How does it work?
Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.
See our road trips below, or check out our quiz and trip map to help find your perfect adventure.
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Road Trip Gift Card
Regular price $74.00 CADUnit price perGive the gift of a one-day surprise road trip with Guess Where Trips®! The recipient can then choose a surprise trip that suits them! -
Treats & Trails
$39 CADIs there anything better than a leisurely day sipping coffee, enjoying tasty treats and meandering along easy boardwalk trails? We think not!- Kid-Friendly
- Dog-Friendly
- Accessible
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Groves, Gardens & Grapevines
$39 CADThis incredibly picturesque road trip is full of whimsical gardens, lookout points, wineries, and easy strolls along forest paths. We think it's an area you'll want to come back to time and time again.- Kid-Friendly
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Sweet Sensations
$39 CADBetween making a furry friend at a farm, enjoying local eateries, walking to quirky ruins in the woods and exploring the sweetest small town, this trip will make all five senses come to life all day!- Kid-Friendly
- Accessible