Destination: Surprise!

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5/4/2018Updated: 10/8/2018

The day before their flight, Briston Brenton and his girlfriend, Sarah O’Hearn, readied their suitcases for a vacation that had been two months in the works. The catch: They had no idea where they were headed.

So began what Brenton would later call “the best trip of [their] life,” a “surprise trip” organized by travel agency The Vacation Hunt.

Founded in 2016 by husband-and-wife team Roshni Agarwal and Jeff Allen, The Vacation Hunt is part of a growing breed of travel agencies that specialize in “surprise” or “mystery” travel.

For a fee, they use a survey to match travelers with a destination, book transportation and accommodation, and recommend—and sometimes arrange, depending on the company—an itinerary of activities. But the travelers themselves are kept in the dark until just before the trip, when a secret envelope with all the details arrives in the mail.

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It’s a quirky twist on bespoke travel, one that elevates the personalized experience with a dose of kid-on-Christmas-morning excitement.

“I think there’s a fun playfulness about it,” said Lillian Rafson, founder and CEO of surprise travel agency Pack Up & Go. “There are so few things in life that are genuinely a surprise.”

These agencies want to remedy that by introducing that rare, inherent joy of a true surprise into the travel experience. Between the thrill of the unknown, the giddy anticipation during the wait, and the high of the final reveal, the excitement begins long before the trip itself.

Options are available for a range of budgets—and bravery levels—from Pack Up & Go’s three-day weekend getaways across the United States, starting at $400 per person, to luxury adventure tour company Black Tomato’s extreme, “Survivor”-style trips to unknown destinations (think arctic treks or rafting down the Amazon), starting at a cool $20,000.

The Vacation Hunt offers both domestic and international trips. Two months after Brenton and O’Hearn first contacted the travel company, the couple uncovered their destination: Dublin, Ireland. There, they toured the Guinness brewery, explored Celtic castles, watched working sheepdogs in action, and hiked the Wicklow Mountains.

Ireland, one of The Vacation Hunt's possible surprise destinations. (Courtesy of The Vacation Hunt) — Ireland, one of The Vacation Hunt's possible surprise destinations. Courtesy of The Vacation Hunt

But the surprises didn’t end with the reveal.

Six hours after landing, in the middle of a cathedral, Brenton proposed. He had planned to do so regardless of their destination, and the Vacation Hunt team didn’t have a clue beforehand.

”[I] had to keep it a surprise,” Brenton said.

Briston Brenton and Sarah O'Hearn's trip to Dublin kicked off with another surprise: a proposal in the middle of a cathedral. (Courtesy of Briston Brenton and Sarah O'Hearn) — Briston Brenton and Sarah O'Hearn's trip to Dublin kicked off with another surprise: a proposal in the middle of a cathedral. Courtesy of Briston Brenton and Sarah O'Hearn

Letting Go

Much of the appeal of the surprise trip lies in the hands-free approach to planning.

“With information overload from the internet, there are just too many choices when trying to plan and research anything, much less a vacation,” Agarwal said. The stress of vacation planning, from deciding on a destination and researching activities, to coordinating transportation and lodging—all while staying within budget—can significantly detract from the actual pleasure. Handing the reins to someone else can feel liberating.

Beyond that, though, there’s also a unique spirit of spontaneity and adventure. A surprise trip offers a chance for travelers to discover a new destination, perhaps one they might not have chosen on their own, and let themselves be, well, surprised by it.

Santorini, Greece. (Courtesy of The Vacation Hunt) — Santorini, Greece. Courtesy of The Vacation Hunt

It’s an exercise in open-mindedness. Free of preconceived notions about a place, travelers are open to experiencing the wealth of all it has to offer.

For Brenton, “that was the fun part,” he said. “We just didn’t know what to expect. We didn’t look anything up when we went. We just showed up.”

Rafson delights in using surprise trips as an opportunity to show off the charm of more overlooked cities and small towns in the United States. Her inspiration for Pack Up & Go arose from her own experience. Hit with the travel bug early in her career, the Pittsburgh native and New York transplant escaped to backpack in far-off places, but found herself guilty of overlooking the treasures closer to home.

“I’ve made my way to Riga, Latvia, but I’ve never been to Charleston, South Carolina,” she recalled thinking at the time. “And I realized there are so many places right in my own backyard that I had never explored, and never made the time to, and didn’t really think of as destinations.”

Pack Up & Go’s domestic trips often highlight those backyard destinations. Even with more popular choices, itineraries strike a balance between touristy spots and hidden gems.

“I love the idea that every city has so much to offer, and it’s all about your mindset and why you travel, and broadening your horizons,” Rafson said.

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Vacation Matchmaking

It all starts with a survey. Rafson likens it to a dating profile, with the purpose of capturing her travelers’ character and what they’re looking for in a trip. History buff seeking cultural immersion, or nature geek seeking wilderness retreat? Comedy shows or boutique shopping? Farmers markets or fine dining? Where would they like to go, or avoid?

Some questions are more practical: Dates and budgets set basic parameters, and listing past and planned trips ensures no repeat destinations.

Answers can be as vague or specific as customers like. For those still reluctant to let loose, Rafson encourages being outspoken about any strong preferences and providing as much information as necessary.

“I want our travelers to know that there is a human on the other side of the screen who’s looking at their survey and reading their responses, and thinking about where they should go very personally,” she said.

From there, it becomes a bit of a logic puzzle. Balancing interests with budget, distance, and availability, travel agents piece together their best match.

For lovers of craft beer and the great outdoors, that might be a weekend trip to Denver or Portland, Oregon. Or for recent visitors to Miami with a penchant for live music and cocktail bars, it could be a rowdy getaway to New Orleans.

“Occasionally, we’ve picked their whole destination because we’re excited about something we have planned for them,” Agarwal said. The Vacation Hunt has whisked a culinary arts student away to Paris for a behind-the-scenes tour of a French bakery, and spirited a Christmas enthusiast to Munich to explore its famed Christmas markets.

Munich's famed Christmas markets. (Foottoo/Shutterstock) — Munich's famed Christmas markets. Foottoo/Shutterstock

For the travelers, their destination date remains a blind one until the last minute. Pack Up & Go sends a weather forecast a week in advance, for ease of packing, and The Vacation Hunt offers the option of receiving a series of riddle-like clues leading up to the trip, but full booking details and itineraries don’t arrive until a week, or even a few days, before departure.

For maximum effect, wait until the final hours. Pack Up & Go, for instance, informs travelers of their designated airport, but challenges them to not open their sealed envelope until they arrive.

Trending in Travel

The surprise trip is trending, with people looking more than ever for unique, customized travel experiences—or simply a more carefree escape from the daily grind.

Magical Mystery Tours has been organizing trips since 2009, and founder Denise Weaver has seen a continuing rise in popularity.

“People are looking for something new, and as more people hear about mystery travel, it seems less crazy,” she said.

Returning customers are also common. Six months later, The Vacation Hunt is already planning the now-engaged Brenton and O’Hearn’s next surprise: their honeymoon, in August.

The growth aligns with an increasing interest in travel in general, Rafson noted, as people are becoming more aware of its healing benefits and embracing it as a means of discovery, connection, and personal growth.

The surprise is just the cherry on top.