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Guess Where Trips
Top 50 Startup
2022
One-day surprise road trips in Canada

At Guess Where Trips, we live for creating exciting road trips that allow travellers to discover new places they never would have discovered on their own.

🇨🇦 One-day surprise road trips in Canada
💌 A series of 4 envelops with your itinerary
⌛️ Most trips are between 6-8 hours

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1 month ago
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Ian
Founder, Travel Massive

Hey Jessica, thanks for sharing Guess Where Trips with the Travel Massive community. What a great idea to bring visitors to new destinations!

I can imagine that the anticipation of going on a mystery road trip would also be an exciting lead up to the adventure — have any of your customers explored every trip?

1 month ago (edited)
Founder, Guess Where Trips Inc.

Yes! We've had quite a few that have explored all the trips offered within their area.

1 month ago
COO, Follow The Camino / One Foot Abroad

That is actually quite a neat idea. Well done

1 month ago
Founder, Guess Where Trips Inc.

Guess Where Trips started a few years ago and have evolved SO much. We're now across Canada and hope to be in the states very soon! Let me know if anyone has any good day trip suggestions for surprise road trips.

1 month ago
Content & Community, Travel Massive

This is a great idea! What would be the first destinations in the US? Are you looking for any local hosts or partners?

1 month ago
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