For a compulsive planner like Jancee Dunn, setting off on a trip with no idea where she was going was a nightmare scenario. Which is exactly why she decided to give it a try.

Credit: Lyndon Hayes

I used to be the sort of freewheeling traveler who rolled into a new country with no itinerary and nothing to guide me but a map. Then I hit my forties, my bravado ebbed, and I became a raging control freak. Now I spend weeks before a trip combing through TripAdvisor and Yelp so that, upon arrival, I know exactly what the showerhead in my hotel room will look like. I already know where I will dine and what I will order, because I’ve memorized the menus online.

So when I came across a new bespoke service offered by a high-end travel agency, in which you have no idea what your destination is until you show up at the airport, my initial thought was: nightmare. The Journey with No Destination, as London-based Brown & Hudson calls it, is a unique trip crafted on the basis of a lengthy interview designed to evaluate your previous travel experiences, likes, dislikes, tolerance for risk, and desired mind-set upon return. “Then,” its website reads, “you will leave everything up to us.”

For a martinet like myself, the enterprise had the whiff of a sinister Stephen King short story, in which a small sign in a shop window reads “Trips of a lifetime—inquire within.” Or echoes of the David Fincher film The Game, in which Michael Douglas’s character, a jaded financier in need of perspective, receives a kind of life-threatening live-action game for his birthday. But the more I thought about it, the more I began to find the idea of complete loss of control strangely appealing. As long as I didn’t end up entombed in a Mexican cemetery, as Douglas did, perhaps it would be liberating—rejuvenating, even—to set off on a journey into the unknown.

And so, perversely, I decided to give it a go. My “evolving dialogue” with Brown & Hudson began over the phone, with an affable trip planner named Chris. For an hour and a half, he gently peppered me with questions, gradually building a profile, the short version being: Former footloose Rolling Stone writer, now a frazzled mom, seeks tranquillity away from the noise of New York City.

His queries grew more probing: When was I most content as a child? What were my passions? If I was captivated by Peruvian textiles, he explained, he could pair me with a preeminent expert in the field. There is nothing like an interview with a luxury travel consultant to reveal your embarrassing lack of passions. Would it count if I mentioned interests, like Greek surrealist poetry, that I had every intention of cultivating one day very, very soon?

Instead, I found myself confessing that during my years as a music writer, I might have resembled a hard-partying rock chick, but my actual interests were always much gentler. Things like baking and walking in nature.

“Maybe the birth of your daughter just brought all this out?” Chris offered gently. I asked him if he had a degree in psychology. “Geography, actually,” he said. “So in putting my psychologist hat on, I’m being a bit of a fraud.” I said, “I frequently feel that way. Aren’t we all frauds, really?” We shared a companionable silence. Then he hung up and got to work.

The idea for the Journey with No Destination came about when the staff of Brown & Hudson was tossing around ideas one afternoon. Someone mentioned The Game; another brought up Alain de Botton’s The Art of Travel, in which the author explores why we leave home, rather than where we choose to go. “We then talked about how experiential travel could morph into travel therapy,” says agency founder Philippe Brown. “It’s about being open to different things, being curious and playful.”

A week after my interview, a book on the science of surprise arrived from Chris, along with travel dates and a thematic goal: contentment, summed up by the words of Buddhist monk Thich Nhat Hanh. “Many people think excitement is happiness.... But when you are excited you are not peaceful. True happiness is based on peace.”

With these words ringing in my ears, there was nothing to do but wait. In the days leading up to my departure, I speculated endlessly. It was a four-day trip, so presumably the flight from New York would be fairly short. What was reachable in a day, but still unusual? Cuba? Iceland? Sayulita? The day before takeoff, my only directive was to pack layers (OK, so Mexico was out).

Approaching the airline counter a few hours before my departure, I was practically hyperventilating. I reached for my ticket, eyes wide, palms clammy, and asked the puzzled airline clerk where I was going.

She squinted at the monitor. “St. John’s,” she replied. “Ooh, the Virgin Islands!” I said. She shook her head. “Nope. Newfoundland.”

As it turned out, my destination was Fogo Island, a remote fishing village off Newfoundland’s northern coast. “We couldn’t think of a place that contrasts more starkly to New York City,” read a card at my hotel, the Fogo Island Inn, a hypermodern glass palace designed by Newfoundland native Todd Saunders.

Well, I wanted remote, and remote is what I got. Outside my window, herds of caribou nibbled moss against the background of hulking icebergs on a slow drift from Greenland. Immediately after breakfast, a card directed me to the home of a local baker named Mona. In her warm, lived-in kitchen, we made partridgeberry tarts as her two cats drowsed on a chair. Mona then delivered another card directing me to the Lion’s Den, a hiking trail that wound around the remains of ancient settlements.

After a brief rest, another missive summoned me to a “shed party” at Phil’s, a cheerful, ramshackle venue where I caught a set by folk musician Aaron Cobb, whose traditional Newfoundland music focused, unsurprisingly, on fishing (“Let Me Fish off Cape St. Mary’s,” “Saltwater Joys.”) Needless to say, quite a contrast to my glitzy Rolling Stone days.

While I occasionally felt like a fourth-grader racing to soccer practice, every one of my nine “exercises” steered me toward my goal of being calm in body and stimulated in mind. As Chris suspected, letting go summoned the freedom of my younger days, when half the fun was not knowing what would happen next.

The service isn’t cheap (weeklong trips start at $18,500 per person), but it did prompt me to reconsider the way I travel, and that’s something hard to put a price on. Rather than beginning with the question of where—a destination to be briskly crossed off my list—I’ve vowed to put more thought into why I want to go, and what I hope the trip will bring. And no more squeezing the life out of each excursion by planning every last detail in advance. Because when you’re experiencing a place for the first time, the last thing you want to feel is déjà vu.