Travel Advisors Work in Mysterious Ways to Put Discovery Into Vacations

With Instagram, travel planning websites, advice from oh-so-well-traveled friends and Google, the experience of discovering a new place is often lost during the intensive planning process for the perfect trip.

Putting back that sense of discovery is behind the growing concept of mystery travel, one where travel advisors keep trip details a secret from their clients until departure.

“How cool would it be to really go to a place and explore it for the first time?” said Jose Pablo Toscano, co-founder and CEO of Jubel, a Mexico City-based travel agency. “Because when you do a bunch of research before planning your trip you kind of spoil the actual trip. You set expectations that probably aren’t going to be met.”

Mysterious Trend

The idea of putting together a trip while hiding nearly every aspect of it from the traveler has spread over the past decade. Several companies are now specializing in different types of “mystery trips” that are catching on with clients.

“I’m not sure how it all happened. We started really small,” said Denise Chaykun Weaver, who started Magical Mystery Tours 10 years ago when designing a trip for a friend who needed a vacation but was too busy to get involved with planning it. “I said I will plan it, and it clicked.”

Since then, a number of other companies have popped up with a variety of mystery offerings. Some specialize in quick weekend getaways within the U.S., while others offer more elaborate multi-destination, multi-week international trips-of-a-lifetime.

“We just went from having a few requests [when we launched] to having thousands,” Toscano said.

Built on Trust

The process of planning a mystery vacation for a traveler is one that is built completely on trust, especially considering that some trips cost thousands of dollars per person. In many cases, companies begin the process of planning a surprise trip by asking travelers to fill out a form about their travel history and preferences. Questions may involve destination choices, where they have traveled recently, places they visit often on business and of any other upcoming trips.

Do they like the beach or city? Culture? Mountains or desert? Nightlife? Infrastructure or remote?

“Some travelers leave it blank while some write five-paragraph essays,” said Lillian Rafson, CEO and founder of Pack Up + Go. “It’s a two-part process. One is kind of matchmaking, looking at the personality and their interests and trips they’ve taken recently to match the traveler with the personality with the city.”

Part two is logistics. Are flights available? Is there a convention happening in a city that might have been a good fit?

Once a destination is set, travelers on Magical Mystery Tours trips receive an email one week before with a very rough weather report and any special information for items to pack that are out of the ordinary.

A few days before the trip, the agency sends clients a big packet of envelopes that isn’t to be opened until the departure date at the airport.

On Weaver’s own honeymoon, she opted to let her co-founder plan a mystery trip for her. She didn’t open the envelope until reaching airport security, discovering her destination was the French Riviera.

“It’s nerve-wracking in a good way, but it was amazing,” Weaver said.

“Doing it for a honeymoon is the perfect trip because you are already at capacity. It is the most fun kind of anticipation. You know something good is coming. You know it’s going to be great. You just don’t know what it is. You can drive yourself crazy thinking of the possibilities.”

Last-Minute Challenges

The biggest challenge for mystery travel providers is the weather, Weaver and others said.

There have been times when Weaver has been forced to plan an entirely new trip for a client the week before when inclement weather intervenes.

“We’ve had times when we scramble and realize this is going to be a lousy location,” Weaver said. “It’s not their fault, anybody would be upset.”

When that occurs, which has happened about 10 times in the company’s history, Magical Mystery Tours takes the financial hit.

“Those are painful because we are planning two trips and the second one is planned at the very last minute,” Weaver said.

Not all agencies that do mystery trips foreswear everything else. Jubel, for example, started with mystery trips but has become a full-service travel agency “with a focus on tech-based, algorithmic trip-planning,” Toscano said.

Likewise, Weaver said 25 percent of Mystery Trips’ business is of the more traditional variety.

Unfortunately in the world of surprise trips, there is always the possibility that a guest doesn’t like their final destination, but the founders of the companies that Skift spoke with all agreed that the types of people who are willing to take a gamble on these trips are the types of open-minded travelers that find a way to enjoy their destinations.

Pack Up + Go has a disclaimer in its FAQ that reads: “Here at Pack Up + Go, we know that every city has a lot to offer. We celebrate open-mindedness, and encourage you to do the same. We’re sure that with your city guide toolkit in hand, you’ll stumble upon some hidden treasures no matter where you go, and you might just fall in love with a place you knew nothing about.”