Why Even Control Freaks Are Opting for ‘Surprise Vacations’

This is the last possible minute.

My phone alerts me to an email from Jordan Tobe, the director of travel operations for Pack Up + Go. The subject line reads “Open Your Envelope! *Do NOT open this email until your envelope is open!*”

Feeling a little like a finalist on a game show, I take a deep breath, tear into the envelope and pull out a sheet of heavyweight paper. In made-for-Instagram teal script, it says: “You’re going to Chicago!”

My studio audience—a pair of heavily armed National Guardsmen standing nearby—didn’t seem to share my enthusiasm, but maybe they’ve seen it all before. After all, this is becoming something of a familiar scene in airports across the country. Companies like Magical Mystery Tours and the Vacation Hunt, both based in Washington, D.C., have made surprise vacations their specialty, while more traditionally oriented operations like Rustic Pathways, which focuses on teen travel, and London-based luxury outfitter Brown + Hudson have added mystery trips to their already robust lineups.

I snapped a picture of my placard and sent it to my wife, then opened the email. In it was a link to my boarding pass for an American Airlines flight, set to depart in two hours. To pass the time, I went into the lounge to look through the rest of the envelope. It held a sheaf of papers about the hotel they’d booked me into, the stylish, centrally located Kimpton Grey hotel; a $70 gift card toward a meal that evening at the Michelin-starred restaurant Sepia; and an admission ticket to the Art Institute of Chicago the next day. There were also three pages of recommended activities curated for me. For the remainder of my Chicago stay, I could mix and match these diversions, or strike off on my own.

For some people, the suspense of opening that envelope is reason enough to sign up. But this kind of travel certainly isn’t for everyone. Sitting there waiting for my flight, I still wasn’t sure it was for me. I have a travel bucket-list as deep as the Mariana Trench. I research my trips ardently, even obsessively. Why would I ever want to cede control? Tom Marchant knows why. The founder of Black Tomato, a luxury travel agency that last year branched into mystery travel with its Get Lost program, said he’s noticed a growing trend toward FOMO among his customer base. In his world, FOMO doesn’t stand for “Fear of Missing Out,” but rather, “Fear of Mind Overload.”

“Option paralysis can kick in,” said Mr. Marchant. When people become so set on ensuring that every experience is a peak experience, they get consumed with worry that they might “come back from somewhere and haven’t done it quite right.” Jubel, a travel agency based in California, began offering Surprise Adventures in 2015. Jubel co-founder Nico Bergengruen says mystery destinations are gaining favor because it’s become too easy to “Google delight away.”

In her book “The Happy Traveler: Unpacking the Secrets of Better Vacations,” author Jaime Kurtz, an associate professor of psychology at James Madison University, describes us compulsive researchers as “maximizers.” While there may not be a cure, she recommends “surrogation.” That is, “surrendering control and outsourcing some of the decision making. People report finding this to be a relief.”

Of course, it’s only a relief if the surprise is a good one. “When we were new, that kept me up at night,” said Denise Chaykun Weaver, co-founder of Magical Mystery Tours, about matching travelers with destinations. “This isn’t some game show where it’s like, ‘Can we make you cry?’”

So, how does a destination get chosen? Most American mystery travel companies, including Pack Up + Go, require clients to take a survey. When booking my trip, I was asked where I’d been recently, and where I’d be heading soon, so the company could avoid those places. I was also asked to select from a long checklist of interests and to write in additional comments. I didn’t request a warmer destination, though I easily could have.

“It is almost like a dating profile—we’re really trying to extract your personality from these surveys,” said Lillian Rafson, Pack Up + Go’s founder when I asked her how they matchmade me with Chicago and not one of the other 69 North American cities they spring on unsuspecting travelers. “I remembered seeing on your survey that you wanted a culturally oriented trip, that you had an interest in food and drink, and that you didn’t mind the cold.”

Sometimes the matchmakers also engage in detective work, said Roshni Agarwal, co-founder of the Vacation Hunt. “We actually ask to follow our travelers’ social media accounts so I can look at their pictures and their Facebook profiles and I can kind of see where they have been, or what they like doing,” she said. “We recently sent a couple to Paris. Looking at their Instagram, we realized that he really likes cooking and baking, so we set up some amazing bakery tours for them.”

Brown + Hudson, the company behind Journey with No Destination, went so far as to consult with a psychologist when formulating the best approach to sussing out where to send their clients. With highly detailed itineraries, their vacations can run into the six-figures for a weeklong trip that’s engineered for maximum personal growth and psychological insight (actors may be involved). Inspired by Alain de Botton’s book “The Art of Travel,” which explores why we traverse the world, company founder Philippe Brown found himself wondering, “What are the benefits of not knowing where you’re going? Is it liberating? Are you more a blank canvas when you arrive? Do you have fewer preconceptions?”

Remaining preconception-free as the trip approaches is not always easy, but it is worthwhile. “The last few weeks before departure are always agonizing, in the best way,” said Marie Chalkley, 33, who has taken two surprise trips with Magical Mystery Tours, including one that sent her to Athens and Santorini, Greece for a 10-day, roughly $2,900 trip last summer. Like me, Ms. Chalkley received pre-trip weather updates on her destination to help with packing. “That’s when the fun really starts,” she said. “I’ve done polls among my friends to see where people think I’m going based on the weather alone.”

Shanna Bober, a 17-year-old high school junior from Boca Raton, Fla., signed on for a guided mystery trip with Rustic Pathways last summer. She had to fight the urge to scour images on the company’s website for clues as to where she was headed (Thailand and Myanmar, it turned out, with a group of similarly adventurous teens). “It was hard,” she said, “But it was actually more rewarding. Learning everything there, in the moment, was so much cooler.”

Surrogating the biggest decisions of my own leap-of-faith trip—where to stay, where to eat that first night and, indeed, even the destination itself—freed me up to relish the smaller choices. One morning, I looked over Pack Up + Go’s guide to the city and decided that Uncle Mike’s Place, “a cozy Filipino diner with the BEST effing breakfast in Chicago,” spoke to me (how could it not? I’m now inclined to believe the encomium). A post-museum drink in the lounge of the stunning Venetian Gothic Chicago Athletic Association hotel was another detour I might have missed without their recommendations.

I wandered freely. And if I stumbled on something good—like an early evening showing of the 1958 film version of Graham Greene’s “The Quiet American”—I didn’t have a self-imposed, overachieving itinerary to prod me on. Giving up control felt like taking a trust fall. With luggage. The surprise—more than the destination—was how liberating that was.

BLINDFOLD, PLEASE // ‘SURPRISE’ GETAWAY OPTIONS—FROM BUDGET TO BLOWOUT

With Jubel’s Surprise Adventures, a flexible-budget option, you fill out a survey, in which you create your “travel style” (are you more “culturist” or “party purist”?) and establish dates and budget. Jubel then sends a proposal—you’ll be able to spell out how much information you want them to share in advance. Average trip budget is $1,000 a week, per person, jubel.co.

Pack Up + Go offers three day, two night trips to 70 cities in the Continental U.S. From $400 per person for a road-trip, and $650 per person for “Plane, Train or Bus,” packupgo.com.

On the higher end of the spectrum, Black Tomato’s Get Lost option deposits you in one of five environments—Polar, Jungle, Desert, Mountain or Coastal (your choice or not)—and challenges you to trek your way back to civilization. Your route may involve luxury camps, exotic modes of transport and unexpected encounters. Just out of sight are support staff, should you need them. At the end, there’s always a party. From about $20,000 per person for a long weekend, blacktomato.com.

Brown + Hudson‘s Journey with No Destination starts with an extensive interview, more like a session with a psychotherapist than a chat with a travel agent. The company will then craft a guided experience around a destination, which could be anywhere from New Guinea to Newfoundland. From about $27,700 per person, all inclusive brownandhudson.com.

Magical Mystery Tours takes particular pride in finding destinations that are both a perfect fit, and a touch obscure (for instance, Croatia’s coast might satisfy your Adriatic dreams more completely—and affordably than Italy’s ). From $1,500 for a two person weekend away, magical-mystery-tours.com.

Rustic Pathways is best known for creating domestic and international trips for teens. While the Mystery Trip promises adventure for the teens who go on it, the real growth may be for the parents who let their kids go. From $5,195 plus airfare for two weeks, rusticpathways.com.

The Vacation Hunt offers simple flat-fee options for both “All-American Adventures” and “International Intrigue” trips, along with surprise package vacations to the Caribbean, Mexico and Latin America. From $750 per person for a 3-4 day domestic trip, thevacationhunt.com

AMAZING RACES // ACTION-ORIENTED VERSIONS FOR COMPETITIVE TRAVELERS

If your idea of a vacation victory is finishing a piña colada without brain freeze, stop reading now. But if you’ve got a competitive streak and a willingness to start each day with no idea what where you’ll be going or what you’ll be doing, consider a “gamified” vacation.

Each year, the Global Scavenger Hunt, familiar to any fan of TV’s Amazing Race, takes between 10 and 15 two-person teams to at least 10 countries in 23 days, covering 24 time zones, so they can battle for the title of “World’s Greatest Traveler.” Last year’s Hunt involved tasks like finding and riding a water buffalo in Hanoi and finagling a dinner invitation from a family in Egypt. Hotels range from the very comfortable to the downright luxurious. “I want [participants] to have an oasis to go to,” said founder William Chalmers. Along with bragging rights, the winners (last year, a 14-year-old girl and her father triumphed) get to do it again for free. This year’s hunt runs from April 13-May 5. $12,500 per person, including airfare, hotels and most meals, globalscavengerhunt.com

For scavengers with fewer vacation days, Competitours, which involves 10 two-person teams, spans over 11 days and four European countries. Though there is $6,600 in prize money at stake, Competitours does not encourage an “I’m not here to make friends” approach to competition. Itineraries are family-friendly and designed for maximum cultural immersion. Last year’s tour, for instance, involved racing toboggans in the Swiss Alps and a cooking contest in San Sebastian, Spain, requiring contestants to hunt down ingredients in the city’s markets (and to ask for them in Basque). Though hotels are generally of the four-star variety, “This is not about going to the spa,” said company founder Steve Belkin. “It’s not about you having people schlep your luggage from the bus. You’re a traveler, not a tourist.” July 16-27, $3,975 per person, double occupancy, includes inter-European transport, lodging, breakfast and activities, competitours.com

Kudos Life Experiences, which specializes in luxury trips to Greece, recently introduced an “experiential luxury travel game” bearing the unwieldy name Kudos OneLife with Hublot. The private tour, scheduled this year for September, takes participants all over the country, by land, sea and air, in search of “elements” of the Antikythera mechanism, a mysterious ancient Greek analog computer, retrieved from a shipwreck in 1902. In the game’s final stage, participants remotely pilot an undersea 3D drone at the wreck site. The winner receives a working replica of the mechanism, made by Swiss watch company Hublot. Roughly $100,000 for a family of four, kudoslifeexperiences.com

Sign up for the two-day Headlands Gamble and you’ll be expected to track down a missing racehorse in Northern California. You are tasked with going from town to picturesque town in the headlands of Marin County to find it. Actors posing as characters in the mystery will provide clues, as will your smartphone (or a provided tablet). For the basic package, you use your own car and device, while the All-Inclusive and Perfecta packages include use of a tablet and a convertible, with “at least one shocking secret stashed within the vehicle, waiting to be discovered.” From $612 per person, including one-night lodging, theheadlandsgamble.com