Destination unknown: Guess Where Trips plans surprise road trip itineraries

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Guess Where Trips lets travellers partake in exploration of Canadian locations, like Brooks Falls, Emsdale.Handout

Jessica Off started her company just before the pandemic in January, 2020, as a little side hobby to keep her (more) busy while she was on maternity leave. Called Guess Where Trips, her company offers surprise itineraries for people who crave adventure on road trips – without having to do any of the research required to find all the hidden gems that make an open-road experience so memorable.

Day trippers begin by choosing one of eight cities – such as Vancouver, Calgary, Toronto and Halifax – as a starting point. From there, they pick a theme such as Weird and Wonderful or Historic Haunts, but don’t actually know where they’re going until they open the package of four sealed envelopes, each containing a stop for the day. It might be a hike, an Instagram-worthy cul-de-sac or a lunch stop. The mystery of how the day will be spent is part of the fun.

Each envelope contains a stop for the day.Lianne Gravitis/Handout

During the first few months after launching, she sold about five trips a day. Word spread quickly on social media and by the end of last summer, daily orders for Guess Where’s curated Road Trip Kits, which are $55 by mail and $39 for a digital version, had jumped to 200-plus a day.

“I never expected it to take off like this,” says Off, who quit her full-time job as a travel planner in March, 2020, to devote herself entirely to growing Guess Where Trips. “With the pandemic, people couldn’t really travel and they were desperate to get out of the house,” says Off, 32. “It gave them something to look forward to. Plus, who doesn’t love a good road trip?”

Indeed, many people do. According to a survey in May by Leger Marketing, commissioned by Toyota Canada, 49 per cent of Canadians planned to take a road trip last summer, a 10 per cent increase from the previous year.

Lianne Gravitis is a repeat customer from Oakville, Ont., who has done four Guess Where Trips in and around the Greater Toronto area. She heard about them through a friend and booked her first one, Wine Time and Hidden Gems, with five girlfriends for her birthday last summer. She’s since done Vistas and Caves, the Butter Tart Trail, and Bridges to Beaches.

Lianne Gravitis, left, who has done four Guess Where Trips, poses outside the motel from the show Schitt's Creek.Lianne Gravitis/Handout

“Guess Where Trips was the ultimate find during COVID,” Gravitis says. “They breathed some life into my year.

“I auditioned for The Amazing Race Canada a long time ago in hopes to open those iconic envelopes and get to travel to places I’ve never been,” she says. “So when I found out how Guess Where works, with their four mystery envelopes, I booked right away. I like them because they send me to places I hadn’t been to and I’d never think of going. They’re spontaneous adventure.”

Initially, Off curated the trips herself but, as demand has grown, she’s hired some travel bloggers to help craft itineraries. The mandate is simple: quirky, interesting, nature-filled and sometimes downright weird. One stop, for example, is Screaming Heads, an outdoor art installation tucked away in a field north of Toronto by a man who has pieces hanging in both the Vatican and Buckingham Palace. In British Columbia, day trippers might be sent to Spirit Trail, a mystical scavenger hunt of sorts that is the perfect follow-up to the Sasquatch Museum.

“The element of surprise is key,” Off says. “That’s what keeps our customers coming back.”

Every Guess Where road trip accommodates up to five people; the itineraries are self-guided and nothing needs to be booked in advance. Information about COVID protocols is included and the kits come with suggestions for where to eat and drink (usually small, local businesses that are little-known gems). In the last year, Off estimates she has sold 10,000 kits, with 30 per cent of them purchased as gifts.

Alejandra Gutierrez, a single mom with two kids aged 12 and 14, bought her first trip in August last year. She has done five since, with her children, her mom and girlfriends.

“I just love the idea of heading on a planned surprise road trip,” says Gutierrez, 41, who lives in Toronto. “When I bought my first one I was afraid it would send me to some places I had already visited because I’ve done a lot of hiking and sightseeing in Ontario. I was wrong. Every single trip has sent me to new destinations and hidden treasures in Ontario.”

They have also helped keep her children happy and engaged. “They love opening the first envelope and find out where we are going,” she says. “Then they get excited after we’re done each stop and it’s time to open a new one,” says Gutierrez, who adds that a recent highlight was a donkey sanctuary.

“When you travel by road you see and hear everything. You meet new people and learn new things. Road trips remind me how much this world has to offer, right outside our door.”