Get someone to plan a mystery vacation for you

When Alicia Ellington and her fiancé Stephan began planning their wedding last year, honeymoon arrangements quickly sank to the bottom of their to-do list. “We had zero time to plan it,” recalls the seniors caregiver from Chelsea, Que. “But we really wanted to add some surprise and excitement to the process.”

The solution? They let someone else organize their once-in-a-lifetime escape—without telling them where they were going.

“Mystery travel” has been a persistent lure for holiday makers over the years. Secret bus tours were once wildly popular, while latter-day “blind booking” deals such as Priceline’s “Name Your Own Price” promotions attract those happy to gamble on sleep overs in specific cities. But the latest trend takes the concept much further. And while hiring planners to arrange your holidays saves time and effort, of course, the main appeal comes from unwrapping a complete itinerary that feels like a custom-made gift.

“You tell us what you want—perhaps a beach vacation or a trip to a country you’ve never visited—and we plan everything. The twist is you have no idea where you’re going until you get to the airport,” says Denise Chaykun president of Magical Mystery Tours. The Virginia-based firm is one of several, including Brown & Hudson and Travel By Surprise, that specialize in the potentially nerve-wracking approach. Vacations start at US$1,500 for a two-person weekend jaunt in North America, though US$5,000 is typical for a week-long international trip. There’s a flat US$300 research fee but the customer’s budget underpins the entire process.

“We start by asking lots of questions,” explains Chaykun. “We want to know all about your previous trips: what you’ve loved, whether you’re a budget traveller or if you crave high-end hotels, for example.”

Ellington says she took the interrogation very seriously. “We filled out their detailed questionnaire and told them we wanted beach time, cultural outings and also some downtime. We didn’t care about accommodations, so long as they were at least two stars and had private bathrooms.”

Next came the operation’s clandestine planning phase. “Once we’ve built the trip and received final payment, they can start pondering where they might be going,” says Chaykun, adding that her head-scratching holiday makers receive general packing tips and weather reports to help decide what to bring.

For Ellington, this was a challenge. “The information was very generic so packing was quite tough. If I’d known where we were actually going, I would have packed some nicer clothing—although it gave me an excuse to shop when we landed!”

The hotly anticipated itinerary arrived in a sealed envelope a few days before departure and Ellington remembers they couldn’t wait to discover where they’d be honeymooning. “We turned it into a game at our wedding with everyone trying to guess the destination,” she says. “We weren’t really nervous about it but we were guessing right up until we got to the airport.”

With Stephan videoing the big reveal, the secret was finally out. “We were thrilled it was Italy. We discovered we’d be visiting Naples, Capri and Rome and we couldn’t have been more excited. I’m a big Italian food fan and my husband is a total history nut.”

It’s the kind of response Chaykun’s company aims for, although she agrees mystery vacations aren’t for everyone. “It’s for travellers who are open to surprises and can have fun with that idea,” she says, adding that they also provide conventional trip planning for those of a more nervous disposition.

The honeymoon, recalls Ellington, was breathtaking. “Our itinerary was full of surprises: We dined with locals, swam at beaches that weren’t full of tourists and even had shoes made by a local shoemaker,” she says, adding that they still talk about their adventurous holiday all the time.

What does she think is the secret to having a successful mystery trip? “You need to be detailed and honest about the kind of vacation you’re looking for. We also had nonstop email conversations with the planners,” she says, adding the payoff of close communication was a stress-free trip with every detail carefully covered.

“We’ll never forget our honeymoon. Opening the package just before boarding and discovering we were going to Italy was one of the highlights of my life,” Ellington recalls. And while the memories endure, the couple remains hooked on the idea of not knowing where they’re going. “A mystery trip was one of the best decisions we’ve ever made and we’ll definitely be doing it again.”