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!

Jess Off


The woman who started it all! Jess 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


JB is in charge of the day-to-day operations of Guess Where Trips. Implementing ideas, creating timelines, sending out marketing emails, overseeing the fulfillment departments in both Ontario and Florida, and making website edits are just a few of the things she might do in a day. Her job roll is often referred to "Manager of Everything Else" - or "Yapasaurus Rex" on an especially chatty day.

Fun fact: She has a two-year-old Chiweenie who occasionally works security for the team.

Sydney Schouten


Sydney was Guess Where Trips' very first hire! Her days are now split between creating content for Instagram, and planning out new road trips. She has tested out more road trips than anyone else on the team, and knows how to get the perfect videos for our reels. She doesn't consider a road trip complete until she's scoured the internet for every piece of historical information available on a business or building!

Fun fact: Sydney used to live in Liverpool, and is known to fly back out for a long weekend here and there.

Hannah Elias


Hannah joined the team last year, and our road trip production has been through the roof ever since! While we used to create 10-15 road trips per year, we're now creating upwards of 50! She has a meticulous eye for detail, and the best dance moves on the team.

Fun fact: Hannah is a professional dancer and has choreographed many musical theatre productions in London, Ontario!

Marilu McKinley


Marilu also joined us last year to help with emails and shipping. She quickly got the handle of things, and now heads her own department! She has a hand in the entire order process, from helping customers pick out the right road trip, to shipping it out to them. She's also one of the last people to proof-read a new trip, as she has a keen eye for typos (more than that, we think she actually enjoys finding them).

Fun fact: Marilu is the proud dog-mom to a yellow lab named Franki - short for Frankincense, of course.

Brian Bax


While Brian technically only started here in May of this year, he's  been behind the scenes periodically over the past two years, helping us get orders out at our busiest times. Brian works closely with Marilu to make sure trips are fully stocked, and we've put him in charge of our least favourite (but most necessary) piece of machinery: the envelope stuffer (pictured here with him).

Fun fact: Brian worked for Apple for over a decade, and is our go-to tech guy.


We're here to help

How much does shipping cost?

You have two shipping options when checking out.  Our expedited option is $8.70, with tracking, and it takes between 5-7 business days. We also have an Xpresspost option for $12, which will take 2-5 business days. If you spend more than $100, we will ship your package for free via expedited mail.

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?.’ This will then take your order to a zero balance.

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?

Most of our trips are dog-friendly! Before purchasing a trip, check to ensure it’s dog-friendly.