You are currently viewing Vacation Roulette? This Travel Agency Plans Your Trip—and Keeps It a Surprise – Robb Report

Vacation Roulette? This Travel Agency Plans Your Trip—and Keeps It a Surprise – Robb Report

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In a travel landscape where nearly every detail can be planned, controlled, and optimized, a quiet countertrend is emerging—one that celebrates the unknown. For travelers accustomed to having access to the best of everything, mystery travel offers something rarer still: a complete surprise.

I didn’t know if I was the kind of person who could hand over control of an entire vacation—let alone our 20th anniversary trip—to strangers. But when I l discovered Journee, a travel company that keeps your destination a secret until the day you leave, something in me lit up. It sounded thrilling, a little audacious, but also strangely freeing. After years of meticulous trip planning, could I just…let go?
I first heard about Journee at a party, when a friend casually mentioned they’d booked a “mystery trip.” The idea stuck, and after a late-night search I was hooked. Founded in 2019 by three former Depop colleagues—Ed Tribe, Megha Chaturvedi, and James Gillard—Journee was created to strip the stress and sameness out of travel planning. Their promise: spend 15 minutes filling out a detailed online questionnaire, and they’ll match you with a tailor-made, experience-first trip to a destination you won’t learn until the airport. After scrolling through truly stellar Trustpilot reviews and grinning at the giddy airport-reveal videos on their Facebook page, my husband and I decided to take the leap and fill out the survey
We cast a pretty wide net in our intake form—saying yes to mountains, beaches, and cities—prioritizing somewhere truly beautiful, colorful, and photogenic. We ranked being outdoors at the top of our list: surrounded by nature, wandering through charming villages, and eating our way through the region’s food scene. (Others might prioritize museums, performances, and historic landmarks, but for us, that was secondary.) We eagerly approved nearly every type of excursion (canyoning, caving, sailing) but we also wanted some slower moments (food tours, spa treatments, wine tastings). We were flexible on accommodations, whether a private house or hotel, but requested a few luxuries like a pool and private balcony. We also included plenty of locations we didn’t want them to send us, mostly because we’d already visited them and wanted this to be a completely new experience. Finally, we set a total trip budget—and within 24 hours, we received our first proposal. 

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It was vague enough to keep the mystery alive (“…an extremely picturesque region that can really only be described as paradise—remote, pristine, and virtually untouched, with everything from stunning beaches to vivid blue lakes, majestic green forests, and bright florals…”) yet with details specific enough to hook us (“…a canyoning experience where you’ll explore a river interspersed with peaceful natural pools…”). 
We had five days to approve it or request a re-match. Full disclosure: we requested several proposals—each one intriguing—before choosing our favorite. Once we said yes, the four-month countdown began to guess our excursion-filled destination. Greece? Croatia? Norway? Madeira?
The shift toward experience-first travel has been building for years. McKinsey reports that today’s most discerning travelers increasingly prioritize immersive, individualized journeys over destination alone. Marriott’s 2025 Intentional Traveler study shows a rising demand in the past decade—particularly post-pandemic—for trips that offer emotional resonance, connection, and authenticity. Preferred Hotel & Resorts echoes this shift in its first-ever Luxury Travel Report (2025), noting that travelers now seek “the unrepeatable—places that excite, environments that surprise, and experiences rooted in individuality.”
Journee embraces this evolution with a growing catalog of more than 90 destinations—many selected because they’re under the radar. “We’ve seen that more affluent travelers are increasingly drawn to places that feel undiscovered,” says Lakeim Knights, a member of Journee’s Community team. One of Knights’s favorite parts of the job is expanding the catalog with destinations that are immersive, perhaps off the beaten path. Some standout matches include Slovenia’s alpine lakes and storybook towns, Albania’s rugged coasts and Ottoman-era villages, and Cyprus’s sun-soaked ruins and hidden coves. Other Journee travelers have traced the winding streets of Porto, ridden camels across the Sahara at sunrise, and basked in Malta’s crystalline waters—all without knowing their destination until the day they left.

For those looking to elevate their trip, they can request upgraded flights, private airport transfers, and exclusive dining reservations. “No matter how specific your request, we encourage you to reach out and we’ll accommodate you,” says Knights. By late August 2025, these options will be formally built into the proposal process for higher-budget trips, with the team proactively reaching out about high-end preferences.
I won’t lie: the four-month countdown was pure anticipatory bliss. Journee kept the suspense alive with playful hints, then sent a detailed packing list and weather report a week before we left. “We build as much excitement as we can through the clues,” Knights says, “spreading everything out to heighten the anticipation.”
So… drumroll… 
We were going to the Azores—the remote, rugged group of Portuguese islands in the Atlantic, about 850 miles from mainland Europe. After opening our reveal envelope and finding our departure gate, we did some last-minute Googling to learn about the archipelago. But once we let go and let the itinerary unfold, we found a rare kind of peace.
The Azores were breathtaking: crater lakes ringed by emerald hills, volcanic cliffs plunging into the Atlantic, steaming hot springs, and small cities filled with warm, welcoming people. Over the course of a week, we enjoyed five thoughtfully planned excursions: a mix of half-day and full-day adventures. We went on a food tour through the cobbled streets of Ponta Delgada, sipped fresh-brewed tea at a tea plantation, and circled the rim of a dormant volcano by ATV. We spotted whales cresting the waves on the open Atlantic, and—my favorite!—canyoned through a rainforest, rappelling down waterfalls and zipping through the jungle on lines our guides strung up on the spot. With no expectations and no list to check off, we wandered, reconnected with each other, and explored a pristinely beautiful paradise we might never have chosen for ourselves—but that turned out to be exactly what we needed.
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