Destination unknown

The surprise travel sector has been a bright spot for an industry battered by the pandemic. And by keeping things simple and local, Guess Where Trips has carved itself a tidy little niche

Photo: Guess Where Trips founder, Jessica Off

IT’S A WEEKEND morning — road trip day. You have four envelopes, delivered in the mail a few days earlier, with instructions not to open them until you’re ready to head off.

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You have, at this point, the barest idea of where you’re heading, what to pack and when you should leave. Most other aspects of your trip — the destination, the route — remain a mystery, four surprises in four envelopes. Until you crack the seal on envelope number one, punch in the address and hit the road.

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In a time when vacations are often obsessively planned and scheduled, Jessica Off is gambling on surprise and spontaneity. Guess Where Trips, a ‘surprise travel’ business she started last July, seemed perfectly timed to satisfy itchy travellers who found themselves grounded all summer.

When flying was out of the question and even interprovincial travel triggered a host of quarantine requirements, Guess Where Trips leaned into surprise road trips — affordable day-long vacation schedules that were self-guided and required no pre-booking.

“Let’s simplify the business model. Let’s make it a one-day trip where everything’s self-guided and nothing needs to be booked in advance, and support local businesses that more people need to know about” —Jessica Off

“I started this as a bit of a side project, and at first it was surprise overnight getaways,” recalls Off. “Then it was scavenger hunts; there were some logistical issues with that.”

How about one-day surprise trips? she thought. “I’m going to source the best stops, create road trip themes and just make a road trip that everyone will like and will encourage travellers to explore their own backyard.”

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The business officially launched in July 2020, and to say it was well-timed might be an understatement. “In our first six months. we sold 10,000 trips,” Off recalls. “It was a really busy first six months.”

Surprise travel is a growing niche within the travel industry, ranging from short daytrips to elaborate and luxurious mysteries. One American operator, Black Tomato, offers a package called Get Lost where keen travellers are ferried into “uncharted and unknown” environments and tasked with figuring their way out. Packages for that start at (Cdn) $25,000 per person.

But what Off is doing with Guess Where Trips “has never been done before,” she says.

“Let’s simplify the business model,” she says of her approach. “Let’s make it a one-day trip where everything’s self-guided and nothing needs to be booked in advance, and support local businesses that more people need to know about.”

Simplifying this way gave Guess Where Trips its own corner of the market at a price point nobody else was able to offer. One of the best-known surprise travel companies, Pack Up and Go, offers road trip plans starting at (US) $400; a Guess Where Trip costs just over 50 bucks, and even less if you want a digital copy of the itinerary. They also make great gifts, accounting for around 40 per cent of sales.

To Off, this isn’t just a pandemic business model, but a way to reinvigorate the idea that tourism can start in your own backyard.

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“Everyone has a few days in the year where you want to go out and explore locally,” Off says. “People were doing that before [the pandemic] and people will continue to do that even if they have the opportunity to travel internationally.”

Since launching with itineraries focusing on Southwestern Ontario, Guess Where Trips now offers a variety of curated packages in eight geographic areas across the country, including Halifax, Ottawa, Winnipeg, Calgary and Vancouver.

Destination unknown guess where trips Tourism

When purchasing an excursion, visitors to the Guess Where Trips website can select a daytrip based on interests or travel preferences. Or they can opt to take a quiz asking questions about preferred trip duration, style and accompaniment (kids or no kids, for instance), which will in turn return suggested trips for the region, including road trips themed by season or occasion (think food-centric or Halloween).

Much of Off’s marketing so far has relied on word-of-mouth; she says that Instagram lifestyle and travel influencers have proven to be the most effective marketing approach for a team that remains small — just Off and three employees.

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Ask Off where she thinks this business model can take her, and like a lot of travellers are apt to do, she lets herself dream a little bit.

“I would love to be — honestly? ― all over the world,” Off says. “I want to be like the red tour bus, the hop-on-hop-off buses that you see in every major city. I know that’s thinking big, but I do think with the demand here that we can.” Destination unknown guess where trips Tourism Kieran Delamont

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