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 USDUnit 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! -
The Taste Trail
$65 USDThis road trip will take you to some funky eateries, family farms, wineries, cideries, and a whole lot more. To offset the treats, we've included a few whimsical hikes to end your day.- Accessible
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Chasing Waterfalls
$65 USDDon't let TLC lead you astray. You should definitely go chasing waterfalls! This trip is jam-packed with good food, picturesque waterfalls, and quirky gems.- Dog-Friendly
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Secrets on the Scenic Route
$65 USDThis trip combines iconic attractions and quite a few hidden gems before ending in one of the coolest villages in Canada. Can you guess where? Perfect for those wanting to explore this famous route in more detail.- Dog-Friendly