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. Like most great ideas, Guess Where Trips didn’t begin as a business plan.
“I wanted to give them an experience that was nicely presented.”
It All Started With a Gift
Back in 2019, I was trying to come up with a Christmas gift idea for my parents. Not another “thing.” Not another dinner reservation. Something they’d actually remember.
They loved road tripping, but I didn't just wanted to print off an itinerary and a hotel reservation confirmation. I wanted to present it to them differently.
So I booked them a weekend away in Prince Edward County here in Ontario. But I knew I wanted to make the long drive there more interesting. So I created my first surprise road trip, complete with envelopes, clues, and hidden destinations they wouldn’t discover until the moment they opened each stop.
After seeing how much they loved it, I couldn't stop thinking: What if other people would love this too?
My parents before heading out on their first road trip I gifted them for Christmas:
“I had no idea if it would work. I just knew it was something I would buy, and something my friends would love.”
From $80 to a Business Idea
I didn’t start with investors, a big team, or a polished brand. I didn't have a lot of money when I first started out. I went to Staples and bought the cheapest printer on the shelves.
At the time, I was pregnant with my first son and building this all from my small living room floor in Toronto: printing, folding, and assembling trips by hand. Orders started trickling in one by one… then (surprisingly) picked up through the pandemic. Things were growing faster than I expected!
The first few orders that came in:
When Things Took Off (Fast)
What began as a side project quickly turned into something much bigger.
People weren’t just buying trips, they were sharing them, gifting them, and telling their friends.
I focused on tapping into three key elements:
- The joy of surprise
- The ease of a pre-planned experience
- The feeling of discovering something new, close to home
And suddenly, this small idea started scaling.
My family helping me out when I couldn't keep up with the orders:
“It went from ‘this is a fun little idea’ to ‘okay… this is actually a real business.’”
The Part You Don't Always See
Growth was super exciting, but it was also overwhelming. Packing orders. Managing customer questions. Keeping up with demand.
At a certain point, I realized this was something I couldn't do on my own.
That shift from doing everything myself to building a strong, capable team truly helped turn Guess Where Trips into what it is today!
“One of the biggest turning points was realizing I needed to build a team and trust them to help shape what this could become.”
Where Guess Where Trips is Now
Today, Guess Where Trips has helped hundreds of thousands of people explore their own backyards in a completely new way.
From its humble beginnings in Toronto, to dozens of cities across North America, the idea has grown, but the heart behind it hasn’t changed.
It’s still about:
- Creating meaningful experiences
- Making travel feel easy and exciting
- Turning ordinary adventures into something memorable
“At the end of the day, it’s about helping people spend quality time together and discover places they never would have found otherwise.”
Ready to Experience it Yourself?
If you’re new here, there’s no better way to understand Guess Where Trips than to try one.
👉 Take our quiz to find your perfect surprise road trip
👉 Or explore our most popular trips to get started
Because the best stories aren’t just read, they’re experienced.
