Surprise travel: 10 Unconventional ways to plan your next trip

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If you love to travel, you’re probably already a fan of novelty and the unexpected. So why not really shake things up: Send your inner control freak on a little solo vacay and try surprise travel!

You can start out gently with a fare map and an open mind, or jump in with both feet and let someone else book your whole trip without telling you where you’re going. Sound fun? Here are some ways to get started.


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Surprise Trips

Surprise Trips Departures from UK and Ireland to 77 European destinations, for holders of UK, IE, CA, AUS, NZ, US and EU passports only. Includes flights and accommodations for 2, 3 or 4 nights. Choose departure city and date, number of nights, budget and up to three cities you would like excluded from consideration (other than Paris, Barcelona or any UK cities, which have already been excluded because “everyone’s been there already”). You’re promised your flights will be no longer than 3.5 hours, but you won’t know where you’re going until 2 hours before you take off. This is the ultimate in surprise travel: You won’t know where you’re going until it’s time to leave!

Spoiler alert: Although all the fun here is in the surprise, there is a way to find out both what airline(s) you’re flying and where you’re staying. At the bottom of the booking page is a link to rules and restrictions, including cancellation and refund info. You are given fair warning that following the link will reveal all.

And here’s the problem with that: You can take that info, do a little research, and see what it would cost to book the same trip yourself. One sample trip came up with a cost of $470 USD, but booking the flights through Skyscanner (the search app Surprise Trips is built on) and the hotel through comes to just $340. Is it worth it to pay 40% more for a surprise destination? Only you can decide.


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MeTripping Currently departures from India only, but with destinations all over the world. Book flights and accommodations together or separately. Enter your departure city and dates, then either list up to three places you’d like to go or choose “Inspire me.” Select your area of interest (global cities, popular destinations, top destinations or exploring the world), type of trip (relaxation, magical sights, adventure & thrill or a bit of everything) and kind of lodging, if any (only the best, good hotels, within budget or with locals), set your budget and currency, and click “Start tripping” for a ranked list of trips that meet your criteria.

A sample trip found the price quoted for airfare was actually a couple of dollars less than the same flights on Skyscanner, which powers MeTripping’s flight search, although a different airline offered slightly lower prices. The price quoted for the hotel was also a little less than

MeTripping offers just a momentary surprise but may actually save money over booking on your own. It will be interesting to see if they expand departure options in the future.


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Pack Up + Go

Pack Up + Go Arranges 3-day trips to mid-size American cities, transportation and accommodation included. Choose road trip or plane, train or bus; specify solo or multi-traveler; and give your maximum budget. This leads you to a survey form covering not only interests but also dietary restrictions and whether there is anything special about your trip (eg, honeymoon, birthday, etc.).

A week before you leave you get an email telling you when and where to go to start your trip, what kind of weather is forecast, and what to bring (eg, swimsuit, hiking boots). You also receive an envelope in the mail with directions to your accommodation and a city guide; you are instructed not to open the envelope until you are on your way.

Cons: All trips are 3 days, 2 nights, period, and destinations are limited. You have to provide personal info on all travelers and wait for a human to research your trip and get back to you. Also, trips are pretty expensive; a solo road trip has a minimum budget of $700. Pro: And this is a big pro — if you want to travel as a group but not everyone is departing from the same place, they’ll coordinate everyone’s arrival without revealing the mystery destination.


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Departure Roulette

Departure Roulette Search hotels and cars in the usual way, but search airfare by setting departure city, dates and budget, then “spinning” for flights. If you don’t like the first destination that comes up, spin again. The higher your budget, of course, the more options you will have.

This is another app built on Skyscanner. It’s a fun idea, but results can be disappointing. When you spin for a flight you’re given a destination and “starting from” price, but there’s no explanation for where that number comes from, and trying to view the flights more often than not returns either a “Sorry,  we couldn’t find any live results” or flights double the “starting from” price. No response so far from the developer to questions about this, but this post will be updated if one is received.


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Lufthansa Surprise

Lufthansa Surprise Fun but limited short trip planner, flights only. Departures are from Frankfurt or Munich. Weekend trips are for 1 or 2 nights; “between weekends” trips may be up to 4 nights. Choose a “pool” or type of trip (eg, cities, shopping, nature) and see a selection of between 7 and 12 possible destinations; choose any or all that are acceptable to you.

Give dates of earliest departure (within about 6 weeks) and latest return (within about 10 weeks), specify when during the week or weekend to go, and minimum and maximum number of nights. You’ll get the price of your airfare but won’t know the destination (or dates or number of nights, if you’ve specified a range) until after you make your nonrefundable payment. It looks like you’ll probably save money over booking directly, but can’t really tell without completing payment.


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Magical Mystery Tours

Magical Mystery Tours Similar in concept to Pack Up + Go but a bit more hands on. First you give them your personal info, then they contact you with a detailed questionnaire before they begin researching your trip. They state up front that they charge $300 for their service and prefer to begin 6 to 8 weeks before you plan to travel. You get the email about weather and packing, and the sealed envelope with destination guide. They will also help plan traditional travel to a destination of your choosing.


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Priceline You can still bid on hotels and cars, but not on flights. For cars you give your pick-up and drop-off locations and dates, type of car, and how much you want to pay per day. If your bid is too low to have much chance of success you’ll be told so and given a suggested minimum price, although you can stick with your original bid. You then enter your payment information and hope for the best. If your bid is accepted your nonrefundable payment will be processed and you’ll find out which rental company you’re booked with; if your bid is unsuccessful you won’t be charged.

For hotels you give a city and dates, then choose which area(s) of the city you’d like, the quality of the hotel in stars, and your per-night bid. As with cars, your bid may or may not be successful and you won’t know which hotel until after your nonrefundable payment is processed.


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Skyscanner You can book flights, hotels and cars, but only flights have any element of surprise and that’s only momentary. Enter your departure city and dates and choose “Everywhere” as your destination. Select “search flights” for a list of possibilities, or select “map” from the upper right hand corner to see a map of non-stop and 1+ stop destinations and the lowest prices found in the previous 15 days. Selecting one of the cities gets you a popup box where you can play around with dates and then search for available tickets.


– 9 – Enter your departure city and “Anywhere” as your destination. You can give a specific departure date, a range of dates, or for the ultimate in flexibility choose “Anytime.” You have the same options for your return date, with the additional choice of 0 to 31 nights or any range of nights therein. You’ll get a map showing all your possibilities and best prices, along with a grid arrangement of tempting destination photos.


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Wing It TravelWing It Travel Mobile app for both iOS and Android, powered by Skyscanner. Enter your departure city, dates and budget and get back flights and hotel with trips of varying destination and duration. Selecting “more info” about either the flights or the hotel will take you out of the app to another booking engine where you may have additional options. Flight prices are same as through Skyscanner and hotel prices seem even better. Fun app that can be a little buggy; sometimes flight parameters don’t transfer over to the booking engine, or you may not be able to back up to Wing It.



– Update –



Vueling has a nifty “search by budget” feature. Pick departure city, month of travel (within a 5-month span) and budget, and get suggestions on where you might go. Click on any destination for a fare map to further refine your search.


– Update 2.0 –



easyJet also has a search features called “Inspire Me.” Give your departure city, dates or date range, and budget to see a map of possibilities. You can search by season, and within the season you can further specify one way, weekend break, 1 week return or 2 week return (that’s just to get started; you can change the dates as you like). You can also filter by type of trip (eg, winter sports, city breaks).

Of course easyJet charges for everything from seat selection to checked bags, but this well-designed app has lots of cool features including 3 day, 3 week and full year fare calendars.

25 thoughts on “Surprise travel: 10 Unconventional ways to plan your next trip

    1. It’s both scary and liberating, right? Just pack your bag and go . . . no research, no worrying. I’d love to hear about your adventures.

  1. Pack Up + Go sounds like it could be a lot of fun when I’m back in the states for a few months in between international travels. Will definitely be looking into that! Vueling and the other search by budget ones will be good as well so I can see how far I get once I spend all of current travel money hahah 😛

    1. But isn’t it mindblowing to see that even your last few travel dollars (or pounds or francs or kroner . . .) can still get you someplace cool!

    1. So glad to know I’ve shared something you didn’t already know about! I was surprised to find so many as well.

  2. I haven’t tried booking to any of these apps/sites yet, but it’s good to know about them. At least there are many options to choose from as to where to get good deals for future travels.

    1. I think travel is like any pursuit where you gain knowledge and skills along the way — the better you get at it, the more you want to challenge yourself. You never know what you’ll enjoy five years from now . . .

  3. I LOVE the idea of “mystery” trips! It sounds so fun and adventurous. I’m kind of a spontaneous, go with the flow kind of traveler anyways, so this is right up my alley! Definitely saving this for future reference.

  4. I don’t think I would ever go with the surprise trips website but some of the other ones look worth looking into. Wing it sounds pretty cool. I usually go with skyscanner or expedia or google flights but being able to get some options to choose from for the app would be great.

    1. Wing It uses Skyscanner as a search engine and builds on that. As mentioned I did find it a bit buggy, but hopefully it will do well and they’ll keep updating it.

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