How Jessica Off launched a viral travel brand with $80 – and a little mystery
Travel11.07.2025
Ever since she can remember, Jessica Off has always wanted to work in the travel industry.
But, after pursuing a hospitality and tourism degree, an internship with the Cook Islands Ministry of Tourism, and a stint with G Adventures tour company, she found herself freelancing, travel blogging, and unsure of her next career steps.
“I didn’t know what I was doing,” she said, laughing.
That winding path eventually led her back to Canada – and to a business idea sparked by a simple gift she gave her parents: a surprise itinerary for a road trip.
“They love experiences, and I wanted to make a formal itinerary that felt more exciting and personal,” she said. “I loved doing it so much, and they loved the experience! And the way they spoke to their family and friends about how excited they were, I knew that I had a bit of a business idea there.”
Today, Off is the founder of Guess Where Trips, a travel company built on curiosity, surprise and helping people rediscover the uniqueness of the areas that surround them.
Customers simply choose a region, intended travel distance and type of adventure – Local Markets & Picturesque Towns is the company’s current top seller – and then receive a collection of envelopes in the mail (or a digital version) and hit the road for a surprise one-day road trip.
Depending on the style of adventure you choose – some are based on scenery, local eats, or outdoor adventuring – each trip outlines stops along the way, businesses to visit, places to grab a snack, or spots to take an Instagram-worthy picture. The trips kick off with a handy “before you go” guide, which is followed by four surprise stops. At each destination, you’ll find a booklet filled with personalized tips, maps, fun facts, and must-see spots.
And while Off focused initially on building multi-day surprise adventures, it was the pandemic that transformed the business into what it is today.
After incorporating Guess Where Trips in January 2020 and giving birth to her first baby in early March, everything fell apart.
“The pandemic hit days after, and everyone cancelled their trip that I had worked so hard on,” she said. “I remember thinking, ‘Oh my gosh, all of this time and money that I spent, and I don’t have a company anymore.'”
But a few months later, something shifted. People were itching to get out of the house, and with borders closed and long trips off the table, they started looking closer to home. Off quickly pivoted the business to focus on single-day surprise itineraries – and Guess Where Trips took off.
Expanding borders
The business now includes trips in Ontario, Nova Scotia, Alberta, B.C., and several cities throughout the U.S., but the charm remains in the details. Each itinerary is still carefully crafted, often requiring weeks (or even months) of research.
“We look at every travel book, every forum, every Pinterest rabbit hole,” she said. “We talk to local tourism offices and business owners. Then we drive it ourselves to make sure the route makes sense.”
Some destinations have been easier than others. “I thought Florida would be great,” she said. “Turns out it’s not that popular.” Heavy traffic and sprawling cities, she learned, also aren’t ideal for surprise day trips.
Instead, the team now prioritizes places that are scenic, easily accessible by car, and filled with charm. Demand also helps guide the map – customers can now join waitlists to request routes in their area.
“My favourite feedback is actually from a business saying, ‘Oh my gosh, thank you so much for including us. You brought us customers from a completely different city, who then have told other friends of family about us,'” she said. “It’s really heartwarming.”
A big year ahead
Since launching in 2020, Guess Where Trips has continued to grow. In 2023, Off even brought the company to Dragon’s Den, where she landed an investment deal.
“It was surreal,” she said. “I’ve always been the kind of person who watches entrepreneur stories to get inspired, so being on the other side of that was wild.”
And the momentum isn’t stopping.
Later this year, Guess Where Trips will open its first physical storefront in London, Ontario, at 100 Kellogg Lane – the former Kellogg cereal factory that has been transitioned into an entertainment hub.
Off says the team is also launching a new travel guide brand and a stationary line that will help travellers navigate some of the major travel routes in Ontario, such as Ottawa to Toronto or Ottawa to Sudbury.
The 300-page Detour Diary will be chock full of unexpected detours and roadside gems, said Off, something for which they have had ample requests.
“This is a really good tool to have in your glove box,” she said. “It will give people a chance to see some fun things along the way that they may not know about.”
The challenge of entrepreneurship
Looking back on the success of the past five years, Off’s advice for other founders is simple: start your business before it’s ready.
“If you start when it’s ready, you’ve started too late,” she said. “It doesn’t have to be perfect, and you don’t have to invest your life savings into a business. I spent $80 on a printer to get the business started and didn’t even have a website when I launched!”
Figuring it out has always been a theme for Off – from scrappy beginnings to navigating what she calls the “constant guilt” of balancing work and motherhood.
“There’s no such thing as perfect balance,” she said. “Some weeks, my kids need me more, and some weeks, I have a million deadlines.”
When her second child was born, she remembers replying to emails while having contractions. “That was a choice I made,” she said. “But because of that early sacrifice and dedication, I’m now where I want to be and can have a good work-life balance.”
At the end of the day, Off doesn’t pretend to have it all figured out.
“I’m not a typical founder,” she said. “I’m not organized. I’m a little messy. But I care deeply about what our customers think – and that’s what keeps me connected to the people we’re building this for.”
