Exploring New Cities with Strayboots

When you plan a vacation, you tend to ask yourself a couple of key questions:

  • Where should I stay?
  • Where and what should I eat?
  • What should I wear?

And inevitably…

  • What should I do?

How you answer that last question can differ significantly depending on your personality, but your answer to the question of how best to occupy your time tends to fall into two general categories. If you’re like me, you do a bunch of research, make lists, and try to come up with a plan based on criteria such as affordability, enjoyability, and uniqueness. However, if you’re like my husband, then you probably eschew the list-making entirely and just show up in the city. My husband revels in spontaneity, taking each hour as it comes and chatting to locals for recommendations. 

His methodology tends to stress me out, but I have grown to really appreciate hours spent wandering through an unfamiliar city, watching people go about their daily lives in random non-touristy neighborhoods. We have stumbled upon some amazing discoveries this way, ranging from architectural to anecdotal to culinary. That being said, I still need a little structure or “just wandering” leaves me wondering what I might be missing.

Bridging that travelers’ gap between structure and spontaneity is a really fun app called Stray BootsSimply put, Stray Boots is a city tour-turned-scavenger hunt. Each Stray Boots tour guides you through a particular city district, introducing you to the history, culture, commerce, etc., of the area through a series of clever clues. You can play alone or in a team; all you need is a smart phone and a couple of hours!

Portland with Stray Boots 

I’m an unashamed, dedicated fan of The Amazing Race, so any opportunity to run around a city searching for hidden clues makes me happy. This app is particularly fantastic though for a number of reasons:

It’s a great way to get an overview of a city.
The scavenger hunt usually covers a 1-2 sq. mile radius but directs you to the most significant or most fascinating things to see and learn about while moving you along at a steady pace. Along the way you can expect to see both the “famous” parts of a city and the quieter gems off the beaten track. Because the app has no time limit, you can pause in any particular area that interests you for a longer period of time or make a note to come back another time. 

Old Town San Diego with Stray Boots 

  • It gamifies the classic tour.
    Learning about new places becomes interactive and fun through the form of a scavenger hunt. It is more likely you will remember what you learned because you weren’t just passively listening to a guide drone on. 
  • It’s a fantastic means to build community.
    While you can Stray Boots alone, they’re way more fun in a team. Whether your team is family, friends, or colleagues, it’s so much fun to try crack the puzzles together. You also learn quite a bit about your teammates and how they think or how they see the world. I’ve done all my Stray Boots experiences with family members and learned that my dad has a fantastic eye for spotting obscure details! 
  • You can meet interesting individuals.
    Besides your teammates, you also get to interact with vendors and locals on the tours to obtain answers. This is a handy way to break the ice with strangers and have a more robust conversation about their experience of the city. (Especially if you are a shy introvert like myself.)
  • You will end up with a fun set of souvenir photos from the hunt!
    I am really bad at remembering to take photos when I’m exploring cities. As part of Stray Boots, you are typically required to snap a few memorable moments with key landmarks. These assignments mean I am guaranteed to leave the city with some tangible (and postable) memories.

Pikes Market in Seattle with Stray Boots 

While Stray Boots isn’t necessarily for everyone–it’s still too much structure for my husband–they provide a great starting point for general wandering. In my family, there are several of us who stick closely to the Stray Boots path, while the others weave back and forth, forging their own destiny and occasionally crossing paths with the Stray Booters. It has proved to be the perfect vacation foundation, minimizing the urge to spend money on numerous attractions and opening up cities in fresh new ways.

So far I’ve done tours in San Diego, Portland, OR, and Seattle, and they were all amazing. I’d love to hear your experiences and see pictures from other tours. Here’s a tip: check Groupon first to see if they have any deals going on. (They usually do.) 
If you do a Stray Boots tour, let me know in the comments!

Featured image is courtesy of Wikimedia and provided for use under CC 2.0.

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  1. Rachel, this sounds perfect for our trip to Charleston at the end of July. I’ll let you know if we do it! Thanks 🙂

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