Launched in February by Groupon founder Andrew Mason, the Detour iOS app is a location-aware audio walking tour with multiple “Detours” highlighting various communities in San Francisco like North Beach.

Detour is a fully immersive experience with a narrator that guides single people or synced-up groups through San Francisco’s back streets to learn about the area’s history and visit local establishments. It’s ideal, if rather impractical at even a small scale, and starting out in San Francisco doesn’t really grasp the challenge of doing this in other popular travel destinations around the world. More cities are under development beginning with Austin, and Mason says an Android app will be ready by the end of the year.

The “Beat Generation” tour begins at the City Lights bookstore, which was the first paperback bookstore in America and a primary base camp for the Beat writers. Across Jack Kerouac Alley, where quotes from Beat writers are engraved in steel plates in the pavement, Vesuvio Cafe is lined with black and white photos depicting Beat writers passing through in the 1950s.

Detour is designed so you can walk the 90-minute route with your iPhone in your pocket. The narrator guides you from street to street and pauses for you to cross intersections. She tells you when to hop on the cable car, and she recommends you take out your ear buds before entering City Lights, Vesuvio Cafe and Caffe Trieste because the locals frown on that kind of thing.

At the beginning of the tour, the narrator’s daughter asks you to physically confirm that you’re aware it’s more important to watch for oncoming traffic at intersections than listen to her mother, which is accomplished by clicking an icon on your screen.

With so much interest in authentic local travel, Detour provides a compelling and affordable ($4.99) experience that immerses you in the community and makes you stop and really see it, feel it and better understand it. Because you can start the tour anywhere along the route, and pause the narration at any time depending on how long you want to stop somewhere, Detour is highly customizable for the individual user because you have the freedom to spontaneously explore on your own also.

Allen Ginsberg’s landmark Howl poem was first read in public in what was once a small bar on Grant Avenue, which to this day is a popular street for locals. Upon arriving at Caffe Trieste nearby, the narrator tells you to turn her off, buy a cup of coffee from the Iranian barista, and grab a seat at one of the tables in the back.

When you turn Detour back on while enjoying your coffee, the narrator explains how Ginsberg wrote some of Howl and Kerouac penned some of On The Road at these tables. Francis Ford Coppola also wrote much of the first Godfather script here. She adds that the jukebox plays mostly opera, although you can find some old Marty Robbins tunes too.

The Beat Generation content is excellent at explaining the famous court case that ruled Howl and its homosexual content was not obscene, which helped pave the way for protected free speech in America and establish San Francisco as a bastion for liberal social discourse. Along the way, you’ll walk by the house where Ginsberg lived, see where Bruce Lee taught kung fu in Chinatown, discover some great Italian restaurants, sit in a park with locals, and visit the bookstore where banned books were once sold out in the open.

By the end of the tour, you’ll feel an appreciation for this community that would be very difficult to accomplish any other way, unless you had a well educated friend who lived here. We spoke with Mason to get some background on the development of Detour.

Skift: Why did you create Detour?

Andrew Mason: I’ve been thinking about a product like this really since my wife and I were visiting Rome back in 2006 before the iPhone even came out. We didn’t want to go on a guided tour. We didn’t want to be with a group of tourists where the tours tend to be these 2- or 3-hour ordeals with lots of history and facts and figures, and you get bored pretty quickly. You feel chained to those groups of people and it’s difficult to explore in a place like the Coliseum. You always want the freedom to explore.

And guidebooks always feel like a lot of work because you have to have your nose in them reading stuff the whole time. So we downloaded an audio tour that we found online and just loaded it on our iPod, and we each put a bud in our ear and walked around. There was something freeing about the experience and we really enjoyed that way of learning about that place.

Skift: Have you come across anything similar to Detour?

Mason: So whenever I’ve traveled, I looked for something similar and it was always hit or miss. Sometimes you couldn’t find anything, sometimes you could but it wasn’t very good. And so when the iPhone came out and the App Store came out, I thought somebody should build something that would be a marketplace for walking audio content. Then as the phone got more mature and they put a GPS in them, etc., I realized all that stuff opens up a whole new world of possibilities to create layers of audio accompanying what you’re seeing, and it opens up dimensions of history as you’re moving around a place.

So after Groupon, I realized that’s what I wanted to build, and we started by looking what else is out there. There have been attempts but I think very few people would claim any of them are good. Usually the content is terrible and the technology is always terrible. There are some really excellent city walking tours but they’re old school tech running off of a CD. Some are well produced but produced in a way that isn’t applicable, or the content isn’t appealing, for people who want to do something like this, which is to find a way to connect with place through the people in places.

Skift: How do you describe the Detour user experience?

Mason: I wanted to build something that would create a better way for people to connect with place than anything that’s out there, where you feel like you’re walking around with a local who really understands the people in a place, and that person feels like they’re there with you. And that’s what we built. It took over a year to get a product out the door because getting the technology right and making it feel simple and seamless is a tricky thing. The way Detour works, your phone is pretty much in your pocket for the whole experience and a narrator is talking to you and guiding you along a path, and if you stop, or if you’re crossing a street, the narrator waits for you.

All the Detours are scored. There’s soundscapes or music going on in the background so it feels immersive, almost like you’re walking around inside a movie. You can also sync up with friends because walking tours are always usually socially isolating. And Detours are a great social activity because a group of people can hear the same thing at the same time. If one person pauses it pauses for everybody so it makes it a fun thing to do.

Skift: Can you describe the tech behind Detour in layman’s terms?

Mason: Using GPS and other sensors on the phone to geolocate you, the narration is almost put together like it would in a video game. It’s divided up into a bunch of different chunks that are triggered as you move in different regions in a place. There’s separate layers of voice and music and ambience that are mixed in real time in the app that allows you to have these non-linear experiences. Some of the stuff that we’re working on now are actually conditional experiences, where depending on the time of day you’re taking a Detour, it might follow a different route based on opening hours of business or something like that. Or depending on how much time you have to complete your Detour.

So that’s one of the biggest technology innovations. The second one is the group-sync thing that we’ve built. So in order to allow a group of people to be connected to each other at all times, we’re using peer-to-peer Bluetooth networking and cloud-based networking—two redundant networks that combine to keep people synced at all times—that again allows you to have a social experience, which we think is kind of a must-have for something like this to be mainstream. Groups of two are the most common, but we’ve seen groups of 12 or 16 syncing up at the same time, and it works. I don’t know if that necessarily is the best experience but it’s doable and those people have had a blast.

Skift: What’s the most popular Detour so far?

Mason: The most popular Detour so far is “Cool Gray City,” which is based on a book by a local historian named Gary Kamiya. It takes you through San Francisco history chapter by chapter, starting with when the mastodons were tromping around, through the gold rush, etc., and it has some really beautiful views.

Skift: We spoke with Kimpton Hotels, who are based in San Francisco, about Detour. The executive we talked to said this could be an interesting partnership between you and them. Are you open to that?

Mason: We love that idea and we think it would be great for hotels. Right now we’re making all the Detours ourselves because they’re so hard to do frankly, and we’re spending as much time on the actual creation tools as we are on the consumer app. That’s because we want to release these creation tools to the public and open it up as a platform in a marketplace where anyone can produce and release or even sell their own Detours.

In the short term, we love the idea of partnering with anyone just as an opportunity to learn. But in the long term, we’ve perceived so many different applications for this that we think keeping the technology to ourselves would be restrictive and not the most innovative way to approach it.

Greg Oates covers hospitality and tourism development. Email him at go@skift.com.

Photo Credit: Detour.com homepage. Detour