Surprise Travel: The Cure to Vacation Decision Fatigue

Do you ever crave a vacation getaway but have trouble deciding where to go? Do the pressures of decision-making lead you to procrastinate the planning of your next vacation? Look to surprise travel companies, who plan the trip for you and keep the destination completely secret until you step onto the plane. In this new trend, the thrill of the unknown adds to your adventure.

Companies like Pack Up + Go, Journee, and Magical Mystery Tours have gained popularity in the last five years for their customized vacation planning services. Keep reading for a free Sass-approved surprise daytrip itinerary!

“We took our paper envelope with the trip details to the airport for a 5 a.m. flight, and opened it there,” said Rachel Vinciguerra of Pittsburgh, PA, who was sent to New Orleans by Pack Up + Go.

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Travel advisors have been around for decades – mapping out your itinerary, providing excursion suggestions, and listing the best places to grab a bite, but surprise travel companies add an element of mystery that caters especially to spontaneous travelers seeking a stress-free yet adventurous experience.

“As someone who is usually the planner for our trips, the idea of having someone else plan everything was really nice,” said Rachel Vinciguerra.

Planning Your Trip

The process begins with a survey that asks about your travel preferences.

“It was super easy. You put in your likes, dislikes, places you have already been, and places you don’t want to visit. I told them I like to keep busy, am a foodie, love fun cocktails, and go on adventures, and they planned it way better than I could have!” said Stephanie Schwartz of Clearwater, FL, who went on a surprise trip to Chicago.

Lisa Williams of Atlanta, GA went to Denver. “You actually get a weather forecast and a few suggested packing items about a week out. Flight departure times were also on that email. We were given just enough details to have no idea where we were going.”

The Wait and Surprise

Anticipation, excitement, and perhaps a few nerves build in the days leading up to your mystery vacation. It is during this time that you receive an envelope revealing your trip destination.

“It just sits, tempting you, but we held out!” said Lisa Williams.

Some travelers wait to open their envelope until they arrive at the airport. Others may choose to have a more elaborate reveal, like Kendall Bush of Nashville, TN, who is a repeat client of Pack Up + Go.

“We have done this twice. The first time we had a reveal party, and it was fun to know ahead of time. The second time we found out once we got to our gate!”

What Do You Get?

Surprise travel companies provide a detailed itinerary, including a list of recommended excursions, coupons, and reservations.

“They gave us a list of activities, points of interest, and events. They had some activities booked for us and made a few meal reservations too. They included hotel details, transportation options, and an Uber voucher,” said Lisa Williams about Pack Up + Go.

“We saw every part of the city in five days, including the monuments, Fulton Market
District, Old Town, and Millennium Park, and we still got to be foodies and shop,” said Stephanie Schwartz of her surprise trip to Chicago.

So Why Let Someone Else Plan Your Trip?

In a world where vacation planning can feel overwhelming and time-consuming,
surprise travel companies offer a refreshing and adventurous alternative. More and
more modern travelers are embracing the concept of leaving their vacation plans in the hands of experts, and the personalized itineraries do not disappoint.

“I appreciate the labor that went into curating our experience. The element of surprise left little room for expectations and I believe that also contributed to us being able to just go and enjoy what the city had to offer,” said Lisa Williams of her trip to Denver.

If you find yourself longing for a getaway, but can’t decide where to go, consider letting a surprise travel company craft a one-of-a-kind journey for you. You might just discover that the best adventures are the ones you never saw coming.

Start Your First Surprise Adventure

Now that you know all about surprise travel, we are excited to introduce a Sass-approved, surprise day trip in downtown Frederick! Perfect for a girls’ day, our curated experience will help you discover new eats, exciting activities, and must-see spots as you explore downtown in a new way.

To unlock the fully planned day of adventures, click below!

Lucy Curtis-Cherry

Lucy Curtis-Cherry is a student at Middlebury College studying American Studies and Film & Media Culture. As President of her school’s chapter of The Women’s Network, intern at Sass Magazine, and Marketing Coordinator for Escape This Frederick, Lucy is passionate about creative storytelling and female empowerment through community.