Interactive Walking Tour

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Strolling around town while you get to know each other can make for a nice date, but throw in fun riddles and photo challenges during a cell phone walking tour and you might just have an awesome date!

The idea is simple: buy the tour ($12/person) from StrayBoots.com, text a code when you get to the starting location, and spend the next 2-3 hours following clues to a bunch of historic spots where you learn fun facts about the city. And I don't have to tell you how sexy history can be!

For my tour, we showed up at one of the big signs in downtown San Diego and sent off our code. A few seconds later we received basic instructions about the hunt and our first clue, which was directions to an old hotel and a riddle about a woman in the bar. We went to the hotel and searched through the old photographs on the walls, broke hotel rules by going upstairs, and poked our noses into other questionable places before settling on a name and texting it off. We quickly got the 'CORRECT!' reply and a factoid about the hotel, along with our next clue. We also thought "Hey, that was sorta fun!"

We spent the next 3 hours checking out a bunch of historical sites and asking confused and suspicious employees a lot of questions. Expect plenty of strange looks and those annoying I'm-being-polite-but-I-think-you're-up-to-something questions. Of course San Diego is a brand new addition so the confusion will probably fade soon.

All in all we had a good time being able to go at our own pace, which you can't do on regular tours, and stopping whenever or wherever we wanted for lunch, ice cream, and to look around. As a date, it gives you flexibility to go off on your own and plenty to talk about while you walk around. Plus, working on the riddles together makes you feel like a team. (bonus!)

I kinda wish the riddles were a little more challenging, especially since you have 2 chances to answer (with a hint if you miss the first time) and the ability to skip any ones you like by texting 'SKIP.' Though you do receive points for correct answers, so skipping is pretty much out of the question.

As of now they have tours set up in Boston, Chicago, Las Vegas, Los Angeles, Nashville, New Orleans, New York, Philadelphia, Portland, San Diego, San Francisco, Seattle, and Washington D.C.