Travel Talk is a new Sosauce blog series in which we chat with our favorite travel experts about celebrating the saucy side of travel. With such successful experiences in travel media, we want to highlight their journeys from turning a passion for wanderlust into a profession, their travel plans for 2010, and how they document and share their own travel experiences.

You can read our previous traveler spotlight interviews here.

Avi Millman of Stray Boots

This week we chat with Avi Millman, co-creator of a fun scavenger hunt travel company called Stray Boots. Based in New York City and inspired by past global trips, Stray Boots provides tourists and travelers interactive games and trivia to make exploring cities fun and engaging. Team Sosauce even got to try a demo scavenger hunt of New York: The Game last fall, and we had such a blast, we recommend you all try it too! Read our interview below to learn more about Stray Boots, what trivia games you should incorporate in your next trip, and how you can score discounts on tourist attractions as well.



When did the travel bug first bite you?

It’s funny. I remember loving travel from the get-go, even though when I was young we never went anywhere that interesting. But even just boarding a plane to Florida to visit my grandparents was exhilarating as a 6 year old. I still love the smell of chlorine, just because I associate it with my first trips. If I walk by a YMCA, I start dreaming of childhood vacations.

But I think when I left the country for the first time at age 13 – when I went to Brazil with my club soccer team – was when I really was bitten. After that I made a trip out of the country every year, to Greece and France with my family in ’97 and ’98, and then to Sweden and Denmark on my own in ’99 with another soccer program.

How can trivia games and activities like scavenger hunts enhance one’s travel experience?

Don’t get me wrong; traditional forms of travel are great. But the outstanding majority of existing tour concepts are very ‘one-directional.’  You listen to a tour-guide who educates you about something you’re observing (or perhaps tasting or smelling, as the case may be). Or you read a guidebook that tells you about that stuff instead. When you explore a city through a scavenger hunt you’re taking an active part in your discovery of that place. You’re getting to know the area, learning to navigate it, and finding the information for yourself. Not only is it amazingly fun, but you actually retain what you learn much better than when you’re just taught it.

What inspired you and your business partner, Scott to start Stray Boots?

I actually got the idea while traveling in Italy in 2008 with my parents and my sister (sort of a reunion trip from those ones we took when I was in high school). As I was visiting various sites in Rome, looking for specific points of interest from my guidebook, I realized that much of travel is already like a scavenger hunt. You’re trying to check things you want to do off a list and find various spots you think are interesting. I got this idea that if you actually made a sightseeing game, it could be loads of fun, and a really great way to get to know a city and a culture (and maybe a way to stop arguing with your family). When I got back to NYC, I looked into what existed and no one was really doing scavenger hunts in a way that would be accessible for travelers and great way for them to explore the city. I talked to Scott over some beers (we used to work together) and he loved the idea. We got to work bringing this idea to life in NYC. We played around with tons of different ways to do it, including scavenger hunts where you collect things and ones where there’s an official starting time and meeting place. Ultimately, we decided to go with a version that people can play on their own schedules and at their own pace, since we thought that the best part of travel is seeing things your own way and not being rushed through stuff you actually want to check out. In August of 2009, we launched New York: The Game, the City’s first sightseeing scavenger hunt.

Search the Sosauce Guide for new points of interests, travel resources, and reviews around the world on the destinations of your choice!

Currently, Stray Boots offers scavenger hunts only in New York. What are some other cities you hope to bring Stray Boots to and why?

This is one of my favorite subjects, because it’s way more fun for me to dream about other places than my native New York, even if it’s the greatest city in the world. We’ve discussed US cities like Boston, Philly, and San Francisco, as well as European cities like Rome, Barcelona, London, and Paris. In my opinion scavenger hunts lend themselves to walking cities, so you don’t have to spend too much time in a car or on a subway. You’d rather spend your time exploring the streets, finding weird places and people, than in a stuffy car or underground. I actually think European cities lend themselves to this the best, because they tend to be a bit smaller than US cities and many are great walking cities. They also have tons more history than US cities (I was a history major), so I think they can make for more interesting facts as well. My ideal would be Brussels, because I love the culture, and you can pretty much get around the whole city on foot.

Stray Boots participants outside Rockefeller Center after seeing the Rockettes

How can participants document their travel experiences with Stray Boots?

Well, it’s nice because an integral part of New York: The Game is documenting your experience. Within each Game Zone (that’s what we call a neighborhood you choose to play), there are several clues where you take photos. So you’re naturally documenting as you go. Moreover the string of text messages you’re left with at the end of The Game is great documentation of the route you traveled and the information you learned.

As a Stray Boots partner, Sosauce allows scavenger hunt players to recreate and share their travel experiences with our powerful online tools. Upload your photos, pin POIs on your own map with friends, and write reviews on the places you visited all on Sosauce!

Do you think there is a connection between Travel Geeks and Stray Boots gamers?

Oh, totally. While we’ve made New York: The Game fairly mainstream, it’s really built for people who love solving puzzles and playing games (aka geeks). The people who have the best time are those who are always looking for new, fun things to do, and who revel in finding those one or two things off the beaten path that they never expected to find.

How has your experience been so far working in the New York travel start-up scene?

It’s been absolutely amazing so far. I can’t imagine how difficult it would have been ten or twenty years ago to get noticed in this industry. For a company that can’t afford brochures in hotels or people in vests harassing you in Times Square, we’ve found it so easy to reach customers both in NYC and on the other side of the world. Tools like Twitter and Facebook, as well as just basic stuff we all take for granted like Google and TripAdvisor, have made it so much easier for us to find customers and, as importantly, for customers to find us.

On top of that, we’ve just had an amazingly positive experience on a personal level. It’s funny that NYC is depicted as a harsh and unwelcoming place and the travel industry as super-competitive with huge barriers to entry, because we’ve found the individuals to be incredibly friendly, welcoming, and eager to collaborate. In fact, we’ve gotten some of the most generous responses from people at companies you’d expect to be our direct competitors.

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As a native New Yorker born and raised in the city, what do you think makes New York unique for visiting travelers and tourists?

Well, New York is obviously ridiculously great in a number of ways. It’s got world famous landmarks, amazing nightlife, tons of history: the whole shebang. But I think what it has over other cities is its diversity and the effect that its diversity has had on its culture and history. It’s sort of like 20 cities in one, all piled up on top of one another. It’s been called a ‘Melting Pot’ for over a century, so I’m not exactly the first to make this extraordinarily keen observation.

But this is definitely something I didn’t notice growing up, and totally took for granted. In fact, it wasn’t until I started leaving New York on a more regular basis that I noticed how different the City is.

What makes the City so interesting and so compelling is the way different cultures interact: mixing, but also maintaining their unique identities. You get the amazing old ethnic pockets: Chinese in Chinatown, African Americans in Harlem, or Poles in Greenpoint. But even more interesting to me is how you get people of different backgrounds and lifestyles thrown together, be it hipsters riding the subway in from Williamsburg alongside orthodox Jews, or yuppies, hippies, and children sharing the Great Lawn in Central Park. It’s this element of NYC that we’ve tried to capture in New York: The Game. Each Game Zone tries to show you what that area is all about, but also tries to illuminate the diversity and nuances of it too.

What’s next in 2010 for Stray Boots?

I think it’s safe to say that at this point no one really knows about us. We plan to change that in 2010, now that New York: The Game is complete and tested. So this year, we want anyone and everyone to come try New York: The Game.

In fact, and some people think we’re crazy for this, we’re offering a money back guarantee, where customers who aren’t satisfied after an hour of playing can get a full refund. So help us out and tell everyone you know that they should come out and play now that the weather’s warm. There’s absolutely nothing to lose!

What other ways can Travel Geeks get involved at Stray Boots?

We just came out with a product testing program where New Yorkers who are interested can do our scavenger hunts for free in return for feedback about their experience. We’re also looking for a few talented interns to join our ranks this spring and summer. Anyone interested in learning more should drop us a line.



Thanks to Avi for talking travel with us. Look out for Stray Boots in nearby cities in the tri-state area in the future, and be sure to sign up for New York: The Game now to receive $10 discount. Let us know how it goes!

Read more posts by Alisha

This entry was posted on Wednesday, April 28th, 2010 at 2:08 PM and is filed under Spotlight, Traveler. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.