Destination Unknown: The Ultimate Surprise Trip

16.08.2023 - 06:09 / forbes.com

Would you pay someone to plan a trip for you and only learn where you’re going when you arrive at the airport?

That’s the premise of Destination Unknown, a trip-planning company that’s part of Seattle’s Explorer X. Michael Bennett is a co-founder of both and finds himself in the center of this new travel trend, with a small but growing group of core travelers reaching out to him to plan their trips.

Where are they going? They’ll find out when they get to the airport.

That’s how New Yorkers Christine and Paul Groppe found themselves at JFK and learned they were heading to Slovenia in July 2022 to celebrate her 60th birthday. They were so delighted with the trip that they asked Destination Unknown to plan another one for them last March. That was a trip to Andalucia, Spain.

Other clients include a Seattle couple that Bennett met at the airport with their tickets and itinerary and sent to Chile during the holidays. He’s sent honeymooners on a surprise trip to Vietnam and Cambodia and arranged a solo trip to Greenland.

Who would entrust a company, albeit one with a well-traveled and qualified staff, to organize such a trip for them?

“Our travelers tend to be in the 40’s and up, mid-career, with no time to plan,” Bennett says. “Also, they can’t decide where they want to go. Sometimes that’s because of information overload or paralysis by analysis. Some are so busy they don’t have time to dream about where they want to go.”

Bennett says that some travelers care more about when they go or what they do rather than a specific destination. They might be looking for more off-the-beaten-path destinations or want excitement in their travels but don’t know how to find it.

How does the company determine where to send them on a trip that will ideally result in delighted clients? Destination Unknown steers these travelers through a learning process — for both sides — to create a journey that matches their desires and needs. They have a Dream Sheet for people’s desires and wishes. They look at each client’s travel history, where they ‘ve been, and what they liked about it. If they’ve had life-changing experiences, Destination Unknown also wants those in the mix.

“Maybe they’ll tell us that they want to go somewhere in December, and they want a foodie trip and leave the rest to us,” Bennett says. But the pre-planning goes deeper than that.

It might be date-specific or activity specific. Is this dream destination a classic or an emerging one, what Bennett calls a “hidden gem.” Do they want a particular environment — a desert, a city, or the seaside? What is their wish list of places they want to go? And importantly, what places do they not want to go?

They compile the information along with the budget consideration and