Meet the Founder
How I Started Guess Where Trips If you’ve ever opened one of our trips and thought “this is such a fun idea, how did this even start?”… you’re not alone....
Meet the Founder
How I Started Guess Where Trips If you’ve ever opened one of our trips and thought “this is such a fun idea, how did this even start?”… you’re not alone....
How We Plan the Perfect Road Trip
Ever wondered how a perfect road trip comes together? Go behind the scenes to see how each Guess Where Trip is researched, tested, and thoughtfully designed.
How We Plan the Perfect Road Trip
Ever wondered how a perfect road trip comes together? Go behind the scenes to see how each Guess Where Trip is researched, tested, and thoughtfully designed.
10 Things to Do in Cold Spring, NY: The Best Da...
As road trip experts, we know that the best small towns have a little bit of everything. That’s why Cold Spring, NY needs to be on your radar! Whether you...
10 Things to Do in Cold Spring, NY: The Best Da...
As road trip experts, we know that the best small towns have a little bit of everything. That’s why Cold Spring, NY needs to be on your radar! Whether you...
10 Things to Do in Stratford, ON for a Charming...
As road trip experts with a soft spot for storybook small towns, Stratford, Ontario is exactly the kind of place we love to send travellers. Below is our list of...
10 Things to Do in Stratford, ON for a Charming...
As road trip experts with a soft spot for storybook small towns, Stratford, Ontario is exactly the kind of place we love to send travellers. Below is our list of...
Things to Do in Banff, Alberta: Hidden Gems + I...
As road trip experts, we believe the best way to experience Banff, Alberta is by mixing its iconic highlights with quieter trails and local-approved stops that show you a different...
Things to Do in Banff, Alberta: Hidden Gems + I...
As road trip experts, we believe the best way to experience Banff, Alberta is by mixing its iconic highlights with quieter trails and local-approved stops that show you a different...
Things To Do In Collingwood For the Perfect Day...
As Ontario road trip experts, we’ve spent countless hours researching, scouting, and personally experiencing destinations across the province -- and Collingwood continues to stand out as a favourite. That’s exactly...
Things To Do In Collingwood For the Perfect Day...
As Ontario road trip experts, we’ve spent countless hours researching, scouting, and personally experiencing destinations across the province -- and Collingwood continues to stand out as a favourite. That’s exactly...
