About Us
Our ultimate goal is to create a memorable experience that will inspire you to try, see, and do something you've never done before. We encourage you to step out of your comfort zone, take the road less traveled, and support local businesses along the way.
Meet the Team
And check out a blog post on how we create the perfect road trip here!
Jessica Off
founder
The woman who started it all! Jessica got the idea for this company after creating a scavenger-style road trip as a gift for her parents. Armed with a laptop and a printer, she launched the company in January 2020 from her living room floor - did we mention she was six months pregnant with her first son at the time?! Today, she focuses on the big picture and helps guide the team through new launches and business ideas.
Fun fact: Jess used to teach English in North Korea!
Jessica Bax
DIRECTOR OF OPERATIONS
Jessica (JB) keeps the wheels turning at Guess Where Trips as our Operations Manager. She leads the day-to-day operations of the business: turning big ideas into action, building timelines, overseeing marketing campaigns, managing fulfillment centres, and making sure the website (and everything else) stays up to date. From big-picture planning to the tiniest details, JB helps keep the entire team organized, aligned, and moving forward.
Fun fact: Her chiweenie occasionally works security for the team, though he's been written up a few times for bad behaviour.
Sydney Schouten
MARKETING COORDINATOR
Sydney was Guess Where Trips’ very first hire - you probably recognize her from our Instagram reels! As our Marketing Coordinator, she keeps all of our marketing efforts aligned and on track. Sydney truly embodies the Guess Where Trips voice, brand, and spirit, which shines through in everything she creates.
Fun fact: Sydney once lived in Liverpool and is known to hop on a plane for the occasional long weekend back there.
Hannah Elias
PRODUCT MANAGER
Hannah joined the team in 2023, and since then has helped to grow our brand in so many different directions. From product launch strategy to research & development (and even writing our new Detour Diaries book!), she continues to find new ways to improve our road trip products for our customers. She has a meticulous eye for detail, and the best dance moves on the team.
Fun fact: Hannah went to Italy for professional dance training, and now she directs/choreographs musical theatre productions across London, ON!
Brian Bax
FULFILLMENT MANAGER
Brian is the powerhouse behind our fulfillment operations. As our Fulfillment Manager, he handles everything from printing and assembling each road trip to tying them up and sending them off to our shipping partners. He also keeps a close eye on inventory to make sure we’re always stocked and ready for your next adventure. If a Guess Where Trip makes it to your doorstep, it’s because Brian made sure it got there.
Fun fact: Brian worked for Apple for over a decade, and is our go-to tech guy.
Jessi-Rae Schroeder
STORE AND WHOLESALE MANAGER
Jessi-Rae is our Store Manager and the friendly face behind so much of what we do day to day. She leads all things in-store while also overseeing customer service and wholesale, making sure every customer and retail partner has a great experience with Guess Where Trips. Jessi-Rae works closely with both Jessicas to keep operations running smoothly and ensure the magic carries from our team to every road trip that goes out the door.
Fun fact: Jessi-Rae competed in figure skating growing up, still plays competitive soccer (despite breaking her leg playing last year!)
FREQUENTLY ASKED QUESTIONS
We're here to help
Can I add on a hotel stay to make it an overnight trip.
We highly recommend turning your day trip into an overnight getaway. We pack so much into the itinerary you won’t run out of activities. Once your trip is booked, we automatically email you a list of recommended accommodations within the finishing area. Unfortunately, we can’t book these for you.
How do I redeem my giftcard?
After choosing a trip, please enter your 16-character code on the checkout page in the field under ‘Have a Gift Card?.’
How long are your trips?
Most trips are between 6-8 hours, which includes the driving and time spent at each stop. When selecting a trip, we’ll provide you with more information on approximate driving times and distances.
Are your trips kid friendly?
Yes! Almost all of our trips are kid-friendly. We recommend choosing trips shorter in driving length to ensure it’s a pleasant drive for everyone.
Does the trip include any activities?
Most of the activities and attractions we recommend are free or have a minimal entrance cost (under $10/per person). We note the approximate costs per person in each trip package. If there is a higher entrance fee, we will recommend a free nearby alternative.
Are your trips dog friendly?
Many of our trips are dog-friendly! Before purchasing a trip, check to ensure it’s dog-friendly.
