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! -
Quaint Corners
$39 USDCozy cafes, countryside drives, gorgeous lookouts and quirky roadside stops are just some of the things you'll discover on your surprise road trip!- Accessible
- Dog-Friendly
- Kid-Friendly
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A Drive Back in Time
$39 USDThe perfect day for the more leisurely road tripper. A Drive Back in Time isn't too far from the city and is full of cute towns, cafes, funky photo ops and so much more.- Accessible
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Wacky Wonders
$39 USDA little funky, a little unexpected, and totally unforgettable—this road trip is a whirlwind of colorful folk art, quirky roadside stops, scenic detours, and bites worth savoring. The only rule? Embrace the unexpected.