Last week on the Hotelsbyday blog we gave our readers four great startups to use on their daycation to explore their destinations with ease. While most most of the applications we showcased in that post concentrated on coordinating activities on the fly, Strayboots was the one outlier in which the service itself was the activity. Instead of just finding things to do, Strayboots pits you and a group of friends against each other on a scavenger game against time to see who can find the most landmarks within the desired area of play. By gamifying the traditional sightseeing experience, Strayboots has found an entertaining way to get everybody involved in exploring their daystay destinations.

So, to prove that we here at the HBD blog team don’t just write about the travel industry, we went on our own Strayboots adventure in the financial district of New York City. Here’s what went down…

Getting Ready…

One of the most important things to have a proper Strayboots scavenger hunt, is the right team. Meeting up at the office at 10 A.M., all the members of the HBD blog came in early to see who they were going to play with later on that afternoon. Elesha, our marketing director, was the mastermind behind everything that day and split the whole team into two groups. We were considering a silly guys vs girls theme earlier on until we realized that the gender ratio on the HBD team was a bit off.

By the end, I was a part of a team that had Trevor (writer/intern), Steven (SEO intern), and Eddy (writer/intern), all who I felt would make us the powerhouse team of HBD. We definitely had a decent chunk of the brains and the brawn of HBD on lock. However, on the other side was Elesha’s team, with Katrina (writer/intern), Kellie (writer/social media guru), and Brian (market manager). Now while I was pretty confident in my team, Elesha’s team was also not to be played with. She also knew more about Strayboots than anybody, so I knew this wasn’t going to be a walk in the park.

We had all earlier agreed to have our scavenger hunt in the financial district in New York City, and were soon off to our starting point: the New York stock exchange.

The Hunt Begins…

Once both Eddy and Elesha entered their game codes into the Strayboots website on their phone, both teams immediately split off. The actual game part of Strayboots requires you to read hints (usually of street names and locations) that point you to a specific landmark and answer a question/riddle once you get to that location. For us that day, these questions ranged from finding obscure island names on the engravings on the pavement in parks nearby to unscrambling letters once we got on top of a hotel building to look across East River to find the solution.

Dispersed in between these questions are mandatory silly photo ops, that not only prove you aren’t googling your answers (the highest offense in the world of Strayboots!), but gives you some time to goof around in midst of your race to finish thirty questions. Yup, you heard that right, thirty four questions is the total in which your team should aim to finish within your Strayboots race. For my team, our halfway point was when the game told us we had to take a group picture in front of the worldtrade center.

"Take a group selfie in front of the One World Trade Center!"
Now, while we were having a blast sprinting back and forth from location to location, fatigue finally caught up with us. We realized that thirty four questions was a lot more questions than we had anticipated originally, with each question taking us at least five to ten minutes to solve. So, here’s a pro Strayboots tip from us at Hotelsbyday: make sure you bring plenty of water and snacks with you so you won’t be exhausted by the end of your scavenger hunt. The summer heat in New York City probably didn’t help either, especially in such a densely packed area of the city.

The Winner is…

Once our time had run out, we all met back back at the New York stock exchange where our race started. Elesha tallied up the points for both teams and crowned us the Hotelsbyday Strayboots winner! As a prize, everyone in the team all received the sweet little prize of a $10 amazon gift card. Even though we were all sweaty and tired, there was no doubt that everyone on the team had a fun time working together against the clock. Since both teams had the same questions, just scrambled in a different order, it was also pretty interesting to see what different tactics the other team pulled in order to rack up points as near the end game.

So the next time you book a dayroom with us at Hotelsbyday, take out an hour or two out of your daycation to explore your destination with some friends with Strayboots!

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Sean Park

Media Intern at Hotels By Day
Currently a Journalism and Integrated Digital Media student at NYU.