Click photo to enlarge
Stray Boots, a new scavenger hunt app, sends tourists and locals alike on a foodie tour of San Francisco's Chinatown and North Beach. Image courtesy of Stray

Cocktails before noon in North Beach? Our iPhone made us do it.

And the fact that it was a fruity pink, rum-laced Jack Kerouac cocktail was not our fault either. The app was very specific -- and it promised cannoli to come.

These days, you can find outdoor foodie adventures in every corner of the Bay Area -- from touring farmers markets with pros, to chocolate tasting with a guide, or winery-hopping through the Livermore Valley and Santa Cruz Mountains. But the advent of apps-fueled scavenger hunts has brought a tasty new wrinkle to the game, turning cities into playgrounds as tourists and locals alike scamper gleefully down sidewalks chasing down clues.

There's much to be said for a map where X marks the spot, of course, but a series of bizarre, trivia-rich clues that take you through the tea shops of San Francisco's Chinatown or the espresso houses of North Beach? So. Much. Better.

Stray Boots is the brainchild of Avi Millman, a New York entrepreneur who took the concept of touristy walking tours, added a hefty dose of whimsy and packaged it into an apps-driven scavenger hunt. Download the app, and you can search for clues amid the medieval armor at New York's Metropolitan Museum, chase down books and brews in Portland, Ore., or explore historic or food-centric neighborhoods in more than a dozen cities.

Each stop along the course yields intriguing sights, historic tidbits and a 10- or 20-point question that requires some serious exploration of the surroundings. That is how we ended up in Kerouac's favorite bar, Vesuvio, on a recent sunny Sunday, sipping fruity booze as instructed while trying to figure out who the heck the Frisco Kid was and what time his friends arrived. Or what that even meant.

The Stray Boots in North Beach is essentially a two-hour foodie trawl, following the footsteps of ravioli makers, Beat poets and Gold Rush hatmakers in a neighborhood where cafes dot the sidewalks and aromas fill the air. In fact, it can be tough to keep your mind on trivia questions and -- heavens, what is that intoxicating fragrance? Eau de pesto? -- we were forced to take a few delicious detours.

The genius of the app lies in the esoteric questions it poses, and the way it sends you into shops, alleys and byways in search of answers. You don't get the next clue until you've figured out the previous one, though you're allowed to get hints. (Or cheat and look up an answer online, as we finally did when faced with a closed sausage shop that contained a historic piece of equipment.)

By the end of the hunt, we'd sipped, noshed and explored, chatted up a Beat poet expert and gotten some fresh air and exercise, too. We even had photos to remember the day by; several challenges involved posing in specific places. What we didn't have were the sweets promised by a hunt dubbed "Leave the Pun, Take the Cannoli." Millman says that's an oops -- the original hunt had a cannoli stop, but the route has evolved.

To which we say, progress is not always a good thing. Leave the pun, make a stop at Stella Pastry, 446 Columbus Ave. Tell them the Frisco Kid sent you.

Stray Boots

This app offers DIY scavenger hunts through historic and food-centric neighborhoods in 15 cities, from San Francisco to New York. The app is free; the hunts are $12 per person, plus whatever you spend on drinks, food or museum admission. Details: www.strayboots.com.
There are four themed scavenger hunts in San Francisco, with a fifth -- a romantic Valentine's romp -- coming online Feb. 14. Foodies will most enjoy "North Beach: Leave the Pun, Take the Cannoli" and "Chinatown: Hot Buns, Good Funs," an interactive trek through dim sum restaurants, tea parlors, markets and temples.