Ever wonder how we create the perfect road trip?

Ever wonder how we create the perfect road trip?

Hint: It involves a lot of research

Behind the scenes of every memorable road trip lies meticulous planning, research, and a touch of magic. At Guess Where Trips, this magic takes the form of a unique process that transforms mere destinations into immersive experiences, leaving travelers with memories to cherish for a lifetime. Keep reading to learn how we do it.

The Travel Planners, Sydney and Hannah, working on a new launch.

The Travel Planners, Sydney and Hannah, working on a new launch.


Did you know? Our 121 (soon to be 135) trips were created by a team of two! Sydney and Hannah, pictured above, are currently working on another 13 road trips that will launch in Michigan, Ohio and Indiana June 20th.  

So how long does it take to create a road trip, and what goes into it?

Long story short: it takes our Travel Planners about 40 hours to create one new road trip, or 6-10 full weeks to launch trips in a new region!

How do they do it? 

Step 1: Which Region? 

The journey begins long before the wheels hit the pavement, as Sydney, Hannah, and founder, Jessica Off, sit down together to narrow down regions ripe for exploration. Armed with curiosity and a passion for uncovering hidden gems, they delve into the heart of each potential location, eager to unearth its secrets and stories.

Step 2: The "Magic Map"

Central to their methodology is a "magic map" – a digital canvas that evolves year-round as the team adds small businesses, scenic trails, historic landmarks, and even haunted buildings. This map serves as the foundation for crafting road trip itineraries, providing a rough outline of potential stops and experiences waiting to be discovered.

This is just one section of the Magic Map!

This is just one section of the Magic Map!

Step 3: Testing Out the Trip

As the outline of the new trips take shape, Hannah and Sydney hit the road to scour every corner of the region for unique attractions and off-the-beaten-path treasures. Armed with 30-50 spots to check out per potential road trip, they decide which spots make the cut, and which fail to deliver. Along the road, they also keep their eyes peeled for hidden gems that may have eluded them during the planning phase. It's a tough job, but someone has to do it 😉

Step 4: The Final Details

Upon returning to their home base in London, Ontario, they set out to bring their road trips to life through engaging narratives and meticulously planned routes. Every detail is considered, from the timing of pit stops to the flow of experiences along the journey. The designing and printing of the booklets also happens on-site, where they go through one final proof-read by Jessica to make sure they meet our expectations.

Step 5: It's Never Really Finished!

The road trip may be ready, but the work isn't yet done! Every member of the team plays a role in the next stage of launching a new trip, from creating the websites to making sure they're properly integrated with our quiz and map, sending out launch emails, and printing and stuffing the trips. Even after a trip is launched, we continue to monitor the stops to ensure the hours and locations stay up-to-date.

Just one question remains... Are you ready for a road trip?

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