The 10 Best Companies for Surprise Vacations

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What if you got ready for a vacation and showed up at the airport with no idea where your plane was headed? That’s the idea behind a new type of travel agency that will plan surprise vacations for very adventurous travelers. At the airport, you’ll receive a destination and custom itinerary (usually based on a survey or interview to determine your travel style). The idea is that you leave the planning, details, and logistics to someone else, and just pack up and go. Here’s how to take a surprise vacation of a lifetime with the help of these 10 travel companies.

Two people relaxing on beach chairs in front of a pool at sunset — Song_about_summer | Adobe Stock

BlackTomato

If you’ve always wanted to test your survival skills, Bear Grylls-style, BlackTomato’s elaborate surprise adventure tours might be the next best thing. Choose between terrains like “Polar, Jungle, Desert, Mountain, and Coastal,” and BlackTomato’s experts will figure out a country to drop you in—with advice on how to train for your expedition beforehand. Then it’s up to you to navigate through a series of checkpoints (with BlackTomato ops teams watching from afar to make sure all is well).

Imagine a surprise honeymoon where stressed-out couples didn’t have to plan anything at all. That idea kickstarted the luxury travel agency Blind Experiences, which then expanded into putting together tailored itineraries for families with young kids and multi-generational groups— with more surprises gradually revealed throughout the trip via sealed envelopes

Jubel

The surprise trip survey for Jubel begins by narrowing in on a country, continent or destination (beach or mountains?), then asks whether you’re more of a museum or nightlife person (you can pick both, for example). Jubel’s experts go from there to put together a proposal for you that’s just vague enough that your vacation is still a big surprise.

Magical Mystery Tours

The founders of Magical Mystery Tours started their surprise travel agency back in 2009, and they’ve planned many customized vacations since then. The questionnaire quizzes travelers on everything from whether seasickness is a concern to which places they’ve visited and absolutely loved.

Pack Up & Go

Looking to go on a surprise road trip, a plane or train trip, or even a staycation in your own town? Those are the types of trips that Pack Up & Go specializes in, and travelers have headed off to 125 U.S. cities for a fun and completely unexpected trip with a planned-out itinerary of activities and meals.

SkipTown

Spontaneous and courageous travelers are the ideal clients for SkipTown, an agency that will plan short surprise trips for you—even if you can only get away for one day. A “daycation” includes one night’s accommodation, one meal reservation, and one activity, all of which will be unexpected.

Surprisit

With Surprisit, you’ll find out your unique surprise destination a few days before your vacation begins (in case you need a bit of time for some Googling). The agency plans surprise trips in the Caribbean in addition to the U.S. and Canada, as well as a “Eurotrip” where you head off to a new European city every three days.

The Vacation Hunt

If you’re a beach person, but you still want a big surprise, The Vacation Hunt will set you up with an all-inclusive resort in the Caribbean, Mexico or Latin America. Other surprise destinations for this travel agency include a trip within Europe or the United States, or you can open it up to any destination in the world. Surprise honeymoons are a speciality for The Vacation Hunt as well.

Whisked Away

Leave the real-world behind for a while with Whisked Away, which will plan surprise week-long flying or driving trips. The idea is to make this the easiest vacation ever for honeymooners, solo vacationers, families, girls’ groups, or anyone who wants an out-of-the-ordinary experience.

Whym

Splurge trips, surprise vow renewals, solo adventures: Whym will plan a surprise vacation for all sorts of travelers. At the moment, the travel agency is only sending travelers out in the U.S.—and the surprises keep coming throughout the vacation, with blank spaces in your itinerary that are revealed gradually via “whymsies” text messages.

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