Destination Unknown: 4 Travel Companies That Offer Surprise Vacations

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Curious about booking yourself a vacation to an unknown destination or sending a loved one on a surprise trip? Check out these four travel companies specializing in mystery travel.

It may not be everyone’s cup of tea, but, mystery vacations can be the ideal style of travel for the true surprise-loving, thrill-seeking adventurers.
Picture arriving at an airport without knowing where you’re headed. Or “Amazing Race”-inspired vacations where envelopes arrive, instructing you on your next activity. Or being dropped off in an exotic, remote locale and having to find your own way out.
Curious about booking yourself a vacation to an unknown destination or sending a loved one on a surprise trip? Check out these four travel companies specializing in mystery travel.


Black Tomato

This bespoke travel agency prides itself on offering high-end curated travel experiences that get you off the beaten path. One such experience is the Get Lost service, designed for adventurers who want to challenge themselves.


Befitting of its name, Get Lost sees travellers dropped off in a far-flung, remote environment (they can choose, at the time of planning, from a polar, jungle, desert, mountain or coastal terrain, or leave it up to Black Tomato) with the equipment and supplies they need to succeed. Each day, they’ll use clues and navigational technology to make their way to check-in points, all while an out-of-sight safety team tracks them. When they successfully complete their expedition, they’ll be rewarded with a surprise luxury prize.


Whisked Away

How about a game of travel roulette? That’s the novelty vacation planning experienced offered by Whisked Away. In 10 minutes, you can have a vacation that’s booked and paid for; you just won’t know anything about it. Here’s how it works. Travellers pick their desired region—North America, Europe, or Latin America—and provide their budget, dates, and airport. They’re then guided through a quick survey designed to help customize their trip, with questions about trip type (family vacation or romantic celebration, for instance), accommodation preference (Airbnbs or hotels), previously visited destinations, and vacation activity interests.


That’s it. Then, two weeks before their departure date, travellers get an email with a weather forecast, packing list and instructions on when to be at the airport. One week before, they’ll receive a mailed envelope containing the surprise destination and itinerary. The budget covers accommodation and travel, and Whisked Away provides an extensive list of food and activity recommendations based on the traveller’s survey responses.


The Vacation Hunt

The Vacation Hunt offers three specific kinds of surprise vacations to Canadian and American travellers. There’s the U.S surprise package, which covers American destinations in the 48 contiguous states. The “International Intrigue” package covers all destinations outside of the U.S., as well as Hawaii, Alaska, Puerto Rico, and the U.S. Virgin Islands. Then there’s the all-inclusive package, for resort-style vacations in the Caribbean, Mexico or Latin America.


Like Whisked Away, Vacation Hunt has travellers complete a trip survey to help tailor their surprise travel and sends the big reveal in an envelope in the days before the flight. Trip prices include flights and accommodations, along with some pre-booked activities. Custom packages and surprise honeymoon planning services are available, too.



This travel company helped pioneer surprise travel back in 2015. Years of experience translate to a seamless booking experience that all but guarantees an incredible trip. Jubel has identified five travel styles—Culturist, Active Nature, Chill Nature, Oceanist, and Party Purist—that it uses to help travellers clarify exactly what they’re looking for. There’s a survey component that drills down further, plus a spot to indicate the desired level of surprise. Choose to know nothing at all, learn the continent or be told of the country.


Jubel’s strongest advantage is its proposal feature. Travellers can review a personalized travel plan that provides an overview of weather, logistics, accommodation style and final price, without giving away the surprise. This way, if travellers aren’t entirely sold, they can request a rework before booking.

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