Talking tech since 2003

I’ve been on my fair share of last-second trips and I’m sure many of you are no exception. Most of these trips were weekenders, where I’d simply get on a car or hop on a train and ride to Pittsburgh or Philadelphia to visit with friends. Nothing wild and crazy. My ability to do so now is hampered by many things, one being a job that I can’t just disappear from and a dog that needs taken care of in my absence. But I do still get the urge to take off, and newly launched FlyRoulette is hoping that others feel the same way.

flyroulette-logoFlyRoulette is a travel service aimed at those who want to engage in spontaneous travel and want zero say in the matter. The company, founded by a couple of college graduates, is led by CEO Andrew Condurache. In the words of Condurache, “Last minute spontaneous group travel is practically impossible. With FlyRoulette, you can still be spontaneous with friends whilst on a tight budget.”

When you set your travel budget and the level of luxury you want in your trip, FlyRoulette gets to work trying to find a suitable trip for you, and then books it. But here’s where the “spontaneous” part comes in; your trip could happen anytime within the next 30 days and FlyRoulette won’t let you know where or when you’re going until 24-48 hours before departure.

So, theoretically, if you set a high enough budget, FlyRoulette could book you a room in Paris and have you on a plane in two days. Or five days. Or fifteen days. And it might not be Paris. It might be Orlando. You really won’t have a clue until 24-48 hours before you’re sitting on the plane. Good luck filling out that leave slip.

I’m not the most tied down person in the world and yet I still can’t envision myself being able to swing this. To do so, you’d likely have to be someone with very few responsibilities — a college student, perhaps? I shared this observation with Condurache and he agreed that the service only targeted those who could leave on a whim.

FlyRoulette could widen its audience by simply dropping the random departure aspect and leaving the destination open to chance, though that would kill the feeling of spontaneity that the company is trying to instill in its customers. As of now, the company claims to have booked 350 trips with little marketing, so there are travelers interested in this kind of thing. Are there enough to sustain and scale a company? That’s the question.

You can check out FlyRoulette at If you decide to book some spontaneous travel through the service, be sure to let us know how it goes.

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