Skip to content
Link copied to clipboard

How to get someone to plan your vacation for you, and why more people are opting for a surprise getaway

Why plan a vacation when you can be surprised?

Kate (left) and Tess Donlevie open a mystery envelope from a travel agent that specializes in mystery trips. The mother and daughter opened their surprise travel itinerary at the Philadelphia International Airport.
Kate (left) and Tess Donlevie open a mystery envelope from a travel agent that specializes in mystery trips. The mother and daughter opened their surprise travel itinerary at the Philadelphia International Airport.Read moreJESSICA GRIFFIN / Staff Photographer

Kate Donlevie and her daughter Tess struggled to open the large red envelope that would announce their weekend travel destination. Instructed not to open it until they were in Philadelphia International Airport’s Terminal F, they were anxious with anticipation.

“Savannah!” they announced at the same time.

Kate had been there briefly before and was excited to be going back. “It was just an overnight when I was taking one of my daughters back to college and it was almost 100 degrees,” said Kate, 59, from Ocean City. “I always said I wanted to go back when it was more decent weather.”

They had only planned the Magical Mystery Tours trip about two weeks earlier. “I thought a mystery trip sounded fun,” Kate said. “I hate planning.” After filling out an extensive questionnaire, the tour company did all the legwork.

“I’ve never done anything like this,” added Tess, 23, from Northern Liberties. “I’m a nervous traveler, so why not throw myself completely out of my comfort zone.”

Surprise trips are about adventure while leaving the time-consuming and stressful planning behind. If there isn’t a natural planner in your circle of friends, lots of companies will do the work for you. Clients get a thorough questionnaire to narrow down their likes and dislikes, where they’ve traveled previously and details including whether they like to wake up and get going or linger through a leisurely breakfast. Is their ideal afternoon spent poolside or hiking? Questions cover hobbies, food preferences, distance they are willing to travel, and vital statistics including passport number.

And interest in these types of trips is growing. “Ten years ago everybody thought, ‘I have the internet, I can plan a trip,’ whereas now, they think ‘There are a million options on the internet and it’s hard to plan a trip,'” said Denise Chaykun Weaver, president of Magical Mystery Tours in Drexel Hill.

Pinterest saw a 192 percent growth in pins for surprise trips year-over-year from January through September 2018, said Larkin Brown, Pinterest user researcher and in-house stylist. “It’s about putting your own spin on a vacation, elevating the everyday,” she said. “What we see in our pins is that it’s mostly about that process and how to go about it in a way that will make people excited and not anxious, more than about any particular destination.”

Kelley Gorman, 29, is a planner but instead of going with a company like Magical Mystery Tours, she offered to organize the trip herself when her group of five friends decided to go on vacation last November. Each agreed on a $1,300 budget to cover all expenses for their four-day getaway.

“It started out as a joke but my friends trusted in me to plan an awesome trip for them,” recalled Gorman, from Society Hill, who let one friend help with the planning. She kept the destination mum for the rest until the last second. “A week prior to leaving, I sent them all a packing list of what to bring, including a few items to throw them off, like a snow hat and aqua shoes.”

She even had them meet at the wrong airport terminal. “We didn’t want them to connect the dots of the flights at the terminal,” she said. They played a guessing game at the airport to reveal the destination — Sausalito, Calif. “The surprise element made it that much more fun.”

Trip highlights included a beautiful Airbnb overlooking San Francisco, hikes through Muir Woods and Hawk Hill, exploring Sausalito and hitting great bars and restaurants.

“It was a really memorable and great trip,” said Gorman, who would happily do it again.

“If you go in with the right attitude, it’s a good surprise,” said Chaykun Weaver. She started planning covert getaways in 2010. The anticipation is often as fun as the trip itself, she said. About a week before your trip, you’ll get the weather forecast at your destination, what to pack for your trip and when and where you’ll need to be. Travelers get an envelope with their travel documents and itinerary several days before leaving, but are urged not to open it until the last minute.

Magical Mystery Tours started serendipitously when Weaver offered to plan a trip for a friend in 2010, and now has five employees and an expected revenue of $1 million in 2019, up from about $300,000 three years ago. Weaver thinks the recent surge comes from exposure of mystery trips through media, social media, and word of mouth.

Customized vacations start at $900 for a weekend getaway for one, to tens of thousands for luxury group excursions. The tour company takes $300 for planning, commissions from hotels, and additional fees to set up excursions.

The trip Justin Shaffer planned to celebrate his 10th anniversary with his wife, Amanda, last March was a double surprise. Knowing that their vacation preferences don’t always align, he gave Magical Mystery Tours a budget and a list of things the couple both enjoyed, but didn’t tell Amanda.

“Not only could somebody plan it for me, but it was also a surprise and I had no hand in the mix because I didn’t even know where we were going,” said Justin, 33.

They ended up in St. Lucia, staying at Crystals, tree top villas in a mango tree grove — “not your typical beach resort where a lot of people would flock,” said Amanda, 33. The couple loved the trip and the process, and can’t wait to do it again.

Surprise Me! Trips, based in Austin, Texas, launched in early 2017, with 18 trips the first year. Last year, they booked close to 50, mostly millennials and Gen Xers. “A lot of millennials were going with groups of friends, though there were some couples and bucket listers,” said Judi Johnson, partner in Surprise Me! Trips, where packages start at $600 per person for two people for a weekend escape. “More Gen Xers were doing anniversaries and birthdays, mother/adult child trips, road trips and multigenerational cruises.”

Tina Barkers of Birmingham, Ala., discovered the City of Brotherly Love on her Pack Up + Go Surprise trip in October 2018. An avid traveler, she wanted to celebrate her friend Philip Gentry’s 49th birthday, but decided to leave the planning hassles to someone else.

“When I finally released the power and let someone else plan the trip, I welcomed it because they had everything so well planned,” said Barkers, 51. “It took the headache away from talking to folks, being on the internet — all that extra work. You didn’t have to do anything but prepare to go.”

Their $650 per person three-day package included their flights, Sonesta Hotel stay, restaurants and all the highlights — the Rocky statue, a run up the steps of the Philadelphia Museum of Art, visits to the Liberty Bell and Reading Terminal Market, a carriage ride and more.

“You have to be open minded to do something like this because you have no control until you actually get there,” she said.