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Guess Where Trips takes NC on a (mystery) ride.
Seeking a surprise-filled saunter? Well, buckle up. If you’ve ever wanted to take an adventurous and off-the-beaten-path road trip without all the planning, Guess Where Trips has got you covered.
The brainchild of Jessica Off, what began as a creative Christmas present to her parents has since blossomed into a full-blown biz sending travelers to a slew of surprise scenic spots based on their trip style. The road trip venture touts starting points in cities in Canada and the Southern U.S.—with NC most recently making the list (!).
Guess Where Trips offers five ubercool and curated NC trip itineraries—with Raleigh and Charlotte-area launch pads—ranging from a leisurely travel day to overnight/weekend excursions. For our Raleigh roamers, a “Sandhills Sauntering” could be just the ticket for a low-maintenance warm weather foray (hey, picturesque drives, trail trekking, art explorations and one-of-a-kind photo ops!).
Each trip includes four planned stops and an explanation of what to know before you go—with just enough deets to keep you prepped without ruining the surprise. To wit, the creative travel company doesn’t send travelers out on expeditions they haven’t tried and tested themselves. The team’s boots-on-the-ground approach ensures your mystery adventure will be well planned—with delightful destinations sprinkled along the road less traveled, plus myriad choices to appeal to all types of interests.
“It was so interesting to research all the hidden gems around North Carolina,” says Off. “There are so many historic and quaint towns, fantastic restaurants, photo moments, and scenic roads that made it really easy to plan a road trip there.”
And amping up Raleigh’s road trip appeal, the City of Oaks is Guess Where Trips’ most popular sauntering select in the state—leading Off to consider creating another Raleigh-area trip based on the high demand.
“There’s still so much you can do in the state. I didn’t think I wanted to come home—it was beautiful in North Carolina and I was very in love with it,” laughs Sydney Schouten, trip producer. … Obviously, we have to agree.
As they look to the horizon, the wanderlust enterprise plans to expand excursion opps into the Baltimore and DC area in the near future. … Ready to guess where you’re going next? guesswheretrips.com
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