Touring becomes a hunt

Editor’s note: PAW senior writer Mark F. Bernstein ’83 took a walking tour of New York City designed by Avi Millman ’05.

What color “hair” does rambutan have?

I had no idea who — or what — a rambutan was, and the first two people I asked on the streets of New York City looked at me blankly. The third person I approached, a young woman at a Chinese produce stand on Baxter Street, jerked her head toward a pile of bright magenta fruit. A rambutan, I discovered, is an exotic Asian fruit covered with green tendrils that might as well be hair. So my wife typed “green” into her iPhone and instantly learned that our correct answer earned us 20 points. Pleased with ourselves, we moved down the street toward our next clue.

We were taking a walking tour of New York City’s Chinatown and Little Italy offered by Stray Boots, a company co-founded in 2008 by Avi Millman ’05. Stray Boots offers 60 tours in 14 U.S. cities and two in Great Britain, spicing up the traditional neighborhood walk by turning it into a scavenger hunt. Download the app (www.strayboots.com), sign up for a tour (there are 17 in New York alone), and let each clue guide you toward the next site. One of the clues on our tour, for example, told us to head to the first seafood market we encountered on Mott Street and find out what is kept in the waist-high gray buckets. [Spoiler alert: frogs.] Each correctly answered question earns points; the object is to earn as many points as possible, which makes it fun for groups that want to divide into teams.

Millman got the idea for the business while traveling with his family in Rome. “It felt like a scavenger hunt,” he recalls, “and it got me thinking about how passive a lot of sightseeing is. I thought it would be a lot more interactive if you turned it into a game.”

As of the end of March, 75,000 people have purchased tours, which cost $12 (in a few cities Stray Boots also offers multi-tour packages, which cost more). Millman wrote all the tours himself until last year, when the business got too big and it became necessary to hire local writers. Each tour tries to give a sense of an area, encompassing ­cultural, historical, culinary, and recreational sites. His sister, Noemi ’02, joined him in 2010 and is now the company’s chief technology officer.

The iPhone app was introduced a few months ago and is available for tours only in New York and a handful of other cities, although Millman says the company is trying to convert all its tours to the app as quickly as possible. In cities where the app has not been introduced, clues are given by text message.

“People seem to really enjoy everything we are doing,” Millman says. “Our challenge is to tell people about it, because once people [take a tour], they tend to come back and take ­others.”

After sampling the lotus buns of Chinatown and the cannolis of Little Italy, a few more walks would do me good.