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What You Need to Know About Taking a Mystery Trip

Travelers typically don’t find out their destination until the last minute for a true surprise

an airplane flying out of a suitcase
A recent survey found that 52 percent of global travelers want to book trips where the destination remains a mystery until arrival.
Photo Collage: AARP;(Source: Sarah Rogers; Getty Images(4))
By

Sheryl Jean,

 
AARP
Published April 19, 2024

All Kaye and Jim Peloquin stipulated before their first “mystery” trip was that they wanted to go somewhere warm for four days and that they liked food and history. When they arrived at the airport, they opened an envelope to learn they were headed to New Orleans.

“The funny thing was that New Orleans was a place we had always talked about wanting to visit,” says Kaye, 59, who lives in Lancaster County, Pennsylvania. “It was like Pack Up + Go was fulfilling a dream of ours.”

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The Peloquins paid that Pittsburgh-based company to plan their mystery trip, which included airfare, hotel, a food tour and tickets to the National WWII Museum. They enjoyed the hassle-free experience so much that they’ve taken two other trips around the country.

a sheet of paper that says new orleans
Kaye and Jim Peloquin found out they were going on a surprise trip to New Orleans when they opened an envelope at the airport.
Kaye Peloquin

They’re not alone. A recent Booking.com survey found that 52 percent of global travelers want to book trips where the destination remains a mystery until arrival.

Mystery or “surprise” vacations where the destination is hidden until the last minute are gaining in popularity as travel continues to rebound to pre-pandemic levels and people seek more spontaneity and less stress in their vacation planning.

At least 15 web-based companies offer mystery travel packages either in the U.S. or internationally.

Vacationers 50-plus comprise a large share of mystery travelers, some companies say. Pack Up + Go notes 33 percent of participants are 50-plus, including empty nesters, people too busy to plan a trip and those celebrating a milestone.

Trusting someone else to plan a trip can be a little scary, but it also provides a sense of freedom and adventure.

“My husband and I were like, ‘What if this is horrible?’ ” Kaye Peloquin says. “But I was really busy in my career, and I just didn’t have the time to plan travel. It’s exhausting, and it takes a lot of research.”

a stream running through a forest with rocks along the sides
Kaye and Jim Peloquin explored this trail recommended by Pack Up + Go on a surprise trip to Ithaca, New York.
Kaye Peloquin

How it works

Although there are small differences between companies, the general concept of mystery travel is similar. You choose how to travel (by plane, train or car) and provide a financial budget based on how many people will travel for how many days. Then you fill out a 10-15-minute survey about past trips (so you aren’t sent somewhere you’ve been), interests, preferences (Do you like the beach or the mountains?) and any dietary or mobility restrictions.

London-based Brown & Hudson uses a psychological-based survey to tailor surprise travel worldwide to each traveler’s personality. Pack Up + Go’s pre-trip survey includes a checklist of about 35 interests. Because of that, “no two trips are the same,” says Lillian Rafson, who founded Pack Up + Go in 2016.

Travelers usually receive a weather forecast, a packing list and instructions on when to arrive at an airport or train station before departure. They learn their destination at the airport in an Instagram-worthy moment of ripping open an envelope to reveal the place. Most companies provide clues in a series of envelopes mixed with emails to heighten the anticipation. The exact timing of deliverables differs from company to company.

Whym Travel doesn’t reveal departure details until 24 hours beforehand and the destination two to three hours before departure. With Black Tomato, a New York-based luxury travel company that offers Get Lost mystery adventures, travelers don’t learn of their destination until they get there.

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The cost varies — from $30 for a road trip itinerary to tens of thousands of dollars for a multi-week, survival-type adventure overseas. Most trips don’t include food unless they’re billed as all-inclusive.

Pack Up + Go’s average price for a plane trip for two people for four days and three nights is $2,700, Rafson says. That includes airfare, accommodations, a guaranteed activity, dinner reservations and recommendations. If any budget is left over, it goes toward other activities. Train or car trips start at about $1,000 for two nights. All travelers receive printed and digital itineraries.

Another mystery travel company, Guess Where Trips offers one-day digital road trip itineraries for $39, or $65 for a “pretty package” that arrives in the mail, founder Jessica Off says. Prices exclude overnight lodgings but include recommendations. In the mailing, travelers don’t learn their final destination until the last of five envelopes.

What are the options?

Some surprise travel companies focus on shorter domestic trips.

“One day appeals to people because many don’t want to pay for a multiday surprise trip because it’s a little risky,” says Off, whose 2019 Christmas gift to her parents inspired her to start Guess Where Trips a year later.

The Canada-based company offers road trips in that country and certain U.S. cities in about a dozen states plus Washington, D.C. California was added this year, and Michigan, Ohio, Washington and Texas are also on tap for 2024, Off says.

Guess Where Trips’ 50-60-page itineraries include maps, facts, at least one free stop such as a walk, and recommended pay stops such as museums. Off boasts that the company sends someone to test “every single road trip.”

One California Day provides day trip itineraries in that state mapped with four surprise stops. It’s the least expensive option at $30 for a downloadable PDF.

Because Guess Where Trips’ and One California Day’s “itineraries to go” don’t include bookings, travelers can use them whenever it suits them.

Mercedes “Mercy” Mesa, 49, and husband Eduardo, 50, have taken two Guess Where road trips with their 20-something daughters near their home in Miami. She liked the affordability, easy-to-follow directions and the lack of crowds wherever they went.

food stand in miami florida
Guess Where Trips sent Mercy Mesa and her family to Cauley Square Historic Village in Miami as part of a Florida road trip that included this food stand.
Mercy Mesa

“The Everglades was fantastic,” Mesa says. “We went to a little store that had so much history, and we got to meet the owner. We also went to the smallest post office in the U.S. [in Ochopee, Florida]. I was born and raised here, and I didn’t even know those places existed.”

Ramping up options

For more adventure, some companies offer mystery mixed with physical challenges similar to The Amazing Race television show.

On Competitours’ worldwide trips, teams compete in daily surprise challenges to win prizes. Most 10-day trips cost about $4,000 per person.

Black Tomato’s Get Lost trips go even farther — into remote areas on every continent. Travelers choose a terrain (polar, jungle, desert, mountain or coastal), and the company might plan trekking in Borneo or navigating the desert in Jordan, including any necessary visas, says Rob Murray-John, head of special projects. The company provides survival-skills training pre-trip and upon arrival, where travelers are outfitted on site with everything needed, including a satellite phone for emergencies, he adds. Trips start around $15,000.

Because of Get Lost’s complexities, travelers should start the process at least six months ahead. With other companies, such as Guess Where Trips, the planning process can take as little as two weeks.

Some companies, including Guess Where Trips and Pack Up + Go, offer wheelchair-accessible options.

Peloquin already is thinking about her next surprise trip — maybe this fall or next year.

“We love to travel, but I can only handle planning one big thing a year,” she says of herself and her husband. “It’s nice to go to places in the U.S. where we haven’t been.”

Sheryl Jean is a contributing writer who covers aging, business, technology, travel, health and human-interest stories. A former reporter for several daily metropolitan newspapers, her work also has appeared in the Chicago Tribune and The Dallas Morning News and on the American Heart Association’s website.

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