symbols related to alchemy, Masonry, the Knights Templar and other occult orders.
“This is the rebirth process,” said Susana as we made our way through a tunnel at the bottom of the initiation well toward the sound of rushing water. “You are buried in the earth. You go through the dark, this tunnel, until you come out and are born again. The entrance of the cave is …” She trailed off.
“A vagina?” I offered.
“Yes, like a vagina,” Susana said, as we entered a labyrinthic grotto, then made our way out one-by-one by balancing on steppingstones.
Next we headed to the nearby wine region of Colares for a tour of the lush, hilltop grounds of the 18th-century Casal Sta. Maria wine estate overlooking the Atlantic Ocean. The tour ran late, so I had to power through the tasting at the end, throwing back each glass of savory sea notes like Jäger shots at a college bar if we were going to make it in time for the next activity: a private yoga session on the beach.
One of Portugal’s most beautiful beaches, Praia da Adraga, is vast and windswept, with jagged, dark cliffs rising out of golden sand.
“I don’t usually teach on the beach!” shouted the instructor over the wind and crashing waves as we both struggled to keep our balance in the sloping, shifting sand.
“I don’t usually do yoga after a wine tasting!” I shouted back, collapsing halfway through another sun salutation as a local family gawked.
What does it all mean?
Was this transformational travel? I was struggling to see how. All of these places and activities were interesting and beautiful, yet there was little time to absorb anything, to get lost in my thoughts. If anything, as I fumbled out of my sandy clothes in the back seat of a car speeding back to Lisbon where I was booked for dinner and a fado show, it felt more like a random jumble of transformational travel imagery, like being trapped inside a constantly updating Instagram feed. If I thought back to the times I really felt altered by travel, these were generally not reproducible, let alone monetizable, experiences. If anything, my most transformational experiences tended to be the least engineered. They were what happened when whatever I was trying to do got derailed.
And yet. Something did begin to happen, particularly when I was sent off on my own in a rental car to tour Alentejo in the south, with its rolling sunbaked fields of twisted cork oaks and olive trees, and then up through the white sand beaches and medieval hilltop towns of the Silver Coast in the west.
Even as I reflexively recoiled from Michael’s emails that continued to arrive intermittently over the next week, prompting me to describe myself in three to five words and ask myself how I wanted my “experience of life” to change, they did most likely have something to do with the reflective mind state in which I soon found myself. I cut myself off from life back at home. I found time to write.
Not that the rest of the trip went off without a hitch. The hybrid rental car’s battery died in Santiago do Cacém, and it took four hours, three jump-starts and at least two linguistically treacherous phone calls to get it up and running. Using Google maps to find my way to a horseback-riding tour along the beach of Melides led me to a sodden field that turned out to be the private property of an angry farmer. Would I have chosen to take a three-hour cooking class at a hotel in Santiago do Cacém with a silent, middle-aged German couple? Doubtful, but I also may never have driven the Portuguese coast alone through a pulsing corridor of umbrella pines or seen an Alentejo sunset over the ocean from the back of a horse, traversing dusty, fragrant sand dunes overgrown with juniper, pine shrubs and wild orchids. I wouldn’t have met Edgar or Susana or the motley crew of young hotel staff who spent hours in a sweltering parking lot trying to restart my car.
If in an age of over-tourism, companies like Explorer X helped some people embrace a more thoughtful, sustainable form of travel, how could I justify my derision?
It was almost dusk on the last day of the trip by the time I reached hotel Rio do Prado, an eco-retreat hidden amid the lush marshland on the outskirts of the walled, medieval town of Óbidos. I checked in and was led to one of 15 grass-covered, concrete-and-eucalyptus-wood structures, designed by the Portuguese architect Jorge Sousa Santos. I fired up the wood-burning stove and let the concrete bathing basin fill with solar-heated water. Birdsong glutted the evening air.
By then I had grown tired of focusing on myself. I thought about my friends and family, about how and why people travel. I thought about the fact that the so-called transformation economy is arguably propelled by millennials, a generation — my generation — coming-of-age in precarity, without the social, political or economic stability that was once taken for granted. Maybe you can’t buy a house or have a kid or trust that a future illness won’t lead to your financial ruin, but with a few thousand dollars you can buy yourself “a transformational journey.” Was this a good trade-off? I was hard-pressed to say. But that night in Óbidos felt almost transformational.
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