Let's be honest: The idea of an audio tour typically conjures visions of droning museum headsets and selfie-stick clutching tourists. Enter Detour, a walking tour audio app developed by Groupon founder Andrew Mason. The app uses your iPhone's GPS to sync the pre-recorded audio with your location as you stroll the Castro, North Beach, Golden Gate Park, Oakland and beyond.
Touting themes like "The Black Panthers," "The Fisherman's Fisherman's Wharf," and, simply, "Trash" (an India Basin stroll that examines San Francisco's mission to eliminate landfills by 2020), Detour bills its jaunts as atypical walking tours. So we put that claim to the test, downloading the least conventional-seeming walk of the 14 currently available: "Our Tenderloin" ($5 per tour; $20 for an unlimited yearlong subscription). Led by Kathleen Lee, a former drug addict and longtime TL dweller, the tour weaves through the city's most crime-ridden neighborhood. Touristy, it's not: The starting point is at the CVS on Market and 7th Streets, where—after a brief safety warning—Lee encourages listeners to purchase a pair of socks or a pack of cough drops to donate at Saint Boniface, the church and homeless sanctuary you'll be visiting later in the trip—and to bring enough cash for a drink. (If rambling around the Tenderloin with earbuds in, staring at your iPhone seems ill-advised, take note: The storytellers give spoken directions as you walk, so you can keep your head up and your phone in your pocket. Since the app is GPS-activated, the next chapter won't play until arrive at the intended destination.)
Throughout the Detour, you'll be guided along by proud locals, not academics, making the experience more akin to listening to a This American Life or Pop-Up Magazine story than a lecture. (Coincidentally, radio reporter Marianne McCune, formerly of NPR's Planet Money, is one of Detour's producers.) On the Tenderloin tour, transgender pioneer Felicia Flames recalls memories of the Compton's Cafeteria Riot of 1966, a turning point in the fight for transgender rights, as you stand beside the site. When you approach the Tenderloin Police Station on Eddy Street, officers Joe Juarez and Gary Peachey pipe up about the neighborhood's continued struggles with crime. And Pam Coates, a jazz singer who lives in a Tenderloin SRO, leads you inside Saint Boniface, a homeless haven thanks to a program called Project Gubbio ("Don't worry, you're welcome here," she purrs, soothingly. "You're with me.") Over the course of the 50-minute walk, you'll hear an insider's take on the neighborhood's art, history, housing and conflicts, all skillfully interwoven with sound clips and music.
Fittingly for this off-the-beaten-path excursion, the Tenderloin walk concludes at Aunt Charlie's, the neighborhood's last remaining gay bar, where drag queens stalk the stage and suggestive art covers the walls. Sitting in the bar's neon-red glow, with the narrators' voices swirling around in your head (and booze in your glass), it’s enough to turn locals into tourists—and maybe even the other way around.