As the old saying goes, if you see enough ads for something on Instagram, eventually you might just buy it. But in all seriousness, I’ve been wanting to try out a Guess Where Trip for at least a year and finally decided a girls’ day out to celebrate my 30th was the perfect moment.
Firstly, what even is a Guess Where Trip? Essentially, they offer hundreds of different surprise trips departing from various cities across the US & Canada. You simply input the city you’re located in or departing from and then can browse different options. Each trip specifies if it’s kid or dog-friendly, the average duration, whether it’s more active (think hikes) or passive (think city walks), but then it’s time to forget about planning and prepare for your one-day Amazing Race-like adventure.
I chose to receive the pretty printed package, though you can opt for a PDF version. Inside, you’ll find a pre-departure envelope with useful information on what to pack for the day, any important considerations, a reminder to check the website for last-minute location updates, and then it’s off to the races.
We opted for the Winding Roads & Historic Gems route, which took us into Northern Virginia. Without spoiling the trip, the photos below might give it away, so… you know, reader beware and all that. Each stop offered a few options on where to go, field notes to acquaint you with the spots you’re seeing, and some bonus detours if you were inclined.
Even though we had been to this area several times before, everything we did felt fresh and new!
