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For those not in the know, Groupon is the brainchild of Andrew Mason, a company that offers discounts on just about anything you can think of, from restaurant dinners to deep sea diving excursions. The idea is that a potential discount is posted and if a threshold of people signs up, each gets the discount. Last year, Mason was fired from the very company he created because of plummeting share prices and quarterly reports, just 32 when he was let go. For lesser souls, this would be a devastating event in their lives, causing a premature life crisis and wondering just where they went wrong. But for Mason, it was little more than a learning experience he’d use to create his new venture, an app called Detour that would host individual guided tours for travelers.

Taking a Detour on Vacation

Mason’s app called Detour is an app travelers can use to go on self-guided walking tours in cities they visit. All they have to do is download it to an iOS-enabled device, hit play, and then get on their way. At first, it’s only available for five walking tours in San Francisco, but Mason plans for more to come so travelers in cities all around the world can enjoy it. The entrepreneur has said the idea came to him while he was still the CEO of Groupon, when he was on a Roman holiday with his wife.

Mason’s decision to form Detour came because of his travels and the way he wanted to experience cities. He realized that many walking tours drag on for hours, boring the travelers with sights and sounds they don’t necessarily want to hear. And so, he wondered if there wasn’t possibly a better way to do this such that travelers could explore cities entirely on their own schedule, while still getting that yearned-for insider scoop that an actual resident can provide

What to Expect When Taking a Detour

Right now, Detour is free and still in beta testing and when it goes into regular mode, each tour will sell for under $10 (the regular version will arrive in 2015). When iPhone users download it, they’ll be greeted with just a few screens, making Detour a streamlined app that’s fast to load and easy to use and navigate. Each tour is themed and narrated by a different person, with each highlighting various places in San Francisco a tourist wouldn’t know to go.

One self-guided tour on Detour is narrated by American poet and former Wyoming cattle rancher John Perry Barlow, which takes you through San Francisco’s Tenderloin area so you can check out a hidden art salon, discover books that teach you about the city’s history, and then drops you of at a hipster espresso café.

Another tour called Beat Generation is narrated by a radio host and producer named Ninna Gaensler-Debs, and this tour takes you through all the local hotspots where prominent members of the Beat generation frequented. As you wander through their various watering holes and walk their after-bar paths home, you’ll get to hear interviews with the Beats themselves, hosted by San Francisco icon Lawrence Ferlinghetti.

For a change of scenery, take one of the tours through the Marina District, which is narrated by philosopher Ulrich Fürst (a friend of Mason’s who narrates while adopting the voice and cadence of filmmaker Werner Herzog). It’s a cupcake-themed tour, and you’ll be going to snack on local pastries and baked goods.

Where a Detour Can Take You in the Future

Mason has big plans for Detour envisioning the app in all major cities around the world. It’s a pretty big task, considering he has to get narrators on board, talk to the locals about what each city’s hotspots are, and then code everything into the app. But if or when it becomes a global reality, it has the potential to change how travel takes place.

Imagine if you decide to go to Istanbul or Kuala Lumpur one day on a lark, having heard of how cheap each city is and the gorgeous landmarks that occupy both locations. You’ve bought the plane ticket, more or less figured out where you’re going to stay, and excitedly disembark on the plane. It’s one thing to be wandering around your native Chicago or New York, where you have a pretty decent sense of what to check out, and quite another to travel around the world and have no idea what to see or where they are.

But by downloading the app, all you’d have to do is switch it on and let the voice guide you. In an instant, you’d be one of the locals, loping around the city with earbuds in your ear and frequenting the spots that tourists have no idea exists. Of course, you’ll want to take in the world-famous landmarks, but part of the appeal of travel is to get off the beaten path and discover what really drives a city.

And with Detour, you’ll be able to.

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